Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0763)
Drug Name
GV-150526
Synonyms
Gavestinel; Gavestinel (USAN/INN); Gavestinel [USAN:INN:BAN]; SCHEMBL1721070; SCHEMBL678632; (E)-4,6-Dichloro-3-(3-oxo-3-(phenylamino)-1-propenyl)-1H-indole-2-carboxylic acid; 153436-22-7; 1H-Indole-2-carboxylic acid, 4,6-dichloro-3-((1E)-3-oxo-3-(phenylamino)-1-propenyl)-; 1H-Indole-2-carboxylic acid, 4,6-dichloro-3-(3-oxo-3-(phenylamino)-1-propenyl)-, (E)-; 318X4QY113; 4,6-Dichloro-3-((E)-2-(phenylcarbamoyl)vinyl)indole-2-carboxylic acid; AC1O51WR; CHEMBL44793; GV 150526; GV 150526X; GV-150526X; UNII-318X4QY113
Indication Cerebral stroke [ICD11: 8B11] Discontinued [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 375.2 Topological Polar Surface Area 82.2
Heavy Atom Count 25 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
6450546
PubChem SID
11972111 ; 14877626 ; 43041642 ; 47206237 ; 49983607 ; 50438457 ; 57370215 ; 85788700 ; 103227166 ; 103956928 ; 114525294 ; 134339038 ; 134340043 ; 135236023 ; 137132921 ; 137249725 ; 142472724 ; 162221852 ; 179322268 ; 184596079 ; 198982944 ; 226973454 ; 227903014 ; 242057623
ChEBI ID
CHEBI:92867
CAS Number
153436-22-7
TTD Drug ID
D0O6AQ
Formula
C18H12Cl2N2O3
Canonical SMILES
C1=CC=C(C=C1)NC(=O)C=CC2=C(NC3=CC(=CC(=C32)Cl)Cl)C(=O)O
InChI
1S/C18H12Cl2N2O3/c19-10-8-13(20)16-12(17(18(24)25)22-14(16)9-10)6-7-15(23)21-11-4-2-1-3-5-11/h1-9,22H,(H,21,23)(H,24,25)/b7-6+
InChIKey
WZBNEZWCNKUOSM-VOTSOKGWSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Gavestinel acyl glucuronid DM005607 N. A. Conjugation - Glucuronidation 1 [2]
p-Hydroxygavestinel DM005606 N. A. Oxidation - Hydrolyzationn 1 [3]
p-OH-gavestinel DM005604
10548468
Oxidation - Aromatic hydroxylation 1 [2]
TGavestinel sulfate (M1) DM005605
154699638
Unclear 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005976 GV-150526 p-OH-gavestinel Oxidation - Aromatic hydroxylation CYP2C9 [2]
MR005978 GV-150526 p-Hydroxygavestinel Oxidation - Hydrolyzationn CYP2C9 [3]
MR005979 GV-150526 Gavestinel acyl glucuronid Conjugation - Glucuronidation UGT1A9 ... [2]
MR005977 GV-150526 TGavestinel sulfate (M1) Unclear SULT [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[2]
References
1 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800007924)
2 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
3 DrugBank(Pharmacology-Metabolism): GV-150526 Tretazicar

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