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

General Information of Drug (ID: DR0212)
Drug Name
GS-9883
Synonyms
Bictegravir; Bictegravir (USAN/INN); Bictegravir [INN]; Bictegravir [USAN:INN]; SB18851; SOLUWJRYJLAZCX-LYOVBCGYSA-N; (2R,5S,13aR)-8-hydroxy-7,9-dioxo-N-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide; 1611493-60-7; 8GB79LOJ07; BCP25703; BDBM330048; CHEMBL3989866; DB11799; GS 9883; GS-9883; GS-9883-01; SCHEMBL15914278; UNII-8GB79LOJ07
Indication Human immunodeficiency virus infection [ICD11: 1C60] Phase 1 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 449.4 Topological Polar Surface Area 99.2
Heavy Atom Count 32 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
90311989
CAS Number
1611493-60-7
Formula
C21H18F3N3O5
Canonical SMILES
C1CC2CC1N3C(O2)CN4C=C(C(=O)C(=C4C3=O)O)C(=O)NCC5=C(C=C(C=C5F)F)F
InChI
1S/C21H18F3N3O5/c22-9-3-14(23)12(15(24)4-9)6-25-20(30)13-7-26-8-16-27(10-1-2-11(5-10)32-16)21(31)17(26)19(29)18(13)28/h3-4,7,10-11,16,29H,1-2,5-6,8H2,(H,25,30)/t10-,11+,16+/m0/s1
InChIKey
SOLUWJRYJLAZCX-LYOVBCGYSA-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
GS-9883 Metabolite M15 DM003459 N. A. Conjugation - Glucuronidation 1 [3]
GS-9883 Metabolite M21 DM003460 N. A. Oxidation - Oxidationn 1 [3]
GS-9883 Metabolite M22 DM003455 N. A. Reduction - Defluorination 1 [3]
GS-9883 Metabolite M23 DM003457 N. A. Oxidation - Oxidationn 1 [3]
GS-9883 Metabolite M20 DM003458 N. A. Conjugation - Sulfation 2 [3]
GS-9883 Metabolite M9 DM003456 N. A. Conjugation - Cysteine conjugation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003907 GS-9883 GS-9883 Metabolite M22 Reduction - Defluorination Unclear [3]
MR003909 GS-9883 GS-9883 Metabolite M23 Oxidation - Oxidationn Unclear [3]
MR003911 GS-9883 GS-9883 Metabolite M15 Conjugation - Glucuronidation Unclear [3]
MR003912 GS-9883 GS-9883 Metabolite M21 Oxidation - Oxidationn Unclear [3]
MR003908 GS-9883 Metabolite M22 GS-9883 Metabolite M9 Conjugation - Cysteine conjugation Unclear [3]
MR003910 GS-9883 Metabolite M23 GS-9883 Metabolite M20 Conjugation - Sulfation Unclear [3]
⏷ Show the Full List of 6 MR(s)
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
[2]
References
1 ClinicalTrials.gov (NCT02400307) Pharmacokinetics of Bictegravir in Adults With Normal and Impaired Renal Function.
2 Bictegravir, a novel integrase inhibitor for the treatment of HIV infection. Drugs Today (Barc). 2019 Nov;55(11):669-682.
3 Human and nonclinical disposition of [(14)C]bictegravir, a potent integrase strand-transfer inhibitor for the treatment of HIV-1 infection

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