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

• ChemBase ID: 920
• Molecular Formular: C14H18N6O
• Molecular Mass: 286.33232
• Monoisotopic Mass: 286.15420923
• SMILES: c12c(n(cn2)[C@@H]2C[C@@H](C=C2)CO)nc(nc1NC1CC1)N
• Canonical SMILES: OC[C@@H]1C=C[C@@H](C1)n1cnc2c1nc(N)nc2NC1CC1
• InChI: InChI=1S/C14H18N6O/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19)/t8-,10+/m1/s1
• InChIKey: MCGSCOLBFJQGHM-SCZZXKLOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl]methanol
• IUPAC Traditional name: abacavir; @abacavir; [(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl]methanol
• Brand Name: Ziagen
• Synonyms: (1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol; (1S-cis)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol; 1592U89; Abacavir(see A105000); ABC; Abacavir; Ziagen; Abacavir

Database IDs

• CAS Number: 136470-78-5
• PubChem SID: 46505718; 160964383
• PubChem CID: 441300

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.406518
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.38658103
• LogD (pH = 7.4): 0.38677147
• Log P: 0.3867739
• Molar Refractivity: 82.6231 cm^3
• Polarizability: 29.981058 Å^3
• Polar Surface Area: 101.88 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.61
• LOG S: -2.37
• Solubility (Water): 1.21e+00 g/l

PROPERTIES

Physical Property

• Solubility: 77 mg/mL (sulfate salt); DMSO; Methanol
• Hydrophobicity(logP): 1.1

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Mechanism of Action: HIV reverse transcriptase inhibitor

Product Information

• Application(s): Antiviral agent; Shows anti-HIV activity

DETAILS

DrugBank - DB01048

• Drug Groups: approved; investigational
• Description: Abacavir (ABC) is a powerful nucleoside analog reverse transcriptase inhibitor (NRTI) used to treat HIV and AIDS. [Wikipedia]
• Indication: For the treatment of HIV-1 infection, in combination with other antiretroviral agents.
• Pharmacology: Abacavir is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Abacavir is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. The lack of a 3'-OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated.
• Toxicity: Some myocardial degeneration has been noticed in rats and mice
• Affected Organisms: Human Immunodeficiency Virus
• Biotransformation: Hepatic, by alcohol dehydrogenase and glucuronosyltransferase to a 5′-carboxylic acid metabolite and 5′-glucuronide metabolite, respectively. These metabolites have no antiviral activity. Abacavir is not significantly metabolized by cytochrome P450 enzymes.
• Absorption: Rapid and extensive after oral administration (83% bioavailability)
• Half Life: 1.54 ± 0.63 hours
• Protein Binding: Moderate (approximately 50%)
• Elimination: Elimination of abacavir was quantified in a mass balance study following administration of a 600-mg dose of 14C-abacavir: 99% of the radioactivity was recovered, 1.2% was excreted in the urine as abacavir, 30% as the 5′-carboxylic acid metabolite, 36% as the 5′-glucuronide metabolite, and 15% as unidentified minor metabolites in the urine. Fecal elimination accounted for 16% of the dose. Fecal elimination accounted for 16% of the dose. Renal excretion of unchanged abacavir is a minor route of elimination in humans.
• Distribution: * 0.86 ± 0.15 L/kg
• Clearance: * 0.80 +/- 0.24 L/hr/kg [asymptomatic, HIV-1-infected adult patients receiving single (IV dose of 150?mg]
• References: Zucman D, Truchis P, Majerholc C, Stegman S, Caillat-Zucman S: Prospective screening for human leukocyte antigen-B*5701 avoids abacavir hypersensitivity reaction in the ethnically mixed French HIV population. J Acquir Immune Defic Syndr. 2007 May 1;45(1):1-3. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - A104990

A nucleoside reverse transcriptase inhibitor (NRTI).

REFERENCES

• Zucman D, Truchis P, Majerholc C, Stegman S, Caillat-Zucman S: Prospective screening for human leukocyte antigen-B*5701 avoids abacavir hypersensitivity reaction in the ethnically mixed French HIV population. J Acquir Immune Defic Syndr. 2007 May 1;45(1):1-3. Pubmed
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