ContaminantDB: Amprenavir

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (33)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:27 UTC

Update Date

2026-05-14 16:46:28 UTC

Accession Number

CHEM002251

Identification

Common Name

Amprenavir

Class

Small Molecule

Description

Amprenavir is an exogenous antiviral drug and HIV protease inhibitor with the chemical formula C25H35N3O6S. At room temperature, this compound exists as a solid. Amprenavir belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. With an average molecular weight of 505.63 g/mol, Amprenavir is a heavy molecule. The compound is utilized as a biological and chemical HIV protease inhibitor. It has been recorded in seven sources, including healthcare, pharmaceuticals and veterinary products such as antivirals; household cleaning and consumer products, specifically non electric simulated smoking devices; and electrical and electronic equipment, including antennas, magnets, relays, television systems, and video games. The recorded route of exposure for this substance is oral. In terms of protein targets, Amprenavir is an inhibitor of seven recorded proteins. These include the ATP-dependent translocase ABCB1, Cathepsin D (CTSD), Cytochrome P450 3A4 (CYP3A4), and Cytosolic 10-formyltetrahydrofolate dehydrogenase (ALDH1L1), along with three other proteins.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Anti-HIV Agent
Antibiotic, Antitubercular
Drug
Ester
Ether
HIV Protease Inhibitor
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamate	ChEBI
Agenerase	ChEBI
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamic acid	Generator
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulphonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamate	Generator
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulphonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamic acid	Generator
AMP	HMDB
AMV	HMDB
VX-478	HMDB
GlaxoSmithKline brand OF amprenavir	HMDB
Vertex VX478	HMDB
Glaxo wellcome brand OF amprenavir	HMDB
Tetrahydro-3-furyl N-(3-(4-amino-N-isobutylbenzenesulfonamido)-1-benzyl-2-hydroxypropyl)carbamate	HMDB

Chemical Formula

C₂₅H₃₅N₃O₆S

Average Molecular Mass

505.627 g/mol

Monoisotopic Mass

505.225 g/mol

CAS Registry Number

161814-49-9

IUPAC Name

(3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate

Traditional Name

amprenavir

SMILES

CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1

InChI Identifier

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

InChI Key

YMARZQAQMVYCKC-OEMFJLHTSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Aminobenzenesulfonamides

Alternative Parents

Substituents

Aminobenzenesulfonamide
Phenylbutylamine
Amphetamine or derivatives
Benzenesulfonyl group
Aniline or substituted anilines
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Aminosulfonyl compound
Carbamic acid ester
Tetrahydrofuran
Sulfonyl
Carbonic acid derivative
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Amine
Alcohol
Carbonyl group
Primary amine
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

carbamate ester (CHEBI:40050 )
sulfonamide (CHEBI:40050 )
tetrahydrofuryl ester (CHEBI:40050 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Amprenavir Action Pathway	SMP0125931	Not Available
Fosamprenavir Action Pathway	SMP0125938	Not Available
Amprenavir Drug Metabolism Action Pathway	SMP0143145	Not Available
Amprenavir Predicted Metabolism Pathway	SMP0174514	Not Available

Applications

Biological Roles

Chemical Roles

HIV protease inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	4.91e-02 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.049 g/L	ALOGPS
logP	1.85	ALOGPS
logP	2.43	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	2.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	131.19 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	134.08 m³·mol⁻¹	ChemAxon
Polarizability	53.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-022d-8491400000-418cbb7f08471fa84619	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-03kc-7192320000-fa264cdbd41779709c30	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-05mk-2692510000-696582f37a165753c2f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-9000500000-e60fa95c31e43c49b031	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9001100000-2c5d3283dd48ceae82dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9010000000-cd15933ef1ecd45d9b1c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0gbi-4304930000-6cf1884fae8acb8332ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0173-9432500000-a4d70ca4c7ac6bd2930d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9825100000-b5b4efee0204074368f4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0046920000-a443e441b8dc951bec99	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2922000000-15960e61915142ff5b1e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9200000000-78c87a49bf59b5f6c014	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uxr-2302980000-1c2dbf56f0de2b3df597	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-3911710000-48ad17f577dc556faafc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-7900200000-41ad730c9ba505f33793	Spectrum

Toxicity Profile

Route of Exposure

Rapidly absorbed after oral administration in HIV-1-infected patients with a time to peak concentration (T_max) typically between 1 and 2 hours after a single oral dose. The absolute oral bioavailability of amprenavir in humans has not been established.

Mechanism of Toxicity

Amprenavir inhibits the HIV viral proteinase enzyme which prevents cleavage of the gag-pol polyprotein, resulting in noninfectious, immature viral particles.

Metabolism

Hepatic. Amprenavir is metabolized in the liver by the cytochrome P450 3A4 (CYP3A4) enzyme system. The 2 major metabolites result from oxidation of the tetrahydrofuran and aniline moieties. Glucuronide conjugates of oxidized metabolites have been identified as minor metabolites in urine and feces. Half Life: 7.1-10.6 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of HIV-1 infection in combination with other antiretroviral agents.

Minimum Risk Level

Not Available

Health Effects

Not Available