Atazanavir

Summary

Atazanavir (CHEMBL1163) is an approved small-molecule antiviral drug (ATC J05AE08); indicated across 7 conditions including viral infectious disease and hiv infectious disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J05AE08
• Indications: 7 conditions
• Clinical trials: 121
• Chemistry: 704.9 Da · C38H52N6O7

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1163
Name	Atazanavir
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	148192
ChEBI	CHEBI:37924
ATC	J05AE08
Molecular formula	C38H52N6O7
Molecular weight	704.9
InChIKey	AXRYRYVKAWYZBR-GASGPIRDSA-N

SMILES: CC(C)(C)[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@H](CN(CC2=CC=C(C=C2)C3=CC=CC=N3)NC(=O)[C@H](C(C)(C)C)NC(=O)OC)O)NC(=O)OC

IUPAC name: methyl N-[(2S)-1-[2-[(2S,3S)-2-hydroxy-3-[[(2S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl]amino]-4-phenylbutyl]-2-[(4-pyridin-2-ylphenyl)methyl]hydrazinyl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate

ChEBI definition: A heavily substituted carbohydrazide that is an antiretroviral drug of the protease inhibitor (PI) class used to treat infection of human immunodeficiency virus (HIV).

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

Also known as: Atazanavir, BMS-232632, CGP-73547, Reyataz, atazanavir, atrenavir, atazavir, dr7, SID144206632, SID174007480, SID170465290, ATAZANAVIR

Parent form; salt/anhydrous children: CHEMBL1200678

Patent coverage: 5,486 distinct patent families (22,094 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 22,009 (100%) of the total. 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: 14 (assay-derived). Sample: UDP-glucuronosyltransferase 1A1, Solute carrier organic anion transporter family member 1B1, Solute carrier organic anion transporter family member 1B3, Solute carrier organic anion transporter family member 2B1, Cholecystokinin receptor type A, Motilin receptor, Kappa-type opioid receptor, Nuclear receptor subfamily 1 group I member 2, ATP-dependent translocase ABCB1, UDP-glucuronosyltransferase 1A1.

Bioactivity

ChEMBL activities: 16 potent at pChembl ≥ 5 of 21 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
UGT1A1	6.52	IC50	300	nM	CHEMBL_ACT_19207157
UGT1A1	6.52	IC50	300	nM	CHEMBL_ACT_24829595
SLCO1B3	6.43	Ki	370	nM	CHEMBL_ACT_12088925
SLCO1B3	6.4	IC50	400	nM	CHEMBL_ACT_12088926
UGT1A1	6.22	IC50	600	nM	CHEMBL_ACT_19207163
UGT1A1	6.22	IC50	600	nM	CHEMBL_ACT_24829597
P0DTD1	6.15	Ki	703	nM	CHEMBL_ACT_25952223
OPRK1	5.97	AC50	1059	nM	CHEMBL_ACT_25129268
SLCO1B1	5.89	Ki	1300	nM	CHEMBL_ACT_12088927
SLCO1B1	5.85	IC50	1400	nM	CHEMBL_ACT_12088928
ABCB11	5.7	AC50	2000	nM	CHEMBL_ACT_25126936
Q64550	5.47	IC50	3400	nM	CHEMBL_ACT_19207165
Q64550	5.38	IC50	4200	nM	CHEMBL_ACT_19207161
SLCO2B1	5.29	Ki	5100	nM	CHEMBL_ACT_12088923
SLCO2B1	5.28	IC50	5200	nM	CHEMBL_ACT_12088924
MLNR	5.19	AC50	6400	nM	CHEMBL_ACT_25189016

Target pathways

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

Indications & clinical

Indications

7 indications (1 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
viral infectious disease	4	MONDO:0005108	EFO:0000763
HIV infectious disease	3	MONDO:0005109	EFO:0000180
AIDS	3	MONDO:0012268	EFO:0000765
severe acute respiratory syndrome	2	MONDO:0005091	MONDO:0100096
lymphoid neoplasm	1	MONDO:0005157	EFO:0001642
type 1 diabetes mellitus	1	MONDO:0005147	MONDO:0005147

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

Clinical trials

Total trials: 121.

Phase distribution

Phase	Trials
PHASE4	37
PHASE1	26
PHASE3	21
Not specified	18
PHASE2	14
PHASE2/PHASE3	3
PHASE1/PHASE2	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00082394	PHASE4	COMPLETED	A Study Comparing The Safety, Tolerability and Efficacy of Trizivir VS Combivir & Atazanavir In Subjects With HIV
NCT00084136	PHASE4	COMPLETED	Prospective Evaluation of Anti-retroviral Combinations for Treatment Naive, HIV Infected Persons in Resource-limited Settings
NCT00084253	PHASE4	COMPLETED	Study of Boosted Atazanavir (ATV) Versus Non-boosted ATV in Naive Patients
NCT00207142	PHASE4	COMPLETED	Induction-Maintenance With Atazanavir in HIV Naïve Patients (The INDUMA Study)
NCT00224445	PHASE4	COMPLETED	Boosted Atazanavir and Truvada Given Once-Daily - BATON Study
NCT00242216	PHASE4	COMPLETED	The Once A Day Protease Inhibitor Regimens
NCT00312754	PHASE4	TERMINATED	A Phase IV Study of BMS-232632 in HIV+ Patients With Metabolic Syndrome
NCT00355719	PHASE4	COMPLETED	Study to Evaluate the Influence of Nevirapine to Atazanavir in Steady State Equilibrium in HIV Patients
NCT00384904	PHASE4	COMPLETED	Drug Interaction Study of Famotidine and Atazanavir With Ritonavir in HIV-Infected Patients
NCT00385645	PHASE4	COMPLETED	Atazanavir or Lopinavir in HIV Post-exposure Prophylaxis
NCT00389402	PHASE4	COMPLETED	BASIC: Boosted Atazanavir or Saquinavir Induced Lipid Changes
NCT00420355	PHASE4	TERMINATED	Pharmacokinetic Study of Two HIV Protease Inhibitors in Patients
NCT00426296	PHASE4	UNKNOWN	SHARE: Simple HAART With Abacavir, Reyataz, and Epivir
NCT00447070	PHASE4	COMPLETED	Effect of Atazanavir on Endothelial Function in HIV-Infected Patients
NCT00540137	PHASE4	COMPLETED	The CogNaive Study: Assessing Changes in Neurocognitive Function in Treatment Naïve HIV-1 Positive Subjects
NCT00544128	PHASE4	COMPLETED	Comparison of Epzicom and Truvada for the Initial Once Daily HIV Treatment
NCT00552240	PHASE4	COMPLETED	Nevirapine vs. Atazanavir Boosted With Ritonavir on a Background of Truvada in Human Immunodeficiency Virus (HIV) Infected Naive Patients (NEwArT)
NCT00751153	PHASE4	UNKNOWN	Raltegravir and Atazanavir Replacing Current Suppressive Treatment Because of Side Effects in Current Treatment
NCT00757783	PHASE4	COMPLETED	Changes in Triglyceride and Other Lipids (Levels of Fats Found in Blood) When Taking Darunavir Compared to Atazanavir in HIV-infected Patients That Have Never Received Treatment
NCT00869960	PHASE4	COMPLETED	Impact of Menstrual Cycle on Antiretroviral Pharmacokinetics in Healthy Women
NCT00885482	PHASE4	COMPLETED	Atazanavir and Lamivudine for Treatment Simplification
NCT00931801	PHASE4	COMPLETED	BATAR: Individuals Currently Taking Boosted Atazanavir as Part of an HIV Treatment Regimen Will be Evaluated to See if Substituting Raltegravir for Nucleoside Transcriptase Inhibitors Will be Safe and Well Tolerated.
NCT00940771	PHASE4	COMPLETED	Equivalence of Boosted Atazanavir Based Regimens and Currently Effective HAART Regimens
NCT01102972	PHASE4	COMPLETED	A Simplification Study of Unboosted Reyataz With Epzicom (ASSURE)
NCT01105611	PHASE4	UNKNOWN	Safety and Efficacy Study Comparing Raltegravir to a Protease Inhibitor in Treatment-naïve, HIV/Hepatitis C Drug Users
NCT01194856	PHASE4	TERMINATED	Switching From Efavirenz to Atazanavir/ Ritonavir in HIV-infected Subjects With Good Virologic Suppression
NCT01225705	PHASE4	WITHDRAWN	Safety Study of Raltegravir in HIV/HCV Co-infected Patients
NCT01232127	PHASE4	COMPLETED	Effects of Famotidine on the Pharmacokinetics of Atazanavir When Coadministered to Participants With HIV Infection
NCT01274780	PHASE4	COMPLETED	Metabolic Effects of Atazanavir/Ritonavir Versus Darunavir/Ritonavir in Combination With Tenofovir/Emtricitabine in naïve HIV-1 Infected Patients
NCT01332227	PHASE4	COMPLETED	Atazanavir/Ritonavir, Once Daily + Raltegravir, Twice Daily, Switch Study in HIV-1-Infected Patients
NCT01351740	PHASE4	COMPLETED	Switch to Unboosted Atazanavir With Tenofovir Study
NCT01388543	PHASE4	COMPLETED	Genetics and HIV-1 Protease Inhibitors
NCT01445223	PHASE4	COMPLETED	A Study on Antiretroviral Therapy (ART) Naïve Patients On Different Regimens to Treat Hiv (NORTHIV)
NCT01599364	PHASE4	COMPLETED	Atazanavir/r + Lamivudine Dual Therapy
NCT01691794	PHASE4	COMPLETED	Safety Sudy of Atazanavir Boosted With Ritonavir in the Treatment of HIV Infection in Pediatric Patients
NCT01902186	PHASE4	TERMINATED	Bone Mineral Density Changes in HIV-positive Females With Osteopenia Switching to Raltegravir
NCT01928407	PHASE4	COMPLETED	Evaluation of the Efficacy and Safety Between Two Antiretroviral Regimens, in HIV-1-infected Treatment-naïve Subjects With Low CD4 Counts
NCT00013520	PHASE3	COMPLETED	Comparison of Three Different Initial Treatments Without Protease Inhibitors for HIV Infection
NCT00013897	PHASE3	COMPLETED	A Comparison of BMS-232632 With Efavirenz, Each in Combination With Zidovudine-Lamivudine
NCT00028067	PHASE3	TERMINATED	A Comparison of Atazanavir and Nelfinavir, Each in Combination With 2 NRTIs, in Patients Who Have Failed Treatments Without a Protease Inhibitor

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (2) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

Guideline	Source	Gene(s)	Dosing	Recommendation
Annotation of CPIC Guideline for atazanavir and UGT1A1	CPIC	UGT1A1		yes
Annotation of DPWG Guideline for atazanavir and UGT1A1	DPWG	UGT1A1		yes

PharmGKB also curates 17 clinical and 95 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).