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

General Information of Drug (ID: DR0107)
Drug Name
Amprenavir
Synonyms
Agenerase; Amprenavir (agenerase); KVX-478; Prozei; VX 478; VX-478; Vertex; Vertex VX478; amprenavir; (3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamate; 141W94; 161814-49-9; 5S0W860XNR; AMV; C25H35N3O6S; CHEBI:40050; DRG-0258; HSDB 7157; Tetrahydro-3-furyl N-(3-(4-amino-N-isobutylbenzenesulfonamido)-1-benzyl-2-hydroxypropyl)carbamate; UNII-5S0W860XNR
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 505.6 Topological Polar Surface Area 140
Heavy Atom Count 35 Rotatable Bond Count 12
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
65016
PubChem SID
10286 ; 601727 ; 628182 ; 822019 ; 3727052 ; 3727059 ; 7847958 ; 7885327 ; 7978703 ; 8030478 ; 8189448 ; 11528777 ; 12014852 ; 14835820 ; 14884574 ; 26697364 ; 29215412 ; 43121862 ; 46392146 ; 46393211 ; 46507537 ; 53790789 ; 57315242 ; 71821412 ; 74965413 ; 85177028 ; 85177034 ; 85177055 ; 92309266 ; 93166556 ; 97857368 ; 99239834 ; 99239838 ; 99239842 ; 99239846 ; 99239847 ; 99239854 ; 99239856 ; 103179760 ; 104178998 ; 104253275 ; 104332645 ; 104829267 ; 117549941 ; 118048728 ; 125267472 ; 125310993 ; 127310203 ; 127310204 ; 127310205
ChEBI ID
ChEBI:40050
CAS Number
161814-49-9
TTD Drug ID
D0A0OO
Formula
C25H35N3O6S
Canonical SMILES
CC(C)CN(CC(C(CC1=CC=CC=C1)NC(=O)OC2CCOC2)O)S(=O)(=O)C3=CC=C(C=C3)N
InChI
1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1
InChIKey
YMARZQAQMVYCKC-OEMFJLHTSA-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
Amprenavir metabolite M1 DM001364 N. A. Unclear 1 [4]
Amprenavir metabolite M2 DM001365 N. A. Unclear 1 [4]
Amprenavir metabolite M3 DM001366 N. A. Unclear 1 [4]
Amprenavir metabolite M4 DM001367 N. A. Unclear 1 [4]
Amprenavir metabolite M5 DM001368 N. A. Unclear 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000227 Amprenavir Amprenavir metabolite M1 Unclear CYP3A4 ... [4]
MR000228 Amprenavir Amprenavir metabolite M2 Unclear CYP2C9 ... [4]
MR000229 Amprenavir Amprenavir metabolite M3 Unclear CYP3A4 ... [4]
MR000230 Amprenavir Amprenavir metabolite M4 Unclear CYP3A4 [4]
MR000231 Amprenavir Amprenavir metabolite M5 Unclear CYP3A4 ... [4]
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]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
References
1 Fosamprenavir was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Amprenavir: a new human immunodeficiency virus type 1 protease inhibitor. Clin Ther. 2000 May;22(5):549-72.
3 Differential inhibition of cytochrome P450 3A4, 3A5 and 3A7 by five human immunodeficiency virus (HIV) protease inhibitors in vitro. Basic Clin Pharmacol Toxicol. 2006 Jan;98(1):79-85.
4 Oxidative metabolism of amprenavir in the human liver. Effect of the CYP3A maturation. Drug Metab Dispos. 2003 Mar;31(3):275-81.

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