AMPRENAVIR

U.S. Department of Health & Human Services Divider Arrow

National Institutes of Health Divider Arrow

NCATS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H35N3O6S
Molecular Weight	505.627
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of AMPRENAVIR

Structure Search

SMILES

CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CCOC2)S(=O)(=O)C3=CC=C(N)C=C3

InChI

InChIKey=YMARZQAQMVYCKC-OEMFJLHTSA-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

HIDE SMILES / InChI

Molecular Formula	C25H35N3O6S
Molecular Weight	505.627
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:48:47 UTC 2023` Edited by `admin` on `Fri Dec 15 15:48:47 UTC 2023`
Record UNII	5S0W860XNR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMPRENAVIR

Official Name

English

AMPRENAVIR [EMA EPAR]

Common Name

English

VX-478

Code

English

AMPRENAVIR [VANDF]

Common Name

English

AMPRENAVIR [MART.]

Common Name

English

KVX-478

Code

English

(3S-(3R*(1R*,2S*)))-(3-(((4-AMINOPHENYL)SULFONYL)(2-METHYLPROPYL)AMINO)-2-HYDROXY-1-(PHENYLMETHYL)PROPYL) TETRAHYDRO-3-FURANYL CARBAMATE

Common Name

English

AMPRENAVIR [MI]

Common Name

English

AMPRENAVIR [HSDB]

Common Name

English

141W94

Code

English

AMPRENAVIR [ORANGE BOOK]

Common Name

English

J05AE05

Code

English

AMPRENAVIR [USAN]

Common Name

English

AGENERASE

Brand Name

English

AMPRENAVIR [JAN]

Common Name

English

Amprenavir [WHO-DD]

Common Name

English

amprenavir [INN]

Common Name

English

141W94

Code

English

(3S)-Tetrahydro-3-furyl [(αS)-α-[(1R-1-hydroxy-2-(N1-isobutylsulfanilamido)ethyl]phenethyl]carbamate

Common Name

English

Classification Tree Code System Code

EMA ASSESSMENT REPORTS

AGENERASE (WITHDRAWN: HIV INFECTIONS)

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

WHO-ATC

J05AE05

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

NDF-RT

N0000175889

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

NCI_THESAURUS

C97366

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

NDF-RT

N0000000246

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

WHO-VATC

QJ05AE05

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

LIVERTOX

NBK548011

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

Code System Code Type Description

NDF-RT

N0000182141

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

Cytochrome P450 3A4 Inhibitors [MoA]

DAILYMED

5S0W860XNR

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

NDF-RT

N0000185506

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

Cytochrome P450 3A4 Inducers [MoA]

DRUG CENTRAL

200

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

MESH

C095108

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

RXCUI

228656

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

RxNorm

PUBCHEM

65016

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

NCI_THESAURUS

C28824

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

INN

7751

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

EPA CompTox

DTXSID5046061

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

DRUG BANK

DB00701

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

CHEBI

40050

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

USAN

JJ-94

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

ChEMBL

CHEMBL116

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

WIKIPEDIA

AMPRENAVIR

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

FDA UNII

5S0W860XNR

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

MERCK INDEX

m1855

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

Merck Index

NDF-RT

N0000191264

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

P-Glycoprotein Inducers [MoA]

CAS

161814-49-9

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

SMS_ID

100000089388

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

EVMPD

SUB00511MIG

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

HSDB

7157

Created by admin on Fri Dec 15 15:48:47 UTC 2023 , Edited by admin on Fri Dec 15 15:48:47 UTC 2023

PRIMARY

Related Record Type Details


					AIN96D6SGL

OATP1B1

TRANSPORTER -> INHIBITOR


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Comments:

The high affinity binding protein for amprenavir is alpha1-acid glycoprotein (AAG).

Interaction Type:

BINDING

Amount:


					0CVZ0EQN96

AMPRENAVIR MESYLATE

SALT/SOLVATE -> PARENT

Amount:


					LT9O6G74LT

HUMAN IMMUNODEFICIENCY VIRUS TYPE 1 PROTEASE

TARGET -> INHIBITOR

Amount:


					22ES734693

MULTIDRUG RESISTANCE PROTEIN 1

TRANSPORTER -> SUBSTRATE


					5S0W860XNR

EXCRETED UNCHANGED

Qualification:

URINE

Amount:


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

MAJOR

Amount:


					805SU96HKF

CYTOCHROME P450 3A5

METABOLIC ENZYME -> SUBSTRATE

Amount:


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> INHIBITOR

Amount:


					859A956UY8

HUMAN IMMUNODEFICIENCY VIRUS TYPE 1

TARGET ORGANISM->INHIBITOR

Amount:


					66DDF797LP

OATP-8

TRANSPORTER -> INHIBITOR


					76UB6O122H

ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2

TRANSPORTER -> INHIBITOR

Related Record Type Details


					65P19KZ7JJ

R-374699

METABOLITE -> PARENT

Comments:

IN VITRO

Amount:


					QB48RKO9ZK

CARBAMIC ACID, (3-(((4-AMINOPHENYL)SULFONYL)(2-METHYLPROPYL)AMINO)-2-HYDROXY-1-(PHENYLMETHYL)PROPYL)-, 3-HYDROXY-1-(HYDROXYMETHYL)PROPYL ESTER, (1S-(1R*(R*),2S*))-

METABOLITE -> PARENT

Amount:


					WOU1621EEG

PRODRUG -> METABOLITE ACTIVE

Amount:

Related Record Type Details


					5S0W860XNR

ACTIVE MOIETY

Amount:

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Tmax	PHARMACOKINETIC				SINGLE DOSE ORAL ADMINISTRATION

Volume of Distribution	PHARMACOKINETIC

Biological Half-life	PHARMACOKINETIC