Thiotepa

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Structural formula
Structure of thiotepa
General
Non-proprietary name Thiotepa
other names

N , N , N -triethylenethiophosphoric acid triamide

Molecular formula C 6 H 12 N 3 PS
External identifiers / databases
CAS number 52-24-4
EC number 200-135-7
ECHA InfoCard 100,000,124
PubChem 5453
DrugBank DB04572
Wikidata Q416507
Drug information
ATC code

L01 AC01

Drug class

Cytostatic

properties
Molar mass 189.22 g · mol -1
Physical state

firmly

Melting point

54-57 ° C

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
06 - Toxic or very toxic 08 - Dangerous to health

danger

H and P phrases H: 300-350
P: 201-264-301 + 310-308 + 313
Toxicological data

23 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Thiotepa is an alkylating cytostatic agent , which was introduced as early as 1953 for the treatment of cancer diseases ( breast cancer , bladder cancer , ovarian cancer ). It is still used in oncology to this day .

In 2010, Thiotepa was approved throughout the EU - in combination with other chemotherapeutic agents - to prepare patients for hematopoietic stem cell transplantation (HSCT) for the treatment of certain blood disorders (e.g. leukemia ) and for the treatment of solid tumors if HSCT is subsequently performed ( trade name TEPADINA ® , pharmaceutical company ADIENNE Pharma & Biotech ).

Thiotepa was originally developed as an auxiliary substance in cotton production.

It is a crystalline, white powder with a melting point between 54 and 57 degrees Celsius. Thiotepa is only stable for a few days in solutions and must therefore be stored at low temperatures.

In the human and animal organism, thiotepa is converted to the likewise alkylating TEPA (triethylenephosphoric acid triamide).

The use of thiotepa leads to significant side effects. These include anemia and a carcinogenic effect, since leukemia can be induced. Bone marrow toxicity is also known for thiotepa.

Individual evidence

  1. ↑ a b c d e Thio-TEPA data sheet from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).
  2. ^ Sean M. Gallagher, Steven H. Selman: From the battlefield to the bladder: The development of thioTEPA . In: World Journal of Clinical Urology . tape 3 , no. 3 , November 24, 2014, p. 195–200 , doi : 10.5410 / wjcu.v3.i3.195 ( wjgnet.com [accessed December 31, 2018]).
  3. ↑ Tepadina® (thiotepa) - New Drug Approval. Accessed December 31, 2018 .
  4. ↑ Information on Tepadina on the website of the European Medicines Agency .

literature

  • Sykes, MP. et al. (1953): Clinical Studies of triethylenephosphoramide compounds with nitrogen mustard-like activity . Cancer 6 (1); 142-48
  • Maanen, MJ. et al. (2000) . Chemistry, pharmacology and pharmacokinetics of N, N ', N' -triethylenethiophosphoramide (thiotepa) Cancer Treat Rev . 26 (4); 257-68; PMID 10913381
  • Hagen, B. et al. (1990): Long-term pharmacokinetics of thio-TEPA, TEPA and total alkylating activity following iv bolus administration of thio-TEPA in ovarian cancer patients . Cancer Chemother Pharmacol . 25 (4); 257-62; PMID 1688514