ID: ALA542610

Max Phase: Preclinical

Molecular Formula: C21H26ClNO3

Molecular Weight: 339.43

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  Cl.O=C(O)C1CCCN(CCOC(c2ccccc2)c2ccccc2)C1

Standard InChI:  InChI=1S/C21H25NO3.ClH/c23-21(24)19-12-7-13-22(16-19)14-15-25-20(17-8-3-1-4-9-17)18-10-5-2-6-11-18;/h1-6,8-11,19-20H,7,12-16H2,(H,23,24);1H

Standard InChI Key:  YFCBTVWNNHMJCT-UHFFFAOYSA-N

Associated Targets(non-human)

GABA transporter 1 233 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

GABA transporter 190 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Rattus norvegicus 775804 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

GABA transporter 97 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: 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: 339.43Molecular Weight (Monoisotopic): 339.1834AlogP: 3.59#Rotatable Bonds: 7
Polar Surface Area: 49.77Molecular Species: ZWITTERIONHBA: 3HBD: 1
#RO5 Violations: 0HBA (Lipinski): 4HBD (Lipinski): 1#RO5 Violations (Lipinski): 0
CX Acidic pKa: 3.28CX Basic pKa: 9.11CX LogP: 1.15CX LogD: 1.14
Aromatic Rings: 2Heavy Atoms: 25QED Weighted: 0.84Np Likeness Score: -0.65

References

1. Andersen KE, Braestrup C, Grønwald FC, Jørgensen AS, Nielsen EB, Sonnewald U, Sørensen PO, Suzdak PD, Knutsen LJ..  (1993)  The synthesis of novel GABA uptake inhibitors. 1. Elucidation of the structure-activity studies leading to the choice of (R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid (tiagabine) as an anticonvulsant drug candidate.,  36  (12): [PMID:8510100] [10.1021/jm00064a005]
2. Andersen KE, Sørensen JL, Lau J, Lundt BF, Petersen H, Huusfeldt PO, Suzdak PD, Swedberg MD..  (2001)  Synthesis of novel gamma-aminobutyric acid (GABA) uptake inhibitors. 5.(1) Preparation and structure-activity studies of tricyclic analogues of known GABA uptake inhibitors.,  44  (13): [PMID:11405652] [10.1021/jm990513k]
3. Pavia MR, Lobbestael SJ, Nugiel D, Mayhugh DR, Gregor VE, Taylor CP, Schwarz RD, Brahce L, Vartanian MG..  (1992)  Structure-activity studies on benzhydrol-containing nipecotic acid and guvacine derivatives as potent, orally-active inhibitors of GABA uptake.,  35  (22): [PMID:1433224] [10.1021/jm00100a032]
4. Andersen KE, Sørensen JL, Huusfeldt PO, Knutsen LJ, Lau J, Lundt BF, Petersen H, Suzdak PD, Swedberg MD..  (1999)  Synthesis of novel GABA uptake inhibitors. 4. Bioisosteric transformation and successive optimization of known GABA uptake inhibitors leading to a series of potent anticonvulsant drug candidates.,  42  (21): [PMID:10543872] [10.1021/jm980492e]

Source