Atazanavir sulfate

Base Information

• Chemical Name: Atazanavir sulfate
• CAS No.: 229975-97-7
• Molecular Formula: C38H52N6O7^.H2SO4
• Molecular Weight: 802.93
• Hs Code.: 29333990
• European Community (EC) Number: 620-495-2
• UNII: 4MT4VIE29P
• DSSTox Substance ID: DTXSID401017206
• Wikidata: Q27114238
• NCI Thesaurus Code: C28835
• RXCUI: 358299
• ChEMBL ID: CHEMBL1200678
• Mol file: 229975-97-7.mol

Synonyms:232632, BMS;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;atazanavir;atazanavir sulfate;BMS 232632;BMS 232632 05;BMS-232632;BMS-232632-05;BMS232632;BMS23263205;CGP 73547;CGP 75136;CGP 75176;CGP 75355;CGP-73547;CGP-75136;CGP-75176;CGP-75355;CGP73547;CGP75136;CGP75176;CGP75355;Reyataz

Chemical Property of Atazanavir sulfate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 195.0°, or acetone; mp 198-199° (dec)
• Boiling Point: 995.5 °C at 760 mmHg
• Flash Point: 555.8 °C
• PSA: 254.20000
• Density: 1.164g/cm³
• LogP: 6.20320
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: ≥28.7 mg/mL in DMSO with gentle warming; insoluble in H2O; ≥4.05 mg/mL in EtOH with gentle warming and ultrasonic
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 18
• Exact Mass: 802.35712773
• Heavy Atom Count: 56
• Complexity: 1190

Purity/Quality:

98%min ^*data from raw suppliers

AtazanavirBisulfateSalt ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(C(=O)NC(CC1=CC=CC=C1)C(CN(CC2=CC=C(C=C2)C3=CC=CC=N3)NC(=O)C(C(C)(C)C)NC(=O)OC)O)NC(=O)OC.OS(=O)(=O)O
• Isomeric SMILES: CC(C)(C)[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@H](CN(CC2=CC=C(C=C2)C3=CC=CC=N3)NC(=O)[C@H](C(C)(C)C)NC(=O)OC)O)NC(=O)OC.OS(=O)(=O)O
• Recent ClinicalTrials: Phase IIIB Study Evaluating the Effects of Atazanavir Powder With Ritonavir in HIV-infected Pediatric Patients
• Recent EU Clinical Trials: A Phase 3 Randomized, Active-Controlled, Open-Label Clinical Study to Evaluate a Switch to Doravirine/Islatravir (DOR/ISL) Once-Daily in Participants With HIV-1 Virologically Suppressed on Antiretroviral Therapy
• Description: Atazanavir (BMS-232632, III), an azapeptide HIV protease inhibitor, has been developed and launched by Bristol-Myers Squibb (BMS), under worldwide license from Novartis, for the treatment of HIV infection. Atazanavir was launched in the US as Reyataz? in July 2003.
• Uses: Atazanavir is a HIV protease inhibitor with Ki of 2.66 nM Atazanavir Sulfate is an intermediate of Atazanavir(A790051) which is a novel azapeptide HIV protease Inhbitor. Antiviral.

Technology Process of Atazanavir sulfate

There total 21 articles about Atazanavir sulfate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.2%

atazanavir (198904-31-3,1292296-09-3) → atazanavir sulphate (229975-97-7)

Guidance literature:

With sulfuric acid; In acetone; at 0 - 50 ℃; for 2h;

Reference yield: 75.5%

atazanavir (198904-31-3,1292296-09-3) → (3S,8S,9S,12S)-3,12-bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-[[4-(2-pyrimidinyl)phenyl]methyl]-2,5,6,10,13-pentaazatetradecanedioate dimethyl sulfate (229975-97-7)

Guidance literature:

atazanavir; In ethanol; at 25 - 30 ℃; for 0.5h;

With sulfuric acid; In ethanol; n-heptane; acetone; at 15 - 40 ℃; Temperature;

Reference yield:

(S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid (162537-11-3) + 1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride (198904-87-9) → atazanavir sulphate (229975-97-7)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 22 - 25 °C / Large scale

2: sulfuric acid / ethanol / 22 °C / Large scale

With sulfuric acid; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane;

DOI:10.1021/op025504r

upstream raw materials:

atazanavir

L-tert-Leucine

methyl [(2S)-3,3-dimethyl-1-({(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}amino)-1-oxobutan-2-yl]carbamate

1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-N-tert-butoxycarbonylamino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane

Refernces

• 1、 -. "TABLETED COMPOSITIONS CONTAINING ATAZANAVIR". Paragraph 0098; 0099; 0100; 0101; 0102; 0103. . Retrieved 2018/06/01.
• 2、 -. "A atazanavir bisulfate method for preparing A-type crystallization (by machine translation)". Paragraph 0026. . Retrieved 2016/12/12.