Drug Information

General Information
Drug ID
DR00584
Drug Name
Amprenavir
Synonyms
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamate; (3S)-Tetrahydro-3-furyl ((alphaS)-alpha-((1R-1-hydroxy-2-(N(sup 1)-isobutylsulfanilamido)ethyl)phenethyl)carbamate; (3S)-tetrahydro-3-furyl N-[(1S,2R)-3-(4-amino-N-isobutylbenzenesulfonamido)-1-benzyl-2-hydroxy-propyl]carbamate; (3S-(3R*(1R*,2S*)))-(3-(((4-Aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl) tetrahydro-3-furanyl carbamate; 4-Amino-N-((2 syn,3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutyl-benzenesulfonamide; AMV; Agenerase; Agenerase (TM); Agenerase (TN); Amprenavir (JAN/USAN/INN); Amprenavir [USAN]; Amprenavir[usan]; Carbamic acid, ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)-, (3S)-tetrahydro-3-furanyl ester; Carbamic acid, ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)-, (3S)-tetrahydro-3-furanyl ester & Galanthus nivalis agglutinin (GNA); Carbamic acid, ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)-, (3S)-tetrahydro-3-furanyl ester & Hippeastrum hybrid agglutinin(HHA); DRG-0258; GNA & Amprenavir; HHA & Amprenavir; KVX-478; Prozei; Tetrahydro-3-furyl N-(3-(4-amino-N-isobutylbenzenesulfonamido)-1-benzyl-2-hydroxypropyl)carbamate; VX 478; VX-478; VX478; Vertex; Vertex VX478; [(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate; {3-[(4-AMINO-BENZENESULFONYL)-ISOBUTYL-AMINO]-1-BENZYL-2-HYDROXY-PROPYL}-CARBAMIC ACID TETRAHYDRO-FURAN-3-YL ESTER
Drug Type
Small molecular drug
Indication Human immunodeficiency virus infection [ICD11:1C62.Z] Approved [1]
Therapeutic Class
Anti-HIV Agents
Structure
3D MOL 2D MOL
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
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
CAS Number
CAS 161814-49-9
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
XLogP
2.9
PubChem CID
65016
PubChem SID
10286 ,103179760 ,104178998 ,104253275 ,104332645 ,104829267 ,11528777 ,117549941 ,118048728 ,12014852 ,125267472 ,125310993 ,127310203 ,127310204 ,127310205 ,14835820 ,14884574 ,26697364 ,29215412 ,3727052 ,3727059 ,43121862 ,46392146 ,46393211 ,46507537 ,53790789 ,57315242 ,601727 ,628182 ,71821412 ,74965413 ,7847958 ,7885327 ,7978703 ,8030478 ,8189448 ,822019 ,85177028 ,85177034 ,85177055 ,92309266 ,93166556 ,97857368 ,99239834 ,99239838 ,99239842 ,99239846 ,99239847 ,99239854 ,99239856
ChEBI ID
ChEBI:40050
TTD Drug ID
D0A0OO
DT(s) Transporting This Drug P-GP Transporter Info P-glycoprotein 1 Substrate [2]
References
1 Fosamprenavir was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.

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