Thiotepa, チオテパ ,тиотепа , ثيوتيبا , 塞替派 ,

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ChemSpider 2D Image | thiotepa | C6H12N3PS

Thiotepa, チオテパ

  • Use:antineoplastic, alkylating agent
  • Chemical name:1,1′,1”-phosphinothioylidynetrisaziridine
  • Formula:C6H12N3PS
    • MW:189.22 g/mol
    • CAS:52-24-4
    • EINECS:200-135-7
    • LD50:14500 μg/kg (M, i.v.); 38 mg/kg (M, p.o.);
      9400 μg/kg (R, i.v.)
    • Aziridine, 1,1′,1”-phosphinothioylidynetris-
      Aziridine, 1-[bis(1-aziridinyl)phosphinothioyl]-
      Phosphorothioic tri(ethyleneamide)

    JAPAN APPROVED, Rethio, PMDA, 2019/3/26

    тиотепа [Russian] [INN]
    ثيوتيبا [Arabic] [INN]
    塞替派 [Chinese] [INN]

    Thiotepa (INN,[1] chemical name: N,N′,N′′-triethylenethiophosphoramide) is an alkylating agent used to treat cancer.

    Thiotepa is an organophosphorus compound with the formula SP(NC2H4)3.[2] It is an analog of N,N′,N′′-triethylenephosphoramide (TEPA), which contains tetrahedral phosphorus and is structurally akin to phosphate. It is manufactured by heating aziridine with thiophosphoryl chloride.


    Thiotepa was developed by the American Cyanamid company in the early 1950s and reported to media outlets in 1953.[3] In 1959, thiotepa was registered with the Food and Drug Administration (FDA) as a drug therapy for several solid cancers.[4]

    On January 29, 2007, the European Medicines Agency designated thiotepa as an orphan drug. On April 2, 2007, the United States FDA designated thiotepa as a conditioning treatment for use prior to hematopoietic stem cell transplantation.[5] Adienne Pharma & Biotech (Italy), the owner of thiotepa (Tepadina) applied for these designations.


    Thiotepa is indicated for use in combination with other chemotherapeutic agents. This can be with or without total body irradiation (TBI), as a conditioning treatment prior to allogeneic or autologous hematopoietic progenitor cell transplantation (HPCT) in hematological diseases in adult and pediatric patients. These diseases include Hodgkin’s disease and leukaemia. Thiotepa is also used with high-dose chemotherapy with HPCT support to treat certain solid tumors in adult and pediatric patients.[6]

    Thiotepa is used in the palliation of many neoplastic diseases. The best results are found in the treatment of adenocarcinoma of the breast, adenocarcinoma of the ovarypapillary thyroid cancer and bladder cancer. Thiotepa is used to control intracavitary effusions caused by serosal neoplastic deposits.[6]

    Intravesical use

    Thiotepa is used as intravesical chemotherapy in bladder cancer.[7]

    It may be used prophylactically to prevent seeding of tumor cells at cystoscopic biopsy; as an adjunctive agent at the time of biopsy; or as a therapeutic agent to prevent recurrence after cystoscopic resection of bladder tumor (transurethral resection of bladder tumor, TURBT). For intravesical use, thiotepa is given in 30 mg doses weekly, for four to six weeks. Efficacy in tumor control may reach 55 percent. The main toxicity of this therapy is bone marrow suppression due to systemic absorption of the drug.

    Side effects

    The main side effect of thiotepa is bone marrow suppression resulting in leukopeniathrombocytopenia and anemia.[8] Liver and lung toxicity may also occur.


    Image result for thiotepa



    <sup>1</sup>H NMR spectrum of C<sub>6</sub>H<sub>13</sub>N<sub>3</sub>P<sub></sub>S<sub></sub> in CDCL3 at 400 MHz.<br>Click to toggle size.

    Fig 5. 1H NMR spectrum of C6H13N3PS in CDCL3 at 400 MHz.

    R.J. Abraham, M. Mobli Modelling 1H NMR Spectra of Organic Compounds:
      Theory, Applications and NMR Prediction Software, Wiley, Chichester, 2008.


    1. ^ “International Non-Proprietary Names for Pharmaceutical Preparations. Recommended International Non-Proprietary Names (Rec. I.N.N.): List 4” (PDF). World Health Organization. March 1962. p. 111. Retrieved 27 November 2016.
    2. ^ Maanen, M. J.; Smeets, C. J.; Beijnen, J. H. (2000). “Chemistry, pharmacology and pharmacokinetics of N,N’,N” -triethylenethiophosphoramide (ThioTEPA)”. Cancer Treatment Reviews26 (4): 257–268. doi:10.1053/ctrv.2000.0170PMID 10913381.
    3. ^ Sykes, M. P.; Karnofsky, D. A.; Philips, F. S.; Burchenal, J. H. (1953). “Clinical studies on triethylenephosphoramide and diethylenephosphoramide, compounds with nitrogen-mustard-like activity”. Cancer6 (1): 142–148. doi:10.1002/1097-0142(195301)6:1<142::AID-CNCR2820060114>3.0.CO;2-W.
    4. ^ Kim, Kyu-Won; Roh, Jae Kyung; Wee, Hee-Jun; Kim, Chan (2016). Cancer Drug Discovery: Science and History. Springer. p. 82. ISBN 978-94-024-0844-7.
    5. ^ “EMA Grants Adienne Marketing Rights for Tepadina” Drug Discovery & Development. 19 March 2010. Retrieved 25 November 2011.
    6. Jump up to:a b “Urgent, thioTEPA update” (PDF)Food and Drug Administration. Adienne Pharma & Biotech. 5 April 2011. Retrieved 25 November 2011.
    7. ^ Droller M. Urothelial Tumors PMPH-USA, 2004. p. 207 ISBN 1550091735
    8. ^ Agnelli, G.; de Cunto, M.; Gresele, P.; del Favero, A. (1982). “Early onset life-threatening myelosuppression after low dose of intravesical thiotepa”Postgraduate Medical Journal58 (680): 380–381. doi:10.1136/pgmj.58.680.380PMC 2426344PMID 6812036.

    External links


    US 2 670 347 (American Cyanamid; 1954; prior. 1952)

    Clinical data
    AHFS/ Consumer Drug Information
    MedlinePlus a682821
    License data
    • AU: D
    • US: D (Evidence of risk)
    Routes of
    IV, intracavitary, intravesical
    ATC code
    Legal status
    Legal status
    Pharmacokinetic data
    Metabolism Hepatic (CYP2BCYP3A)
    Elimination half-life 1.5–4.1 hours
    Excretion Renal
    6 hours for thiotepa
    8 hours for TEPA
    CAS Number
    PubChem CID
    ECHA InfoCard 100.000.124 Edit this at Wikidata
    Chemical and physical data
    Formula C6H12N3PS
    Molar mass 189.23 g/mol g·mol−1
    3D model (JSmol)

    //////////////Thiotepa, チオテパ   ,тиотепа ثيوتيبا 塞替派 , JAPAN 2019

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