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

General Information of Drug (ID: DR1588)
Drug Name
Tiagabine
Synonyms
Tiagabina; Tiagabina [INN-Spanish]; Tiagabine (INN); Tiagabine [INN:BAN]; Tiagabine [INN]; Tiagabinum; Tiagabinum [INN-Latin]; Gabatril; Gabitril; Gabitril (TN); NO 329; NO-328; NO050328; Z80I64HMNP; tiagabine; (-)-(R)-1-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)nipecotic acid; (R)-1-(4,4-Bis(3-methylthiophen-2-yl)but-3-en-1-yl)piperidine-3-carboxylic acid; (R)-Tiagabine; 115103-54-3; A-70569-1; ABBOTT-70569-1; ABT-569; Abbott-70569; CHEBI:9586; CHEMBL1027; NO328; UNII-Z80I64HMNP
Indication Epilepsy [ICD11: 8A60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 375.6 Topological Polar Surface Area 97
Heavy Atom Count 25 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
60648
PubChem SID
9706 ; 7980788 ; 8186978 ; 14804309 ; 14926800 ; 26758048 ; 43118012 ; 46505560 ; 48416622 ; 50015636 ; 50510996 ; 53787330 ; 92723327 ; 93166176 ; 96025272 ; 103276854 ; 103946490 ; 104321287 ; 117542112 ; 126592912 ; 126617580 ; 128891680 ; 134337484 ; 135016989 ; 137002486 ; 142970946 ; 160847730 ; 160964245 ; 163418753 ; 163850077 ; 164814870 ; 172858819 ; 175268881 ; 178101399 ; 178101520 ; 179116918 ; 184545901 ; 210279817 ; 210282140 ; 223441308 ; 223554966 ; 223655564 ; 224165587 ; 226421082 ; 251916677 ; 251917916 ; 251970975 ; 252357544
ChEBI ID
CHEBI:9586
CAS Number
115103-54-3
TTD Drug ID
D0ED7U
Formula
C20H25NO2S2
Canonical SMILES
CC1=C(SC=C1)C(=CCCN2CCCC(C2)C(=O)O)C3=C(C=CS3)C
InChI
1S/C20H25NO2S2/c1-14-7-11-24-18(14)17(19-15(2)8-12-25-19)6-4-10-21-9-3-5-16(13-21)20(22)23/h6-8,11-12,16H,3-5,9-10,13H2,1-2H3,(H,22,23)/t16-/m1/s1
InChIKey
PBJUNZJWGZTSKL-MRXNPFEDSA-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
5-oxo-tiagabine DM005441 N. A. Oxidation - Oxidationn 1 [4]
Tiagabine glucuronide DM005442 N. A. Conjugation - Glucuronidation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005782 Tiagabine 5-oxo-tiagabine Oxidation - Oxidationn CYP3A4 [4]
MR005783 Tiagabine Tiagabine glucuronide Conjugation - Glucuronidation Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
References
1 Tiagabine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Enzyme induction and inhibition by new antiepileptic drugs: a review of human studies. Fundam Clin Pharmacol. 2000 Jul-Aug;14(4):301-19.
3 Actual and Predicted Pharmacokinetic Interactions Between Anticonvulsants and Antiretrovirals.
4 LABEL:TIAGABINE HYDROCHLORIDE tablet, film coated

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