CAS 198904-31-3|Latazanavir|Atazanavir|Atazanavir sulfate|ATV|atazanavir|methyl N-[(1S)-1-{N'-[(2S,3S)-2-hydroxy-3-[(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanamido]-4-phenylbutyl]-N'-{[4-(pyr...

基本信息

化学结构

分子式

C₃₈H₅₂N₆O₇

分子量

704.85548

精确质量

704.38974803

电荷

InChI

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

InChIKey

AXRYRYVKAWYZBR-GASGPIRDSA-N

Canonic Smiles

COC(=O)N[C@@H](C(C)(C)C)C(=O)NN(Cc1ccc(cc1)c1ccccn1)C[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)(C)C)NC(=O)OC)O

Isomeric Smiles

O[C@H]([C@@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)Cc1ccccc1)CN(NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)Cc1ccc(cc1)c1ncccc1

计算属性

JChem

Acid pKa

11.919422

质子受体

质子供体

LogD (pH = 5.5)

4.5060835

LogD (pH = 7.4)

4.5393934

Log P

4.5398483

摩尔折射率

191.8025

极化性

76.91037

极化表面积

171.22

可自由旋转的化学键

里宾斯基五规则

false

ALOGPS 2.1

Log P

4.08

LOG S

-5.33

溶解度

3.27e-03 g/l

数据来源

学术数据

产品目录

数据来源

名称和标识

商标名

LatazanavirZrivadaReyataz

别名

AtazanavirAtazanavir sulfateATVatazanavirBMS-232632ATZAtazanavir(BMS-232632)Reyataz(3S,8S, 9S, 12S)-2,5,6,13-Pentaazatetradecanedioic AcidCGP-735473,12-Bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-[[4-(2-pyridinyl)phenyl]methyl]-dimethyl Ester

IUPAC传统名

IUPAC标准名

methyl N-[(1S)-1-{N'-[(2S,3S)-2-hydroxy-3-[(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanamido]-4-phenylbutyl]-N'-{[4-(pyridin-2-yl)phenyl]methyl}hydrazinecarbonyl}-2,2-dimethylpropyl]carbamate methyl N-[(1S)-1-{[(2S,3S)-3-hydroxy-4-[(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethyl-N'-{[4-(pyridin-2-yl)phenyl]methyl}butanehydrazido]-1-phenylbutan-2-yl]carbamoyl}-2,2-dimethylpropyl]carbamate

名称和标识

数据登录号

PubChem SID

16096440646508504

PubChem CID

148192

CAS号

198904-31-3

数据登录号

化合物性质

理化性质

产品相关信息

Free Base

下载链接

药理学性质

Proteasome

安全信息

-20°C

-20°C Freezer

下载链接

化合物性质

分子相关蛋白质

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分子图谱

暂无数据

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描述信息

DrugBank

DB01072

Drug Groups

approved; investigational

Description

Atazanavir (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. [Wikipedia]

Indication

Used in combination with other antiretroviral agents for the treatment of HIV-1 infection, as well as postexposure prophylaxis of HIV infection in individuals who have had occupational or nonoccupational exposure to potentially infectious body fluids of a person known to be infected with HIV when that exposure represents a substantial risk for HIV transmission.

Pharmacology

Atazanavir (ATV) is an azapeptide HIV-1 protease inhibitor (PI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Atazanavir binds to the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs. Atazanivir is pharmacologically related but structurally different from other protease inhibitors and other currently available antiretrovirals.

Affected Organisms

Human Immunodeficiency Virus

Biotransformation

Atazanavir is extensively metabolized in humans, primarily by the liver. The major biotransformation pathways of atazanavir in humans consisted of monooxygenation and dioxygenation. Other minor biotransformation pathways for atazanavir or its metabolites consisted of glucuronidation, N-dealkylation, hydrolysis, and oxygenation with dehydrogenation. In vitro studies using human liver microsomes suggested that atazanavir is metabolized by CYP3A.

Absorption

Atazanavir is rapidly absorbed with a T_max of approximately 2.5 hours. Administration of atazanavir with food enhances bioavailability and reduces pharmacokinetic variability. Oral bioavailability is 60-68%.

Half Life

Elimination half-life in adults (healthy and HIV infected) is approximately 7 hours (following a 400 mg daily dose with a light meal). Elimination half-life in hepatically impaired is 12.1 hours (following a single 400 mg dose).

Protein Binding

86% bound to human serum proteins (alpha-1-acid glycoprotein and albumin). Protein binding is independent of concentration.

References

• 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. doi: 10.2165/00003495-200969080-00009. [Pubmed]

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

• Swainston Harrison T, Scott LJ: Atazanavir: a review of its use in the management of HIV infection. Drugs. 2005;65(16):2309-36. [Pubmed]

• Le Tiec C, Barrail A, Goujard C, Taburet AM: Clinical pharmacokinetics and summary of efficacy and tolerability of atazanavir. Clin Pharmacokinet. 2005;44(10):1035-50. [Pubmed]

• Lopez-Cortes LF: [Pharmacology, pharmacokinetic features and interactions of atazanavir] Enferm Infecc Microbiol Clin. 2008 Dec;26 Suppl 17:2-8. [Pubmed]

• Busti AJ, Hall RG, Margolis DM: Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S1457

Research Area: Infection
Biological Activity:
Atazanavir sulfate(BMS-232632-05) is a sulfate salt form of atazanavir (BMS-232632) that is an highly potent HIV protease inhibitor with an EC50 and EC90 of 2.6~5.3 nM and 9~15 nM in cell culture. Atazanavir (BMS-232632) is generally more potent than the five currently approved HIV-1 Prt inhibitors. Atazanavir (BMS-232632) inhibited the proteolytic cleavage of the viral gag precursor p55 polyprotein in a dose-dependent manner, with a EC50 of approximately 47 nM. Furthermore, Atazanavir (BMS-232632) is highly selective for HIV-1 Prt and exhibits cytotoxicity only at concentrations 6,500- to 23,000-fold higher than that required for anti-HIV activity. Atazanavir (BMS-232632) may be an effective HIV-1 inhibitor that may be utilized in a variety of different drug combinations. [1][2]References on Atazanavir sulfate[] ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, Aug. 2000, 44:2093–2099[] Organic Process Research & Development, 2002, 6:323−328

TRC

A790051

Atazanavir is a novel azapeptide HIV protease inhibitor (PI). Antiviral.

描述信息

参考文献

PubChem文献

数据源提供

• Le Tiec C, Barrail A, Goujard C, Taburet AM: Clinical pharmacokinetics and summary of efficacy and tolerability of atazanavir. Clin Pharmacokinet. 2005;44(10):1035-50. Pubmed

• 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. doi: 10.2165/00003495-200969080-00009. Pubmed

• Busti AJ, Hall RG, Margolis DM: Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47. Pubmed

• Swainston Harrison T, Scott LJ: Atazanavir: a review of its use in the management of HIV infection. Drugs. 2005;65(16):2309-36. Pubmed

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

• Lopez-Cortes LF: [Pharmacology, pharmacokinetic features and interactions of atazanavir] Enferm Infecc Microbiol Clin. 2008 Dec;26 Suppl 17:2-8. Pubmed

• http://en.wikipedia.org/wiki/Atazanavir

• Palella, F.J. Jr., et al.: N. Engl. J. Med., 338(13)

• Nolan, D., et al.: Drugs, 63(13)

• 853 (13)

• 2555 (13)

• Musial, B.L., et al.: Am. J. Health Syst. Pharm., 61, 1365 (13)

• Wood, R., et al.: J. Acquir. Immune Defic. Syndr., 36, 684 (13)

参考文献

生物活性

PubChem BioAssay

生物活性

数据来源

学术数据

产品目录

名称和标识

商标名

LatazanavirZrivadaReyataz

别名

IUPAC传统名

IUPAC标准名

数据登录号

PubChem SID

PubChem CID

CAS号

描述信息

DB01072

Drug Groups

approved; investigational

Description

Indication

Pharmacology

Affected Organisms

Human Immunodeficiency Virus

Biotransformation

Absorption

Half Life

Protein Binding

86% bound to human serum proteins (alpha-1-acid glycoprotein and albumin). Protein binding is independent of concentration.

References

• 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. doi: 10.2165/00003495-200969080-00009. [Pubmed]

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

• Swainston Harrison T, Scott LJ: Atazanavir: a review of its use in the management of HIV infection. Drugs. 2005;65(16):2309-36. [Pubmed]

• Le Tiec C, Barrail A, Goujard C, Taburet AM: Clinical pharmacokinetics and summary of efficacy and tolerability of atazanavir. Clin Pharmacokinet. 2005;44(10):1035-50. [Pubmed]

• Lopez-Cortes LF: [Pharmacology, pharmacokinetic features and interactions of atazanavir] Enferm Infecc Microbiol Clin. 2008 Dec;26 Suppl 17:2-8. [Pubmed]

• Busti AJ, Hall RG, Margolis DM: Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S1457

TRC

A790051

Atazanavir is a novel azapeptide HIV protease inhibitor (PI). Antiviral.

参考文献

PubChem文献

数据源提供

• Le Tiec C, Barrail A, Goujard C, Taburet AM: Clinical pharmacokinetics and summary of efficacy and tolerability of atazanavir. Clin Pharmacokinet. 2005;44(10):1035-50. Pubmed

• 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. doi: 10.2165/00003495-200969080-00009. Pubmed

• Busti AJ, Hall RG, Margolis DM: Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47. Pubmed

• Swainston Harrison T, Scott LJ: Atazanavir: a review of its use in the management of HIV infection. Drugs. 2005;65(16):2309-36. Pubmed

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

• Lopez-Cortes LF: [Pharmacology, pharmacokinetic features and interactions of atazanavir] Enferm Infecc Microbiol Clin. 2008 Dec;26 Suppl 17:2-8. Pubmed

• http://en.wikipedia.org/wiki/Atazanavir

• Palella, F.J. Jr., et al.: N. Engl. J. Med., 338(13)

• Nolan, D., et al.: Drugs, 63(13)

• 853 (13)

• 2555 (13)

• Musial, B.L., et al.: Am. J. Health Syst. Pharm., 61, 1365 (13)

• Wood, R., et al.: J. Acquir. Immune Defic. Syndr., 36, 684 (13)

生物活性

PubChem BioAssay

化合物性质

理化性质

产品相关信息

Free Base

下载链接

药理学性质

Proteasome

安全信息

-20°C

-20°C Freezer

下载链接

化合物信息

ID:943