Atazanavir

From Wikipedia, the free encyclopedia

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
SMILES	eMolecules & PubChem
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).

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 reduces 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.

Newer research has been investigating the potential anticancer effects of atazanavir. For example, laboratory studies have found that this drug can inhibit the growth of brain tumor cells in culture. ^[2]

[edit] Adverse effects

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.^[3]

[edit] References

v • d • e Antivirals used against HIV (HAART) (primarily J05) Nucleoside & Nucleotide Reverse Transcriptase Inhibitors (NRTI) Abacavir (ABC)° • Emtricitabine° • Lamivudine (3TC)° • Tenofovir° • Didanosine • Zidovudine (AZT) • Apricitabine† • Stampidine† • Elvucitabine† • Racivir† • Amdoxovir† • Stavudine‡ • Zalcitabine‡ Non-Nucleoside Reverse Transcriptase Inhibitors (NNRTI) Efavirenz° • Nevirapine • Etravirine • Rilpivirine† • Loviride‡ • Delavirdine‡ Protease Inhibitors (PI) Atazanavir° • Fosamprenavir° • Lopinavir° • Darunavir • Nelfinavir • Ritonavir • Saquinavir • Tipranavir • Amprenavir‡ • Indinavir‡ Entry/fusion inhibitors Enfuvirtide • Maraviroc • Vicriviroc† • PRO 140† • Ibalizumab† Integrase inhibitors Raltegravir • Elvitegravir† Maturation inhibitors Bevirimat† • Vivecon™† Combined formulations Combivir • Atripla • Trizivir • Truvada • Kaletra • Epzicom Other & experimental agents Foscarnet • Hydroxyurea • Synergistic enhancers • Epigallocatechin gallate • Portmanteau inhibitors • Globoidnan A • Griffithsin • Diarylpyrimidines • Calanolide A • Cyanovirin-N • Miltefosine • R-roscovitine† °DHHS preferred first-line agent. †Undergoing clinical trials, not FDA approved. ‡Formerly or rarely used agent.