Fosamprenavir

Summary

Fosamprenavir (CHEMBL1664) is an approved small-molecule prodrug (ATC J05AE07); indicated across 4 conditions including viral infectious disease and hiv infectious disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J05AE07
• Indications: 4 conditions
• Clinical trials: 31
• Chemistry: 585.6 Da · C25H36N3O9PS

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1664
Name	Fosamprenavir
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	131536
ChEBI	CHEBI:82941
ATC	J05AE07
Molecular formula	C25H36N3O9PS
Molecular weight	585.6
InChIKey	MLBVMOWEQCZNCC-OEMFJLHTSA-N

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

IUPAC name: [(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-1-phenyl-3-phosphonooxybutan-2-yl]carbamate

ChEBI definition: A sulfonamide with a structure based on that of sulfanilamide substituted on the sulfonamide nitrogen by a (2R,3S)-4-phenyl-2-(phosphonooxy)-3-({[(3S)-tetrahydrofuran-3-yloxy]carbonyl}amino)butyl group. It is a pro-drug of the HIV protease inhibitor and antiretroviral drug amprenavir.

Pharmacological roles (ChEBI): prodrug.

Also known as: Fosamprenavir, GW-433908, GW433908, GW433908A, fosamprenavir, FOSAMPRENAVIR

Parent form; salt/anhydrous children: CHEMBL1200734, CHEMBL2106751

Patent coverage: 3,815 distinct patent families (15,723 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

No target linkage available.

Bioactivity

No ChEMBL bioactivity rows at pChembl ≥ 5 (expected for biologics / antibodies).

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

1 approved indication. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
viral infectious disease	4	MONDO:0005108	EFO:0000763

2 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
HIV infectious disease	3	MONDO:0005109	EFO:0000180
AIDS	3	MONDO:0012268	EFO:0000765

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 31.

Phase distribution

Phase	Trials
PHASE3	9
PHASE1	7
PHASE2	6
PHASE4	5
Not specified	4

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00148785	PHASE4	COMPLETED	A Pharmacokinetic (PK) Study of a Combination of Indinavir, Ritonavir, and Amprenavir
NCT00240552	PHASE4	COMPLETED	Fosamprenavir Expanded Access
NCT00242216	PHASE4	COMPLETED	The Once A Day Protease Inhibitor Regimens
NCT01010399	PHASE4	COMPLETED	Boosted Lexiva With Lovaza Adjunctive Therapy in Hypertriglyceridemic, HIV-Infected Subjects
NCT01222611	PHASE4	COMPLETED	HCV Evolution in HIV/HCV (Genotype 1) Coinfected Patients Treated With Fosamprenavir
NCT00008554	PHASE3	UNKNOWN	Comparison of GW433908 and Nelfinavir in HIV Patients Who Have Not Had Antiretroviral Therapy
NCT00009061	PHASE3	UNKNOWN	Comparison of GW433908/Ritonavir to Nelfinavir When Used With Abacavir and Lamivudine in Patients That Have Not Taken Antiretroviral Drugs
NCT00025727	PHASE3	UNKNOWN	Comparison of Two Dosing Regimens of GW433908/Ritonavir Versus Lopinavir/Ritonavir for 48 Weeks in HIV Patients Who Have Taken Protease Inhibitors and Experienced Virological Failure
NCT00043888	PHASE3	COMPLETED	Study to Explore Safety And Tolerability of Fosamprenavir With or Without Ritonavir in Combination With TRIZIVIR or COMBIVIR
NCT00085943	PHASE3	COMPLETED	KALETRA Or LEXIVA With Ritonavir Combined With EPIVIR And Abacavir In Naive Subjects Over 48 Weeks
NCT00094523	PHASE3	COMPLETED	Fosamprenavir Versus Other Protease Inhibitors
NCT00296504	PHASE3	COMPLETED	A Study To Assess GW433908 (Fosamprenavir) Containing Regimens In HIV-1 Infected Subjects
NCT00363142	PHASE3	COMPLETED	A Study of an Investigational Regimen Combining FDA Approved HIV Drugs in HIV-Infected Subjects
NCT00450580	PHASE3	COMPLETED	HIV-1 Infection Study of Once a Day Versus Twice a Day Protease Inhibitor in Antiretroviral Treatment Naive Adults
NCT06704100	PHASE2	NOT_YET_RECRUITING	Oral Fosamprenavir + Sodium Alginate for GERD
NCT00027339	PHASE2	COMPLETED	Using Drug Levels and Drug Resistance Testing to Select Effective Anti-HIV Drug Combinations in Patients With Drug-resistant HIV
NCT00040664	PHASE2	COMPLETED	A Clinical Study Of An Investigational Regimen Including Marketed HIV Drugs In HIV-1 Pediatric Subjects Ages 2-18 Years
NCT00071760	PHASE2	COMPLETED	Study Of An Investigational Regimen Including FDA Approved HIV Drugs In HIV-Infected Pediatric Subjects
NCT00122603	PHASE2	COMPLETED	Dual Boosted Protease Inhibitor Regimens Without Any Additional Antiretroviral Therapy in HIV-1 Infected Patients (ANRS127)
NCT00764465	PHASE2	COMPLETED	An Interaction Study to Assess Drug Levels in Healthy Adult Subjects
NCT00481182	PHASE1	COMPLETED	Co-Administration Of Fosamprenavir With Methadone: A Drug Interaction Study.
NCT00817765	PHASE1	COMPLETED	Pharmacokinetic Study of Posaconazole Boosted Fosamprenavir
NCT00877591	PHASE1	COMPLETED	Interaction of Buprenorphine With HIV Medications and Tuberculosis Medications
NCT00977301	PHASE1	COMPLETED	Interaction Between Fosamprenavir/Ritonavir and a Single-dose Olanzapine (FORZA)
NCT01140412	PHASE1	TERMINATED	Pharmacokinetic Interaction Between Maraviroc And Fosamprenavir/Ritonavir In Healthy Subjects
NCT01209065	PHASE1	COMPLETED	GSK1349572 Drug Interaction Study With Fosamprenavir/Ritonavir
NCT01290211	PHASE1	COMPLETED	Pharmacokinetic Interaction Between Maraviroc And Fosamprenavir/Ritonavir In Healthy Subjects
NCT00028366	Not specified	COMPLETED	Dual Versus Triple Protease Inhibitor Combinations, Including Ritonavir, in HIV Infected People
NCT00042289	Not specified	COMPLETED	Pharmacokinetic Study of Antiretroviral Drugs and Related Drugs During and After Pregnancy
NCT00614991	Not specified	COMPLETED	An Interaction Study to Assess Drug Levels in Healthy Adult Subjects
NCT00802074	Not specified	COMPLETED	An Interaction Study to Assess Drug Levels in Fasting Healthy Adult Subjects

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).