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Chemical Compound Review

TEPA     1-[bis(aziridin-1- yl)phosphoryl]aziridine

Synonyms: Aphoxide, TAPO, CHEMBL670, NSC-9717, HSDB 1011, ...
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Disease relevance of Triethylenephosphoramide


High impact information on Triethylenephosphoramide

  • An attempt was made to unravel the metabolic profile of the alkylating agent N,N',N''-triethylenethiophosphoramide (thioTEPA). thioTEPA and its metabolite N,N',N-triethylenephosphoramide (TEPA) were quantified in urine of treated patients by gas chromatography with selective nitrogen/phosphorous detection [6].
  • The pharmacokinetics of thiotepa and its principal metabolite TEPA were studied in 23 patients [7].
  • The AUC of TEPA was lower than that previously observed [7].
  • Although these rates are low compared to those catalyzed by phenobarbital-induced liver microsomes (3.5 nmol TEPA/min/mg), they are sufficient to contribute to the systemic metabolism of this drug [8].
  • Alkaline elution studies of L1210 cells that had been incubated with TEPA, alone or in the presence of microsomes and NADPH, demonstrated an elution pattern identical to that produced by thioTEPA in the presence of microsomes and NADPH [9].

Chemical compound and disease context of Triethylenephosphoramide


Biological context of Triethylenephosphoramide

  • SCE frequency was significantly increased even after very low doses of mutagens, while chromosome aberrations were significantly increased only after high doses (0.160 micrograms/ml mitomycin and 10(-5) M TEPA) [3].
  • The results of dominant-lethal and bone-marrow cytogenetic studies in mice after consumption of drinking water containing 1000 mg of 5-NFA/1 for 12 weeks and dosed subsequently with TEPA suggests that 5-NFA has some antimutagenic activity [11].
  • Influence of the tissue distribution of ThioTEPA and its metabolite, TEPA, on the response of murine colon tumours [12].
  • After exposures to TEPA and ECHH, 10.9% of aberrations were undectable in G0 and 3.3% in G1S and G2 phases [10].
  • We found that Thio-TEPA is approximately two-fold more active than TEPA in arresting cell growth (IC50 = 2.8 microM for TEPA and 1.5 microM for Thio-TEPA) [13].

Anatomical context of Triethylenephosphoramide

  • The antineoplastic agents N,N',N''-triethylenethiophosphoramide (thioTEPA) and N,N',N''-triethylenephosphoramide (TEPA) were studied for their interaction with the DNA of L1210 cells in the presence and absence of rat hepatic microsomes and NADPH [9].
  • One of these cell lines proved hypersensitive to TEPA, whereas the other was no more sensitive to TEPA than were lymphoblasts from normal humans [9].
  • We conclude that Cudt containing TEPA depletes exocrine tissue and facilitates pancreas digestion for successful transplantation of islets into the portal system [14].
  • Significantly more eggs were fertilized by untreated than by TEPA-treated spermatozoa [15].
  • For CFU-GM and BFU-E growth in vitro, the IC50(s) of thioTEPA were 83 ng/ml and 16 ng/ml, respectively, and the IC50(s) of TEPA were 141 ng/ml and 47 ng/ml, respectively [16].

Associations of Triethylenephosphoramide with other chemical compounds


Gene context of Triethylenephosphoramide

  • MUC5AC and MUC5B mucin secretion was measured by an enzyme-linked immunosorbent assay (ELISA) using a specific monoclonal antibody NCL-HGM-45M1 and polyclonal antiserum TEPA, respectively [20].
  • Cytochrome P450 isozymes 3A4 and 2B6 are involved in the in vitro human metabolism of thiotepa to TEPA [21].
  • Oxidation of thio-TEPA to TEPA was also catalyzed by purified P-450 PB-4 (Km (app) 19 microM; Vmax (app) = 11 mol thio-TEPA metabolized/min/mol P-450 PB-4) following reconstitution of the cytochrome with NADPH P-450 reductase in a lipid environment [22].
  • After extraction of ThioTEPA and its metabolite, triethylenephosphoramide (TEPA), from plasma using Sep-Pak C18 cartridges, the compounds were separated by capillary chromatography, detected using a nitrogen detector and quantified by reference to an internal standard, hexaethylphosphoramide [23].
  • In both groups early recovery of normal activities was noted, after a mean of respectively 13.6 days (TAPP) and 12.9 days (TEPA) [24].

Analytical, diagnostic and therapeutic context of Triethylenephosphoramide


  1. Phase I/pharmacokinetic reevaluation of thioTEPA. O'Dwyer, P.J., LaCreta, F., Engstrom, P.F., Peter, R., Tartaglia, L., Cole, D., Litwin, S., DeVito, J., Poplack, D., DeLap, R.J. Cancer Res. (1991) [Pubmed]
  2. In the search for new anticancer drugs. 17. Linear and cyclic polyether analogues of N,N:N',N':N'',N''-tri-1,2-ethanediylphosphoric triamide and N,N:N',N':N'',N''-tri-1,2-ethanediylphosphorothioic triamide. Sosnovsky, G., Lukszo, J., Rao, N.U. J. Med. Chem. (1986) [Pubmed]
  3. Effects of alkylating agents on lymphocytes from controls and from patients with Fanconi's anemia. Studies of sister chromatid exchanges, chromosome aberrations, and kinetics of cell division. Novotná, B., Goetz, P., Surkova, N.I. Hum. Genet. (1979) [Pubmed]
  4. Mutagenic effect of epichlorohydrin. I. Testing on human lymphocytes in vitro in comparison with TEPA. Kucerová, M., Polívková, Z., Srám, R., Matousek, V. Mutat. Res. (1976) [Pubmed]
  5. Long-term pharmacokinetics of thio-TEPA, TEPA and total alkylating activity following i.v. bolus administration of thio-TEPA in ovarian cancer patients. Hagen, B., Neverdal, G., Walstad, R.A., Nilsen, O.G. Cancer Chemother. Pharmacol. (1990) [Pubmed]
  6. A search for new metabolites of N,N',N''-triethylenethiophosphoramide. van Maanen, M.J., Tijhof, I.M., Damen, J.M., Versluis, C., van den Bosch, J.J., Heck, A.J., Rodenhuis, S., Beijnen, J.H. Cancer Res. (1999) [Pubmed]
  7. Phase I study of thiotepa in combination with the glutathione transferase inhibitor ethacrynic acid. O'Dwyer, P.J., LaCreta, F., Nash, S., Tinsley, P.W., Schilder, R., Clapper, M.L., Tew, K.D., Panting, L., Litwin, S., Comis, R.L. Cancer Res. (1991) [Pubmed]
  8. 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. Ng, S.F., Waxman, D.J. Cancer Res. (1991) [Pubmed]
  9. Interaction of N,N',N''-triethylenethiophosphoramide and N,N',N''-triethylenephosphoramide with cellular DNA. Cohen, N.A., Egorin, M.J., Snyder, S.W., Ashar, B., Wietharn, B.E., Pan, S.S., Ross, D.D., Hilton, J. Cancer Res. (1991) [Pubmed]
  10. Banding technique used for the detection of chromosomal aberrations induced by radiation and alkylating agents TEPA and epichlorohydrin. Kucerová, M., Polívková, Z. Mutat. Res. (1976) [Pubmed]
  11. Mutagenicity studies with nitrofurans. I. Mutagenicity of nitrofurylacrylic acid for mammals. Srám, R.J., Rössner, P., Zhurkov, V.S., Kodýtková, I. Mutat. Res. (1979) [Pubmed]
  12. Influence of the tissue distribution of ThioTEPA and its metabolite, TEPA, on the response of murine colon tumours. Bibby, M.C., McDermott, B.J., Double, J.A., Phillips, R.M., Loadman, P.M., Burgess, L. Cancer Chemother. Pharmacol. (1987) [Pubmed]
  13. Cellular pharmacology of N,N',N''-triethylene thiophosphoramide. Miller, B., Tenenholz, T., Egorin, M.J., Sosnovsky, G., Rao, N.U., Gutierrez, P.L. Cancer Lett. (1988) [Pubmed]
  14. In vivo depletion of pancreatic acinar tissue simplifies islet preparation for transplantation. Al-Abdullah, I.H., Vulin, C.L., Kumar, M.S. Transplantation (1996) [Pubmed]
  15. Fertilization following mixed insemination with 'cervix-selected' and 'unselected' spermatozoa in the rabbit. Fischer, B., Adams, C.E. J. Reprod. Fertil. (1981) [Pubmed]
  16. Dosing of thioTEPA for myeloablative therapy. Przepiorka, D., Madden, T., Ippoliti, C., Estrov, Z., Dimopoulos, M. Cancer Chemother. Pharmacol. (1995) [Pubmed]
  17. Simultaneous quantification of cyclophosphamide, 4-hydroxycyclophosphamide, N,N',N"-triethylenethiophosphoramide (thiotepa) and N,N',N"-triethylenephosphoramide (tepa) in human plasma by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry. de Jonge, M.E., van Dam, S.M., Hillebrand, M.J., Rosing, H., Huitema, A.D., Rodenhuis, S., Beijnen, J.H. Journal of mass spectrometry : JMS. (2004) [Pubmed]
  18. Population pharmacokinetics of thioTEPA and its active metabolite TEPA in patients undergoing high-dose chemotherapy. Huitema, A.D., Mathôt, R.A., Tibben, M.M., Schellens, J.H., Rodenhuis, S., Beijnen, J.H. British journal of clinical pharmacology. (2001) [Pubmed]
  19. High-performance liquid chromatography of the anti-tumour agent triethylenethiophosphoramide and its metabolite triethylenephosphoramide with sodium sulphide, taurine and o-phthalaldehyde as pre-column fluorescent derivatization reagents. Sano, A., Matsutani, S., Takitani, S. J. Chromatogr. (1988) [Pubmed]
  20. Up-regulation of mucin secretion in HT29-MTX cells by the pro-inflammatory cytokines tumor necrosis factor-alpha and interleukin-6. Smirnova, M.G., Kiselev, S.L., Birchall, J.P., Pearson, J.P. Eur. Cytokine Netw. (2001) [Pubmed]
  21. Cytochrome P450 isozymes 3A4 and 2B6 are involved in the in vitro human metabolism of thiotepa to TEPA. Jacobson, P.A., Green, K., Birnbaum, A., Remmel, R.P. Cancer Chemother. Pharmacol. (2002) [Pubmed]
  22. Biotransformation of N,N',N''-triethylenethiophosphoramide: oxidative desulfuration to yield N,N',N''-triethylenephosphoramide associated with suicide inactivation of a phenobarbital-inducible hepatic P-450 monooxygenase. Ng, S.F., Waxman, D.J. Cancer Res. (1990) [Pubmed]
  23. Gas chromatographic analysis of triethylenethiophosphoramide and triethylenephosphoramide in biological specimens. McDermott, B.J., Double, J.A., Bibby, M.C., Wilman, D.E., Loadman, P.M., Turner, R.L. J. Chromatogr. (1985) [Pubmed]
  24. Laparoscopic transperitoneal versus extraperitoneal inguinal hernia repair: a prospective clinical trial. Van Hee, R., Goverde, P., Hendrickx, L., Van der Schelling, G., Totté, E. Acta chirurgica Belgica. (1998) [Pubmed]
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