Amprenavir

Summary

Amprenavir (CHEMBL116) is an approved small-molecule HIV protease inhibitor (ATC J05AE05); indicated across 3 conditions including hiv infectious disease and viral infectious disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J05AE05
• Indications: 3 conditions
• Clinical trials: 41
• Chemistry: 505.6 Da · C25H35N3O6S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL116
Name	Amprenavir
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	65016
ChEBI	CHEBI:40050
ATC	J05AE05
Molecular formula	C25H35N3O6S
Molecular weight	505.6
InChIKey	YMARZQAQMVYCKC-OEMFJLHTSA-N

SMILES: CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CCOC2)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]-3-hydroxy-1-phenylbutan-2-yl]carbamate

Pharmacological roles (ChEBI): HIV protease inhibitor, antiviral drug.

Also known as: 141 W94, 141W94, Agenerase, Amprenavir, J05AE05, KVX-478, VX-478, amprenavir, SID29215412, AMPRENAVIR

Patent coverage: 7,107 distinct patent families (29,221 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

Broader ChEMBL bioactivity targets: 10 (assay-derived). Sample: Prelamin-A/C, Thromboxane-A synthase, Cannabinoid receptor 1, Motilin receptor, Alpha-1A adrenergic receptor, Cathepsin D, Cytochrome P450 3A5, Cytochrome P450 3A4, Cruzipain, Bile salt export pump.

Bioactivity

ChEMBL activities: 7 potent at pChembl ≥ 5 of 15 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
CYP3A5	6.7	Ki	200	nM	CHEMBL_ACT_6075245
CYP3A4	6.58	Ki	260	nM	CHEMBL_ACT_6075215
CYP3A4	6.43	Ki	370	nM	CHEMBL_ACT_12163655
LMNA	6.2	Potency	631	nM	CHEMBL_ACT_3658210
CYP3A4	6	IC50	1000	nM	CHEMBL_ACT_7637849
TBXAS1	5.17	IC50	6727	nM	CHEMBL_ACT_7639351
MLNR	5.14	AC50	7300	nM	CHEMBL_ACT_25189667

Target pathways

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

Indications & clinical

Indications

3 indications (2 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
HIV infectious disease	4	MONDO:0005109	EFO:0000764
viral infectious disease	4	MONDO:0005108	EFO:0000763
AIDS	1	MONDO:0012268	EFO:0000765

Clinical trials

Total trials: 41.

Phase distribution

Phase	Trials
PHASE2	17
Not specified	12
PHASE1	5
PHASE3	4
PHASE4	2
PHASE2/PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00005017	PHASE4	UNKNOWN	Effectiveness and Safety of Epivir/Ziagen/Zerit (3TC/ABC/d4T) Versus Epivir/Ziagen/Sustiva (3TC/ABC/EFV) Versus Epivir/Ziagen/Agenerase/Norvir (3TC/ABC/APV/RTV) in HIV Patients Who Have Never Received Treatment
NCT00192660	PHASE4	COMPLETED	HIV Infection And Metabolic Abnormalities Protocol 1 (HAMA001)
NCT00002193	PHASE3	COMPLETED	Safety and Effectiveness of Giving Two Nucleoside Reverse Transcriptase Inhibitors Alone or in Combination With 141W94 to HIV-Infected Children Who Have Never Received Protease Inhibitors
NCT00002195	PHASE3	COMPLETED	A Study of Retrovir and Epivir Alone or in Combination With 141W94 in HIV-Infected Patients
NCT00002202	PHASE3	COMPLETED	A Comparison of 141W94 and Indinavir in HIV-Infected Patients
NCT00002245	PHASE3	COMPLETED	A Study of the Effects of Amprenavir, a Protease Inhibitor, on Carbohydrate and Fat Metabolism in HIV-Infected Patients
NCT00038519	PHASE2/PHASE3	COMPLETED	Amprenavir/Ritonavir or Saquinavir/Ritonavir in HIV-Infected Subjects Following Failure With Kaletra as Their Second Protease Inhibitor
NCT00000912	PHASE2	COMPLETED	A Study on Amprenavir in Combination With Other Anti-HIV Drugs in HIV-Positive Patients
NCT00000918	PHASE2	COMPLETED	A Study to Compare The Ability of Different Anti-HIV Drugs to Decrease Viral Load After Nelfinavir (an Anti-HIV Drug)Treatment Failure
NCT00000940	PHASE2	COMPLETED	Five-Drug Anti-HIV Treatment Followed by Treatment Interruption in Patients Who Have Recently Been Infected With HIV
NCT00001085	PHASE2	COMPLETED	A Study of 141W94 Used Alone or in Combination With Zidovudine Plus 3TC in HIV-Infected Patients
NCT00001095	PHASE2	COMPLETED	A Study of Three Anti-HIV Drug Combinations in Patients Who Have Taken Amprenavir
NCT00001758	PHASE2	COMPLETED	Continued Antiretroviral Therapy With Abacavir, Amprenavir and Efavirenz
NCT00002213	PHASE2	COMPLETED	The Safety and Effectiveness of 1592U89 Plus 141W94 Plus DMP 266 in Patients With HIV Who Developed a Resistance to Protease Inhibitors
NCT00002233	PHASE2	COMPLETED	A Study of a Combination of Four Drugs in Patients With Recent HIV Infection
NCT00002239	PHASE2	COMPLETED	A Study to Compare Three Doses of T-20 When Given in Combination With Abacavir, Amprenavir, Ritonavir, and Efavirenz to HIV-Infected Adults
NCT00002419	PHASE2	COMPLETED	Safety and Effectiveness of Giving Adefovir Dipivoxil Plus Abacavir Plus Efavirenz Plus Amprenavir to HIV-Infected Patients Who Have Failed to Respond to Previous Protease Inhibitor Treatment
NCT00002423	PHASE2	COMPLETED	A Study to Compare Two Anti-HIV Drug Combinations That Include Amprenavir in HIV-Infected Patients Who Have Failed Anti-HIV Drug Combinations That Did Not Include Amprenavir
NCT00002440	PHASE2	COMPLETED	A Study of 1592U89 in Combination With Protease Inhibitors in HIV-Infected Patients Who Have Never Taken Anti-HIV Drugs
NCT00006152	PHASE2	COMPLETED	A Study to See If Taking One or Two Extra Drugs Can Lower HIV Levels in Patients Who Have Failed Their Anti-HIV Drug Treatment
NCT00038532	PHASE2	COMPLETED	Amprenavir/Ritonavir, Saquinavir/Ritonavir or Efavirenz in HIV-Infected Subjects Following Failure With Kaletra (ABT-378/Ritonavir) as Their First Protease Inhibitor Based HAART
NCT00046033	PHASE2	COMPLETED	Comparing Standard-Dose Versus Adjusted-Dose Lopinavir/Ritonavir Therapy in HIV-Infected Persons With Drug Resistance
NCT00056641	PHASE2	COMPLETED	Dual Boosted - Protease Inhibitor (PI) Pharmacokinetics (PK) Trial (Tipranavir / Ritonavir) in Highly Treatment-experienced HIV-1 Infected Patients
NCT00196625	PHASE2	COMPLETED	Salvage Therapy With Amprenavir, Lopinavir and Ritonavir in HIV-Infected Patients in Virological Failure.
NCT00001766	PHASE1	COMPLETED	Drug Interactions Among Anti-HIV Agents
NCT00001968	PHASE1	COMPLETED	Once-Daily Drug Regimen for HIV-Infected Patients
NCT00002183	PHASE1	COMPLETED	A Phase I Trial to Evaluate the Safety, Pharmacokinetics and Antiviral Activity of 141W94 After Multiple Dosing in Patients With HIV Infection
NCT00002372	PHASE1	COMPLETED	A Study of 141W94 in Combination With Other Anti-HIV Drugs
NCT02182765	PHASE1	TERMINATED	Investigation of the Potential Pharmacokinetic Interaction Between Nevirapine, Abacavir and Amprenavir in HIV-1 Infected Non-Nucleoside Reverse Transcriptase Inhibitor (NNRTI) Naive Adults
NCT00000919	Not specified	COMPLETED	A Study to Evaluate Various Combinations of Anti-HIV Medications to Treat Early HIV Infection
NCT00001119	Not specified	COMPLETED	Effects on the Immune System of Anti-HIV Drugs in Patients Recently Infected With HIV
NCT00002205	Not specified	COMPLETED	An Open-Label Study to Evaluate the Efficacy and Safety of Amprenavir (141W94) and Abacavir Combination Therapy in Protease Inhibitor Experienced Subjects With HIV-1 Infection Who Are Failing Their Current Antiretroviral Treatment Regimen
NCT00002216	Not specified	COMPLETED	A Comparison of Two Multi-Drug Therapies in HIV-Infected Patients Who Have Never Received Anti-HIV Treatment
NCT00002217	Not specified	COMPLETED	A Study of Combivir Plus Abacavir Plus 141W94 in Patients Who Previously Have Used Anti-HIV Drugs
NCT00002405	Not specified	COMPLETED	A Study of Amprenavir in HIV-Infected Patients
NCT00002417	Not specified	COMPLETED	A Study of Amprenavir in Patients With Protease Inhibitor-Related Complications
NCT00005762	Not specified	COMPLETED	Drug Interactions of Amprenavir and Efavirenz, in Combination With a Second Protease Inhibitor, in HIV-Negative Volunteers
NCT00006578	Not specified	WITHDRAWN	Evaluation of Specific Infection-Fighting Cells For Prediction of Immune Response to Anti-HIV and Immune-Boosting Medication
NCT00006591	Not specified	UNKNOWN	Ritonavir and Agenerase Treatment for Patients Who Have Failed Previous Anti-HIV Treatment
NCT00006617	Not specified	COMPLETED	Four-Drug Combination Therapy With Zidovudine, Lamivudine, 1592U89 (Abacavir), and 141W94 (Amprenavir) in HIV-Infected Patients

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 1 clinical and 2 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

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