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

General Information of Drug (ID: DR1829)
Drug Name
GSK-1265744
Synonyms
Cabotegravir; Cabotegravir (GSK744, GSK1265744); Cabotegravir [USAN:INN]; S/GSK1265744; 1051375-10-0; CAB; GSK-1265744; GSK1265744; GSK1265744A; GSK744; GSK744 (S/GSK1265744); GSK744 LA; GSK744 LAP; HMH0132Z1Q; Oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide, N-[(2,4-difluorophenyl)methyl]-2,3,5,7,11,11a-hexahydro-6-hydroxy-3-methyl-5,7-dioxo-, (3S,11aR)-;Oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide, N-[(2,4-difluorophenyl)methyl]-2,3,5,7,11,11a-hexahydro-6-hydroxy-3-methyl-5,7-dioxo-, (3S,11aR)-; UNII-HMH0132Z1Q
Indication Human immunodeficiency virus infection [ICD11: 1C60] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 405.4 Topological Polar Surface Area 99.2
Heavy Atom Count 29 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
54713659
PubChem SID
17424254 ; 36462227 ; 76221742 ; 138088923 ; 162108745 ; 174502414 ; 198940204 ; 198993890 ; 226461534 ; 244829189 ; 249732325
CAS Number
1051375-10-0
TTD Drug ID
D08LDB
Formula
C19H17F2N3O5
Canonical SMILES
CC1COC2N1C(=O)C3=C(C(=O)C(=CN3C2)C(=O)NCC4=C(C=C(C=C4)F)F)O
InChI
1S/C19H17F2N3O5/c1-9-8-29-14-7-23-6-12(16(25)17(26)15(23)19(28)24(9)14)18(27)22-5-10-2-3-11(20)4-13(10)21/h2-4,6,9,14,26H,5,7-8H2,1H3,(H,22,27)/t9-,14+/m0/s1
InChIKey
WCWSTNLSLKSJPK-LKFCYVNXSA-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
Cabotegravir M1 DM005019 N. A. Conjugation - Glucuronidation 1 [2]
Cabotegravir M2 DM005021 N. A. Conjugation - Glucose Conjugation 1 [2]
Cabotegravir M3 DM005020 N. A. Multi-steps Reaction - Oxidationn defluorination; glutathione conjugation 1 [2] , [3]
Cabotegravir M4 DM005022 N. A. Multi-steps Reaction - Oxidationn defluorination; glutathione conjugation 1 [2]
Cabotegravir M5 DM005023 N. A. Oxidation - Oxidationn 1 [2]
GSK-1265744 M1 DM006872 N. A. Conjugation - O-glucuronidation 1 [2]
GSK-1265744 M2 DM006873 N. A. Conjugation - O-glucuronidation 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005445 GSK-1265744 Cabotegravir M1 Conjugation - Glucuronidation Unclear [2]
MR005446 GSK-1265744 Cabotegravir M3 Multi-steps Reaction - Oxidationn defluorination; glutathione conjugation UGT1A1 ... [2], [3]
MR005447 GSK-1265744 Cabotegravir M2 Conjugation - Glucose Conjugation Unclear [2]
MR005448 GSK-1265744 Cabotegravir M4 Multi-steps Reaction - Oxidationn defluorination; glutathione conjugation Unclear [2]
MR005449 GSK-1265744 Cabotegravir M5 Oxidation - Oxidationn Unclear [2]
MR007469 GSK-1265744 GSK-1265744 M1 Conjugation - O-glucuronidation UGT1A1 ... [2]
MR007470 GSK-1265744 GSK-1265744 M2 Conjugation - O-glucuronidation UGT1A1 ... [2]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_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 800029709)
2 Disposition and metabolism of cabotegravir: a comparison of biotransformation and excretion between different species and routes of administration in humans. Xenobiotica. 2016;46(2):147-62.
3 Correction to "Mechanistic Basis of Cabotegravir-Glucuronide Disposition in Humans"

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