An inhibitor of HIV-1 protease
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Labeled Version(s)
26456Atazanavir-d6
Metabolite(s)
27372Des(benzylpyridyl) Atazanavir
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Atazanavir

Item No. 11733

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3S,12S-bis(1,1-dimethylethyl)-8S-hydroxy-4,11-dioxo-9S-(phenylmethyl)-6-[[4-(2-pyridinyl)phenyl]methyl]-2,5,6,10,13-pentaazatetradecanedioic acid, 1,14-dimethyl ester
CAS Number
198904-31-3
Synonyms
  • BMS 232632
  • CGP 73547
Molecular Formula
C38H52N6O7
Formula Weight
704.9
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMF:PBS (pH 7.2) (1:8): 0.1 mg/mlDMSO: 16 mg/mlEthanol: 2 mg/ml
λmax
252, 280 nm
SMILES
COC(N[C@@H](C(C)(C)C)C(N[C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC2=CC=C(C3=NC=CC=C3)C=C2)NC([C@@H](NC(OC)=O)C(C)(C)C)=O)=O)=O
InChi Code
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
InChi Key
AXRYRYVKAWYZBR-GASGPIRDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Atazanavir is an azapeptide inhibitor of HIV-1 protease (Ki = 2.66 nM).1 It has antiviral activity against a variety of HIV-1 strains in several cell types with EC50 values ranging from 2.62 to 5.28 nM. Atazanavir exhibits a minor synergistic effect when used in combination with the reverse transcriptase inhibitor zidovudine (Item No. 15492) in HIV-1-infected human peripheral blood mononuclear cells (PBMCs) and an additive effect when used in combination with several additional reverse transcriptase or HIV-1 protease inhibitors. Atazanavir also inhibits UDP-glucuronyltransferase 1A1 (UGT1A1), which is involved in bilirubin clearance.2 Formulations containing atazanavir have been used in combination therapy for the treatment of HIV-1 infection.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Robinson, B.S., Riccardi, K.A., Gong, Y.F., et al. BMS-232632, a highly potent human immunodeficiency virus protease inhibitor that can be used in combination with other available antiretroviral agents. Antimicrob. Agents Chemother. 44(8), 2093-2099 (2000).

    2. Michaud, V., Bar-Magen, T., Turgeon, J., et al. The dual role of pharmacogenetics in HIV treatment: Mutations and polymorphisms regulating antiretroviral drug resistance and disposition. Pharmacol. Rev. 64(3), 803-833 (2012).