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ThioTEPA

Thiotepa
Systematic (IUPAC) name
1,1',1''-phosphorothioyltriaziridine
Clinical data
AHFS/Drugs.com
MedlinePlus
Pregnancy cat.
Legal status
Routes IV, intracavitary, intravesical
Pharmacokinetic data
Metabolism Hepatic (CYP2B, CYP3A)
Half-life 1.5-4.1 hours
Excretion Renal
6 hours for ThioTEPA
8 hours for TEPA
Identifiers
CAS number  YesY
ATC code L01
PubChem
DrugBank
ChemSpider  YesY
UNII  YesY
KEGG  YesY
ChEMBL  YesY
Chemical data
Formula C6H12N3PS 
Mol. mass 189.23 g/mol
 N   

N,N'N'-triethylenethiophosphoramide (ThioTEPA or thiotepa) is an alkylating agent used to treat cancer.

ThioTEPA is an

  • Thiotepa Official FDA information, side effects and uses on Drugs.com
  • Thiotepa on cancer.org

External links

  1. ^ Maanen, M. J.; Smeets, C. J.; Beijnen, J. H. (2000). "Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA)". Cancer Treatment Reviews 26 (4): 257–268.  
  2. ^ 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". Cancer 6 (1): 142–148.  
  3. ^ "EMA Grants Adienne Marketing Rights for Tepadina". dddmag.com. Drug Discovery & Development. 19 March 2010. Retrieved 25 November 2011. 
  4. ^ a b "URGENT – THIOTEPA UPDATE".  
  5. ^ Agnelli, G.; de Cunto, M.; Gresele, P.; del Favero, A. (1982). "Early onset life-threatening myelosuppression after low dose of intravesical thiotepa" (pdf). Postgraduate Medical Journal 58 (680): 380–381.  

References

Thiotepa synthesis: U.S. Patent 2,670,347 JP 55218 

Synthesis

Thiotepa main toxicity is myelosuppression. The most serious complication of excessive therapy is bone marrow depression, causing leukopenia, thrombocytopenia, and anemia.[5] Serious toxicity involving the hematologic, hepatic and respiratory system were considered as expected consequences of the conditioning regimen and transplant process.

For therapeutic usage, thiotepa is given in 30 mg doses intravesically weekly for 4–6 weeks. Many studies have reported up to 55% of success rate. Main toxicity of intravesical therapy is due to systemic absorption causing myelosupression, which results in thrombocytopenia and leukopenia.

Thiotepa is also used as intravesical chemotherapy in bladder cancer. Three patterns of usage is identified. 1) prophylactic - before taking cystoscopic biopsy, to prevent seeding of tumor cells; 2) adjunctive- at the time of biopsy; 3) therapeutic - to prevent recurrence after cystoscopic resection of bladder tumor (transurethral resection of bladder tumor - TURBT)

Thiotepa has been previously used in the palliation of a wide variety of neoplastic diseases. The more consistent results have been seen in: adenocarcinoma of the breast, adenocarcinoma of the ovary, superficial papillary carcinoma of the urinary bladder and for controlling intracavitary effusions secondary to diffuse or localized neoplastic diseases of various serosal cavities.[4]

  • with or without total body irradiation (TBI), as conditioning treatment prior to allogeneic or autologous haematopoietic progenitor cell transplantation (HPCT) in haematological diseases in adult and paediatric patients;
  • when high dose chemotherapy with HPCT support is appropriate for the treatment of solid tumours in adult and paediatric patients.[4]

Thiotepa is indicated, in combination with other chemotherapy medicinal products:

ThioTEPA has been designated as orphan drug by the European Medicines Agency on January 29, 2007, and by the United States Food and Drug Administration (FDA) on April 2, 2007, as a conditioning treatment prior to haematopoietic stem cell transplantation.[3] The applicant for these orphan drug designations was the Italian company ADIENNE Pharma & Biotech, owner of the drug TEPADINA (INN: thiotepa).

ThioTEPA was first developed by American Cyanamid company in the early 1950s and was reported in 1953.[2] ThioTEPA has been in use since the 1960s.

History and use

Contents

  • History and use 1
  • Synthesis 2
  • References 3
  • External links 4

. thiophosphoryl chloride and aziridine. It is derived from phosphate). This molecule features tetrahedral phosphorus and is structurally akin to TEPA It is an analogue of N,N',N''- triethylenephosphoramide ([1]

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