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...

General Information

Structure

Molecular Formula

C₃₈H₅₂N₆O₇

Molecular Mass

704.85548

Exact Mass

704.38974803

Charge

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

Calculated Properties

JChem

Acid pKa

11.919422

H Acceptors

H Donor

LogD (pH = 5.5)

4.5060835

LogD (pH = 7.4)

4.5393934

Log P

4.5398483

Molar Refractivity

191.8025

Polarizability

76.91037

Polar Surface Area

171.22

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

4.08

LOG S

-5.33

Solubility (Water)

3.27e-03 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Brand Name

LatazanavirZrivadaReyataz

Synonyms

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 Traditional name

IUPAC name

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

Names and Identifiers

Registration numbers

PubChem SID

16096440646508504

PubChem CID

148192

CAS Number

198904-31-3

Registration numbers

Properties

Physical Property

Solubility

Free base slightly soluble (4-5 mg/mL)

Methanol

Hydrophobicity(logP)

4.5

Apperance

Off-White Solid

Melting Point

207-209°C

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Pharmacology Properties

Target

Proteasome

Safety Information

Storage Condition

-20°C

-20°C Freezer

MSDS Link

Download link

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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.

Molecule Details

References

PubChem Literature

From Data Sources

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

• 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

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

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

• 853 (13)

• 2555 (13)

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

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

• Nolan, D., et al.: Drugs, 63(13)

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

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

Brand Name

LatazanavirZrivadaReyataz

Synonyms

IUPAC Traditional name

IUPAC name

Registration numbers

PubChem SID

16096440646508504

PubChem CID

148192

CAS Number

198904-31-3

Properties

Physical Property

Solubility

Free base slightly soluble (4-5 mg/mL)

Methanol

Hydrophobicity(logP)

4.5

Apperance

Off-White Solid

Melting Point

207-209°C

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Pharmacology Properties

Target

Proteasome

Safety Information

Storage Condition

-20°C

-20°C Freezer

MSDS Link

Download link

Molecule Details

DrugBank

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.

References

PubChem Literature

From Data Sources

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

• 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

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

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

• 853 (13)

• 2555 (13)

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

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

• Nolan, D., et al.: Drugs, 63(13)

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

Bioactivity

PubChem BioAssay

Molecule

ID:943