Abacavir Hemisulfate;ABC sulfate

Base Information

• Chemical Name: Abacavir Hemisulfate;ABC sulfate
• CAS No.: 188062-50-2
• Molecular Formula: C28H38N12O6S
• Molecular Weight: 670.74
• Hs Code.: 2933595960
• European Community (EC) Number: 620-488-4
• Mol file: 188062-50-2.mol

Synonyms:188062-50-2;1955524-04-5;Abacavir Hemisulfate;ABC sulfate;AB17664;PD086804;FT-0621705;FT-0660941;EN300-297824;(1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol sulfate;Sulfuric acid, bis({4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol);sulfuric acid;bis({4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol);Sulfuricacid,bis({4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol)

Chemical Property of Abacavir Hemisulfate;ABC sulfate

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: 222-225 °C
• Boiling Point: 636 °C at 760 mmHg
• Flash Point: 338.4 °C
• PSA: 153.63000
• LogP: 2.65440
• Storage Temp.: -20°C Freezer
• Solubility.: H2O: ≥17mg/mL
• Water Solubility.: 1.68ug/L(32 oC)
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 8
• Exact Mass: 670.27579815
• Heavy Atom Count: 47
• Complexity: 496

Purity/Quality:

99%min ^*data from raw suppliers

Abacavir, Sulfate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 63-40
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1NC2=C3C(=NC(=N2)N)N(C=N3)C4CC(C=C4)CO.C1CC1NC2=C3C(=NC(=N2)N)N(C=N3)C4CC(C=C4)CO.OS(=O)(=O)O
• Recent EU Clinical Trials: A randomised non-inferiority trial with nested PK to assess DTG/3TC fixed dose formulations for the maintenance of virological suppression in children
• Description: Abacavir sulfate was first launched as Ziagen in the US for the treatment of human immunodeficiency virus (HIV) infection, in combination with other antiretroviral drugs. Abacavir is a carbocyclic nucleoside reverse transcriptase inhibitor (nRTI); it is one of the most potent anti-HIV agents to date. In vitro, Abacavir is a potent and selective inhibitor of HIV-1 and HIV-2 replication. Resistance to Abacavir develops more slowly than for other anti-HIV agents. Abacavir is highly synergistic with protease inhibitors such as Amprenavir. In clinical trials for HIV infections in adults, it produced durable suppression in viral load. Combinations with different protease inhibitors such as Nelfinavir, Saquinavir or Indinavir markedly reduced plasma viral load to undetectable levels for at least 48 weeks, and significantly raised CD4+ cell counts in adults with HIV infection, especially nRTI-naive patients. Abacavir has a good oral availability and its penetration into CSF is much more significant than for other anti-HIV drugs. The two major metabolites identified in humans were the 5'-carboxylate and the 5'-glucuronide, mainly excreted via the renal route.
• Uses: Abacavir sulfate is a nucleoside reverse transcriptase inhibitor (NRTI) used for the treatment of HIV-1 infection and anti-AIDS drug. It has been used in the cytotoxicity to test its tumour promoting activity U937 cells.
• Therapeutic Function: Antiviral

Technology Process of Abacavir Hemisulfate;ABC sulfate

There total 3 articles about Abacavir Hemisulfate;ABC 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: 97.0%

(-)-N-{6-(cyclopropylamino)-9-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-enyl]-9H-purin-2-yl}isobutyramide (136470-88-7) → {(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol sulphate (188062-50-2,216699-07-9)

Guidance literature:

(-)-N-{6-(cyclopropylamino)-9-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-enyl]-9H-purin-2-yl}isobutyramide; With sodium hydroxide; water; isopropyl alcohol; for 1h; Heating / reflux;

With sulfuric acid; In tert-butyl methyl ether; Product distribution / selectivity;

Reference yield: 95.0%

abacavir (136470-78-5,128131-83-9,136470-79-6) → {(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol sulphate (188062-50-2,216699-07-9)

Guidance literature:

With sulfuric acid; In water; isopropyl alcohol; at 50 - 55 ℃; for 2h; Concentration; Temperature; Solvent;

Reference yield:

abacavir (136470-78-5,128131-83-9,136470-79-6) → abacavir sulfate (188062-50-2,216699-07-9)

Guidance literature:

With sulfuric acid; In ethyl acetate; at 20 ℃; for 3h; Purification / work up;

upstream raw materials:

abacavir

(-)-N-{6-(cyclopropylamino)-9-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-enyl]-9H-purin-2-yl}isobutyramide

Refernces

• 1、 -. "Process for the Preparation of Abacavir". Page/Page column 2-3. . Retrieved 2010/02/16.
• 2、 -. "Process for the preparation of abacavir". Page/Page column 7. . Retrieved 2008/12/06.