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Identification
NameAtazanavir
Accession NumberDB01072  (APRD00804)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Atazanavir (formerly known as BMS-232632) is an antiretroviral drug of the protease inhibitor (PI) class. Like other antiretrovirals, it is used to treat infection of human immunodeficiency virus (HIV). Atazanavir is distinguished from other PIs in that it can be given once-daily (rather than requiring multiple doses per day) and has lesser effects on the patient’s lipid profile (the amounts of cholesterol and other fatty substances in the blood). Like other protease inhibitors, it is used only in combination with other HIV medications. The U.S. Food and Drug Administration (FDA) approved atazanavir on June 20, 2003. [Wikipedia]

Structure
Thumb
Synonyms
Atazanavirum
ATV
ATZ
Latazanavir
Zrivada
External Identifiers
  • BMS-232632
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Reyatazcapsule, gelatin coated300 mg/1oralE.R. Squibb & Sons, L.L.C.2003-06-24Not applicableUs
Reyatazcapsule, gelatin coated300 mg/1oralA S Medication Solutions Llc2003-06-24Not applicableUs
Reyatazcapsule100 mgoralBristol Myers Squibb CanadaNot applicableNot applicableCanada
Reyatazcapsule, gelatin coated200 mg/1oralA S Medication Solutions Llc2003-06-24Not applicableUs
Reyatazcapsule300 mgoralBristol Myers Squibb Canada2007-05-31Not applicableCanada
Reyatazcapsule, gelatin coated150 mg/1oralREMEDYREPACK INC.2013-03-262016-03-31Us
Reyatazcapsule200 mgoralBristol Myers Squibb Canada2004-01-09Not applicableCanada
Reyatazpowder50 mg/1oralE.R. Squibb & Sons, L.L.C.2014-12-19Not applicableUs
Reyatazcapsule150 mgoralBristol Myers Squibb Canada2004-01-09Not applicableCanada
Reyatazcapsule, gelatin coated200 mg/1oralE.R. Squibb & Sons, L.L.C.2003-06-24Not applicableUs
Reyatazcapsule, gelatin coated300 mg/1oralPhysicians Total Care, Inc.2007-12-04Not applicableUs
Reyatazcapsule, gelatin coated150 mg/1oralE.R. Squibb & Sons, L.L.C.2003-06-24Not applicableUs
Reyatazcapsule, gelatin coated150 mg/1oralPhysicians Total Care, Inc.2003-07-16Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
LatazanavirNot Available
ZrivadaNot Available
Brand mixtures
NameLabellerIngredients
EvotazE.R. Squibb & Sons, L.L.C.
Salts
Name/CASStructureProperties
Atazanavir sulfate
229975-97-7
Thumb
  • InChI Key: DQSGVVGOPRWTKI-QVFAWCHISA-N
  • Monoisotopic Mass: 802.35712729
  • Average Mass: 802.934
DBSALT000426
Categories
UNIIQZU4H47A3S
CAS number198904-31-3
WeightAverage: 704.8555
Monoisotopic: 704.389748048
Chemical FormulaC38H52N6O7
InChI KeyInChIKey=AXRYRYVKAWYZBR-GASGPIRDSA-N
InChI
InChI=1S/C38H52N6O7/c1-37(2,3)31(41-35(48)50-7)33(46)40-29(22-25-14-10-9-11-15-25)30(45)24-44(43-34(47)32(38(4,5)6)42-36(49)51-8)23-26-17-19-27(20-18-26)28-16-12-13-21-39-28/h9-21,29-32,45H,22-24H2,1-8H3,(H,40,46)(H,41,48)(H,42,49)(H,43,47)/t29-,30-,31+,32+/m0/s1
IUPAC Name
methyl N-[(1S)-1-{[(2S,3S)-3-hydroxy-4-[(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethyl-N'-{[4-(pyridin-2-yl)phenyl]methyl}butanehydrazido]-1-phenylbutan-2-yl]carbamoyl}-2,2-dimethylpropyl]carbamate
SMILES
COC(=O)N[[email protected]](C(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC1=CC=C(C=C1)C1=CC=CC=N1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C(C)(C)C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPhenylpyridines
Direct ParentPhenylpyridines
Alternative Parents
Substituents
  • 2-phenylpyridine
  • Alpha-amino acid amide
  • Phenylbutylamine
  • Amphetamine or derivatives
  • N-substituted-alpha-amino acid
  • Phenylmethylamine
  • Benzylamine
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid hydrazide
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationUsed in combination with other antiretroviral agents for the treatment of HIV-1 infection, as well as postexposure prophylaxis of HIV infection in individuals who have had occupational or nonoccupational exposure to potentially infectious body fluids of a person known to be infected with HIV when that exposure represents a substantial risk for HIV transmission.
PharmacodynamicsAtazanavir (ATV) is an azapeptide HIV-1 protease inhibitor (PI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Atazanavir binds to the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs. Atazanivir is pharmacologically related but structurally different from other protease inhibitors and other currently available antiretrovirals.
Mechanism of actionAtazanavir selectively inhibits the virus-specific processing of viral Gag and Gag-Pol polyproteins in HIV-1 infected cells by binding to the active site of HIV-1 protease, thus preventing the formation of mature virions. Atazanavir is not active against HIV-2.
Related Articles
AbsorptionAtazanavir is rapidly absorbed with a Tmax of approximately 2.5 hours. Administration of atazanavir with food enhances bioavailability and reduces pharmacokinetic variability. Oral bioavailability is 60-68%.
Volume of distributionNot Available
Protein binding86% bound to human serum proteins (alpha-1-acid glycoprotein and albumin). Protein binding is independent of concentration.
Metabolism

Atazanavir is extensively metabolized in humans, primarily by the liver. The major biotransformation pathways of atazanavir in humans consisted of monooxygenation and dioxygenation. Other minor biotransformation pathways for atazanavir or its metabolites consisted of glucuronidation, N-dealkylation, hydrolysis, and oxygenation with dehydrogenation. In vitro studies using human liver microsomes suggested that atazanavir is metabolized by CYP3A.

Route of eliminationNot Available
Half lifeElimination half-life in adults (healthy and HIV infected) is approximately 7 hours (following a 400 mg daily dose with a light meal). Elimination half-life in hepatically impaired is 12.1 hours (following a single 400 mg dose).
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Human Immunodeficiency Virus
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7997
Blood Brain Barrier-0.9409
Caco-2 permeable-0.7017
P-glycoprotein substrateSubstrate0.832
P-glycoprotein inhibitor IInhibitor0.81
P-glycoprotein inhibitor IINon-inhibitor0.844
Renal organic cation transporterNon-inhibitor0.924
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6463
CYP450 1A2 substrateNon-inhibitor0.7553
CYP450 2C9 inhibitorNon-inhibitor0.7041
CYP450 2D6 inhibitorNon-inhibitor0.848
CYP450 2C19 inhibitorNon-inhibitor0.5948
CYP450 3A4 inhibitorNon-inhibitor0.8425
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7718
Ames testNon AMES toxic0.6714
CarcinogenicityNon-carcinogens0.7261
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7082 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9766
hERG inhibition (predictor II)Inhibitor0.6538
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral
Capsuleoral100 mg
Capsuleoral150 mg
Capsuleoral200 mg
Capsuleoral300 mg
Capsule, gelatin coatedoral150 mg/1
Capsule, gelatin coatedoral200 mg/1
Capsule, gelatin coatedoral300 mg/1
Powderoral50 mg/1
Prices
Unit descriptionCostUnit
Reyataz 300 mg capsule36.63USD capsule
Reyataz 150 mg capsule18.49USD capsule
Reyataz 200 mg capsule18.49USD capsule
Reyataz 100 mg capsule18.12USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2250840 No2006-07-042017-04-14Canada
CA2317736 No2004-11-022018-12-22Canada
US5849911 Yes1997-12-202017-12-20Us
US6087383 Yes1999-06-212019-06-21Us
US8148374 No2009-09-032029-09-03Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilityFree base slightly soluble (4-5 mg/mL)Not Available
logP4.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00327 mg/mLALOGPS
logP4.08ALOGPS
logP4.54ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)11.92ChemAxon
pKa (Strongest Basic)4.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area171.22 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity191.8 m3·mol-1ChemAxon
Polarizability76.83 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US5849911
General References
  1. Croom KF, Dhillon S, Keam SJ: Atazanavir: a review of its use in the management of HIV-1 infection. Drugs. 2009 May 29;69(8):1107-40. doi: 10.2165/00003495-200969080-00009. [PubMed:19496633 ]
  2. von Hentig N: Atazanavir/ritonavir: a review of its use in HIV therapy. Drugs Today (Barc). 2008 Feb;44(2):103-32. doi: 10.1358/dot.2008.44.2.1137107. [PubMed:18389089 ]
  3. Swainston Harrison T, Scott LJ: Atazanavir: a review of its use in the management of HIV infection. Drugs. 2005;65(16):2309-36. [PubMed:16266202 ]
  4. Le Tiec C, Barrail A, Goujard C, Taburet AM: Clinical pharmacokinetics and summary of efficacy and tolerability of atazanavir. Clin Pharmacokinet. 2005;44(10):1035-50. [PubMed:16176117 ]
  5. Lopez-Cortes LF: [Pharmacology, pharmacokinetic features and interactions of atazanavir]. Enferm Infecc Microbiol Clin. 2008 Dec;26 Suppl 17:2-8. doi: 10.1016/S0213-005X(08)76613-8. [PubMed:20116610 ]
  6. Busti AJ, Hall RG, Margolis DM: Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47. [PubMed:15585441 ]
External Links
ATC CodesJ05AE08J05AR15
AHFS Codes
  • 08:18.08.08
PDB EntriesNot Available
FDA labelDownload (412 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with Atazanavir.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Atazanavir.
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Atazanavir.
AlmotriptanThe serum concentration of Almotriptan can be increased when it is combined with Atazanavir.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Atazanavir.
AlosetronThe serum concentration of Alosetron can be increased when it is combined with Atazanavir.
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Atazanavir.
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Atazanavir resulting in a reduced serum concentration and potentially a decrease in efficacy.
AmiodaroneThe serum concentration of Amiodarone can be increased when it is combined with Atazanavir.
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Atazanavir.
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Atazanavir.
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Atazanavir.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Atazanavir.
AstemizoleThe serum concentration of Astemizole can be increased when it is combined with Atazanavir.
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Atazanavir.
AvanafilThe serum concentration of Avanafil can be increased when it is combined with Atazanavir.
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Atazanavir.
BarnidipineThe serum concentration of Barnidipine can be increased when it is combined with Atazanavir.
BatimastatThe serum concentration of Atazanavir can be increased when it is combined with Batimastat.
BedaquilineThe serum concentration of Bedaquiline can be increased when it is combined with Atazanavir.
BelinostatThe serum concentration of Belinostat can be increased when it is combined with Atazanavir.
BepridilThe metabolism of Bepridil can be decreased when combined with Atazanavir.
BexaroteneThe serum concentration of Atazanavir can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Atazanavir can be decreased when it is combined with Boceprevir.
BortezomibThe serum concentration of Bortezomib can be increased when it is combined with Atazanavir.
BosentanThe serum concentration of Atazanavir can be decreased when it is combined with Bosentan.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Atazanavir.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Atazanavir.
BrexpiprazoleThe serum concentration of Brexpiprazole can be increased when it is combined with Atazanavir.
BrinzolamideThe serum concentration of Brinzolamide can be increased when it is combined with Atazanavir.
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Atazanavir.
BuprenorphineThe serum concentration of Atazanavir can be decreased when it is combined with Buprenorphine.
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Atazanavir.
CabozantinibThe serum concentration of Cabozantinib can be increased when it is combined with Atazanavir.
Calcium carbonateCalcium carbonate can cause a decrease in the absorption of Atazanavir resulting in a reduced serum concentration and potentially a decrease in efficacy.
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Atazanavir.
CarbamazepineThe metabolism of Atazanavir can be increased when combined with Carbamazepine.
CeritinibThe serum concentration of Ceritinib can be increased when it is combined with Atazanavir.
ChlorotrianiseneThe serum concentration of Chlorotrianisene can be decreased when it is combined with Atazanavir.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Atazanavir.
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Atazanavir.
CimetidineThe serum concentration of Atazanavir can be decreased when it is combined with Cimetidine.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Atazanavir.
CitalopramAtazanavir may increase the QTc-prolonging activities of Citalopram.
ClarithromycinThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Atazanavir.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Atazanavir.
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Atazanavir.
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Atazanavir.
CyclophosphamideThe risk or severity of adverse effects can be increased when Atazanavir is combined with Cyclophosphamide.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Atazanavir.
DabrafenibThe serum concentration of Atazanavir can be decreased when it is combined with Dabrafenib.
DaclatasvirThe serum concentration of Daclatasvir can be increased when it is combined with Atazanavir.
DapoxetineThe serum concentration of Dapoxetine can be increased when it is combined with Atazanavir.
DasatinibThe serum concentration of Dasatinib can be increased when it is combined with Atazanavir.
DeferasiroxThe serum concentration of Atazanavir can be decreased when it is combined with Deferasirox.
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Atazanavir.
DidanosineThe serum concentration of Atazanavir can be decreased when it is combined with Didanosine.
DienogestThe serum concentration of Dienogest can be increased when it is combined with Atazanavir.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Atazanavir.
DisulfiramThe therapeutic efficacy of Disulfiram can be decreased when used in combination with Atazanavir.
DofetilideAtazanavir may increase the QTc-prolonging activities of Dofetilide.
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Atazanavir.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Atazanavir.
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Atazanavir.
DronedaroneThe serum concentration of Dronedarone can be increased when it is combined with Atazanavir.
DutasterideThe serum concentration of Dutasteride can be increased when it is combined with Atazanavir.
EfavirenzThe serum concentration of Atazanavir can be decreased when it is combined with Efavirenz.
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Atazanavir.
EliglustatThe serum concentration of Eliglustat can be increased when it is combined with Atazanavir.
EluxadolineThe serum concentration of Eluxadoline can be increased when it is combined with Atazanavir.
ElvitegravirThe serum concentration of Elvitegravir can be increased when it is combined with Atazanavir.
EnfuvirtideThe serum concentration of Enfuvirtide can be increased when it is combined with Atazanavir.
EplerenoneThe serum concentration of Eplerenone can be increased when it is combined with Atazanavir.
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Atazanavir.
EsomeprazoleThe serum concentration of Atazanavir can be decreased when it is combined with Esomeprazole.
EstazolamThe serum concentration of Estazolam can be increased when it is combined with Atazanavir.
EtizolamThe serum concentration of Etizolam can be increased when it is combined with Atazanavir.
EtonogestrelThe serum concentration of Etonogestrel can be increased when it is combined with Atazanavir.
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Atazanavir.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Atazanavir.
FamotidineThe serum concentration of Atazanavir can be decreased when it is combined with Famotidine.
FentanylThe serum concentration of Fentanyl can be increased when it is combined with Atazanavir.
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Atazanavir.
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Atazanavir.
FluconazoleThe metabolism of Atazanavir can be decreased when combined with Fluconazole.
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Atazanavir.
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Atazanavir.
Fluticasone PropionateThe serum concentration of Fluticasone Propionate can be increased when it is combined with Atazanavir.
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Atazanavir.
Fusidic AcidThe serum concentration of Atazanavir can be increased when it is combined with Fusidic Acid.
GarlicThe serum concentration of Atazanavir can be decreased when it is combined with Garlic.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Atazanavir.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Atazanavir.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Atazanavir.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Atazanavir.
GoserelinAtazanavir may increase the QTc-prolonging activities of Goserelin.
GuanfacineThe serum concentration of Guanfacine can be increased when it is combined with Atazanavir.
HalofantrineThe serum concentration of Halofantrine can be increased when it is combined with Atazanavir.
HydrocodoneThe serum concentration of Hydrocodone can be increased when it is combined with Atazanavir.
IbrutinibThe serum concentration of Ibrutinib can be increased when it is combined with Atazanavir.
IdelalisibThe serum concentration of Atazanavir can be increased when it is combined with Idelalisib.
IfosfamideThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Atazanavir resulting in a loss in efficacy.
IloperidoneThe serum concentration of the active metabolites of Iloperidone can be increased when Iloperidone is used in combination with Atazanavir.
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Atazanavir.
ImidafenacinThe serum concentration of Imidafenacin can be increased when it is combined with Atazanavir.
IndinavirThe risk or severity of adverse effects can be increased when Atazanavir is combined with Indinavir.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Atazanavir.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Atazanavir.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Atazanavir.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Atazanavir.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Atazanavir.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Atazanavir.
IrinotecanThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Atazanavir.
IsavuconazoniumThe serum concentration of the active metabolites of Isavuconazonium can be increased when Isavuconazonium is used in combination with Atazanavir.
IsoflurophateThe serum concentration of Atazanavir can be increased when it is combined with Isoflurophate.
IvabradineThe serum concentration of Ivabradine can be increased when it is combined with Atazanavir.
IvacaftorThe serum concentration of Ivacaftor can be increased when it is combined with Atazanavir.
IxabepiloneThe serum concentration of Ixabepilone can be increased when it is combined with Atazanavir.
LacosamideThe serum concentration of Lacosamide can be increased when it is combined with Atazanavir.
LamotrigineThe serum concentration of Lamotrigine can be decreased when it is combined with Atazanavir.
LansoprazoleThe serum concentration of Atazanavir can be decreased when it is combined with Lansoprazole.
LapatinibThe serum concentration of Lapatinib can be increased when it is combined with Atazanavir.
LercanidipineThe serum concentration of Lercanidipine can be increased when it is combined with Atazanavir.
LeuprolideAtazanavir may increase the QTc-prolonging activities of Leuprolide.
LevobupivacaineThe serum concentration of Levobupivacaine can be increased when it is combined with Atazanavir.
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Atazanavir.
LevonorgestrelThe serum concentration of Levonorgestrel can be increased when it is combined with Atazanavir.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Atazanavir.
LomitapideThe serum concentration of Lomitapide can be increased when it is combined with Atazanavir.
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Atazanavir.
LuliconazoleThe serum concentration of Atazanavir can be increased when it is combined with Luliconazole.
LurasidoneThe serum concentration of Lurasidone can be increased when it is combined with Atazanavir.
MacitentanThe serum concentration of MACITENTAN can be increased when it is combined with Atazanavir.
Magnesium hydroxideMagnesium hydroxide can cause a decrease in the absorption of Atazanavir resulting in a reduced serum concentration and potentially a decrease in efficacy.
Magnesium oxideMagnesium oxide can cause a decrease in the absorption of Atazanavir resulting in a reduced serum concentration and potentially a decrease in efficacy.
MaravirocThe serum concentration of Maraviroc can be increased when it is combined with Atazanavir.
Medroxyprogesterone acetateThe serum concentration of Medroxyprogesterone Acetate can be increased when it is combined with Atazanavir.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Atazanavir.
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Atazanavir.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Atazanavir.
MifepristoneThe serum concentration of Mifepristone can be increased when it is combined with Atazanavir.
MinocyclineThe serum concentration of Atazanavir can be decreased when it is combined with Minocycline.
MinoxidilThe serum concentration of Minoxidil can be increased when it is combined with Atazanavir.
MitotaneThe serum concentration of Atazanavir can be decreased when it is combined with Mitotane.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Atazanavir.
NefazodoneThe serum concentration of Nefazodone can be increased when it is combined with Atazanavir.
NelfinavirThe metabolism of Atazanavir can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Atazanavir can be increased when it is combined with Netupitant.
NevirapineThe serum concentration of Nevirapine can be increased when it is combined with Atazanavir.
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Atazanavir.
NimodipineThe serum concentration of Nimodipine can be increased when it is combined with Atazanavir.
NisoldipineThe serum concentration of Nisoldipine can be increased when it is combined with Atazanavir.
NizatidineThe serum concentration of Atazanavir can be decreased when it is combined with Nizatidine.
NorethisteroneThe serum concentration of Norethindrone can be increased when it is combined with Atazanavir.
OlaparibThe serum concentration of Olaparib can be increased when it is combined with Atazanavir.
OmeprazoleThe serum concentration of Atazanavir can be decreased when it is combined with Omeprazole.
OspemifeneThe serum concentration of Ospemifene can be increased when it is combined with Atazanavir.
OxybutyninThe serum concentration of Oxybutynin can be increased when it is combined with Atazanavir.
OxycodoneThe risk or severity of adverse effects can be increased when Atazanavir is combined with Oxycodone.
PaclitaxelThe serum concentration of Paclitaxel can be increased when it is combined with Atazanavir.
PalbociclibThe serum concentration of Palbociclib can be increased when it is combined with Atazanavir.
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Atazanavir.
PantoprazoleThe serum concentration of Atazanavir can be decreased when it is combined with Pantoprazole.
ParecoxibThe serum concentration of Parecoxib can be increased when it is combined with Atazanavir.
ParicalcitolThe serum concentration of Paricalcitol can be increased when it is combined with Atazanavir.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Atazanavir.
PethidineThe risk or severity of adverse effects can be increased when Atazanavir is combined with Pethidine.
PhenytoinThe metabolism of Atazanavir can be increased when combined with Phenytoin.
PimecrolimusThe metabolism of Pimecrolimus can be decreased when combined with Atazanavir.
PimozideThe serum concentration of Pimozide can be increased when it is combined with Atazanavir.
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Atazanavir.
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Atazanavir.
PosaconazoleThe serum concentration of Atazanavir can be increased when it is combined with Posaconazole.
PranlukastThe serum concentration of Pranlukast can be increased when it is combined with Atazanavir.
PrasugrelThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Atazanavir resulting in a loss in efficacy.
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Atazanavir.
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Atazanavir.
PropafenoneThe serum concentration of Propafenone can be increased when it is combined with Atazanavir.
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Atazanavir.
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Atazanavir.
RabeprazoleThe serum concentration of Atazanavir can be decreased when it is combined with Rabeprazole.
RamelteonThe serum concentration of Ramelteon can be increased when it is combined with Atazanavir.
RanitidineThe serum concentration of Atazanavir can be decreased when it is combined with Ranitidine.
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Atazanavir.
RegorafenibThe serum concentration of Regorafenib can be increased when it is combined with Atazanavir.
RepaglinideThe serum concentration of Repaglinide can be increased when it is combined with Atazanavir.
RetapamulinThe serum concentration of Retapamulin can be increased when it is combined with Atazanavir.
RifabutinThe serum concentration of the active metabolites of Rifabutin can be increased when Rifabutin is used in combination with Atazanavir.
RifampicinThe serum concentration of Atazanavir can be decreased when it is combined with Rifampicin.
RilpivirineThe serum concentration of Rilpivirine can be increased when it is combined with Atazanavir.
RiociguatThe serum concentration of Riociguat can be increased when it is combined with Atazanavir.
RitonavirThe serum concentration of Ritonavir can be increased when it is combined with Atazanavir.
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Atazanavir.
RosiglitazoneThe serum concentration of Rosiglitazone can be increased when it is combined with Atazanavir.
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Atazanavir.
RuxolitinibThe serum concentration of Ruxolitinib can be increased when it is combined with Atazanavir.
SalmeterolThe serum concentration of Salmeterol can be increased when it is combined with Atazanavir.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Atazanavir.
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Atazanavir.
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Atazanavir.
SiltuximabThe serum concentration of Atazanavir can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Atazanavir.
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Atazanavir.
Sodium bicarbonateSodium bicarbonate can cause a decrease in the absorption of Atazanavir resulting in a reduced serum concentration and potentially a decrease in efficacy.
SonidegibThe serum concentration of Sonidegib can be increased when it is combined with Atazanavir.
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Atazanavir.
St. John's WortThe serum concentration of Atazanavir can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Atazanavir can be increased when it is combined with Stiripentol.
SuvorexantThe serum concentration of Suvorexant can be increased when it is combined with Atazanavir.
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Atazanavir.
TadalafilThe serum concentration of Tadalafil can be increased when it is combined with Atazanavir.
TamsulosinThe serum concentration of Tamsulosin can be increased when it is combined with Atazanavir.
TasimelteonThe serum concentration of Tasimelteon can be increased when it is combined with Atazanavir.
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Atazanavir.
TemsirolimusThe risk or severity of adverse effects can be increased when Atazanavir is combined with Temsirolimus.
TenofovirThe serum concentration of Atazanavir can be decreased when it is combined with Tenofovir.
TerfenadineThe serum concentration of Terfenadine can be increased when it is combined with Atazanavir.
TicagrelorThe serum concentration of the active metabolites of Ticagrelor can be reduced when Ticagrelor is used in combination with Atazanavir resulting in a loss in efficacy.
TipranavirThe serum concentration of Atazanavir can be decreased when it is combined with Tipranavir.
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Atazanavir.
TocilizumabThe serum concentration of Atazanavir can be decreased when it is combined with Tocilizumab.
TofacitinibThe serum concentration of Tofacitinib can be increased when it is combined with Atazanavir.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Atazanavir.
TolterodineThe serum concentration of Tolterodine can be increased when it is combined with Atazanavir.
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Atazanavir.
ToremifeneThe risk or severity of adverse effects can be increased when Atazanavir is combined with Toremifene.
TrabectedinThe serum concentration of Trabectedin can be increased when it is combined with Atazanavir.
TramadolThe serum concentration of Tramadol can be increased when it is combined with Atazanavir.
Trastuzumab emtansineThe serum concentration of the active metabolites of ado-trastuzumab emtansine can be increased when ado-trastuzumab emtansine is used in combination with Atazanavir.
TrazodoneThe serum concentration of Trazodone can be increased when it is combined with Atazanavir.
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Atazanavir.
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Atazanavir.
Valproic AcidThe serum concentration of Valproic Acid can be decreased when it is combined with Atazanavir.
VardenafilThe serum concentration of Vardenafil can be increased when it is combined with Atazanavir.
VemurafenibThe serum concentration of Vemurafenib can be increased when it is combined with Atazanavir.
VilazodoneThe serum concentration of Vilazodone can be increased when it is combined with Atazanavir.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Atazanavir.
VincristineThe serum concentration of Vincristine can be increased when it is combined with Atazanavir.
VindesineThe serum concentration of Vindesine can be increased when it is combined with Atazanavir.
VorapaxarThe serum concentration of Vorapaxar can be increased when it is combined with Atazanavir.
VoriconazoleThe serum concentration of Voriconazole can be decreased when it is combined with Atazanavir.
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Atazanavir.
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Atazanavir.
ZopicloneThe serum concentration of Zopiclone can be increased when it is combined with Atazanavir.
ZuclopenthixolThe serum concentration of Zuclopenthixol can be increased when it is combined with Atazanavir.
Food Interactions
  • Administration with food reduces pharmacokinetic variability.
  • Food increases product absorption.

Targets

Kind
Protein
Organism
Human immunodeficiency virus 1
Pharmacological action
yes
Actions
inhibitor
General Function:
Aspartic-type endopeptidase activity
Specific Function:
Not Available
Gene Name:
pol
Uniprot ID:
Q72874
Molecular Weight:
10778.7 Da
References
  1. Dierynck I, De Wit M, Gustin E, Keuleers I, Vandersmissen J, Hallenberger S, Hertogs K: Binding kinetics of darunavir to human immunodeficiency virus type 1 protease explain the potent antiviral activity and high genetic barrier. J Virol. 2007 Dec;81(24):13845-51. Epub 2007 Oct 10. [PubMed:17928344 ]
  2. Dandache S, Sevigny G, Yelle J, Stranix BR, Parkin N, Schapiro JM, Wainberg MA, Wu JJ: In vitro antiviral activity and cross-resistance profile of PL-100, a novel protease inhibitor of human immunodeficiency virus type 1. Antimicrob Agents Chemother. 2007 Nov;51(11):4036-43. Epub 2007 Jul 16. [PubMed:17638694 ]
  3. Wood R: Atazanavir: its role in HIV treatment. Expert Rev Anti Infect Ther. 2008 Dec;6(6):785-96. doi: 10.1586/14787210.6.6.785. [PubMed:19053892 ]
  4. Le Tiec C, Barrail A, Goujard C, Taburet AM: Clinical pharmacokinetics and summary of efficacy and tolerability of atazanavir. Clin Pharmacokinet. 2005;44(10):1035-50. [PubMed:16176117 ]
  5. Pyrko P, Kardosh A, Wang W, Xiong W, Schonthal AH, Chen TC: HIV-1 protease inhibitors nelfinavir and atazanavir induce malignant glioma death by triggering endoplasmic reticulum stress. Cancer Res. 2007 Nov 15;67(22):10920-8. [PubMed:18006837 ]
  6. Menendez-Arias L, Tozser J: HIV-1 protease inhibitors: effects on HIV-2 replication and resistance. Trends Pharmacol Sci. 2008 Jan;29(1):42-9. Epub 2007 Dec 4. [PubMed:18054799 ]
  7. Lopez-Cortes LF: [Pharmacology, pharmacokinetic features and interactions of atazanavir]. Enferm Infecc Microbiol Clin. 2008 Dec;26 Suppl 17:2-8. doi: 10.1016/S0213-005X(08)76613-8. [PubMed:20116610 ]
  8. Busti AJ, Hall RG, Margolis DM: Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47. [PubMed:15585441 ]
  9. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Le Tiec C, Barrail A, Goujard C, Taburet AM: Clinical pharmacokinetics and summary of efficacy and tolerability of atazanavir. Clin Pharmacokinet. 2005;44(10):1035-50. [PubMed:16176117 ]
  2. Busti AJ, Hall RG, Margolis DM: Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47. [PubMed:15585441 ]
  3. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Busti AJ, Hall RG, Margolis DM: Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47. [PubMed:15585441 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Perloff ES, Duan SX, Skolnik PR, Greenblatt DJ, von Moltke LL: Atazanavir: effects on P-glycoprotein transport and CYP3A metabolism in vitro. Drug Metab Dispos. 2005 Jun;33(6):764-70. Epub 2005 Mar 11. [PubMed:15764714 ]
  2. Lucia MB, Golotta C, Rutella S, Rastrelli E, Savarino A, Cauda R: Atazanavir inhibits P-glycoprotein and multidrug resistance-associated protein efflux activity. J Acquir Immune Defic Syndr. 2005 Aug 15;39(5):635-7. [PubMed:16044020 ]
  3. Chinn LW, Gow JM, Tse MM, Becker SL, Kroetz DL: Interindividual variability in the effect of atazanavir and saquinavir on the expression of lymphocyte P-glycoprotein. J Antimicrob Chemother. 2007 Jul;60(1):61-7. Epub 2007 May 17. [PubMed:17510066 ]
  4. Wood R: Atazanavir: its role in HIV treatment. Expert Rev Anti Infect Ther. 2008 Dec;6(6):785-96. doi: 10.1586/14787210.6.6.785. [PubMed:19053892 ]
  5. Janneh O, Anwar T, Jungbauer C, Kopp S, Khoo SH, Back DJ, Chiba P: P-glycoprotein, multidrug resistance-associated proteins and human organic anion transporting polypeptide influence the intracellular accumulation of atazanavir. Antivir Ther. 2009;14(7):965-74. doi: 10.3851/IMP1399. [PubMed:19918100 ]
  6. Storch CH, Theile D, Lindenmaier H, Haefeli WE, Weiss J: Comparison of the inhibitory activity of anti-HIV drugs on P-glycoprotein. Biochem Pharmacol. 2007 May 15;73(10):1573-81. Epub 2007 Jan 24. [PubMed:17328866 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Transporter activity
Specific Function:
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency.
Gene Name:
ABCC1
Uniprot ID:
P33527
Molecular Weight:
171589.5 Da
References
  1. Janneh O, Anwar T, Jungbauer C, Kopp S, Khoo SH, Back DJ, Chiba P: P-glycoprotein, multidrug resistance-associated proteins and human organic anion transporting polypeptide influence the intracellular accumulation of atazanavir. Antivir Ther. 2009;14(7):965-74. doi: 10.3851/IMP1399. [PubMed:19918100 ]
  2. Lucia MB, Golotta C, Rutella S, Rastrelli E, Savarino A, Cauda R: Atazanavir inhibits P-glycoprotein and multidrug resistance-associated protein efflux activity. J Acquir Immune Defic Syndr. 2005 Aug 15;39(5):635-7. [PubMed:16044020 ]
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Drug created on June 13, 2005 07:24 / Updated on July 27, 2016 03:12