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

General Information of Drug (ID: DR1834)
Drug Name
GS-9620
Synonyms
Vesatolimod; Vesatolimod (USAN/INN); Vesatolimod [INN]; Vesatolimod [USAN:INN]; 1228585-88-3; 4-Amino-2-butoxy-8-(3-(pyrrolidin-1-ylmethyl)benzyl)-7,8-dihydropteridin-6(5H)-one; 4-amino-2-butoxy-8-[[3-(pyrrolidin-1-ylmethyl)phenyl]methyl]-5,7-dihydropteridin-6-one; 4-azanyl-2-butoxy-8-[[3-(pyrrolidin-1-ylmethyl)phenyl]methyl]-5,7-dihydropteridin-6-one; O8M467C50G; 8-(3-(pyrrolidin-1-ylmethyl)benzyl)-4-amino-2-butoxy-7,8-dihydropteridin-6(5H)-one; CHEMBL2424780; GS 9620; GS-9620; GS9620; SCHEMBL10083191; UNII-O8M467C50G
Indication Viral hepatitis [ICD11: 1E51] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 410.5 Topological Polar Surface Area 96.6
Heavy Atom Count 30 Rotatable Bond Count 8
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
46241268
PubChem SID
96103174 ; 120493416 ; 140852686 ; 162109056 ; 163620976 ; 163686300 ; 172821359 ; 174508709 ; 175452601 ; 185974265 ; 198935848 ; 235421727 ; 247178727 ; 252151325 ; 252451782 ; 252811246
CAS Number
1228585-88-3
TTD Drug ID
D08JWC
Formula
C22H30N6O2
Canonical SMILES
CCCCOC1=NC2=C(C(=N1)N)NC(=O)CN2CC3=CC(=CC=C3)CN4CCCC4
InChI
1S/C22H30N6O2/c1-2-3-11-30-22-25-20(23)19-21(26-22)28(15-18(29)24-19)14-17-8-6-7-16(12-17)13-27-9-4-5-10-27/h6-8,12H,2-5,9-11,13-15H2,1H3,(H,24,29)(H2,23,25,26)
InChIKey
VFOKSTCIRGDTBR-UHFFFAOYSA-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-9620 M11 DM006864 N. A. Oxidation - Hydrolyzationn 1 [3]
GS-9620 M12 DM006866 N. A. Oxidation - Oxidationn 1 [3]
GS-9620 M13 DM006871 N. A. Oxidation - Oxidationn 1 [3]
GS-9620 M16 DM006869 N. A. Unclear 1 [3]
GS-9620 M2 DM006867 N. A. Oxidation - Hydrolyzationn 1 [3]
Unclear DM009999 N. A. Unclear 1 [3]
Unclear DM009999 N. A. Oxidation - Dehydrogenation 1 [3]
Unclear DM009999 N. A. Oxidation - Hydrolyzationn 1 [3]
GS-9620 M17 DM006870 N. A. Unclear 2 [3]
GS-9620 M18 DM006865 N. A. Oxidation - Oxidationn 2 [3]
GS-9620 M4 DM006868 N. A. Oxidation - Oxidationn 2 [3]
Unclear DM009999 N. A. Oxidation - Hydrolyzationn 2 [3]
Unclear DM009999 N. A. Oxidation - Hydrolyzationn 3 [3]
⏷ Show the Full List of 13  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007458 GS-9620 GS-9620 M11 Oxidation - Hydrolyzationn Unclear [3]
MR007461 GS-9620 GS-9620 M12 Oxidation - Oxidationn Unclear [3]
MR007463 GS-9620 GS-9620 M2 Oxidation - Hydrolyzationn Unclear [3]
MR007465 GS-9620 GS-9620 M16 Unclear Unclear [3]
MR007467 GS-9620 GS-9620 M13 Oxidation - Oxidationn Unclear [3]
MR007468 GS-9620 Unclear Oxidation - Hydrolyzationn Unclear [3]
MR007459 GS-9620 M11 GS-9620 M18 Oxidation - Oxidationn Unclear [3]
MR007462 GS-9620 M12 Unclear Oxidation - Hydrolyzationn Unclear [3]
MR007466 GS-9620 M16 GS-9620 M17 Unclear Unclear [3]
MR007464 GS-9620 M2 GS-9620 M4 Oxidation - Oxidationn Unclear [3]
MR007460 GS-9620 M18 Unclear Oxidation - Hydrolyzationn Unclear [3]
⏷ Show the Full List of 11 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]
References
1 Pharmacokinetic and pharmacodynamic properties of GS-9620, a novel Toll-like receptor 7 agonist, demonstrate interferon-stimulated gene induction without detectable serum interferon at low oral doses. J Pharmacol Exp Ther. 2014 Jan;348(1):96-105.
2 The oral toll-like receptor-7 agonist GS-9620 in patients with chronic hepatitis B virus infection. J Hepatol. 2015 Aug;63(2):320-8.
3 Metabolism of vesatolimod in rat, dog, and human liver microsomes: Metabolic stability assessment, metabolite identification, and interspecies comparison

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