Thiotepa
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MedKoo CAT#: 100860

CAS#: 52-24-4

Description: Thiotepa is a polyfunctional, organophosphorus alkylating agent and a stable derivative of N,N',N''-triethylenephosphoramide (TEPA), with antineoplastic activity. Upon administration, thiotepa is converted into highly reactive ethylenimine groups, which covalently bind to nucleophilic groups in DNA and demonstrate a preference for the N7 position of guanine bases. This induces crosslinking of alkylated guanine bases in double-stranded DNA, interferes with both DNA replication and cell division, and results in both the induction of apoptosis and the inhibition of cell growth.


Price and Availability

Size Price Shipping out time Quantity
200mg USD 90 2 Weeks
500mg USD 150 2 Weeks
1g USD 250 2 Weeks
2g USD 450 2 Weeks
5g USD 850 2 Weeks
10g USD 1450 2 Weeks
20g USD 2350 2 Weeks
50g USD 4250 2 Weeks
100g USD 7650 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-28. Prices are subject to change without notice.

Thiotepa, purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 10g may be 2 weeks..


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100860
Name: Thiotepa
CAS#: 52-24-4
Chemical Formula: C6H12N3PS
Exact Mass: 189.04895
Molecular Weight: 189.22
Elemental Analysis: C, 38.09; H, 6.39; N, 22.21; P, 16.37; S, 16.95


Synonym: AI3 24916; AI324916; AI3-24916; NSC-6396; NSC 6396; NSC6396; Girostan; thiophosphamide; thiophosphoramide; triethylene thiophosphoramide. US brand names: Girostan; STEPA; TESPA; Thiofozil; Thioplex; Tifosyl. Foreign brand names: Ledertepa; Onco Tiotepa; Oncotiotepa; Tespamin; Tespamine; Thiotef; TioTEF; Abbreviation: TSPA. Code name: WR 45312; WR45312; WR45312.

IUPAC/Chemical Name: tri(aziridin-1-yl)phosphine sulfide

InChi Key: FOCVUCIESVLUNU-UHFFFAOYSA-N

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

SMILES Code: S=P(N1CC1)(N2CC2)N3CC3


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Safety Data Sheet (SDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001


References

1: Oh DH, Chua N, Street L, Stewart DA. Treatment of secondary central nervous system lymphoma patients with high-dose Busulfan/Thiotepa-based conditioning and autologous stem cell transplantation. Leuk Lymphoma. 2015 Mar 9:1-23. [Epub ahead of print] PubMed PMID: 25747968.

2: Srour SA, Borders EB, Cherry MA, Holter J, Herman T, Selby GB. Role of topotecan, vinorelbine, thiotepa, and gemcitabine (TVTG) chemotherapy in relapsed/refractory adult acute leukemia. Leuk Lymphoma. 2015 Feb 26:1-11. [Epub ahead of print] PubMed PMID: 25721752.

3: Baronciani D, Depau C, Targhetta C, Derudas D, Culurgioni F, Tandurella I, Latte G, Palmas A, Angelucci E. Treosulfan-fludarabine-thiotepa conditioning before allogeneic haemopoietic stem cell transplantation for patients with advanced lympho-proliferative disease. A single centre study. Hematol Oncol. 2015 Jan 28. doi: 10.1002/hon.2187. [Epub ahead of print] PubMed PMID: 25626861.

4: Thust SC, Blanco E, Michalski AJ, Chong WK, Gaze MN, Phipps K, Mankad K. MRI abnormalities in children following sequential chemotherapy, hyperfractionated accelerated radiotherapy and high-dose thiotepa for high-risk primitive neuroectodermal tumours of the central nervous system. J Med Imaging Radiat Oncol. 2014 Dec;58(6):683-90. doi: 10.1111/1754-9485.12232. Epub 2014 Sep 16. PubMed PMID: 25224299.

5: Chen YB, Batchelor T, Li S, Hochberg E, Brezina M, Jones S, Del Rio C, Curtis M, Ballen KK, Barnes J, Chi AS, Dietrich J, Driscoll J, Gertsner ER, Hochberg F, LaCasce AS, McAfee SL, Spitzer TR, Nayak L, Armand P. Phase 2 trial of high-dose rituximab with high-dose cytarabine mobilization therapy and high-dose thiotepa, busulfan, and cyclophosphamide autologous stem cell transplantation in patients with central nervous system involvement by non-Hodgkin lymphoma. Cancer. 2015 Jan 15;121(2):226-33. doi: 10.1002/cncr.29023. Epub 2014 Sep 9. PubMed PMID: 25204639; PubMed Central PMCID: PMC4293259.

6: Lee SH, Son MH, Sung KW, Choi YB, Lee NH, Yoo KH, Koo HH, Lim do H, Shin HJ. Toxicity of tandem high-dose chemotherapy and autologous stem cell transplantation using carboplatin-thiotepa-etoposide and cyclophosphamide-melphalan regimens for malignant brain tumors in children and young adults. J Neurooncol. 2014 Dec;120(3):507-13. doi: 10.1007/s11060-014-1576-1. Epub 2014 Aug 10. PubMed PMID: 25108776.

7: Samtsevych AI, Bulavin LA, Sukhodub LF, Nikolaienko TIu. [Interaction of DNA nucleotide bases with anticancer drug ThioTEPA: molecular docking and quantum-mechanical analysis]. Ukr Biokhim Zh. 2014 Mar-Apr;86(2):50-9. Ukrainian. PubMed PMID: 24868911.

8: Gato R, Lees RS, Bruzon RY, Companioni A, Menendez Z, González A, Rodríguez M. Large indoor cage study of the suppression of stable Aedes aegypti populations by the release of thiotepa-sterilised males. Mem Inst Oswaldo Cruz. 2014 Jun;109(3):365-70. Epub 2014 May 23. PubMed PMID: 24863972; PubMed Central PMCID: PMC4131792.

9: Welch MR, Sauter CS, Matasar MJ, Faivre G, Weaver SA, Moskowitz CH, Omuro AM. Autologous stem cell transplant in recurrent or refractory primary or secondary central nervous system lymphoma using thiotepa, busulfan and cyclophosphamide. Leuk Lymphoma. 2015 Feb;56(2):361-7. doi: 10.3109/10428194.2014.916800. Epub 2014 Jun 27. PubMed PMID: 24745937.

10: Marec-Berard P, Segura-Ferlay C, Tabone MD, Pacquement H, Lervat C, Gentet JC, Schmitt C, Gaspar N, Brugières L. High Dose Thiotepa in Patients with Relapsed or Refractory Osteosarcomas: Experience of the SFCE Group. Sarcoma. 2014;2014:475067. doi: 10.1155/2014/475067. Epub 2014 Feb 4. PubMed PMID: 24672280; PubMed Central PMCID: PMC3941142.

11: Gato R, Companioni A, Bruzón RY, Menéndez Z, González A, Rodríguez M. Release of thiotepa sterilized males into caged populations of Aedes aegypti: life table analysis. Acta Trop. 2014 Apr;132 Suppl:S164-9. doi: 10.1016/j.actatropica.2013.09.024. Epub 2013 Oct 25. PubMed PMID: 24513037.

12: Kokolo MB, Fergusson D, O'Neill J, Tay J, Tinmouth AT, Stewart D, Bredeson C. Effectiveness and safety of thiotepa as conditioning treatment prior to stem cell transplant in patients with central nervous system lymphoma. Leuk Lymphoma. 2014 Dec;55(12):2712-20. doi: 10.3109/10428194.2014.889825. Epub 2014 Mar 26. PubMed PMID: 24491026.

13: Kosuri S, van Besien K. Great expectations? Conditioning with busulfan, melphalan and thiotepa in recurrent Hodgkin lymphoma. Leuk Lymphoma. 2014 Mar;55(3):476-7. doi: 10.3109/10428194.2014.887715. PubMed PMID: 24471910.

14: Bergthold G, El Kababri M, Varlet P, Dhermain F, Sainte-Rose C, Raquin MA, Kieffer V, Goma G, Grill J, Valteau-Couanet D, Dufour C. High-dose busulfan-thiotepa with autologous stem cell transplantation followed by posterior fossa irradiation in young children with classical or incompletely resected medulloblastoma. Pediatr Blood Cancer. 2014 May;61(5):907-12. doi: 10.1002/pbc.24954. Epub 2014 Jan 28. PubMed PMID: 24470384.

15: Henes JC, Koetter I, Horger M, Schmalzing M, Mueller K, Eick C, Bauer A, Vogel W, Kanz L. Autologous stem cell transplantation with thiotepa-based conditioning in patients with systemic sclerosis and cardiac manifestations. Rheumatology (Oxford). 2014 May;53(5):919-22. doi: 10.1093/rheumatology/ket464. Epub 2014 Jan 22. PubMed PMID: 24459219.

16: Dertinger SD, Phonethepswath S, Avlasevich SL, Torous DK, Mereness J, Cottom J, Bemis JC, Macgregor JT. Pig-a gene mutation and micronucleated reticulocyte induction in rats exposed to tumorigenic doses of the leukemogenic agents chlorambucil, thiotepa, melphalan, and 1,3-propane sultone. Environ Mol Mutagen. 2014 May;55(4):299-308. doi: 10.1002/em.21846. Epub 2014 Jan 21. PubMed PMID: 24449360.

17: Shukla N, Kobos R, Renaud T, Steinherz LJ, Steinherz PG. Phase II trial of clofarabine with topotecan, vinorelbine, and thiotepa in pediatric patients with relapsed or refractory acute leukemia. Pediatr Blood Cancer. 2014 Mar;61(3):431-5. doi: 10.1002/pbc.24789. Epub 2013 Sep 24. PubMed PMID: 24115731.

18: Comte A, Jdid W, Guilhaume MN, Kriegel I, Piperno-Neumann S, Dieras V, Dorval T, Pierga JY, Cottu PH, Mignot L, Bidard FC. Survival of breast cancer patients with meningeal carcinomatosis treated by intrathecal thiotepa. J Neurooncol. 2013 Dec;115(3):445-52. doi: 10.1007/s11060-013-1244-x. Epub 2013 Sep 17. PubMed PMID: 24043602.

19: Le Rhun E, Taillibert S, Devos P, Zairi F, Turpin A, Rodrigues I, Cazin JL, Pierret MF, André C, Dubois F, Bonneterre J, Chamberlain MC. Salvage intracerebrospinal fluid thiotepa in breast cancer-related leptomeningeal metastases: a retrospective case series. Anticancer Drugs. 2013 Nov;24(10):1093-7. doi: 10.1097/CAD.0000000000000010. PubMed PMID: 23962903.

20: Bains T, Chen AI, Lemieux A, Hayes-Lattin BM, Leis JF, Dibb W, Maziarz RT. Improved outcome with busulfan, melphalan and thiotepa conditioning in autologous hematopoietic stem cell transplant for relapsed/refractory Hodgkin lymphoma. Leuk Lymphoma. 2014 Mar;55(3):583-7. doi: 10.3109/10428194.2013.806659. Epub 2013 Jun 24. PubMed PMID: 23697844.