TEPA | CAS# 545-55-1 | Antineoplastic agent

MedKoo Cat#: 571153 | Name: TEPA

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

TEPA is an insect chemosterilant and an antineoplastic agent. It inhibits carcinoma growth.

Chemical Structure

TEPA

CAS#545-55-1

Theoretical Analysis

MedKoo Cat#: 571153

Name: TEPA

CAS#: 545-55-1

Chemical Formula: C6H12N3OP

Exact Mass: 173.0718

Molecular Weight: 173.16

Elemental Analysis: C, 41.62; H, 6.99; N, 24.27; O, 9.24; P, 17.89

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 300.00
25mg	USD 450.00
50mg	USD 715.00

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Related CAS #

No Data

Synonym

TEPA; Aphoxide; A 6366; A-6366; A6366; NSC 9717; NSC-9717; NSC9717

IUPAC/Chemical Name

Tris(1-aziridinyl)phosphine oxide

InChi Key

FYAMXEPQQLNQDM-UHFFFAOYSA-N

InChi Code

InChI=1S/C6H12N3OP/c10-11(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2

SMILES Code

O=P(N1CC1)(N2CC2)N3CC3

Appearance

Solid powder

Purity

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

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

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 173.16 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Zhou X, Wang X, Song Q, Yang H, Zhu X, Yu J, Song G, Di L, Ren J, Shao H, Lyerly HK. Transformation of alkylating regimen of thiotepa into tepa determines the disease progression through GSTP1 gene polymorphism for metastatic breast cancer patients receiving thiotepa containing salvage chemotherapy. Int J Clin Pharmacol Ther. 2015 Nov;53(11):914-22. doi: 10.5414/CP202391. PubMed PMID: 26396136. 2: Zaker F, Nasiri N, Oodi A, Amirizadeh N. Evaluation of umbilical cord blood CD34 (+) hematopoietic stem cell expansion in co-culture with bone marrow mesenchymal stem cells in the presence of TEPA. Hematology. 2013 Jan;18(1):39-45. doi: 10.1179/1607845412Y.0000000034. Epub 2012 Nov 19. PubMed PMID: 23321686. 3: Torabifard H, Fattahi A. Mechanisms and kinetics of thiotepa and tepa hydrolysis: DFT study. J Mol Model. 2012 Aug;18(8):3563-76. doi: 10.1007/s00894-012-1354-y. Epub 2012 Feb 14. PubMed PMID: 22331106. 4: Hagen B. Pharmacokinetics of thio-TEPA and TEPA in the conventional dose-range and its correlation to myelosuppressive effects. Cancer Chemother Pharmacol. 1991;27(5):373-8. PubMed PMID: 1705489. 5: Li S, Zhang J, Yang H, Wu C, Dang X, Liu Y. Copper depletion inhibits CoCl2-induced aggressive phenotype of MCF-7 cells via downregulation of HIF-1 and inhibition of Snail/Twist-mediated epithelial-mesenchymal transition. Sci Rep. 2015 Jul 15;5:12410. doi: 10.1038/srep12410. PubMed PMID: 26174737; PubMed Central PMCID: PMC4502431. 6: Hagen B, Neverdal G, Walstad RA, Nilsen OG. Long-term pharmacokinetics of thio-TEPA, TEPA and total alkylating activity following i.v. bolus administration of thio-TEPA in ovarian cancer patients. Cancer Chemother Pharmacol. 1990;25(4):257-62. PubMed PMID: 1688514. 7: Sosnovsky G, Li SW. In the search for new anticancer drugs XI. Anticancer activity of nitroxyl labeled phosphoric N,N;N',N';N",N"-tris[1,2-ethanediyl]triamide(TEPA) and phosphorothioic N,N;N',N';N",N"-tris[1,2-ethanediyl]triamide(thio-TEPA) derivatives. Cancer Lett. 1985 Jan;25(3):255-60. PubMed PMID: 2578867. 8: van Maanen MJ, Doesburg Smits K, Damen JM, Heck AJ, Beijnen JH. Stability of thioTEPA and its metabolites, TEPA, monochloroTEPA and thioTEPA-mercapturate, in plasma and urine. Int J Pharm. 2000 May 10;200(2):187-94. PubMed PMID: 10867248. 9: Ekhart C, Doodeman VD, Rodenhuis S, Smits PH, Beijnen JH, Huitema AD. Polymorphisms of drug-metabolizing enzymes (GST, CYP2B6 and CYP3A) affect the pharmacokinetics of thiotepa and tepa. Br J Clin Pharmacol. 2009 Jan;67(1):50-60. doi: 10.1111/j.1365-2125.2008.03321.x. Epub 2008 Nov 17. PubMed PMID: 19076156; PubMed Central PMCID: PMC2668084. 10: Breau AP, Field L, Mitchell WM. Thiono compounds. 4. In vitro mutagenic and antineoplastic activity of TEPA and thio-TEPA. Cell Biol Toxicol. 1984 Oct;1(1):21-30. PubMed PMID: 6086064. 11: Hagen B, Dale O, Neverdal G, Azri S, Nilsen OG. Metabolism and alkylating activity of thio-TEPA in rat liver slice incubation. Cancer Chemother Pharmacol. 1991;28(6):441-7. PubMed PMID: 1718615. 12: Sosnovsky G, Lukszo J, Konieczny M, Purgstaller K, Laib F. In the search for new anticancer drugs. 26. A comparison of anticancer activities of several TEPA, thio-TEPA, Seleno-TEPA, and azetidine analogs, including congeners containing an aminoxyl moiety. J Pharm Sci. 1994 Jul;83(7):982-8. PubMed PMID: 7525922. 13: Dale O, Thommesen L, Mortensen B, Hagen B. Gender aspects of liver slice incubations with N,N,N-triethylene-thiophosphamide (Thio-TEPA) in rats and mice. Pharmacol Toxicol. 1999 Mar;84(3):122-4. PubMed PMID: 10193672. 14: Huitema AD, Mathôt RA, Tibben MM, Schellens JH, Rodenhuis S, Beijnen JH. Population pharmacokinetics of thioTEPA and its active metabolite TEPA in patients undergoing high-dose chemotherapy. Br J Clin Pharmacol. 2001 Jan;51(1):61-70. PubMed PMID: 11167666; PubMed Central PMCID: PMC2014425. 15: Hagen B, Nilsen OG. The binding of thio-TEPA in human serum and to isolated serum protein fractions. Cancer Chemother Pharmacol. 1987;20(4):319-23. PubMed PMID: 3121202. 16: Ng SF, Waxman DJ. N,N',N''-triethylenethiophosphoramide (thio-TEPA) oxygenation by constitutive hepatic P450 enzymes and modulation of drug metabolism and clearance in vivo by P450-inducing agents. Cancer Res. 1991 May 1;51(9):2340-5. PubMed PMID: 1707751. 17: van Maanen MJ, Smits KD, Beijnen JH. Simultaneous determination of thioTEPA, TEPA and a novel, recently identified thioTEPA metabolite, monochloroTEPA, in urine using capillary gas chromatography. J Chromatogr B Biomed Sci Appl. 2000 Jun 9;742(2):335-43. PubMed PMID: 10901138. 18: Kheffache D, Ouamerali O. Some physicochemical properties of the antitumor drug thiotepa and its metabolite tepa as obtained by density functional theory (DFT) calculations. J Mol Model. 2010 Aug;16(8):1383-90. doi: 10.1007/s00894-010-0658-z. Epub 2010 Feb 14. PubMed PMID: 20155478. 19: Hagen B, Walseth F, Walstad RA, Iversen T, Nilsen OG. Single and repeated dose pharmacokinetics of thio-TEPA in patients treated for ovarian carcinoma. Cancer Chemother Pharmacol. 1987;19(2):143-8. PubMed PMID: 3105905. 20: Jacobson PA, Green K, Birnbaum A, Remmel RP. Cytochrome P450 isozymes 3A4 and 2B6 are involved in the in vitro human metabolism of thiotepa to TEPA. Cancer Chemother Pharmacol. 2002 Jun;49(6):461-7. Epub 2002 Apr 23. PubMed PMID: 12107550.