Atazanavir

drugbox
IUPAC_name = methyl "N"- [(1"S")-1- [(2"S",3"S")-2-hydroxy-3- [(2"S")-
2-(methoxycarbonylamino)-3,3-dimethyl-butanoyl]
amino] -4-phenyl-butyl] - [(4-pyridin-2-ylphenyl)
methyl] amino] carbamoyl] -2,2-dimethyl-propyl]
carbamate


CAS_number = 198904-31-3
ATC_prefix = J05
ATC_suffix = AE08
ATC_supplemental =
PubChem = 148192
DrugBank = APRD00804
C = 38 | H = 52 | N = 6 | O = 7
molecular_weight = 704.856 g/mol
smiles = COC(=O)N [C@H] (C(=O)N [C@@H] (Cc1ccccc1) [C@@H] (O)CN(Cc1ccc(cc1)c1ccccn1)NC(=O) [C@@H] (NC(=O)OC)C(C)(C)C)C(C)(C)C
bioavailability = 60-68%
protein_bound = 86%
metabolism = Hepatic (CYP3A4-mediated)
elimination_half-life = 6.5 hours
excretion = Fecal and renal
pregnancy_AU = B2
pregnancy_US = B
legal_UK = POM
legal_US = Rx-only
routes_of_administration = 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).

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. [cite news | title = Bristol wins U.S. approval for single anti-HIV pill | publisher = Reuters | date = 2006-10-20 | accessdate = 2006-10-25 | url = http://today.reuters.co.uk/news/articlenews.aspx?type=healthNews&storyID=2006-10-20T184537Z_01_WEN7494_RTRIDST_0_HEALTH-BRISTOLMYERS-DC.XML&WTmodLoc=SciHealth-C4-Health-5 ] 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. [ cite journal |title=HIV-1 protease inhibitors nelfinavir and atazanavir induce malignant glioma death by triggering endoplasmic reticulum stress|journal= Cancer Research |volume=67|pages=10920–8|year=2007 |doi=10.1158/0008-5472.CAN-07-0796 |author=Pyrko, P. |pmid=18006837]

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. [cite journal | title=Prolonged QT interval and torsades de pointes associated with atazanavirtherapy | author=Ly T, Ruiz M | journal=Clin Infect Dis | year=2007 | volume=44 | issue=6 | pages=e67–8 |month=Mar |pmid=17304444 | doi=10.1086/511875]

References