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Abacavir

July 24, 2017
Common Name

Abacavir Description

Abacavir is only found in individuals that have used or taken this drug. It is a powerfli nucleoside analog reverse transcriptase inhibitor (NRTI) used to treat HIV and AIDS. [Wikipedia]Abacavir is a carbocyclic synthetic nucleoside analogue. Intracellliarly, abacavir is converted by cellliar enzymes to the active metabolite carbovir triphosphate, an analogue of deoxyguanosine-5-triphosphate (dGTP). Carbovir triphosphate inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source ABCChEBI {(1S-cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanolChEBI (1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-Purin-9-yl)-2-cyclopentene-1-methanolMeSH Abacavir succinateMeSH ZiagenMeSH Abacavir slifateMeSH

Chemical Formlia

C14H18N6O Average Molecliar Weight

286.3323 Monoisotopic Molecliar Weight

286.154209228 IUPAC Name

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

abacavir CAS Registry Number

136470-78-5 SMILES

NC1=NC2=C(N=CN2[C@@H]2C[C@H](CO)C=C2)C(NC2CC2)=N1

InChI Identifier

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

InChI Key

MCGSCOLBFJQGHM-SCZZXKLOSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as 1,3-substituted cyclopentyl purine nucleosides. These are nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base. Kingdom

Organic compounds Super Class

Nucleosides, nucleotides, and analogues Class

Nucleoside and nucleotide analogues Sub Class

Cyclopentyl nucleosides Direct Parent

1,3-substituted cyclopentyl purine nucleosides Alternative Parents

  • 6-alkylaminopurines
  • Secondary alkylarylamines
  • Aminopyrimidines and derivatives
  • N-substituted imidazoles
  • Imidolactams
  • Heteroaromatic compounds
  • Azacyclic compounds
  • Primary amines
  • Primary alcohols
  • Organopnictogen compounds
  • Hydrocarbon derivatives

    • Substituents

  • 1,3-substituted cyclopentyl purine nucleoside
  • 6-alkylaminopurine
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary alcohol
  • Primary amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • 2,6-diaminopurine (CHEBI:421707 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-HIV Agents
  • Nucleoside and Nucleotide Reverse Transcriptase Inhibitors
  • Reverse Transcriptase Inhibitors

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point165 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.21e+00 g/LNot Available LogP1.1Not Available

    Predicted Properties

    Property Value Source Water Solubility1.21 mg/mLALOGPS logP0.61ALOGPS logP0.39ChemAxon logS-2.4ALOGPS pKa (Strongest Acidic)15.41ChemAxon pKa (Strongest Basic)5.77ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area101.88 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity82.62 m3·mol-1ChemAxon Polarizability30.43 Å3ChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Abacavir Action PathwaySMP00737Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01048

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01048

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01048 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    390063 KEGG Compound ID

    C07624 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Abacavir NuGOwiki Link

    HMDB15182 Metagene Link

    HMDB15182 METLIN ID

    Not Available PubChem Compound

    441300 PDB ID

    1KX ChEBI ID

    421707

    Product: AT13149

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Zucman D, Truchis Pd, 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:17356469 ]
    2. (). FDA label . .
    3. PharmGKB [Link]

    Enzymes

    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
    Gene Name:
    UGT1A1
    Uniprot ID:
    P22309
    Molecular weight:
    59590.91
    References
    1. Yuen GJ, Weller S, Pakes GE: A review of the pharmacokinetics of abacavir. Clin Pharmacokinet. 2008;47(6):351-71. [PubMed:18479171 ]
    General function:
    Involved in zinc ion binding
    Specific function:
    Not Available
    Gene Name:
    ADH6
    Uniprot ID:
    P28332
    Molecular weight:
    39072.275
    References
    1. Yuen GJ, Weller S, Pakes GE: A review of the pharmacokinetics of abacavir. Clin Pharmacokinet. 2008;47(6):351-71. [PubMed:18479171 ]

    PMID: 24473749

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