Posted inUncategorized

Azathioprine

July 24, 2017
Common Name

Azathioprine Description

Azathioprine is only found in individuals that have used or taken this drug. It is an immunosuppressive pro-drug. It is converted into 6-mercaptopurine in the body where it blocks purine metabolism and DNA synthesis.Azathioprine antagonizes purine metabolism and may inhibit synthesis of DNA, RNA, and proteins. It may also interfere with cellliar metabolism and inhibit mitosis. Its mechanism of action is likely due to incorporation of thiopurine analogues into the DNA structure, causing chain termination and cytotoxicity. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-1H-purineChEBI 6-(1'-Methyl-4'-nitro-5'-imidazolyl)-mercaptopurineChEBI ImuranChEBI AzathioprinHMDB AzatioprinHMDB AzothioprineHMDB Azathioprine sodium saltMeSH Azathioprine sodiumMeSH Azathioprine slifateMeSH ImmuranMeSH ImurelMeSH Sodium, azathioprineMeSH

Chemical Formlia

C9H7N7O2S Average Molecliar Weight

277.263 Monoisotopic Molecliar Weight

277.038193193 IUPAC Name

6-[(1-methyl-4-nitro-1H-imidazol-5-yl)slifanyl]-7H-purine Traditional Name

azathioprine CAS Registry Number

446-86-6 SMILES

CN1C=NC(=C1SC1=NC=NC2=C1NC=N2)[N+]([O-])=O

InChI Identifier

InChI=1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)

InChI Key

LMEKQMALGUDUQG-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as diarylthioethers. These are organoslifur compounds containing a thioether group that is substituted by two aryl groups. Kingdom

Organic compounds Super Class

Organoslifur compounds Class

Thioethers Sub Class

Aryl thioethers Direct Parent

Diarylthioethers Alternative Parents

  • 6-thiopurines
  • Nitroimidazoles
  • Nitroaromatic compounds
  • Pyrimidines and pyrimidine derivatives
  • Imidolactams
  • N-substituted imidazoles
  • Heteroaromatic compounds
  • Slifenyl compounds
  • Propargyl-type 1,3-dipolar organic compounds
  • Azacyclic compounds
  • Organic oxoazanium compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Organic zwitterions
  • Organonitrogen compounds
  • Organopnictogen compounds

    • Substituents

  • Diarylthioether
  • 6-thiopurine
  • Imidazopyrimidine
  • Purine
  • Nitroaromatic compound
  • Nitroimidazole
  • N-substituted imidazole
  • Imidolactam
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • C-nitro compound
  • Organic nitro compound
  • Azacycle
  • Organic oxoazanium
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Slifenyl compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic zwitterion
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • C-nitro compound (CHEBI:2948 )
  • aryl slifide (CHEBI:2948 )
  • imidazoles (CHEBI:2948 )
  • thiopurine (CHEBI:2948 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antirheumatic Agents
  • Immunosuppressive Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point243.5 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.07e+00 g/LNot Available LogP0.7Not Available

    Predicted Properties

    Property Value Source Water Solubility1.07 mg/mLALOGPS logP0.84ALOGPS logP1.17ChemAxon logS-2.4ALOGPS pKa (Strongest Acidic)8.65ChemAxon pKa (Strongest Basic)4ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area118.1 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity70.95 m3·mol-1ChemAxon Polarizability24.26 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-000x-0950000000-b6de6073310270167ffbView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-001l-2950000000-4d3fb67844876c217814View in MoNA 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

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Azathioprine Metabolism PathwaySMP00645Not Available Azathioprine PathwaySMP00427Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00993

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00993

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-4 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-2 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00993 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

    2178 KEGG Compound ID

    C06837 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Azathioprine NuGOwiki Link

    HMDB15128 Metagene Link

    HMDB15128 METLIN ID

    Not Available PubChem Compound

    2265 PDB ID

    Not Available ChEBI ID

    2948

    Product: Talabostat (mesylate)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Download (PDF) General References
    1. Woodroffe R, Yao GL, Meads C, Bayliss S, Ready A, Raftery J, Taylor RS: Clinical and cost-effectiveness of newer immunosuppressive regimens in renal transplantation: a systematic review and modelling study. Health Technol Assess. 2005 May;9(21):1-179, iii-iv. [PubMed:15899149 ]
    2. Gombar VK, Enslein K, Blake BW: Carcinogenicity of azathioprine: an S-AR investigation. Mutat Res. 1993 May;302(1):7-12. [PubMed:7683109 ]
    3. Konstantopoulou M, Belgi A, Griffiths KD, Seale JR, Macfarlane AW: Azathioprine-induced pancytopenia in a patient with pompholyx and deficiency of erythrocyte thiopurine methyltransferase. BMJ. 2005 Feb 12;330(7487):350-1. [PubMed:15705694 ]

    Enzymes

    General function:
    Involved in oxidoreductase activity
    Specific function:
    Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
    Gene Name:
    XDH
    Uniprot ID:
    P47989
    Molecular weight:
    146422.99
    References
    1. Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [PubMed:15354273 ]
    General function:
    Involved in thiopurine S-methyltransferase activity
    Specific function:
    Catalyzes the S-methylation of thiopurine drugs such as 6-mercaptopurine.
    Gene Name:
    TPMT
    Uniprot ID:
    P51580
    Molecular weight:
    28180.09
    References
    1. Sahasranaman S, Howard D, Roy S: Clinical pharmacology and pharmacogenetics of thiopurines. Eur J Clin Pharmacol. 2008 Aug;64(8):753-67. doi: 10.1007/s00228-008-0478-6. Epub 2008 May 28. [PubMed:18506437 ]
    General function:
    Involved in hypoxanthine phosphoribosyltransferase activity
    Specific function:
    Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
    Gene Name:
    HPRT1
    Uniprot ID:
    P00492
    Molecular weight:
    24579.155
    References
    1. Anstey A, Lear JT: Azathioprine: clinical pharmacology and current indications in autoimmune disorders. BioDrugs. 1998 Jan;9(1):33-47. [PubMed:18020555 ]
    2. Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [PubMed:15354273 ]

    PMID: 11906293

    Last updated on