Abacavir

Base Information

• Chemical Name: Abacavir
• CAS No.: 136470-78-5
• Molecular Formula: C14H18N6O
• Molecular Weight: 286.337
• European Community (EC) Number: 620-487-9
• UNII: WR2TIP26VS
• DSSTox Substance ID: DTXSID4046444
• Nikkaji Number: J825.172J
• Wikipedia: Abacavir
• Wikidata: Q304330
• NCI Thesaurus Code: C61523
• RXCUI: 190521
• Metabolomics Workbench ID: 43289
• ChEMBL ID: CHEMBL1380
• Mol file: 136470-78-5.mol

Synonyms:((1R,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-cyclopent-2-enyl)methanol;((1R,4S)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-enyl)methanol;(+)-abacavir;(+)-abacavir sulfate;(+-)-abacavir sulfate;(-)-cis-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-2-cyclopentene-1-methanol;(1R,4R)-abacavir;(1R,4S)-abacavir sulfate;(1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-2-cyclopentene-1-methanol;(1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-2-cyclopentene-1-methanol succinate (1:1) (salt);1592U89;2-cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-, (1R,4S)-, sulfate (2:1);2-cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-, (1S,4R)-, rel-, sulfate (2:1);2-cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-, hydrochloride, hydrate (1:1:1), (1S,4R)-;abacavir;abacavir enantiomer;abacavir hydrochloride monohydrate;abacavir succinate;abacavir sulfate;abacavir sulfate racemic;abacavir sulfate, (+)-;abacavir sulfate, (+-)-;abacavir sulfate, (1R,4S)-;abacavir sulphate;abacavir, (+)-;abacavir, (1R,4S)-;abacavir, trans-;abacavir, trans-, (+-)-;Abamune;avacavir;DRG 0257;DRG-0257;DRG0257;trans-abacavir;trans-abacavir R,R-;Ziagen

Chemical Property of Abacavir

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 4.77E-17mmHg at 25°C
• Melting Point: 165°
• Refractive Index: 1.864
• Boiling Point: 636 °C at 760 mmHg
• PKA: 5.01(at 25℃)
• Flash Point: 338.4 °C
• PSA: 101.88000
• Density: 1.7 g/cm³
• LogP: 1.74650
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 286.15420922
• Heavy Atom Count: 21
• Complexity: 414

Purity/Quality:

99% ^*data from raw suppliers

Abacavir ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiviral Agents
• Canonical SMILES: C1CC1NC2=C3C(=NC(=N2)N)N(C=N3)C4CC(C=C4)CO
• Isomeric SMILES: C1CC1NC2=C3C(=NC(=N2)N)N(C=N3)[C@@H]4C[C@@H](C=C4)CO
• Recent ClinicalTrials: A Study to Evaluate the Pharmacokinetics, Safety, Tolerability, and Antiviral Activity of Rilpivirine (TMC278) in Human Immunodeficiency Virus Infected Adolescents and Children Aged Greater Than or Equal to 6 Years
• 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
• Recent NIPH Clinical Trials: Multi-center clinical trial testing efficacy and safety of 1592U89 in patients with relapsed/refractory adult T-cell Leukemia
• Description: The drug is extensively metabolized via stepwise phosphorylation to 5′-mono-, di-, and triphosphate. Abacavir is well absorbed (>75%) and penetrates the CNS. The drug can be taken without regard to meals. The drug does not show any clinically significant drug–drug interactions. Abacavir has been reported to produce life-threatening hypersensitivity reactions. The major use of abacavir appears to be in combination with other nucleoside RT inhibitors. A fixed-combination product has recently been approved by the U.S. FDA consisting of 300 mg of ABC, 150 mg of 3TC, and 300 mg of ZDV (Trizivar). The combination has been shown to be superior to other combinations in reducing viral load as well as to show improvement in CD4 cell count.
• Uses: Abacavir is a commonly used nucleoside analogue with potent antiviral activity against HIV-1. - See more at: http://www.selleckchem.com/products/abacavir-sulfate.html#sthash.lApvcTNO.dpuf A nucleoside reverse transcriptase inhibitor (NRTI).
• Indications: Abacavir (Ziagen) is a guanosine nucleoside analogue indicated for the therapy of HIV-1 infection in adults and children. It is used as part of a multidrug regimen and is available in a fixed-dose combination with zidovudine and lamivudine (Trizivir). It is also used for postexposure HIV infection prophylaxis.
• Therapeutic Function: Antiviral
• Clinical Use: Treatment of HIV infection in adults and children (in combination with other antiretroviral drugs)
• Drug interactions: Potentially hazardous interactions with other drugs Antivirals: possibly reduces effects of ribavirin; concentration reduced by tipranavir. Orlistat: absorption possibly reduced by orlistat.

Technology Process of Abacavir

There total 59 articles about Abacavir 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: 98.0%

(1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol (136522-33-3,172721-00-5) + Cyclopropylamine (765-30-0) → abacavir (136470-78-5,128131-83-9,136470-79-6)

Guidance literature:

In ethanol; at 70 ℃;

DOI:10.1002/cmdc.201800361

Reference yield: 90.0%

Cyclopropylamine (765-30-0) + ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → abacavir (136470-78-5,128131-83-9,136470-79-6)

Guidance literature:

In methanol; at 70 ℃; for 12h;

DOI:10.1080/15257770008033011

Reference yield: 90.0%

(-)-N-{6-(cyclopropylamino)-9-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-enyl]-9H-purin-2-yl}isobutyramide (136470-88-7) → abacavir (136470-78-5,128131-83-9,136470-79-6)

Guidance literature:

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

With hydrogenchloride; In water; isopropyl alcohol; at 20 - 25 ℃; pH=7.0 - 7.5; Product distribution / selectivity;

upstream raw materials:

((1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl acetate

(1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol

Cyclopropylamine

(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene

Downstream raw materials:

methyl ((((1S,4R)-4-(2-amino-6-(cyclopropyl-amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

{(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol sulphate

(5S)-1-{[(4S)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-cyclopent-1-en-1-yl]methyl}-3-phenyl-5-(propan-2-yl)-2-thioxoimidazolidin-4-one

Refernces

• 1、 -. "Abacavir intermediate and method for purifying same". Paragraph 0079-0080. . Retrieved 2018/03/26.
• 2、 Thieme, Niels,Breit, Bernhard. "Enantioselective and Regiodivergent Addition of Purines to Terminal Allenes: Synthesis of Abacavir". supporting information. p. 1520 - 1524. Retrieved 2017/02/05.