Atazanavir

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Atazanavir
Systematic (IUPAC) name
methyl N-[(1S)-1-[[[(2S,3S)-2-hydroxy-3-[[(2S)-
2-(methoxycarbonylamino)-3,3-dimethyl-butanoyl]
amino]-4-phenyl-butyl]-[(4-pyridin-2-ylphenyl)
methyl]amino]carbamoyl]-2,2-dimethyl-propyl]
carbamate
Identifiers
CAS number 198904-31-3
ATC code J05AE08
PubChem 148192
DrugBank APRD00804
Chemical data
Formula C38H52N6O7 
Mol. mass 704.856 g/mol
Pharmacokinetic data
Bioavailability 60-68%
Protein binding 86%
Metabolism Hepatic (CYP3A4-mediated)
Half life 6.5 hours
Excretion Fecal and renal
Therapeutic considerations
Pregnancy cat.

B2(AU) B(US)
Legal status

POM(UK) ℞-only(US)
Routes Oral

Atazanavir, trade name Reyataz®, (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).

Two Reyataz 200 mg capsules
Two Reyataz 200 mg capsules

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. Atazanavir is the first PI approved for once-daily dosing, and also appears to be less likely to cause lipodystrophy and elevated cholesterol as side effects. It may also not be cross-resistant with other PIs. When boosted with ritonavir it is of equivalent potency to lopinavir for use in salvage therapy in patients with a degree of drug resistance; although boosting with ritonavir eliminates the metabolic advantages of atazanavir.

On October 20, 2006, the FDA approved a new formulation of atazanavir (300 mg capsules) to be taken as part of combination drug therapy.[1] This formulation should reduce pill burden, as one 300 mg capsule may replace two 150 mg capsules.

Bilirubin levels in the blood are normally asymptomatically raised with atazanavir. A single case of torsades de pointes attributable to atazanavir therapy has been described.[2]

  1. ^ "Bristol wins U.S. approval for single anti-HIV pill", Reuters, October 20, 2006. Retrieved on 2006-10-25. 
  2. ^ Ly T, Ruiz M (2007). "Prolonged QT interval and torsades de pointes associated with atazanavir therapy". Clin Infect Dis 44 (6): e67. 
v • d • e
Antivirals used against HIV (HAART) (primarily J05)
Nucleoside & Nucleotide
Reverse Transcriptase Inbitors (NRTI)		 Abacavir (ABC) • Didanosine • Emtricitabine° • Lamivudine (3TC)° • Stavudine • Zidovudine (AZT)° • Tenofovir° • Apricitabine† • Stampidine† • Zalcitabine‡
Non-Nucleoside
Reverse Transcriptase Inhibitiors (NNRTI)		 Efavirenz° • Nevirapine • Etravirine† • Rilpivirine† • Loviride‡ • Delavirdine‡
Protease Inhibitors (PI) Atazanavir • Darunavir • Fosamprenavir • Lopinavir° • Nelfinavir • Ritonavir • Saquinavir • Tipranavir • Amprenavir‡ • Indinavir‡
Entry/fusion inhibitors Enfuvirtide • Maraviroc • Vicriviroc†
Integrase inhibitors Raltegravir • Elvitegravir†
Maturation inhibitors Bevirimat† • Vivecon™†
Combined formulations Combivir • Atripla • Trizivir • Truvada • Kaletra • Epzicom
Other & experimental agents Foscarnet • Synergistic enhancers • Epigallocatechin gallate • Portmanteau inhibitors • Globoidnan A • Griffithsin • Diarylpyrimidines • Calanolide A
†Undergoing clinical trials, not FDA approved. ‡Formerly or rarely used agent. °Preferred 1st line agent.
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Retrieved from "http://en.wikipedia.org/wiki/Atazanavir"
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