Atazanavir

Modify Date: 2024-01-02 18:25:09

Atazanavir Structure
Atazanavir structure
 Common Name Atazanavir
CAS Number 198904-31-3 Molecular Weight 704.856
Density 1.2±0.1 g/cm3 Boiling Point N/A
Molecular Formula C38H52N6O7 Melting Point 207-209ºC
MSDS N/A Flash Point N/A

 Use of Atazanavir


Atazanavir(BMS-232632) is an highly potent HIV-1 protease inhibitor.IC50 value:Target: HIV-1 protease inhibitorAtazanavir sulfate is a sulfate salt form of atazanavir that is an highly potent HIV-1 protease inhibitor. It has a pharmacokinetic profile that supports once-daily dosing and has demonstrated a unique resistance profile and superior virologic potency compared with other antiretrovirals in vitro. In subjects with HIV, atazanavir (400 mg once daily) produced rapid and sustained improvements in viral load and CD4 counts in both antiretroviral-naive as well as previously treated patients when used in combination with dual nucleoside reverse transcriptase inhibitor (NRTI) treatment [1].After intravenous (iv), oral (po) and intraportal (ip) administration of ATV at a dosage of 7 mg/kg, AUCs in HL rats were 12.41, 5.24 and 8.89 microg/mLh, respectively, and were significantly higher than those in control rats (4.09, 1.70 and 3.38 microg/mLh). Despite the decrease of distribution volume (Vd(ss)), the terminal half-life (t(1/2)) in HL tended to be shorter than in control, and hepatic distribution of ATV in HL rats was 4.8-fold increases. These results suggested that the uptake of ATV into liver might counteract the decrease of Vd(ss). On the other hand, there was no significant difference in bioavailability, and the lymphatic transport to AUC showed no statistical change. In conclusion, although the protein binding rate and AUC were significantly increased, the pharmacokinetics of ATV might be tolerated in HL [2].Clinical indications: HIV-1 infection Toxicity: torsades de pointes

 Names

Name atazanavir
Synonym More Synonyms

 Atazanavir Biological Activity

Description Atazanavir(BMS-232632) is an highly potent HIV-1 protease inhibitor.IC50 value:Target: HIV-1 protease inhibitorAtazanavir sulfate is a sulfate salt form of atazanavir that is an highly potent HIV-1 protease inhibitor. It has a pharmacokinetic profile that supports once-daily dosing and has demonstrated a unique resistance profile and superior virologic potency compared with other antiretrovirals in vitro. In subjects with HIV, atazanavir (400 mg once daily) produced rapid and sustained improvements in viral load and CD4 counts in both antiretroviral-naive as well as previously treated patients when used in combination with dual nucleoside reverse transcriptase inhibitor (NRTI) treatment [1].After intravenous (iv), oral (po) and intraportal (ip) administration of ATV at a dosage of 7 mg/kg, AUCs in HL rats were 12.41, 5.24 and 8.89 microg/mLh, respectively, and were significantly higher than those in control rats (4.09, 1.70 and 3.38 microg/mLh). Despite the decrease of distribution volume (Vd(ss)), the terminal half-life (t(1/2)) in HL tended to be shorter than in control, and hepatic distribution of ATV in HL rats was 4.8-fold increases. These results suggested that the uptake of ATV into liver might counteract the decrease of Vd(ss). On the other hand, there was no significant difference in bioavailability, and the lymphatic transport to AUC showed no statistical change. In conclusion, although the protein binding rate and AUC were significantly increased, the pharmacokinetics of ATV might be tolerated in HL [2].Clinical indications: HIV-1 infection Toxicity: torsades de pointes
Related Catalog
References

[1]. Gianotti N, Soria A, Lazzarin A. Antiviral activity and clinical efficacy of atazanavir in HIV-1-infected patients: a review. New Microbiol. 2007 Apr;30(2):79-88.

[2]. von Hentig N. Atazanavir/ritonavir: a review of its use in HIV therapy. Drugs Today (Barc). 2008 Feb;44(2):103-32.

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

[4]. 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.

[5]. Bentué-Ferrer D, Arvieux C, Tribut O et al. Clinical pharmacology, efficacy and safety of atazanavir: a review. Expert Opin Drug Metab Toxicol. 2009 Nov;5(11):1455-68.

[6]. Atazanavir

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Melting Point 207-209ºC
Molecular Formula C38H52N6O7
Molecular Weight 704.856
Exact Mass 704.389771
PSA 171.22000
LogP 5.20
Index of Refraction 1.562

 Safety Information

Hazard Codes Xi

 Synthetic Route

 Synonyms

methyl N-[(2S)-1-[2-[(2S,3S)-2-hydroxy-3-[[(2S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl]amino]-4-phenylbutyl]-2-[(4-pyridin-2-ylphenyl)methyl]hydrazinyl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate
Zrivada
Methyl {(5S,10S,11S,14S)-11-benzyl-5-tert-butyl-10-hydroxy-15,15-dimethyl-3,6,13-trioxo-8-[4-(pyridin-2-yl)benzyl]-2-oxa-4,7,8,12-tetraazahexadecan-14-yl}carbamate
Atazanavir
BMS-232632-05
2aqu
[3H]-Atazanavir
(3S,8S,9S,12S)-3,12-Bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-((4-(2-pyridinyl)phenyl)methyl)-2,5,6,10,13-pentaazatetradecanedioic acid Dimethyl Ester
Methyl-{(5S,10S,11S,14S)-11-benzyl-5-tert-butyl-10-hydroxy-15,15-dimethyl-3,6,13-trioxo-8-[4-(pyridin-2-yl)benzyl]-2-oxa-4,7,8,12-tetraazahexadecan-14-yl}carbamat
(3S-(3R*,8R*,9R*,12R*))-3,12-Bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-((4-(2-pyridinyl)phenyl)methyl)-2,5,6,10,13-pentaazatetradecanedioic acid Dimethyl Ester
butanoic acid, 2-[(methoxycarbonyl)amino]-3,3-dimethyl-, 2-[(2S,3S)-2-hydroxy-3-[[(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethyl-1-oxobutyl]amino]-4-phenylbutyl]-2-[[4-(2-pyridinyl)phenyl]methyl]hydrazi
Methyl {(5S,10S,11S,14S)-11-benzyl-10-hydroxy-15,15-dimethyl-5-(2-methyl-2-propanyl)-3,6,13-trioxo-8-[4-(2-pyridinyl)benzyl]-2-oxa-4,7,8,12-tetraazahexadecan-14-yl}carbamate
Reyataz
Butanoic acid, 2-[(methoxycarbonyl)amino]-3,3-dimethyl-, 2-[(2S,3S)-2-hydroxy-3-[[(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethyl-1-oxobutyl]amino]-4-phenylbutyl]-2-[[4-(2-pyridinyl)phenyl]methyl]hydrazide, (2S)-
Methyl {(5S,10S,11S,14S)-11-benzyl-5-tert-butyl-10-hydroxy-15,15-dimethyl-3,6,13-trioxo-8-[4-(pyridin-2-yl)benzyl]-2-oxa-4,7,8,12-tetraazahexadecan-14-yl}carbamate (non-preferred name)
UNII-QZU4H47A3S
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Related Compounds: More...
Atazanavir-d5
1132747-14-8
Atazanavir-d6
1092540-50-5
Atazanavir D9
1092540-51-6
Atazanavir-d18
1092540-52-7
8-epi Atazanavir
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Atazanavir sulfate
229975-97-7
Atazanavir Impurity 6
1006868-81-0
Atazanavir metabolite M7
1354820-56-6
Atazanavir metabolite M1
1354820-55-5
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