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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
SynonymLanguageCode
AtazanavirumNot AvailableNot Available
ATVNot AvailableNot Available
ATZNot AvailableNot Available
LatazanavirNot AvailableNot Available
ZrivadaNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Reyatazcapsule, gelatin coated300 mgoralE.R. Squibb & Sons, L.L.C.2003-06-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Reyatazcapsule, gelatin coated100 mgoralE.R. Squibb & Sons, L.L.C.2003-06-242015-07-31Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Reyatazcapsule, gelatin coated150 mgoralE.R. Squibb & Sons, L.L.C.2003-06-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Reyatazcapsule, gelatin coated200 mgoralE.R. Squibb & Sons, L.L.C.2003-06-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Reyatazpowder50 mgoralE.R. Squibb & Sons, L.L.C.2014-12-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Reyatazcapsule, gelatin coated150 mgoralREMEDYREPACK INC.2013-03-26Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Reyatazcapsule, gelatin coated200 mgoralA S Medication Solutions Llc2003-06-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Reyatazcapsule, gelatin coated300 mgoralA S Medication Solutions Llc2003-06-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Reyatazcapsule, gelatin coated150 mgoralPhysicians Total Care, Inc.2003-07-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Reyatazcapsule, gelatin coated300 mgoralPhysicians Total Care, Inc.2007-12-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Reyatazcapsule150 mgoralBristol Myers Squibb CanadaNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Reyatazcapsule200 mgoralBristol Myers Squibb CanadaNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Reyatazcapsule300 mgoralBristol Myers Squibb CanadaNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
LatazanavirNot Available
ZrivadaNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Atazanavir sulfate
229975-97-7
Thumb
  • InChI Key: DQSGVVGOPRWTKI-QVFAWCHISA-N
  • Monoisotopic Mass: 802.35712729
  • Average Mass: 802.934
DBSALT000426
Categories
CAS number198904-31-3
WeightAverage: 704.8555
Monoisotopic: 704.389748048
Chemical FormulaC38H52N6O7
InChI KeyAXRYRYVKAWYZBR-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[C@H](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.
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 substrateNon-inhibitor0.7041
CYP450 2D6 substrateNon-inhibitor0.848
CYP450 2C19 substrateNon-inhibitor0.5948
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Capsuleoral150 mg
Capsuleoral200 mg
Capsuleoral300 mg
Capsule, gelatin coatedoral100 mg
Capsule, gelatin coatedoral150 mg
Capsule, gelatin coatedoral200 mg
Capsule, gelatin coatedoral300 mg
Powderoral50 mg
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
CountryPatent NumberApprovedExpires (estimated)
Canada22508402006-07-042017-04-14
Canada23177362004-11-022018-12-22
United States58499111997-06-202017-06-20
United States60873831998-12-212018-12-21
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 Reference
  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
  2. von Hentig N: Atazanavir/ritonavir: a review of its use in HIV therapy. Drugs Today (Barc). 2008 Feb;44(2):103-32. Pubmed
  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
  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
  5. Lopez-Cortes LF: [Pharmacology, pharmacokinetic features and interactions of atazanavir] Enferm Infecc Microbiol Clin. 2008 Dec;26 Suppl 17:2-8. Pubmed
  6. Busti AJ, Hall RG, Margolis DM: Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47. Pubmed
External Links
ATC CodesJ05AE08
AHFS Codes
  • 08:18.08.08
PDB EntriesNot Available
FDA labelDownload (412 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AbacavirProtease Inhibitors may decrease the serum concentration of Abacavir.
AcetohexamideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
ado-trastuzumab emtansineCYP3A4 Inhibitors (Strong) may increase serum concentrations of the active metabolite(s) of Ado-Trastuzumab Emtansine. Specifically, strong CYP3A4 inhibitors may increase concentrations of the cytotoxic DM1 component.
AlfuzosinCYP3A4 Inhibitors (Strong) may increase the serum concentration of Alfuzosin.
AlmotriptanCYP3A4 Inhibitors (Strong) may increase the serum concentration of Almotriptan.
AlogliptinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
AlosetronCYP3A4 Inhibitors (Strong) may increase the serum concentration of Alosetron.
AlprazolamProtease Inhibitors may increase the serum concentration of ALPRAZolam.
Aluminum hydroxideMay decrease the absorption of Atazanavir.
AmiodaroneAtazanavir may increase the serum concentration of Amiodarone.
ApixabanCYP3A4 Inhibitors (Strong) may increase the serum concentration of Apixaban.
AripiprazoleCYP3A4 Inhibitors (Strong) may increase the serum concentration of ARIPiprazole.
AstemizoleCYP3A4 Inhibitors (Strong) may increase the serum concentration of Astemizole.
AtorvastatinProtease Inhibitors may increase the serum concentration of AtorvaSTATin.
AvanafilCYP3A4 Inhibitors (Strong) may increase the serum concentration of Avanafil.
AxitinibCYP3A4 Inhibitors (Strong) may increase the serum concentration of Axitinib.
BatimastatMay increase the serum concentration of other Protease Inhibitors.
BedaquilineCYP3A4 Inhibitors (Strong) may increase the serum concentration of Bedaquiline.
BelinostatAtazanavir may increase the serum concentration of Belinostat.
BoceprevirMay decrease the serum concentration of Protease Inhibitors. Protease Inhibitors may decrease the serum concentration of Boceprevir.
BortezomibCYP3A4 Inhibitors (Strong) may increase the serum concentration of Bortezomib.
BosentanMay increase the serum concentration of Bosentan. Bosentan may decrease the serum concentration of Atazanavir.
BosutinibCYP3A4 Inhibitors (Strong) may increase the serum concentration of Bosutinib.
Brentuximab vedotinCYP3A4 Inhibitors (Strong) may increase the serum concentration of Brentuximab Vedotin. Specifically, concentrations of the active monomethyl auristatin E (MMAE) component may be increased.
BrinzolamideCYP3A4 Inhibitors (Strong) may increase the serum concentration of Brinzolamide.
BuprenorphineMay increase the serum concentration of Buprenorphine. Buprenorphine may decrease the serum concentration of Atazanavir.
CabazitaxelCYP3A4 Inhibitors (Strong) may increase the serum concentration of Cabazitaxel.
CabozantinibCYP3A4 Inhibitors (Strong) may increase the serum concentration of Cabozantinib.
Calcium carbonateMay decrease the absorption of Atazanavir.
CanagliflozinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
CarbamazepineMay increase the metabolism of Protease Inhibitors. Protease Inhibitors may decrease the metabolism of CarBAMazepine.
ChlorpropamideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
CilostazolCYP3A4 Inhibitors (Strong) may increase the serum concentration of Cilostazol.
CimetidineH2-Antagonists may decrease the serum concentration of Atazanavir.
CisaprideProtease Inhibitors may increase the serum concentration of Cisapride. This may result in QTc prolongation and malignant cardiac arrhythmias.
ClarithromycinProtease Inhibitors may diminish the therapeutic effect of Clarithromycin. Specifically, certain protease inhibitors may decrease formation of the active 14-hydroxy-clarithromycin metabolite, which may negatively impact clarithromycin effectiveness vs. H. influenzae and other non-MAC infections. Clarithromycin may increase the serum concentration of Protease Inhibitors. Protease Inhibitors may increase the serum concentration of Clarithromycin. Clarithromycin dose adjustment in renally impaired patients may be needed.
ColchicineCYP3A4 Inhibitors (Strong) may increase the serum concentration of Colchicine.
ConivaptanCYP3A4 Inhibitors (Strong) may increase the serum concentration of Conivaptan.
CrizotinibCYP3A4 Inhibitors (Strong) may increase the serum concentration of Crizotinib.
CyclophosphamideProtease Inhibitors may enhance the adverse/toxic effect of Cyclophosphamide. Specifically, the incidences of neutropenia, infection, and mucositis may be increased.
DabrafenibMay decrease the serum concentration of CYP3A4 Substrates.
DapoxetineCYP3A4 Inhibitors (Strong) may increase the serum concentration of Dapoxetine.
DasatinibCYP3A4 Inhibitors (Strong) may increase the serum concentration of Dasatinib.
DeferasiroxMay decrease the serum concentration of CYP3A4 Substrates.
DelavirdineMay increase the serum concentration of Protease Inhibitors. Protease Inhibitors may decrease the serum concentration of Delavirdine.
DesogestrelMay increase the serum concentration of Contraceptives (Progestins).
DidanosineMay decrease the serum concentration of Didanosine. Reported with enteric coated didanosine capsules. Didanosine may decrease the serum concentration of Atazanavir. Specifically, the buffered formulation of didanosine may decrease atazanavir absorption.
DigoxinProtease Inhibitors may increase the serum concentration of Digoxin. Increased serum concentrations of digoxin may increase risk of AV nodal blockade.
DisulfiramMay diminish the therapeutic effect of Disulfiram.
DomperidoneCYP3A4 Inhibitors (Strong) may increase the serum concentration of Domperidone.
DronabinolCYP3A4 Inhibitors (Strong) may increase the serum concentration of Dronabinol.
DronedaroneCYP3A4 Inhibitors (Strong) may increase the serum concentration of Dronedarone.
DrospirenoneMay increase the serum concentration of Contraceptives (Progestins).
DutasterideCYP3A4 Inhibitors (Strong) may increase the serum concentration of Dutasteride.
EfavirenzMay decrease the serum concentration of Atazanavir.
EliglustatCYP3A4 Inhibitors (Strong) may increase the serum concentration of Eliglustat.
EnfuvirtideMay increase the serum concentration of Protease Inhibitors. Protease Inhibitors may increase the serum concentration of Enfuvirtide.
EplerenoneCYP3A4 Inhibitors (Strong) may increase the serum concentration of Eplerenone.
ErlotinibCYP3A4 Inhibitors (Strong) may increase the serum concentration of Erlotinib.
EsomeprazoleProton Pump Inhibitors may decrease the serum concentration of Atazanavir.
EthynodiolMay increase the serum concentration of Contraceptives (Progestins).
EtonogestrelMay increase the serum concentration of Contraceptives (Progestins).
EtravirineAtazanavir may increase the serum concentration of Etravirine. Etravirine may decrease the serum concentration of Atazanavir.
EverolimusCYP3A4 Inhibitors (Strong) may increase the serum concentration of Everolimus.
FamotidineH2-Antagonists may decrease the serum concentration of Atazanavir.
FentanylCYP3A4 Inhibitors (Strong) may increase the serum concentration of FentaNYL.
FesoterodineCYP3A4 Inhibitors (Strong) may increase serum concentrations of the active metabolite(s) of Fesoterodine.
FluvastatinAtazanavir may increase the serum concentration of Fluvastatin.
GliclazideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
GlimepirideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
GliquidoneHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
GlyburideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
GuanfacineCYP3A4 Inhibitors (Strong) may increase the serum concentration of GuanFACINE.
HalofantrineCYP3A4 Inhibitors (Strong) may increase the serum concentration of Halofantrine.
HydrocodoneCYP3A4 Inhibitors (Strong) may increase the serum concentration of Hydrocodone.
IfosfamideCYP3A4 Inhibitors (Strong) may decrease serum concentrations of the active metabolite(s) of Ifosfamide.
IloperidoneCYP3A4 Inhibitors (Strong) may increase serum concentrations of the active metabolite(s) of Iloperidone. Specifically, concentrations of the metabolites P88 and P95 may be increased. CYP3A4 Inhibitors (Strong) may increase the serum concentration of Iloperidone.
ImatinibCYP3A4 Inhibitors (Strong) may increase the serum concentration of Imatinib.
IndinavirMay enhance the adverse/toxic effect of Indinavir. Indinavir may enhance the adverse/toxic effect of Atazanavir.
Insulin AspartHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin DetemirHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin GlargineHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin GlulisineHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin LisproHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin RegularHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin, isophaneHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
IrinotecanCYP3A4 Inhibitors (Strong) may increase serum concentrations of the active metabolite(s) of Irinotecan. Specifically, serum concentrations of SN-38 may be increased. CYP3A4 Inhibitors (Strong) may increase the serum concentration of Irinotecan.
IsoflurophateMay increase the serum concentration of other Protease Inhibitors.
IvacaftorCYP3A4 Inhibitors (Strong) may increase the serum concentration of Ivacaftor.
IxabepiloneCYP3A4 Inhibitors (Strong) may increase the serum concentration of Ixabepilone.
LacosamideCYP3A4 Inhibitors (Strong) may increase the serum concentration of Lacosamide.
LamotrigineMay decrease the serum concentration of LamoTRIgine.
LansoprazoleProton Pump Inhibitors may decrease the serum concentration of Atazanavir.
LapatinibCYP3A4 Inhibitors (Strong) may increase the serum concentration of Lapatinib.
LercanidipineCYP3A4 Inhibitors (Strong) may increase the serum concentration of Lercanidipine.
LevobupivacaineCYP3A4 Inhibitors (Strong) may increase the serum concentration of Levobupivacaine.
LevomilnacipranCYP3A4 Inhibitors (Strong) may increase the serum concentration of Levomilnacipran.
LevonorgestrelMay increase the serum concentration of Contraceptives (Progestins).
LinagliptinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
LomitapideCYP3A4 Inhibitors (Strong) may increase the serum concentration of Lomitapide.
LovastatinProtease Inhibitors may increase the serum concentration of Lovastatin.
LULICONAZOLEMay increase the serum concentration of CYP3A4 Substrates.
LurasidoneCYP3A4 Inhibitors (Strong) may increase the serum concentration of Lurasidone.
MACITENTANCYP3A4 Inhibitors (Strong) may increase the serum concentration of Macitentan.
Magnesium oxideMay decrease the absorption of Atazanavir.
MaravirocCYP3A4 Inhibitors (Strong) may increase the serum concentration of Maraviroc.
Medroxyprogesterone AcetateMay increase the serum concentration of Contraceptives (Progestins).
MestranolMay increase the serum concentration of Contraceptives (Progestins).
MetforminHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
MethylprednisoloneCYP3A4 Inhibitors (Strong) may increase the serum concentration of MethylPREDNISolone.
MidazolamProtease Inhibitors may increase the serum concentration of Midazolam.
MifepristoneCYP3A4 Inhibitors (Strong) may increase the serum concentration of Mifepristone.
MinocyclineMinocycline may decrease the serum concentration of Atazanavir.
MitotaneMay decrease the serum concentration of CYP3A4 Substrates.
NefazodoneProtease Inhibitors may increase the serum concentration of Nefazodone.
NevirapineMay increase the serum concentration of Nevirapine. Nevirapine may decrease the serum concentration of Atazanavir.
NilotinibCYP3A4 Inhibitors (Strong) may increase the serum concentration of Nilotinib.
NisoldipineCYP3A4 Inhibitors (Strong) may increase the serum concentration of Nisoldipine.
NizatidineH2-Antagonists may decrease the serum concentration of Atazanavir.
NorelgestrominMay increase the serum concentration of Contraceptives (Progestins).
NorethindroneMay increase the serum concentration of Contraceptives (Progestins).
NorgestimateMay increase the serum concentration of Contraceptives (Progestins).
OmeprazoleProton Pump Inhibitors may decrease the serum concentration of Atazanavir.
OspemifeneCYP3A4 Inhibitors (Strong) may increase the serum concentration of Ospemifene.
OxybutyninCYP3A4 Inhibitors (Strong) may increase the serum concentration of Oxybutynin.
OxycodoneCYP3A4 Inhibitors (Strong) may enhance the adverse/toxic effect of OxyCODONE. CYP3A4 Inhibitors (Strong) may increase the serum concentration of OxyCODONE. Serum concentrations of the active metabolite oxymorphone may also be increased.
PanobinostatCYP3A4 Inhibitors (Strong) may increase the serum concentration of Panobinostat.
PantoprazoleProton Pump Inhibitors may decrease the serum concentration of Atazanavir.
ParicalcitolCYP3A4 Inhibitors (Strong) may increase the serum concentration of Paricalcitol.
PazopanibCYP3A4 Inhibitors (Strong) may increase the serum concentration of PAZOPanib.
PimecrolimusCYP3A4 Inhibitors (Strong) may decrease the metabolism of Pimecrolimus.
PimozideProtease Inhibitors may increase the serum concentration of Pimozide.
PitavastatinAtazanavir may increase the serum concentration of Pitavastatin.
PonatinibCYP3A4 Inhibitors (Strong) may increase the serum concentration of PONATinib.
PosaconazoleMay increase the serum concentration of Atazanavir.
PranlukastCYP3A4 Inhibitors (Strong) may increase the serum concentration of Pranlukast.
PrasugrelCYP3A4 Inhibitors (Strong) may decrease serum concentrations of the active metabolite(s) of Prasugrel.
PrednisoneCYP3A4 Inhibitors (Strong) may increase the serum concentration of PredniSONE.
PropafenoneCYP3A4 Inhibitors (Strong) may increase the serum concentration of Propafenone.
QuetiapineCYP3A4 Inhibitors (Strong) may increase the serum concentration of QUEtiapine.
QuinidineMay increase the serum concentration of QuiNIDine.
RabeprazoleProton Pump Inhibitors may decrease the serum concentration of Atazanavir.
RanitidineH2-Antagonists may decrease the serum concentration of Atazanavir.
RanolazineCYP3A4 Inhibitors (Strong) may increase the serum concentration of Ranolazine.
RegorafenibCYP3A4 Inhibitors (Strong) may increase the serum concentration of Regorafenib.
RepaglinideMay increase the serum concentration of Repaglinide.
RetapamulinCYP3A4 Inhibitors (Strong) may increase the serum concentration of Retapamulin.
RifabutinAtazanavir may increase serum concentrations of the active metabolite(s) of Rifabutin. Atazanavir may increase the serum concentration of Rifabutin.
RifampicinRifampin may decrease the serum concentration of Atazanavir.
RilpivirineCYP3A4 Inhibitors (Strong) may increase the serum concentration of Rilpivirine.
RiociguatProtease Inhibitors may increase the serum concentration of Riociguat.
RivaroxabanCYP3A4 Inhibitors (Strong) may increase the serum concentration of Rivaroxaban. For clarithromycin, refer to more specific clarithromycin-rivaroxaban monograph recommendations.
RomidepsinCYP3A4 Inhibitors (Strong) may increase the serum concentration of RomiDEPsin.
RosiglitazoneMay increase the serum concentration of Rosiglitazone.
RosuvastatinProtease Inhibitors may increase the serum concentration of Rosuvastatin.
RuxolitinibCYP3A4 Inhibitors (Strong) may increase the serum concentration of Ruxolitinib.
SalmeterolCYP3A4 Inhibitors (Strong) may increase the serum concentration of Salmeterol.
SaxagliptinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
SildenafilProtease Inhibitors may increase the serum concentration of Sildenafil.
SilodosinCYP3A4 Inhibitors (Strong) may increase the serum concentration of Silodosin.
SiltuximabMay decrease the serum concentration of CYP3A4 Substrates.
SimeprevirMay increase the serum concentration of other Protease Inhibitors.
SimvastatinProtease Inhibitors may increase the serum concentration of Simvastatin.
Sodium bicarbonateAntacids may decrease the absorption of Atazanavir.
SorafenibCYP3A4 Inhibitors (Strong) may increase the serum concentration of SORAfenib.
SuvorexantCYP3A4 Inhibitors (Strong) may increase the serum concentration of Suvorexant.
TadalafilCYP3A4 Inhibitors (Strong) may increase the serum concentration of Tadalafil.
TamsulosinCYP3A4 Inhibitors (Strong) may increase the serum concentration of Tamsulosin.
TelaprevirAtazanavir may decrease the serum concentration of Telaprevir. Telaprevir may increase the serum concentration of Atazanavir.
TemsirolimusProtease Inhibitors may enhance the adverse/toxic effect of Temsirolimus. Levels of sirolimus, the active metabolite, may be increased, likely due to inhibition of CYP-mediated metabolism.
TenofovirMay increase the serum concentration of Tenofovir. Tenofovir may decrease the serum concentration of Atazanavir.
TerfenadineCYP3A4 Inhibitors (Strong) may increase the serum concentration of Terfenadine.
TicagrelorCYP3A4 Inhibitors (Strong) may decrease serum concentrations of the active metabolite(s) of Ticagrelor. CYP3A4 Inhibitors (Strong) may increase the serum concentration of Ticagrelor.
TipranavirMay decrease the serum concentration of Protease Inhibitors.
TocilizumabMay decrease the serum concentration of CYP3A4 Substrates.
TofacitinibCYP3A4 Inhibitors (Strong) may increase the serum concentration of Tofacitinib.
TolbutamideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
TolterodineCYP3A4 Inhibitors (Strong) may increase the serum concentration of Tolterodine.
TolvaptanCYP3A4 Inhibitors (Strong) may increase the serum concentration of Tolvaptan.
ToremifeneCYP3A4 Inhibitors (Strong) may enhance the adverse/toxic effect of Toremifene. CYP3A4 Inhibitors (Strong) may increase the serum concentration of Toremifene.
TrabectedinCYP3A4 Inhibitors (Strong) may increase the serum concentration of Trabectedin.
TrazodoneAtazanavir may increase the serum concentration of TraZODone.
TriazolamProtease Inhibitors may increase the serum concentration of Triazolam.
UlipristalCYP3A4 Inhibitors (Strong) may increase the serum concentration of Ulipristal.
VardenafilCYP3A4 Inhibitors (Strong) may increase the serum concentration of Vardenafil.
VemurafenibCYP3A4 Inhibitors (Strong) may increase the serum concentration of Vemurafenib.
VilazodoneCYP3A4 Inhibitors (Strong) may increase the serum concentration of Vilazodone.
VildagliptinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
VorapaxarCYP3A4 Inhibitors (Strong) may increase the serum concentration of Vorapaxar.
VoriconazoleMay decrease the serum concentration of Voriconazole. Atazanavir may increase the serum concentration of Voriconazole. Voriconazole may decrease the serum concentration of Atazanavir.
WarfarinAtazanavir may increase the serum concentration of Warfarin.
ZidovudineProtease Inhibitors may decrease the serum concentration of Zidovudine.
ZopicloneCYP3A4 Inhibitors (Strong) may increase the serum concentration of Zopiclone.
ZuclopenthixolCYP3A4 Inhibitors (Strong) may increase the serum concentration of Zuclopenthixol.
Food Interactions
  • Administration with food reduces pharmacokinetic variability.
  • Food increases product absorption.

Targets

1. Protease

Kind: protein

Organism: Human immunodeficiency virus 1

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
HIV-1 Protease Q72874 Details

References:

  1. Dierynck I, De Wit M, Gustin E, Keuleers I, Vandersmissen J, Hallenberger S, Hertogs K: Binding kinetics of darunavir to HIV-1 protease explain the potent antiviral activity and high genetic barrier. J Virol. 2007 Oct 10;. Pubmed
  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 Next Generation Protease Inhibitor of Human Immunodeficiency Virus Type 1. Antimicrob Agents Chemother. 2007 Jul 16;. Pubmed
  3. Wood R: Atazanavir: its role in HIV treatment. Expert Rev Anti Infect Ther. 2008 Dec;6(6):785-96. Pubmed
  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
  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
  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
  7. Lopez-Cortes LF: [Pharmacology, pharmacokinetic features and interactions of atazanavir] Enferm Infecc Microbiol Clin. 2008 Dec;26 Suppl 17:2-8. Pubmed
  8. Busti AJ, Hall RG, Margolis DM: Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47. Pubmed
  9. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

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
  2. Busti AJ, Hall RG, Margolis DM: Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47. Pubmed
  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

2. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

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

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

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
  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
  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
  4. Wood R: Atazanavir: its role in HIV treatment. Expert Rev Anti Infect Ther. 2008 Dec;6(6):785-96. Pubmed
  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. Pubmed
  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

2. Multidrug resistance-associated protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Multidrug resistance-associated protein 1 P33527 Details

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. Pubmed
  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

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Drug created on June 13, 2005 07:24 / Updated on December 04, 2013 16:12