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Thiotepa

July 24, 2017
Common Name

Thiotepa Description

N,NN-triethylenethiophosphoramide (ThioTEPA) is a cancer chemotherapeutic member of the alkylating agent group, now in use for over 50 years. It is a stable derivative of N,N,N- triethylenephosphoramide (TEPA). It is mostly used to treat breast cancer, ovarian cancer and bladder cancer. It is also used as conditioning for Bone marrow transplantation. Its main toxicity is myelosuppression. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source ThioplexKegg TepadinaKegg GirostanMeSH TespaMeSH TespaminMeSH thio-TepaMeSH thio TepaMeSH TriethylenethiophosphoramideMeSH Tris(1-aziridinyl)phosphine slifideMeSH ThiophosphamideMeSH

Chemical Formlia

C6H12N3PS Average Molecliar Weight

189.218 Monoisotopic Molecliar Weight

189.048954601 IUPAC Name

tris(aziridin-1-yl)-λ⁵-phosphanethione Traditional Name

thiophosphamide CAS Registry Number

52-24-4 SMILES

S=P(N1CC1)(N1CC1)N1CC1

InChI Identifier

InChI=1S/C6H12N3PS/c11-10(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2

InChI Key

FOCVUCIESVLUNU-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as organic thiophosphoric acids and derivatives. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure RP(R)(R)=S, where R,R,R = O,N, halogen residue. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Organic thiophosphoric acids and derivatives Direct Parent

Organic thiophosphoric acids and derivatives Alternative Parents

  • Aziridines
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organonitrogen compounds
  • Hydrocarbon derivatives

    • Substituents

  • Organic thiophosphoric acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Aziridine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound

    • Molecliar Framework

    Aliphatic heteromonocyclic compounds External Descriptors

  • aziridines (CHEBI:9570 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Alkylating Agents
  • Antineoplastic Agents, Alkylating

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility9.27 mg/mLALOGPS logP0.17ALOGPS logP-1ChemAxon logS-1.3ALOGPS pKa (Strongest Basic)-0.3ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area9.03 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity50.72 m3·mol-1ChemAxon Polarizability18.23 Å3ChemAxon Number of Rings3ChemAxon 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 MS

    Mass Spectrum (Electron Ionization)splash10-00kn-6900000000-6d6b7c109663ea65ad79View in MoNA

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04572

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04572

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-5 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-3 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

    DB04572 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

    5254 KEGG Compound ID

    C07641 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Thiotepa NuGOwiki Link

    HMDB15576 Metagene Link

    HMDB15576 METLIN ID

    Not Available PubChem Compound

    5453 PDB ID

    Not Available ChEBI ID

    128310

    Product: Betahistine (dihydrochloride)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Maanen MJ, Smeets CJ, Beijnen JH: Chemistry, pharmacology and pharmacokinetics of N,N,N” -triethylenethiophosphoramide (ThioTEPA). Cancer Treat Rev. 2000 Aug;26(4):257-68. [PubMed:10913381 ]

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585
    References
    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
    Gene Name:
    CYP2B6
    Uniprot ID:
    P20813
    Molecular weight:
    56277.81
    References
    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

    PMID: 22122192

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