ROSUVASTATIN

ID: ALA1496

Max Phase: Approved

First Approval: 2003

Molecular Formula: C22H28FN3O6S

Molecular Weight: 481.55

Molecule Type: Small molecule

Associated Items:

Representations

Synonyms (5): Creston | Rosuvastatin | X-plended | ZD-4522 | ZD4522
Synonyms from Alternative Forms(5):

    Canonical SMILES:  CC(C)c1nc(N(C)S(C)(=O)=O)nc(-c2ccc(F)cc2)c1/C=C/[C@@H](O)C[C@@H](O)CC(=O)O

    Standard InChI:  InChI=1S/C22H28FN3O6S/c1-13(2)20-18(10-9-16(27)11-17(28)12-19(29)30)21(14-5-7-15(23)8-6-14)25-22(24-20)26(3)33(4,31)32/h5-10,13,16-17,27-28H,11-12H2,1-4H3,(H,29,30)/b10-9+/t16-,17-/m1/s1

    Standard InChI Key:  BPRHUIZQVSMCRT-VEUZHWNKSA-N

    Associated Targets(Human)

    HMGCR Tclin HMG-CoA reductase (2475 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    Homo sapiens (32628 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    PC-3 (62116 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    CYP2C8 Tchem Cytochrome P450 2C8 (1492 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
    SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    SLCO2B1 Tchem Solute carrier organic anion transporter family member 2B1 (580 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    Hepatocyte (2737 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    Plasma (7708 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    PDE6D Tclin Phosphodiesterase 6D (241 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
    HRH1 Tclin Histamine H1 receptor (7573 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    KCNH2 Tclin HERG (29587 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    ADRB1 Tclin Beta-1 adrenergic receptor (6630 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
    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
    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
    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
    PTGS2 Tclin Cyclooxygenase-2 (13999 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
    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
    MC3R Tchem Melanocortin receptor 3 (5659 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
    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
    CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    PGR Tclin Progesterone receptor (8562 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    ADRB2 Tclin Beta-2 adrenergic receptor (11824 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)

    Hepatocyte (2621 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    L6 (7924 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    Mus musculus (284745 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    Hmgcr HMG-CoA reductase (1653 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    Hamster (598 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    Cavia porcellus (23802 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    Syrian golden hamster (1610 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    DPP4 Dipeptidyl peptidase IV (170 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    Rattus norvegicus (775804 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    Liver microsomes (8692 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    Plasma (10718 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    Plasmodium falciparum (966862 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    Slco1a1 Solute carrier organic anion transporter family member 1A1 (265 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    Slco1a4 Solute carrier organic anion transporter family member 1A4 (114 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    Liver (4264 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    Plasma (810 Activities)
    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
    SARS-CoV-2 (38078 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

    Molecule Features

    Natural Product: NoOral: YesChemical Probe: NoParenteral: No
    Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
    Chirality: YesAvailability: 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

    Properties

    Molecular Weight: 481.55Molecular Weight (Monoisotopic): 481.1683AlogP: 2.40#Rotatable Bonds: 10
    Polar Surface Area: 140.92Molecular Species: ACIDHBA: 7HBD: 3
    #RO5 Violations: 0HBA (Lipinski): 9HBD (Lipinski): 3#RO5 Violations (Lipinski): 0
    CX Acidic pKa: 4.00CX Basic pKa: CX LogP: 1.92CX LogD: -1.24
    Aromatic Rings: 2Heavy Atoms: 33QED Weighted: 0.47Np Likeness Score: -0.17

    References

    1. Medina-Franco JL, López-Vallejo F, Rodríguez-Morales S, Castillo R, Chamorro G, Tamariz J..  (2005)  Molecular docking of the highly hypolipidemic agent alpha-asarone with the catalytic portion of HMG-CoA reductase.,  15  (4): [PMID:15686898] [10.1016/j.bmcl.2004.12.046]
    2. Thilagavathi R, Kumar R, Aparna V, Sobhia ME, Gopalakrishnan B, Chakraborti AK..  (2005)  Three-dimensional quantitative structure (3-D QSAR) activity relationship studies on imidazolyl and N-pyrrolyl heptenoates as 3-hydroxy-3-methylglutaryl-CoA reductase (HMGR) inhibitors by comparative molecular similarity indices analysis (CoMSIA).,  15  (4): [PMID:15686906] [10.1016/j.bmcl.2004.12.042]
    3. Bratton LD, Auerbach B, Choi C, Dillon L, Hanselman JC, Larsen SD, Lu G, Olsen K, Pfefferkorn JA, Robertson A, Sekerke C, Trivedi BK, Unangst PC..  (2007)  Discovery of pyrrole-based hepatoselective ligands as potent inhibitors of HMG-CoA reductase.,  15  (16): [PMID:17560788] [10.1016/j.bmc.2007.05.031]
    4. Pfefferkorn JA, Song Y, Sun KL, Miller SR, Trivedi BK, Choi C, Sorenson RJ, Bratton LD, Unangst PC, Larsen SD, Poel TJ, Cheng XM, Lee C, Erasga N, Auerbach B, Askew V, Dillon L, Hanselman JC, Lin Z, Lu G, Robertson A, Olsen K, Mertz T, Sekerke C, Pavlovsky A, Harris MS, Bainbridge G, Caspers N, Chen H, Eberstadt M..  (2007)  Design and synthesis of hepatoselective, pyrrole-based HMG-CoA reductase inhibitors.,  17  (16): [PMID:17574412] [10.1016/j.bmcl.2007.05.096]
    5. Larsen SD, Poel TJ, Filipski KJ, Kohrt JT, Pfefferkorn JA, Sorenson RJ, Tait BD, Askew V, Dillon L, Hanselman JC, Lu GH, Robertson A, Sekerke C, Kowala MC, Auerbach BJ..  (2007)  Pyrazole inhibitors of HMG-CoA reductase: an attempt to dramatically reduce synthetic complexity through minimal analog re-design.,  17  (20): [PMID:17764936] [10.1016/j.bmcl.2007.08.004]
    6. Pfefferkorn JA, Choi C, Larsen SD, Auerbach B, Hutchings R, Park W, Askew V, Dillon L, Hanselman JC, Lin Z, Lu GH, Robertson A, Sekerke C, Harris MS, Pavlovsky A, Bainbridge G, Caspers N, Kowala M, Tait BD..  (2008)  Substituted pyrazoles as hepatoselective HMG-CoA reductase inhibitors: discovery of (3R,5R)-7-[2-(4-fluoro-phenyl)-4-isopropyl-5-(4-methyl-benzylcarbamoyl)-2H-pyrazol-3-yl]-3,5-dihydroxyheptanoic acid (PF-3052334) as a candidate for the treatment of hypercholesterolemia.,  51  (1): [PMID:18072721] [10.1021/jm070849r]
    7. Taldone T, Zito SW, Talele TT..  (2008)  Inhibition of dipeptidyl peptidase-IV (DPP-IV) by atorvastatin.,  18  (2): [PMID:18068977] [10.1016/j.bmcl.2007.11.107]
    8. Park WK, Kennedy RM, Larsen SD, Miller S, Roth BD, Song Y, Steinbaugh BA, Sun K, Tait BD, Kowala MC, Trivedi BK, Auerbach B, Askew V, Dillon L, Hanselman JC, Lin Z, Lu GH, Robertson A, Sekerke C..  (2008)  Hepatoselectivity of statins: design and synthesis of 4-sulfamoyl pyrroles as HMG-CoA reductase inhibitors.,  18  (3): [PMID:18155906] [10.1016/j.bmcl.2007.11.124]
    9. Sarver RW, Bills E, Bolton G, Bratton LD, Caspers NL, Dunbar JB, Harris MS, Hutchings RH, Kennedy RM, Larsen SD, Pavlovsky A, Pfefferkorn JA, Bainbridge G..  (2008)  Thermodynamic and structure guided design of statin based inhibitors of 3-hydroxy-3-methylglutaryl coenzyme A reductase.,  51  (13): [PMID:18540668] [10.1021/jm7015057]
    10. Ahmad S, Madsen CS, Stein PD, Janovitz E, Huang C, Ngu K, Bisaha S, Kennedy LJ, Chen BC, Zhao R, Sitkoff D, Monshizadegan H, Yin X, Ryan CS, Zhang R, Giancarli M, Bird E, Chang M, Chen X, Setters R, Search D, Zhuang S, Nguyen-Tran V, Cuff CA, Harrity T, Darienzo CJ, Li T, Reeves RA, Blanar MA, Barrish JC, Zahler R, Robl JA..  (2008)  (3R,5S,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(methyl(1-methyl-1h-1,2,4-triazol-5-yl)amino)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoic acid (BMS-644950): a rationally designed orally efficacious 3-hydroxy-3-methylglutaryl coenzyme-a reductase inhibitor with reduced myotoxicity potential.,  51  (9): [PMID:18412317] [10.1021/jm800001n]
    11. Varma MV, Feng B, Obach RS, Troutman MD, Chupka J, Miller HR, El-Kattan A..  (2009)  Physicochemical determinants of human renal clearance.,  52  (15): [PMID:19445515] [10.1021/jm900403j]
    12. Varma MV, Obach RS, Rotter C, Miller HR, Chang G, Steyn SJ, El-Kattan A, Troutman MD..  (2010)  Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.,  53  (3): [PMID:20070106] [10.1021/jm901371v]
    13. MacDonald ML, Lamerdin J, Owens S, Keon BH, Bilter GK, Shang Z, Huang Z, Yu H, Dias J, Minami T, Michnick SW, Westwick JK..  (2006)  Identifying off-target effects and hidden phenotypes of drugs in human cells.,  (6): [PMID:16680159] [10.1038/nchembio790]
    14. Obach RS, Lombardo F, Waters NJ..  (2008)  Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.,  36  (7): [PMID:18426954] [10.1124/dmd.108.020479]
    15. Wong RP, Davis TM..  (2009)  Statins as potential antimalarial drugs: low relative potency and lack of synergy with conventional antimalarial drugs.,  53  (5): [PMID:19258270] [10.1128/aac.01469-08]
    16. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]
    17.  (2008)  Casarett and Doull's Toxicology The Basic Science of Poisons, 7th edition, 
    18. Pfefferkorn JA, Litchfield J, Hutchings R, Cheng XM, Larsen SD, Auerbach B, Bush MR, Lee C, Erasga N, Bowles DM, Boyles DC, Lu G, Sekerke C, Askew V, Hanselman JC, Dillon L, Lin Z, Robertson A, Olsen K, Boustany C, Atkinson K, Goosen TC, Sahasrabudhe V, Chupka J, Duignan DB, Feng B, Scialis R, Kimoto E, Bi YA, Lai Y, El-Kattan A, Bakker-Arkema R, Barclay P, Kindt E, Le V, Mandema JW, Milad M, Tait BD, Kennedy R, Trivedi BK, Kowala M..  (2011)  Discovery of novel hepatoselective HMG-CoA reductase inhibitors for treating hypercholesterolemia: a bench-to-bedside case study on tissue selective drug distribution.,  21  (9): [PMID:21183342] [10.1016/j.bmcl.2010.11.103]
    19. 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]
    20. Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P..  (2012)  Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions.,  55  (10): [PMID:22541068] [10.1021/jm300212s]
    21. Pfefferkorn JA, Guzman-Perez A, Litchfield J, Aiello R, Treadway JL, Pettersen J, Minich ML, Filipski KJ, Jones CS, Tu M, Aspnes G, Risley H, Bian J, Stevens BD, Bourassa P, D'Aquila T, Baker L, Barucci N, Robertson AS, Bourbonais F, Derksen DR, Macdougall M, Cabrera O, Chen J, Lapworth AL, Landro JA, Zavadoski WJ, Atkinson K, Haddish-Berhane N, Tan B, Yao L, Kosa RE, Varma MV, Feng B, Duignan DB, El-Kattan A, Murdande S, Liu S, Ammirati M, Knafels J, Dasilva-Jardine P, Sweet L, Liras S, Rolph TP..  (2012)  Discovery of (S)-6-(3-cyclopentyl-2-(4-(trifluoromethyl)-1H-imidazol-1-yl)propanamido)nicotinic acid as a hepatoselective glucokinase activator clinical candidate for treating type 2 diabetes mellitus.,  55  (3): [PMID:22196621] [10.1021/jm2014887]
    22. Unpublished dataset, 
    23. Stevens BD, Litchfield J, Pfefferkorn JA, Atkinson K, Perreault C, Amor P, Bahnck K, Berliner MA, Calloway J, Carlo A, Derksen DR, Filipski KJ, Gumkowski M, Jassal C, MacDougall M, Murphy B, Nkansah P, Pettersen J, Rotter C, Zhang Y..  (2013)  Discovery of an intravenous hepatoselective glucokinase activator for the treatment of inpatient hyperglycemia.,  23  (24): [PMID:24239482] [10.1016/j.bmcl.2013.10.057]
    24. 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]
    25. Zimmermann G, Schultz-Fademrecht C, Küchler P, Murarka S, Ismail S, Triola G, Nussbaumer P, Wittinghofer A, Waldmann H..  (2014)  Structure guided design and kinetic analysis of highly potent benzimidazole inhibitors targeting the PDEδ prenyl binding site.,  57  (12): [PMID:24884780] [10.1021/jm500632s]
    26. Kimoto E, Chupka J, Xiao Y, Bi YA, Duignan DB..  (2011)  Characterization of digoxin uptake in sandwich-cultured human hepatocytes.,  39  (1): [PMID:20926619] [10.1124/dmd.110.034298]
    27. Jigorel E, Houston JB..  (2012)  Utility of drug depletion-time profiles in isolated hepatocytes for accessing hepatic uptake clearance: identifying rate-limiting steps and role of passive processes.,  40  (8): [PMID:22593038] [10.1124/dmd.112.045732]
    28. Acimovic J, Korosec T, Seliskar M, Bjorkhem I, Monostory K, Szabo P, Pascussi JM, Belic A, Urleb U, Kocjan D, Rozman D..  (2011)  Inhibition of human sterol Δ7-reductase and other postlanosterol enzymes by LK-980, a novel inhibitor of cholesterol synthesis.,  39  (1): [PMID:20952551] [10.1124/dmd.110.035840]
    29. Kazmi F, Hensley T, Pope C, Funk RS, Loewen GJ, Buckley DB, Parkinson A..  (2013)  Lysosomal sequestration (trapping) of lipophilic amine (cationic amphiphilic) drugs in immortalized human hepatocytes (Fa2N-4 cells).,  41  (4): [PMID:23378628] [10.1124/dmd.112.050054]
    30. Lin X, Skolnik S, Chen X, Wang J..  (2011)  Attenuation of intestinal absorption by major efflux transporters: quantitative tools and strategies using a Caco-2 model.,  39  (2): [PMID:21051535] [10.1124/dmd.110.034629]
    31. Nakakariya M, Ono M, Amano N, Moriwaki T, Maeda K, Sugiyama Y..  (2012)  In vivo biliary clearance should be predicted by intrinsic biliary clearance in sandwich-cultured hepatocytes.,  40  (3): [PMID:22190695] [10.1124/dmd.111.042101]
    32.  (2015)  Rosuvastatin and atorvastatin derivatives, 
    33.  (2015)  Use of rosuvastatin lactols as medicaments, 
    34. WHO Anatomical Therapeutic Chemical Classification, 
    35. Chen M, Suzuki A, Thakkar S, Yu K, Hu C, Tong W..  (2016)  DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.,  21  (4): [PMID:26948801] [10.1016/j.drudis.2016.02.015]
    36.  (2016)  (9): [10.1039/C6MD00235H]
    37. Unpublished dataset, 
    38. Franck Touret, Magali Gilles, Karine Barral, Antoine Nougairède, Etienne Decroly, Xavier de Lamballerie, Bruno Coutard.  (2020)  In vitro screening of a FDA approved chemical library reveals potential inhibitors of SARS-CoV-2 replication,  [10.1101/2020.04.03.023846]
    39. 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]
    40. Tess DA,Eng H,Kalgutkar AS,Litchfield J,Edmonds DJ,Griffith DA,Varma MVS.  (2020)  Predicting the Human Hepatic Clearance of Acidic and Zwitterionic Drugs.,  63  (20): [PMID:32985885] [10.1021/acs.jmedchem.0c01033]
    41. 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]
    42. 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]