(2,8-Bis-trifluoromethyl-quinolin-4-yl)-piperidin-2-yl-methanol

ID: ALA416956

Chembl Id: CHEMBL416956

Cas Number: 53230-10-7

PubChem CID: 4046

Max Phase: Approved

First Approval: 1989

Molecular Formula: C17H16F6N2O

Molecular Weight: 378.32

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Lariam | Mefaquin | Mefloquine | GNF-Pf-5544 | NSC-758233 | RO 21-5998 | RO-215998 | WR 142,490 | mefloquine|49752-90-1|Lariam|GNF-Pf-5544|[2,8-bis(trifluoromethyl)quinolin-4-yl]-piperidin-2-ylmethanol|53230-10-7|[2,8-bis(trifluoromethyl)quinolin-4-yl](piperidin-2-yl)methanol|alpha-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol|threo-MefloquineHydrochloride|CHEMBL416956|alpha-2-Piperidyl-2,8-bis(trifluoromethyl)quinoline-4-methanol|CHEBI:63681|Racemic mefloquine|[2,8-bis(trifluorometShow More

Synonyms from Alternative Forms(11): Mefloquine hydrochloride | Loriam | Mefloquine hcl | Mefloquini hydrochloridum | NSC-157387 | RO 21-5998/001 | RO-21-5998 | RO-215998001 | WR-142490 | Fansimef | Lariam

Canonical SMILES:  OC(c1cc(C(F)(F)F)nc2c(C(F)(F)F)cccc12)C1CCCCN1

Standard InChI:  InChI=1S/C17H16F6N2O/c18-16(19,20)11-5-3-4-9-10(15(26)12-6-1-2-7-24-12)8-13(17(21,22)23)25-14(9)11/h3-5,8,12,15,24,26H,1-2,6-7H2

Standard InChI Key:  XEEQGYMUWCZPDN-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

    ALA416956

    MEFLOQUINE
  2. Alternative Forms:

Associated Targets(Human)

KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALB Tchem Serum albumin (2651 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KB (17409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HT-1080 (3966 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL-2 (46422 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A-431 (6446 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LNCaP (8286 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ZR-75-1 (953 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Huh-7 (12904 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LoVo (4724 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Homo sapiens (32628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LMNA Tbio Prelamin-A/C (36751 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTT Tchem Huntingtin (19182 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TP53 Tchem Cellular tumor antigen p53 (48468 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Brain (33 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasma (7708 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KAT2A Tchem Histone acetyltransferase GCN5 (14285 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RUNX1 Tbio Runt-related transcription factor 1/Core-binding factor subunit beta (7867 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
VDR Tclin Vitamin D receptor (26531 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCB1 Tchem P-glycoprotein 1 (14716 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GMNN Tbio Geminin (128009 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ATXN2 Tbio Ataxin-2 (54410 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GLRA1 Tclin Glycine receptor subunit alpha-1 (392 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR3C1 Tclin Glucocorticoid receptor (14987 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ESR1 Tclin Estrogen receptor alpha (17718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A3 Tclin Dopamine transporter (10535 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRNA4 Tclin Neuronal acetylcholine receptor protein alpha-4 subunit (1265 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCB11 Tchem Bile salt export pump (2311 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRK1 Tclin Kappa opioid receptor (16155 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA1 Tclin Adenosine A1 receptor (17603 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA3 Tchem Adenosine A3 receptor (15931 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD2 Tclin Dopamine D2 receptor (23596 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC29A1 Tclin Equilibrative nucleoside transporter 1 (1711 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACHE Tclin Acetylcholinesterase (18204 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A2 Tclin Norepinephrine transporter (10102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRM1 Tclin Mu opioid receptor (19785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A4 Tclin Serotonin transporter (12625 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA2A Tclin Adenosine A2a receptor (16305 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRD1 Tclin Delta opioid receptor (15096 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAOA Tclin Monoamine oxidase A (11911 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ERBB2 Tclin Receptor protein-tyrosine kinase erbB-2 (7851 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH2 Tclin Histamine H2 receptor (5428 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BDKRB2 Tclin Bradykinin B2 receptor (3970 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCKBR Tclin Cholecystokinin B receptor (3550 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GHSR Tclin Ghrelin receptor (6229 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCKAR Tclin Cholecystokinin A receptor (4460 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EDNRA Tclin Endothelin receptor ET-A (5008 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD1 Tclin Dopamine D1 receptor (9720 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MC3R Tchem Melanocortin receptor 3 (5659 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MC4R Tclin Melanocortin receptor 4 (10016 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE4D Tclin Phosphodiesterase 4D (3546 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NPY1R Tchem Neuropeptide Y receptor type 1 (5019 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR1I2 Tchem Pregnane X receptor (6667 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MLNR Tchem Motilin receptor (1724 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE3A Tclin Phosphodiesterase 3A (3309 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PGR Tclin Progesterone receptor (8562 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD3 Tclin Dopamine D3 receptor (14368 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH3 Tclin Histamine H3 receptor (10389 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH1 Tclin Histamine H1 receptor (7573 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GABRA1 Tclin Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 (1034 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium berghei (192651 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium yoelii (6656 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pfmrk Protein kinase Pfmrk (149 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium yoelii nigeriensis (1119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
L6 (7924 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei rhodesiense (7991 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Histidine-rich protein (528 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium avium complex sp. (178 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium tuberculosis (203094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P388 (20296 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma cruzi (99888 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania donovani (89745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDCK (10148 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RAW264.7 (28094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium vivax (152 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania infantum (5912 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium avium (4587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium malariae (15 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania major (2877 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pmp22 Peripheral myelin protein 22 (1279 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cacna1c Voltage-gated L-type calcium channel alpha-1C subunit (1321 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Grin1 Glutamate (NMDA) receptor subunit zeta 1 (2166 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Gabra1 GABA receptor alpha-1 subunit (2848 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ptgs1 Cyclooxygenase-1 (1373 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ar Androgen Receptor (5522 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc18a2 Synaptic vesicular amine transporter (631 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: YesChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: Yes
Chirality: NoAvailability: YesProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 378.32Molecular Weight (Monoisotopic): 378.1167AlogP: 4.45#Rotatable Bonds: 2
Polar Surface Area: 45.15Molecular Species: BASEHBA: 3HBD: 2
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 13.79CX Basic pKa: 9.46CX LogP: 4.11CX LogD: 2.07
Aromatic Rings: 2Heavy Atoms: 26QED Weighted: 0.76Np Likeness Score: 0.03

References

1. Gamage SA, Tepsiri N, Wilairat P, Wojcik SJ, Figgitt DP, Ralph RK, Denny WA..  (1994)  Synthesis and in vitro evaluation of 9-anilino-3,6-diaminoacridines active against a multidrug-resistant strain of the malaria parasite Plasmodium falciparum.,  37  (10): [PMID:8182707] [10.1021/jm00036a014]
2. Casteel DA, Peri S, Gerena L.  (1993)  Synthesis and antimalarial evaluation of 2,3,5-trioxabicyclo[2.2.3]nonane, a model for the putative pharmacophore of artemisinin,  (8): [10.1016/S0960-894X(00)80047-5]
3. Ayad F, Tilley L, Deady LW..  (2001)  Synthesis, antimalarial activity and inhibition of haem detoxification of novel bisquinolines.,  11  (16): [PMID:11514142] [10.1016/s0960-894x(01)00383-3]
4. Crivori P, Cruciani G, Carrupt PA, Testa B..  (2000)  Predicting blood-brain barrier permeation from three-dimensional molecular structure.,  43  (11): [PMID:10841799] [10.1021/jm990968+]
5. Crivori P, Cruciani G, Carrupt PA, Testa B..  (2000)  Predicting blood-brain barrier permeation from three-dimensional molecular structure.,  43  (11): [PMID:10841799] [10.1021/jm990968+]
6. Girault S, Grellier P, Berecibar A, Maes L, Mouray E, Lemière P, Debreu MA, Davioud-Charvet E, Sergheraert C..  (2000)  Antimalarial, antitrypanosomal, and antileishmanial activities and cytotoxicity of bis(9-amino-6-chloro-2-methoxyacridines): influence of the linker.,  43  (14): [PMID:10893302] [10.1021/jm990946n]
7. Solaja BA, Terzić N, Pocsfalvi G, Gerena L, Tinant B, Opsenica D, Milhous WK..  (2002)  Mixed steroidal 1,2,4,5-tetraoxanes: antimalarial and antimycobacterial activity.,  45  (16): [PMID:12139444] [10.1021/jm020891g]
8. Wiesner J, Mitsch A, Wissner P, Jomaa H, Schlitzer M..  (2001)  Structure-activity relationships of novel anti-malarial agents. Part 2: cinnamic acid derivatives.,  11  (3): [PMID:11212126] [10.1016/s0960-894x(00)00684-3]
9. Avery MA, Muraleedharan KM, Desai PV, Bandyopadhyaya AK, Furtado MM, Tekwani BL..  (2003)  Structure-activity relationships of the antimalarial agent artemisinin. 8. design, synthesis, and CoMFA studies toward the development of artemisinin-based drugs against leishmaniasis and malaria.,  46  (20): [PMID:13678403] [10.1021/jm030181q]
10. Avery MA, Alvim-Gaston M, Vroman JA, Wu B, Ager A, Peters W, Robinson BL, Charman W..  (2002)  Structure-activity relationships of the antimalarial agent artemisinin. 7. Direct modification of (+)-artemisinin and in vivo antimalarial screening of new, potential preclinical antimalarial candidates.,  45  (19): [PMID:12213073] [10.1021/jm020142z]
11. Bhattacharjee AK, Karle JM..  (1996)  Molecular electronic properties of a series of 4-quinolinecarbinolamines define antimalarial activity profile.,  39  (23): [PMID:8917651] [10.1021/jm960358z]
12. Bhattacharjee AK, Karle JM..  (1996)  Molecular electronic properties of a series of 4-quinolinecarbinolamines define antimalarial activity profile.,  39  (23): [PMID:8917651] [10.1021/jm960358z]
13. Brossi A, Venugopalan B, Dominguez Gerpe L, Yeh HJ, Flippen-Anderson JL, Buchs P, Luo XD, Milhous W, Peters W..  (1988)  Arteether, a new antimalarial drug: synthesis and antimalarial properties.,  31  (3): [PMID:3279208] [10.1021/jm00398a026]
14. Griesbeck AG, El-Idreesy TT, Höinck LO, Lex J, Brun R..  (2005)  Novel spiroanellated 1,2,4-trioxanes with high in vitro antimalarial activities.,  15  (3): [PMID:15664819] [10.1016/j.bmcl.2004.11.043]
15. Du LP, Tsai KC, Li MY, You QD, Xia L..  (2004)  The pharmacophore hypotheses of I(Kr) potassium channel blockers: novel class III antiarrhythmic agents.,  14  (18): [PMID:15324906] [10.1016/j.bmcl.2004.06.070]
16. Bhattacharjee AK, Geyer JA, Woodard CL, Kathcart AK, Nichols DA, Prigge ST, Li Z, Mott BT, Waters NC..  (2004)  A three-dimensional in silico pharmacophore model for inhibition of Plasmodium falciparum cyclin-dependent kinases and discovery of different classes of novel Pfmrk specific inhibitors.,  47  (22): [PMID:15481979] [10.1021/jm040108f]
17. Nallan L, Bauer KD, Bendale P, Rivas K, Yokoyama K, Hornéy CP, Pendyala PR, Floyd D, Lombardo LJ, Williams DK, Hamilton A, Sebti S, Windsor WT, Weber PC, Buckner FS, Chakrabarti D, Gelb MH, Van Voorhis WC..  (2005)  Protein farnesyltransferase inhibitors exhibit potent antimalarial activity.,  48  (11): [PMID:15916422] [10.1021/jm0491039]
18. Tobita M, Nishikawa T, Nagashima R..  (2005)  A discriminant model constructed by the support vector machine method for HERG potassium channel inhibitors.,  15  (11): [PMID:15911273] [10.1016/j.bmcl.2005.03.080]
19. Zhang Q, Guan J, Sacci J, Ager A, Ellis W, Milhous W, Kyle D, Lin AJ..  (2005)  Unambiguous synthesis and prophylactic antimalarial activities of imidazolidinedione derivatives.,  48  (20): [PMID:16190773] [10.1021/jm0504252]
20. Singh C, Malik H, Puri SK..  (2006)  Orally active 1,2,4-trioxanes: synthesis and antimalarial assessment of a new series of 9-functionalized 3-(1-arylvinyl)-1,2,5-trioxaspiro[5.5]undecanes against multi-drug-resistant plasmodium yoelii nigeriensis in mice.,  49  (9): [PMID:16640340] [10.1021/jm051130r]
21. Opsenica I, Terzić N, Opsenica D, Angelovski G, Lehnig M, Eilbracht P, Tinant B, Juranić Z, Smith KS, Yang YS, Diaz DS, Smith PL, Milhous WK, Doković D, Solaja BA..  (2006)  Tetraoxane antimalarials and their reaction with Fe(II).,  49  (13): [PMID:16789736] [10.1021/jm050966r]
22. Berger H, Seebacher W, Saf R, Kaiser M, Brun R, Weis R..  (2006)  Antiprotozoal activities of new bis-chlorophenyl derivatives of bicyclic octanes and aza-nonanes.,  16  (20): [PMID:16889962] [10.1016/j.bmcl.2006.07.057]
23. Skinner-Adams TS, Andrews KT, Melville L, McCarthy J, Gardiner DL..  (2007)  Synergistic interactions of the antiretroviral protease inhibitors saquinavir and ritonavir with chloroquine and mefloquine against Plasmodium falciparum in vitro.,  51  (2): [PMID:17088482] [10.1128/aac.00840-06]
24. Huy NT, Uyen DT, Maeda A, Trang DT, Oida T, Harada S, Kamei K..  (2007)  Simple colorimetric inhibition assay of heme crystallization for high-throughput screening of antimalarial compounds.,  51  (1): [PMID:17088494] [10.1128/aac.00985-06]
25. Noedl H, Krudsood S, Leowattana W, Tangpukdee N, Thanachartwet W, Looareesuwan S, Miller RS, Fukuda M, Jongsakul K, Yingyuen K, Sriwichai S, Ohrt C, Knirsch C..  (2007)  In vitro antimalarial activity of azithromycin, artesunate, and quinine in combination and correlation with clinical outcome.,  51  (2): [PMID:17116669] [10.1128/aac.01023-06]
26. Baniecki ML, Wirth DF, Clardy J..  (2007)  High-throughput Plasmodium falciparum growth assay for malaria drug discovery.,  51  (2): [PMID:17116676] [10.1128/aac.01144-06]
27. Terzić N, Opsenica D, Milić D, Tinant B, Smith KS, Milhous WK, Solaja BA..  (2007)  Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives(1).,  50  (21): [PMID:17887664] [10.1021/jm070684m]
28. Schlapper C, Seebacher W, Kaiser M, Brun R, Saf R, Weis R..  (2007)  Bicyclo[2.2.2]octyl esters of dialkylamino acids as antiprotozoals.,  15  (16): [PMID:17544672] [10.1016/j.bmc.2007.05.042]
29. Dodean RA, Kelly JX, Peyton D, Gard GL, Riscoe MK, Winter RW..  (2008)  Synthesis and heme-binding correlation with antimalarial activity of 3,6-bis-(omega-N,N-diethylaminoamyloxy)-4,5-difluoroxanthone.,  16  (3): [PMID:18023189] [10.1016/j.bmc.2007.10.083]
30. Friebolin W, Jannack B, Wenzel N, Furrer J, Oeser T, Sanchez CP, Lanzer M, Yardley V, Becker K, Davioud-Charvet E..  (2008)  Antimalarial dual drugs based on potent inhibitors of glutathione reductase from Plasmodium falciparum.,  51  (5): [PMID:18260613] [10.1021/jm7009292]
31. Opsenica I, Opsenica D, Smith KS, Milhous WK, Solaja BA..  (2008)  Chemical stability of the peroxide bond enables diversified synthesis of potent tetraoxane antimalarials.,  51  (7): [PMID:18330976] [10.1021/jm701417a]
32. Johnson JD, Dennull RA, Gerena L, Lopez-Sanchez M, Roncal NE, Waters NC..  (2007)  Assessment and continued validation of the malaria SYBR green I-based fluorescence assay for use in malaria drug screening.,  51  (6): [PMID:17371812] [10.1128/aac.01607-06]
33. Bermudez LE, Motamedi N, Chee C, Baimukanova G, Kolonoski P, Inderlied C, Aralar P, Wang G, Phan LT, Young LS..  (2007)  EDP-420, a bicyclolide (bridged bicyclic macrolide), is active against Mycobacterium avium.,  51  (5): [PMID:17296742] [10.1128/aac.01303-06]
34. Fivelman QL, Adagu IS, Warhurst DC..  (2007)  Effects of piperaquine, chloroquine, and amodiaquine on drug uptake and of these in combination with dihydroartemisinin against drug-sensitive and -resistant Plasmodium falciparum strains.,  51  (6): [PMID:17404003] [10.1128/aac.01479-06]
35. Zsila F, Visy J, Mády G, Fitos I..  (2008)  Selective plasma protein binding of antimalarial drugs to alpha1-acid glycoprotein.,  16  (7): [PMID:18289858] [10.1016/j.bmc.2008.01.053]
36. Angerhofer CK, Guinaudeau H, Wongpanich V, Pezzuto JM, Cordell GA..  (1999)  Antiplasmodial and cytotoxic activity of natural bisbenzylisoquinoline alkaloids.,  62  (1): [PMID:9917283] [10.1021/np980144f]
37. Cimanga K, De Bruyne T, Pieters L, Vlietinck AJ, Turger CA..  (1997)  In vitro and in vivo antiplasmodial activity of cryptolepine and related alkaloids from Cryptolepis sanguinolenta.,  60  (7): [PMID:9249972] [10.1021/np9605246]
38. Lin LZ, Hu SF, Zaw K, Angerhofer CK, Chai H, Pezzuto JM, Cordell GA, Lin J, Zheng DM..  (1994)  Thalifaberidine, a cytotoxic aporphine-benzylisoquinoline alkaloid from Thalictrum faberi.,  57  (10): [PMID:7528786] [10.1021/np50112a013]
39. Angerhofer CK, Pezzuto JM, König GM, Wright AD, Sticher O..  (1992)  Antimalarial activity of sesquiterpenes from the marine sponge Acanthella klethra.,  55  (12): [PMID:1294700] [10.1021/np50090a014]
40. Opsenica DM, Terzić N, Smith PL, Yang Y, Anova L, Smith KS, Solaja BA..  (2008)  Mixed tetraoxanes containing the acetone subunit as antimalarials.,  16  (14): [PMID:18550377] [10.1016/j.bmc.2008.05.017]
41. O'Neill PM, Park BK, Shone AE, Maggs JL, Roberts P, Stocks PA, Biagini GA, Bray PG, Gibbons P, Berry N, Winstanley PA, Mukhtar A, Bonar-Law R, Hindley S, Bambal RB, Davis CB, Bates M, Hart TK, Gresham SL, Lawrence RM, Brigandi RA, Gomez-delas-Heras FM, Gargallo DV, Ward SA..  (2009)  Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.,  52  (5): [PMID:19222165] [10.1021/jm8012618]
42. Fotie J, Bohle DS, Leimanis ML, Georges E, Rukunga G, Nkengfack AE..  (2006)  Lupeol long-chain fatty acid esters with antimalarial activity from Holarrhena floribunda.,  69  (1): [PMID:16441070] [10.1021/np050315y]
43. MacKinnon S, Durst T, Arnason JT, Angerhofer C, Pezzuto J, Sanchez-Vindas PE, Poveda LJ, Gbeassor M..  (1997)  Antimalarial activity of tropical Meliaceae extracts and gedunin derivatives.,  60  (4): [PMID:9134742] [10.1021/np9605394]
44. Riel MA, Kyle DE, Milhous WK..  (2002)  Efficacy of scopadulcic acid A against Plasmodium falciparum in vitro.,  65  (4): [PMID:11975516] [10.1021/np0105275]
45. Han J, Lee JG, Min SS, Park SH, Angerhofer CK, Cordell GA, Kim SU..  (2001)  Synthesis of new artemisinin analogues from artemisinic acid modified at C-3 and C-13 and their antimalarial activity.,  64  (9): [PMID:11575956] [10.1021/np0101752]
46. Opsenica I, Opsenica D, Lanteri CA, Anova L, Milhous WK, Smith KS, Solaja BA..  (2008)  New chimeric antimalarials with 4-aminoquinoline moiety linked to a tetraoxane skeleton.,  51  (19): [PMID:18774792] [10.1021/jm8006905]
47. O'Neill PM, Shone AE, Stanford D, Nixon G, Asadollahy E, Park BK, Maggs JL, Roberts P, Stocks PA, Biagini G, Bray PG, Davies J, Berry N, Hall C, Rimmer K, Winstanley PA, Hindley S, Bambal RB, Davis CB, Bates M, Gresham SL, Brigandi RA, Gomez-de-Las-Heras FM, Gargallo DV, Parapini S, Vivas L, Lander H, Taramelli D, Ward SA..  (2009)  Synthesis, antimalarial activity, and preclinical pharmacology of a novel series of 4'-fluoro and 4'-chloro analogues of amodiaquine. Identification of a suitable "back-up" compound for N-tert-butyl isoquine.,  52  (7): [PMID:19284751] [10.1021/jm8012757]
48. Lilienkampf A, Mao J, Wan B, Wang Y, Franzblau SG, Kozikowski AP..  (2009)  Structure-activity relationships for a series of quinoline-based compounds active against replicating and nonreplicating Mycobacterium tuberculosis.,  52  (7): [PMID:19271749] [10.1021/jm900003c]
49. Klayman DL, Lin AJ, Acton N, Scovill JP, Hoch JM, Milhous WK, Theoharides AD, Dobek AS..  (1984)  Isolation of artemisinin (qinghaosu) from Artemisia annua growing in the United States.,  47  (4): [PMID:6387056] [10.1021/np50034a027]
50. Likhitwitayawuid K, Angerhofer CK, Cordell GA, Pezzuto JM, Ruangrungsi N..  (1993)  Cytotoxic and antimalarial bisbenzylisoquinoline alkaloids from Stephania erecta.,  56  (1): [PMID:8450319] [10.1021/np50091a005]
51. Kardono LB, Angerhofer CK, Tsauri S, Padmawinata K, Pezzuto JM, Kinghorn AD..  (1991)  Cytotoxic and antimalarial constituents of the roots of Eurycoma longifolia.,  54  (5): [PMID:1800638] [10.1021/np50077a020]
52. Frédérich M, De Pauw M, Prosperi C, Tits M, Brandt V, Penelle J, Hayette M, DeMol P, Angenot L..  (2001)  Strychnogucines A and B, two new antiplasmodial bisindole alkaloids from Strychnos icaja.,  64  (1): [PMID:11170658] [10.1021/np000285t]
53. Jia L, Sun H..  (2008)  Support vector machines classification of hERG liabilities based on atom types.,  16  (11): [PMID:18448342] [10.1016/j.bmc.2008.04.028]
54. Solaja BA, Opsenica D, Smith KS, Milhous WK, Terzić N, Opsenica I, Burnett JC, Nuss J, Gussio R, Bavari S..  (2008)  Novel 4-aminoquinolines active against chloroquine-resistant and sensitive P. falciparum strains that also inhibit botulinum serotype A.,  51  (15): [PMID:18637666] [10.1021/jm800737y]
55. Wright AD, de Nys R, Angerhofer CK, Pezzuto JM, Gurrath M..  (2006)  Biological activities and 3D QSAR studies of a series of Delisea pulchra (cf. fimbriata) derived natural products.,  69  (8): [PMID:16933872] [10.1021/np050510c]
56. Wright AD, König GM, Angerhofer CK, Greenidge P, Linden A, Desqueyroux-Faúndez R..  (1996)  Antimalarial activity: the search for marine-derived natural products with selective antimalarial activity.,  59  (7): [PMID:8759172] [10.1021/np9602325]
57. Böhlke M, Guinaudeau H, Angerhofer CK, Wongpanich V, Soejarto DD, Farnsworth NR, Mora GA, Poveda LJ..  (1996)  Costaricine, a new antiplasmodial bisbenzylisoquinoline alkaloid from Nectandra salicifolia trunk bark.,  59  (6): [PMID:8786363] [10.1021/np960195h]
58. Likhitwitayawuid K, Angerhofer CK, Chai H, Pezzuto JM, Cordell GA, Ruangrungsi N..  (1993)  Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.,  56  (9): [PMID:8254346] [10.1021/np50099a005]
59. Cabral JA, McChesney JD, Milhous WK..  (1993)  A new antimalarial quassinoid from Simaba guianensis.,  56  (11): [PMID:8289064] [10.1021/np50101a014]
60. Likhitwitayawuid K, Angerhofer CK, Chai H, Pezzuto JM, Cordell GA, Ruangrungsi N..  (1993)  Cytotoxic and antimalarial alkaloids from the bulbs of Crinum amabile.,  56  (8): [PMID:8229016] [10.1021/np50098a017]
61. Verotta L, Dell'Agli M, Giolito A, Guerrini M, Cabalion P, Bosisio E..  (2001)  In vitro antiplasmodial activity of extracts of Tristaniopsis species and identification of the active constituents: ellagic acid and 3,4,5-trimethoxyphenyl-(6'-O-galloyl)-O-beta-D-glucopyranoside.,  64  (5): [PMID:11374952] [10.1021/np000306j]
62. Rodenko B, van der Burg AM, Wanner MJ, Kaiser M, Brun R, Gould M, de Koning HP, Koomen GJ..  (2007)  2,N6-disubstituted adenosine analogs with antitrypanosomal and antimalarial activities.,  51  (11): [PMID:17698622] [10.1128/aac.00425-07]
63. Berger H, Weis R, Kaiser M, Brun R, Saf R, Seebacher W..  (2008)  Novel azabicyclo[3.2.2]nonane derivatives and their activities against Plasmodium falciparum K1 and Trypanosoma brucei rhodesiense.,  16  (12): [PMID:18502136] [10.1016/j.bmc.2008.05.007]
64. Chen Y, Lopez-Sanchez M, Savoy DN, Billadeau DD, Dow GS, Kozikowski AP..  (2008)  A series of potent and selective, triazolylphenyl-based histone deacetylases inhibitors with activity against pancreatic cancer cells and Plasmodium falciparum.,  51  (12): [PMID:18494463] [10.1021/jm701606b]
65. de Souza MV, Pais KC, Kaiser CR, Peralta MA, de L Ferreira M, Lourenço MC..  (2009)  Synthesis and in vitro antitubercular activity of a series of quinoline derivatives.,  17  (4): [PMID:19188070] [10.1016/j.bmc.2009.01.013]
66. Mao J, Yuan H, Wang Y, Wan B, Pieroni M, Huang Q, van Breemen RB, Kozikowski AP, Franzblau SG..  (2009)  From serendipity to rational antituberculosis drug discovery of mefloquine-isoxazole carboxylic acid esters.,  52  (22): [PMID:19863050] [10.1021/jm900340a]
67. Lilienkampf A, Pieroni M, Wan B, Wang Y, Franzblau SG, Kozikowski AP..  (2010)  Rational design of 5-phenyl-3-isoxazolecarboxylic acid ethyl esters as growth inhibitors of Mycobacterium tuberculosis. a potent and selective series for further drug development.,  53  (2): [PMID:20000577] [10.1021/jm901273n]
68. Dong Y, Wittlin S, Sriraghavan K, Chollet J, Charman SA, Charman WN, Scheurer C, Urwyler H, Santo Tomas J, Snyder C, Creek DJ, Morizzi J, Koltun M, Matile H, Wang X, Padmanilayam M, Tang Y, Dorn A, Brun R, Vennerstrom JL..  (2010)  The structure-activity relationship of the antimalarial ozonide arterolane (OZ277).,  53  (1): [PMID:19924861] [10.1021/jm901473s]
69. Grimberg BT, Jaworska MM, Hough LB, Zimmerman PA, Phillips JG..  (2009)  Addressing the malaria drug resistance challenge using flow cytometry to discover new antimalarials.,  19  (18): [PMID:19666223] [10.1016/j.bmcl.2009.07.095]
70. Plouffe D, Brinker A, McNamara C, Henson K, Kato N, Kuhen K, Nagle A, Adrián F, Matzen JT, Anderson P, Nam TG, Gray NS, Chatterjee A, Janes J, Yan SF, Trager R, Caldwell JS, Schultz PG, Zhou Y, Winzeler EA..  (2008)  In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen.,  105  (26): [PMID:18579783] [10.1073/pnas.0802982105]
71. Tang Y, Wittlin S, Charman SA, Chollet J, Chiu FC, Morizzi J, Johnson LM, Tomas JS, Scheurer C, Snyder C, Zhou L, Dong Y, Charman WN, Matile H, Urwyler H, Dorn A, Vennerstrom JL..  (2010)  The comparative antimalarial properties of weak base and neutral synthetic ozonides.,  20  (2): [PMID:19962893] [10.1016/j.bmcl.2009.11.088]
72. Mao J, Yuan H, Wang Y, Wan B, Pak D, He R, Franzblau SG..  (2010)  Synthesis and antituberculosis activity of novel mefloquine-isoxazole carboxylic esters as prodrugs.,  20  (3): [PMID:20022500] [10.1016/j.bmcl.2009.11.105]
73. Milner E, McCalmont W, Bhonsle J, Caridha D, Carroll D, Gardner S, Gerena L, Gettayacamin M, Lanteri C, Luong T, Melendez V, Moon J, Roncal N, Sousa J, Tungtaeng A, Wipf P, Dow G..  (2010)  Structure-activity relationships amongst 4-position quinoline methanol antimalarials that inhibit the growth of drug sensitive and resistant strains of Plasmodium falciparum.,  20  (4): [PMID:20097070] [10.1016/j.bmcl.2010.01.001]
74. Milner E, McCalmont W, Bhonsle J, Caridha D, Carroll D, Gardner S, Gerena L, Gettayacamin M, Lanteri C, Luong T, Melendez V, Moon J, Roncal N, Sousa J, Tungtaeng A, Wipf P, Dow G..  (2010)  Structure-activity relationships amongst 4-position quinoline methanol antimalarials that inhibit the growth of drug sensitive and resistant strains of Plasmodium falciparum.,  20  (4): [PMID:20097070] [10.1016/j.bmcl.2010.01.001]
75. Zhang Y, Guiguemde WA, Sigal M, Zhu F, Connelly MC, Nwaka S, Guy RK..  (2010)  Synthesis and structure-activity relationships of antimalarial 4-oxo-3-carboxyl quinolones.,  18  (7): [PMID:20206533] [10.1016/j.bmc.2010.02.013]
76. Shahinas D, Liang M, Datti A, Pillai DR..  (2010)  A repurposing strategy identifies novel synergistic inhibitors of Plasmodium falciparum heat shock protein 90.,  53  (9): [PMID:20349996] [10.1021/jm901796s]
77. Deng X, Nagle A, Wu T, Sakata T, Henson K, Chen Z, Kuhen K, Plouffe D, Winzeler E, Adrian F, Tuntland T, Chang J, Simerson S, Howard S, Ek J, Isbell J, Tully DC, Chatterjee AK, Gray NS..  (2010)  Discovery of novel 1H-imidazol-2-yl-pyrimidine-4,6-diamines as potential antimalarials.,  20  (14): [PMID:20610151] [10.1016/j.bmcl.2010.05.095]
78. Caridha D, Kathcart AK, Jirage D, Waters NC..  (2010)  Activity of substituted thiophene sulfonamides against malarial and mammalian cyclin dependent protein kinases.,  20  (13): [PMID:20627564] [10.1016/j.bmcl.2010.05.039]
79. Eswaran S, Adhikari AV, Chowdhury IH, Pal NK, Thomas KD..  (2010)  New quinoline derivatives: synthesis and investigation of antibacterial and antituberculosis properties.,  45  (8): [PMID:20537437] [10.1016/j.ejmech.2010.04.022]
80. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]
81. Bahl D, Athar F, Soares MB, de Sá MS, Moreira DR, Srivastava RM, Leite AC, Azam A..  (2010)  Structure-activity relationships of mononuclear metal-thiosemicarbazone complexes endowed with potent antiplasmodial and antiamoebic activities.,  18  (18): [PMID:20719524] [10.1016/j.bmc.2010.07.039]
82. Chong CR, Chen X, Shi L, Liu JO, Sullivan DJ..  (2006)  A clinical drug library screen identifies astemizole as an antimalarial agent.,  (8): [PMID:16816845] [10.1038/nchembio806]
83. Nasveld PE, Edstein MD, Reid M, Brennan L, Harris IE, Kitchener SJ, Leggat PA, Pickford P, Kerr C, Ohrt C, Prescott W, Tafenoquine Study Team..  (2010)  Randomized, double-blind study of the safety, tolerability, and efficacy of tafenoquine versus mefloquine for malaria prophylaxis in nonimmune subjects.,  54  (2): [PMID:19995933] [10.1128/aac.00354-09]
84. Rottmann M, McNamara C, Yeung BK, Lee MC, Zou B, Russell B, Seitz P, Plouffe DM, Dharia NV, Tan J, Cohen SB, Spencer KR, González-Páez GE, Lakshminarayana SB, Goh A, Suwanarusk R, Jegla T, Schmitt EK, Beck HP, Brun R, Nosten F, Renia L, Dartois V, Keller TH, Fidock DA, Winzeler EA, Diagana TT..  (2010)  Spiroindolones, a potent compound class for the treatment of malaria.,  329  (5996): [PMID:20813948] [10.1126/science.1193225]
85. Roberts L, Egan TJ, Joiner KA, Hoppe HC..  (2008)  Differential effects of quinoline antimalarials on endocytosis in Plasmodium falciparum.,  52  (5): [PMID:18316523] [10.1128/aac.01478-07]
86. Russell B, Chalfein F, Prasetyorini B, Kenangalem E, Piera K, Suwanarusk R, Brockman A, Prayoga P, Sugiarto P, Cheng Q, Tjitra E, Anstey NM, Price RN..  (2008)  Determinants of in vitro drug susceptibility testing of Plasmodium vivax.,  52  (3): [PMID:18180357] [10.1128/aac.01334-07]
87. Nzila A, Rottmann M, Chitnumsub P, Kiara SM, Kamchonwongpaisan S, Maneeruttanarungroj C, Taweechai S, Yeung BK, Goh A, Lakshminarayana SB, Zou B, Wong J, Ma NL, Weaver M, Keller TH, Dartois V, Wittlin S, Brun R, Yuthavong Y, Diagana TT..  (2010)  Preclinical evaluation of the antifolate QN254, 5-chloro- N'6'-(2,5-dimethoxy-benzyl)-quinazoline-2,4,6-triamine, as an antimalarial drug candidate.,  54  (6): [PMID:20350951] [10.1128/aac.01526-09]
88. Savini H, Bogreau H, Bertaux L, Bouchiba H, Kraemer P, Parzy D, Garnotel E, Rogier C, Simon F, Pradines B..  (2008)  First case of emergence of atovaquone-proguanil resistance in Plasmodium falciparum during treatment in a traveler in Comoros.,  52  (6): [PMID:18411319] [10.1128/aac.00282-08]
89. Lek-Uthai U, Suwanarusk R, Ruengweerayut R, Skinner-Adams TS, Nosten F, Gardiner DL, Boonma P, Piera KA, Andrews KT, Machunter B, McCarthy JS, Anstey NM, Price RN, Russell B..  (2008)  Stronger activity of human immunodeficiency virus type 1 protease inhibitors against clinical isolates of Plasmodium vivax than against those of P. falciparum.,  52  (7): [PMID:18443130] [10.1128/aac.00169-08]
90. Castanys-Muñoz E, Pérez-Victoria JM, Gamarro F, Castanys S..  (2008)  Characterization of an ABCG-like transporter from the protozoan parasite Leishmania with a role in drug resistance and transbilayer lipid movement.,  52  (10): [PMID:18644961] [10.1128/aac.00587-08]
91. Kuhn I, Kellenberger E, Said-Hassane F, Villa P, Rognan D, Lobstein A, Haiech J, Hibert M, Schuber F, Muller-Steffner H..  (2010)  Identification by high-throughput screening of inhibitors of Schistosoma mansoni NAD(+) catabolizing enzyme.,  18  (22): [PMID:20951593] [10.1016/j.bmc.2010.09.041]
92. PubChem BioAssay data set, 
93. PubChem BioAssay data set, 
94. PubChem BioAssay data set, 
95. Gonçalves RS, Kaiser CR, Lourenço MC, de Souza MV, Wardell JL, Wardell SM, da Silva AD..  (2010)  Synthesis and antitubercular activity of new mefloquine-oxazolidine derivatives.,  45  (12): [PMID:20932608] [10.1016/j.ejmech.2010.09.024]
96. Dow GS, Chen Y, Andrews KT, Caridha D, Gerena L, Gettayacamin M, Johnson J, Li Q, Melendez V, Obaldia N, Tran TN, Kozikowski AP..  (2008)  Antimalarial activity of phenylthiazolyl-bearing hydroxamate-based histone deacetylase inhibitors.,  52  (10): [PMID:18644969] [10.1128/aac.00439-08]
97. Gutteridge CE, Hoffman MM, Bhattacharjee AK, Milhous WK, Gerena L..  (2011)  In vitro efficacy of 7-benzylamino-1-isoquinolinamines against Plasmodium falciparum related to the efficacy of chalcones.,  21  (2): [PMID:21168330] [10.1016/j.bmcl.2010.11.099]
98. Starzengruber P, Thriemer K, Haque R, Khan WA, Fuehrer HP, Siedl A, Hofecker V, Ley B, Wernsdorfer WH, Noedl H..  (2009)  Antimalarial activity of tigecycline, a novel glycylcycline antibiotic.,  53  (9): [PMID:19596882] [10.1128/aac.00312-09]
99. Andriantsoanirina V, Ratsimbasoa A, Bouchier C, Jahevitra M, Rabearimanana S, Radrianjafy R, Andrianaranjaka V, Randriantsoa T, Rason MA, Tichit M, Rabarijaona LP, Mercereau-Puijalon O, Durand R, Ménard D..  (2009)  Plasmodium falciparum drug resistance in Madagascar: facing the spread of unusual pfdhfr and pfmdr-1 haplotypes and the decrease of dihydroartemisinin susceptibility.,  53  (11): [PMID:19704124] [10.1128/aac.00610-09]
100. Hasugian AR, Tjitra E, Ratcliff A, Siswantoro H, Kenangalem E, Wuwung RM, Purba HL, Piera KA, Chalfien F, Marfurt J, Penttinen PM, Russell B, Anstey NM, Price RN..  (2009)  In vivo and in vitro efficacy of amodiaquine monotherapy for treatment of infection by chloroquine-resistant Plasmodium vivax.,  53  (3): [PMID:19104023] [10.1128/aac.01511-08]
101. Khan MO, Levi MS, Tekwani BL, Khan SI, Kimura E, Borne RF..  (2009)  Synthesis and antimalarial activities of cyclen 4-aminoquinoline analogs.,  53  (4): [PMID:19171802] [10.1128/aac.01304-08]
102. Brickelmaier M, Lugovskoy A, Kartikeyan R, Reviriego-Mendoza MM, Allaire N, Simon K, Frisque RJ, Gorelik L..  (2009)  Identification and characterization of mefloquine efficacy against JC virus in vitro.,  53  (5): [PMID:19258267] [10.1128/aac.01614-08]
103. Bacon DJ, McCollum AM, Griffing SM, Salas C, Soberon V, Santolalla M, Haley R, Tsukayama P, Lucas C, Escalante AA, Udhayakumar V..  (2009)  Dynamics of malaria drug resistance patterns in the Amazon basin region following changes in Peruvian national treatment policy for uncomplicated malaria.,  53  (5): [PMID:19258269] [10.1128/aac.01677-08]
104. Rush MA, Baniecki ML, Mazitschek R, Cortese JF, Wiegand R, Clardy J, Wirth DF..  (2009)  Colorimetric high-throughput screen for detection of heme crystallization inhibitors.,  53  (6): [PMID:19307367] [10.1128/aac.01466-08]
105. Parquet V, Briolant S, Torrentino-Madamet M, Henry M, Almeras L, Amalvict R, Baret E, Fusaï T, Rogier C, Pradines B..  (2009)  Atorvastatin is a promising partner for antimalarial drugs in treatment of Plasmodium falciparum malaria.,  53  (6): [PMID:19307369] [10.1128/aac.01462-08]
106. Masseno V, Muriithi S, Nzila A..  (2009)  In vitro chemosensitization of Plasmodium falciparum to antimalarials by verapamil and probenecid.,  53  (7): [PMID:19364853] [10.1128/aac.01689-08]
107. Chen N, Chavchich M, Peters JM, Kyle DE, Gatton ML, Cheng Q..  (2010)  Deamplification of pfmdr1-containing amplicon on chromosome 5 in Plasmodium falciparum is associated with reduced resistance to artelinic acid in vitro.,  54  (8): [PMID:20421397] [10.1128/aac.01421-09]
108. Lucumi E, Darling C, Jo H, Napper AD, Chandramohanadas R, Fisher N, Shone AE, Jing H, Ward SA, Biagini GA, DeGrado WF, Diamond SL, Greenbaum DC..  (2010)  Discovery of potent small-molecule inhibitors of multidrug-resistant Plasmodium falciparum using a novel miniaturized high-throughput luciferase-based assay.,  54  (9): [PMID:20547797] [10.1128/aac.00431-10]
109. Price RN, Marfurt J, Chalfein F, Kenangalem E, Piera KA, Tjitra E, Anstey NM, Russell B..  (2010)  In vitro activity of pyronaridine against multidrug-resistant Plasmodium falciparum and Plasmodium vivax.,  54  (12): [PMID:20876370] [10.1128/aac.00801-10]
110. Sinha N, Sen S..  (2011)  Predicting hERG activities of compounds from their 3D structures: development and evaluation of a global descriptors based QSAR model.,  46  (2): [PMID:21185626] [10.1016/j.ejmech.2010.11.042]
111. Siswantoro H, Russell B, Ratcliff A, Prasetyorini B, Chalfein F, Marfurt J, Kenangalem E, Wuwung M, Piera KA, Ebsworth EP, Anstey NM, Tjitra E, Price RN..  (2011)  In vivo and in vitro efficacy of chloroquine against Plasmodium malariae and P. ovale in Papua, Indonesia.,  55  (1): [PMID:20937779] [10.1128/aac.01122-10]
112. Marfurt J, Chalfein F, Prayoga P, Wabiser F, Kenangalem E, Piera KA, Fairlie DP, Tjitra E, Anstey NM, Andrews KT, Price RN..  (2011)  Ex vivo activity of histone deacetylase inhibitors against multidrug-resistant clinical isolates of Plasmodium falciparum and P. vivax.,  55  (3): [PMID:21135175] [10.1128/aac.01220-10]
113. Manzano JI, Carvalho L, Pérez-Victoria JM, Castanys S, Gamarro F..  (2011)  Increased glycolytic ATP synthesis is associated with tafenoquine resistance in Leishmania major.,  55  (3): [PMID:21199921] [10.1128/aac.01545-10]
114. Matthews EJ, Kruhlak NL, Weaver JL, Benz RD, Contrera JF..  (2004)  Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.,  (4): [PMID:16472241] [10.2174/1570163043334794]
115. Opsenica I, Burnett JC, Gussio R, Opsenica D, Todorović N, Lanteri CA, Sciotti RJ, Gettayacamin M, Basilico N, Taramelli D, Nuss JE, Wanner L, Panchal RG, Solaja BA, Bavari S..  (2011)  A chemotype that inhibits three unrelated pathogenic targets: the botulinum neurotoxin serotype A light chain, P. falciparum malaria, and the Ebola filovirus.,  54  (5): [PMID:21265542] [10.1021/jm100938u]
116. Gujjar R, El Mazouni F, White KL, White J, Creason S, Shackleford DM, Deng X, Charman WN, Bathurst I, Burrows J, Floyd DM, Matthews D, Buckner FS, Charman SA, Phillips MA, Rathod PK..  (2011)  Lead optimization of aryl and aralkyl amine-based triazolopyrimidine inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase with antimalarial activity in mice.,  54  (11): [PMID:21517059] [10.1021/jm200265b]
117. Ndakala AJ, Gessner RK, Gitari PW, October N, White KL, Hudson A, Fakorede F, Shackleford DM, Kaiser M, Yeates C, Charman SA, Chibale K..  (2011)  Antimalarial pyrido[1,2-a]benzimidazoles.,  54  (13): [PMID:21644541] [10.1021/jm200227r]
118. Wu T, Nagle A, Kuhen K, Gagaring K, Borboa R, Francek C, Chen Z, Plouffe D, Goh A, Lakshminarayana SB, Wu J, Ang HQ, Zeng P, Kang ML, Tan W, Tan M, Ye N, Lin X, Caldwell C, Ek J, Skolnik S, Liu F, Wang J, Chang J, Li C, Hollenbeck T, Tuntland T, Isbell J, Fischli C, Brun R, Rottmann M, Dartois V, Keller T, Diagana T, Winzeler E, Glynne R, Tully DC, Chatterjee AK..  (2011)  Imidazolopiperazines: hit to lead optimization of new antimalarial agents.,  54  (14): [PMID:21644570] [10.1021/jm2003359]
119. Milner E, Gardner S, Moon J, Grauer K, Auschwitz J, Bathurst I, Caridha D, Gerena L, Gettayacamin M, Johnson J, Kozar M, Lee P, Leed S, Li Q, McCalmont W, Melendez V, Roncal N, Sciotti R, Smith B, Sousa J, Tungtaeng A, Wipf P, Dow G..  (2011)  Structure-activity relationships of 4-position diamine quinoline methanols as intermittent preventative treatment (IPT) against Plasmodium falciparum.,  54  (18): [PMID:21854078] [10.1021/jm200647u]
120. Sá MS, de Menezes MN, Krettli AU, Ribeiro IM, Tomassini TC, Ribeiro dos Santos R, de Azevedo WF, Soares MB..  (2011)  Antimalarial activity of physalins B, D, F, and G.,  74  (10): [PMID:21954931] [10.1021/np200260f]
121. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]
122. Gonçalves RS, Kaiser CR, Lourenço MC, Bezerra FA, de Souza MV, Wardell JL, Wardell SM, Henriques Md, Costa T..  (2012)  Mefloquine-oxazolidine derivatives, derived from mefloquine and arenecarbaldehydes: In vitro activity including against the multidrug-resistant tuberculosis strain T113.,  20  (1): [PMID:22142615] [10.1016/j.bmc.2011.11.006]
123. Zhu S, Chandrashekar G, Meng L, Robinson K, Chatterji D..  (2012)  Febrifugine analogue compounds: synthesis and antimalarial evaluation.,  20  (2): [PMID:22182577] [10.1016/j.bmc.2011.11.053]
124. Tacon C, Guantai EM, Smith PJ, Chibale K..  (2012)  Synthesis, biological evaluation and mechanistic studies of totarol amino alcohol derivatives as potential antimalarial agents.,  20  (2): [PMID:22196513] [10.1016/j.bmc.2011.11.060]
125. Endale M, Ekberg A, Akala HM, Alao JP, Sunnerhagen P, Yenesew A, Erdélyi M..  (2012)  Busseihydroquinones A-D from the roots of Pentas bussei.,  75  (7): [PMID:22709138] [10.1021/np3002223]
126. Fujita R, Ishikawa M, Takayanagi M, Takayanagi Y, Sasaki K..  (2000)  Enhancement of doxorubicin activity in multidrug-resistant cells by mefloquine.,  22  (1): [PMID:11031728] [10.1358/mf.2000.22.5.796646]
127. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 
128. Asif M, Siddiqui AA, Husain A.  (2013)  Quinolone derivatives as antitubercular drugs,  22  (3): [10.1007/s00044-012-0101-3]
129. Murugesan D, Mital A, Kaiser M, Shackleford DM, Morizzi J, Katneni K, Campbell M, Hudson A, Charman SA, Yeates C, Gilbert IH..  (2013)  Discovery and structure-activity relationships of pyrrolone antimalarials.,  56  (7): [PMID:23517371] [10.1021/jm400009c]
130. Ochieng CO, Manguro LA, Owuor PO, Akala H..  (2013)  Voulkensin C-E, new 11-oxocassane-type diterpenoids and a steroid glycoside from Caesalpinia volkensii stem bark and their antiplasmodial activities.,  23  (10): [PMID:23562058] [10.1016/j.bmcl.2013.03.007]
131. Gorka AP, de Dios A, Roepe PD..  (2013)  Quinoline drug-heme interactions and implications for antimalarial cytostatic versus cytocidal activities.,  56  (13): [PMID:23586757] [10.1021/jm400282d]
132. Dartois V, Barry CE..  (2013)  A medicinal chemists' guide to the unique difficulties of lead optimization for tuberculosis.,  23  (17): [PMID:23910985] [10.1016/j.bmcl.2013.07.006]
133. Unpublished dataset, 
134. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]
135. Conyers RC, Mazzone JR, Siegler MA, Tripathi AK, Sullivan DJ, Mott BT, Posner GH..  (2014)  The survival times of malaria-infected mice are prolonged more by several new two-carbon-linked artemisinin-derived dimer carbamates than by the trioxane antimalarial drug artemether.,  24  (5): [PMID:24508128] [10.1016/j.bmcl.2014.01.059]
136. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]
137. PubChem BioAssay data set, 
138. Opsenica IM, Verbić TŽ, Tot M, Sciotti RJ, Pybus BS, Djurković-Djaković O, Slavić K, Šolaja BA..  (2015)  Investigation into novel thiophene- and furan-based 4-amino-7-chloroquinolines afforded antimalarials that cure mice.,  23  (9): [PMID:25801154] [10.1016/j.bmc.2015.02.061]
139. Aroonkit P, Thongsornkleeb C, Tummatorn J, Krajangsri S, Mungthin M, Ruchirawat S..  (2015)  Synthesis of isocryptolepine analogues and their structure-activity relationship studies as antiplasmodial and antiproliferative agents.,  94  [PMID:25747499] [10.1016/j.ejmech.2015.02.047]
140. Wells MM, Tillman TS, Mowrey DD, Sun T, Xu Y, Tang P..  (2015)  Ensemble-based virtual screening for cannabinoid-like potentiators of the human glycine receptor α1 for the treatment of pain.,  58  (7): [PMID:25790278] [10.1021/jm501873p]
141. Korotchenko V, Sathunuru R, Gerena L, Caridha D, Li Q, Kreishman-Deitrick M, Smith PL, Lin AJ..  (2015)  Antimalarial activity of 4-amidinoquinoline and 10-amidinobenzonaphthyridine derivatives.,  58  (8): [PMID:25654185] [10.1021/jm501809x]
142. WHO Anatomical Therapeutic Chemical Classification, 
143. Unpublished dataset, 
144. Sangeun Jeon, Meehyun Ko, Jihye Lee, Inhee Choi, Soo Young Byun, Soonju Park, David Shum, Seungtaek Kim.  (2020)  Identification of antiviral drug candidates against SARS-CoV-2 from FDA-approved drugs,  [10.1101/2020.03.20.999730]
145. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]
146. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]
147. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]
148. Zimmermann M, Zimmermann-Kogadeeva M, Wegmann R, Goodman AL..  (2019)  Mapping human microbiome drug metabolism by gut bacteria and their genes.,  570  (7762): [PMID:31158845] [10.1038/s41586-019-1291-3]