Amprenavir

Protease Inhibitor — ANTIINFECTIVES FOR SYSTEMIC USE

Key facts

Amprenavir is an ofm drug in the Protease Inhibitor class catalogued in DrugCentral. It was first approved by the FDA in 1999. Its mechanism of action is classified as Cytochrome P450 3A4 Inducers, Cytochrome P450 3A4 Inhibitors and HIV Protease Inhibitors. DrugCentral lists 8 molecular targets, including HIV-1 protease, protease and pol. Recorded indications include Human immunodeficiency virus infection.

• Approval status: ofm (first approved 1999 by the FDA).
• Drug class: Protease Inhibitor.
• Mechanism of action: Cytochrome P450 3A4 Inducers; Cytochrome P450 3A4 Inhibitors; HIV Protease Inhibitors.
• Molecular targets: HIV-1 protease, protease, pol and HIV-1 protease (8 listed in DrugCentral).
• Indications: Human immunodeficiency virus infection.
• ATC code: J05AE05 (Protease inhibitors).
• Molecular formula: C25H35N3O6S; molecular weight 505.64 g/mol.

Indications & contraindications

Drug–disease relationships curated by DrugCentral (OMOP / SNOMED concepts).

Indications (1)

• Human immunodeficiency virus infection

Off-label uses (1)

• Prevention of HIV Infection after Exposure

Contraindications (26)

• Acquired hemolytic anemia
• Autoimmune hemolytic anemia
• Blood coagulation disorder
• Breastfeeding (mother)
• Cardiovascular event risk
• Chronic hepatitis C
• Chronic type B viral hepatitis
• Diabetes mellitus
• Disease of liver
• Disorder of coronary artery
• Familial hypercholesterolemia - homozygous
• Hemolytic anemia
• Hereditary factor IX deficiency disease
• Hereditary factor VIII deficiency disease
• Hypercholesterolemia
• Hyperglycemia
• Hypertensive disorder
• Hypertriglyceridemia
• Ketoacidosis in diabetes mellitus
• Kidney stone
• Lipodystrophy
• Liver function tests abnormal
• Myocardial infarction
• Obesity
• Smokes tobacco daily
• Vitamin K Deficiency Induced Hypoprothrombinemia

Mechanism & targets

• Mechanism of action (MoA): Cytochrome P450 3A4 Inducers; Cytochrome P450 3A4 Inhibitors; HIV Protease Inhibitors; P-Glycoprotein Inducers
• Established pharmacologic class: Protease Inhibitor

Molecular targets (8)

Target	Gene	Action	Activity
Protease	HIV-1 protease	unknown	Ki 10.52
Protease	protease	unknown	Ki 10.44
Pol polyprotein	pol	inhibitor	Ki 10.40
Protease	HIV-1 protease	unknown	Ki 9.82
Cytochrome P450 3A4	CYP3A4	unknown	IC50 6.00
Thromboxane-A synthase	TBXAS1	unknown	IC50 5.17
Cathepsin D	CTSD	unknown	IC50 4.82
Gag-Pol polyprotein	gag-pol	unknown	—

Regulatory approvals (2)

Date	Agency	Marketed as	Applicant	Orphan
2000-10-20	EMA	—	—
1999-04-15	FDA	—	GLAXOSMITHKLINE

ATC classification

ATC code	Therapeutic hierarchy
J05AE05	ANTIINFECTIVES FOR SYSTEMIC USE › ANTIVIRALS FOR SYSTEMIC USE › DIRECT ACTING ANTIVIRALS › Protease inhibitors

Reported adverse-event signals

Strongest FDA FAERS disproportionality signals (log-likelihood ratio). A signal is a statistical association in spontaneous reports, not proof that the drug causes the event.

MedDRA term	LLR
Viral mutation identified	273.5
Virologic failure	270.7
Pathogen resistance	204.6

Chemical structure

• Molecular formula: C₂₅H₃₅N₃O₆S
• Molecular weight: 505.64 g/mol
• CAS number: —
• InChIKey: YMARZQAQMVYCKC-OEMFJLHTSA-N
• PubChem CID: 65016

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

Frequently asked questions

Answers are generated from the structured data on this page, not written by hand.

What is Amprenavir used for?

DrugCentral lists the following indications for Amprenavir: Human immunodeficiency virus infection.

How does Amprenavir work?

Amprenavir is classified as Cytochrome P450 3A4 Inducers, Cytochrome P450 3A4 Inhibitors and HIV Protease Inhibitors; its molecular targets in DrugCentral include HIV-1 protease, protease, pol (inhibitor) and HIV-1 protease.

When was Amprenavir first approved?

Amprenavir was first approved by the FDA in 1999.

What drug class does Amprenavir belong to?

Amprenavir is in the Protease Inhibitor class.

What is the chemical formula of Amprenavir?

Amprenavir has the molecular formula C25H35N3O6S and a molecular weight of 505.64 g/mol.

Sources

• DrugCentral drug card 200 — structure, indications, targets, approvals, pharmacologic classes (CC BY-SA 4.0)
• ChEMBL CHEMBL116 — compound record and bioactivity
• PubChem CID 65016 — chemical identifiers
• DrugBank DB00701 — drug record
• FDA UNII 5S0W860XNR — substance identity
• DailyMed: FDA labels for Amprenavir — current prescribing information (label search)
• UniProt P08684 (CYP3A4) — target protein
• UniProt P24557 (TBXAS1) — target protein
• UniProt P07339 (CTSD) — target protein
• FDA Adverse Event Reporting System (openFDA FAERS) — adverse-event signals, as aggregated by DrugCentral

How this page is built: methodology · editorial policy & corrections.