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QuickView for Thiotepa (compound)

Summary
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PubChem

PubChem Compound 5453

PubChem Compound 5453

Name:	Thiotepa
PubChem Compound ID:	5453
Description:	A very toxic alkylating antineoplastic agent also used as an insect sterilant. It causes skin, gastrointestinal, CNS, and bone marrow damage. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), thiotepa may reasonably be anticipated to be a carcinogen (Merck Index, 11th ed).
Molecular formula:	C₆H₁₂N₃PS
Molecular weight:	189.219 g/mol
Synonyms:	Triaziridinylphosphine sulfide; Phosphorothioic triamide, N,N',N''-triethylene; WR-45312; Thiophosphoramide, N, N',N''-tri-1,2-ethanediyl-; BRN 0145978; Ledertepa; 52-24-4; Tris(1-aziridinyl)phosphine sulfide; Phosphoric tri(ethyleneamide); Tespamine. show more » Triaziridinylphosphine sulfide; Phosphorothioic triamide, N,N',N''-triethylene; WR-45312; Thiophosphoramide, N, N',N''-tri-1,2-ethanediyl-; BRN 0145978; Ledertepa; 52-24-4; Tris(1-aziridinyl)phosphine sulfide; Phosphoric tri(ethyleneamide); Tespamine; NSC6396; N,N',N''-Triethylenethiophosphortriamide; NSC 6396; Tri-1-aziridinylphosphine sulfide; Tris(aziridinyl)phosphine sulfide; Thiotepa [USAN:BAN:INN:JAN]; KBio3_002688; Thioplex (TN); Girostan; Stepa; Thiotepa; Oncothio-tepa; Thio-TEPA; NCI60_013117; Triethylenethiophosphoramide; KBio1_000817; Thio-tep; Phosphine sulfide, tris(1-aziridinyl)-; KBio2_004737; AI3-24916; N,N',N-Triethylenethiophosphamide; Phosphorothioic triamide, N,N',N-triethylene-; N,N',N-Triethylenethiophosphoramide; Tifosyl; EINECS 200-135-7; Tris(ethylenimino)thiophosphate; Tri(ethyleneimino)thiophosphoramide; Thiophosphamidum; KBio2_002169; AIDS112651; 4-20-00-00052 (Beilstein Handbook Reference); Aziridine, 1,1',1''-phosphinothioylidynetris-; SK 6882; C07641; 1,1',1''-Phosphinothioylidynetrisaziridine; N,N', N''-Triethylenephosphorothioic triamide; Thioplex; Thiotepa (JP15/USP); N,N',N''-Tri-1,2-ethanediylphosphorothioic triamide; Thio-tepa S; Aziridine, 1,1,1-phosphinothioylidynetris-; CBC 806495;Girostan; KBio2_007305; TSPA; Thiofozil; CCRIS 586; Tio-tef; Thiotriethylenephosphoramide; Tio TEF; Thiophosphoramide, N,N',N'' -triethylene-; Thiotepum [INN-Latin]; Tiofosyl; Thiophosphoramide, N,N',N-triethylene-; NINDS_000817; Tespamin; Thiophosphoramide, N,N',N''-tri-1,2-ethanediyl-; Phosphorothioic triamide, N,N',N''-tri-1, 2-ethanediyl-; Triethylene thiophosphoramide; Spectrum4_000208; Phosphorothioic triamide, N,N',N''-tri-1,2-ethanediyl-; Oncotiotepa; Tespa; NSC-6396; Phosphine sulfide, tris (1-aziridinyl)-; AIDS-112651; Spectrum3_001594; Triethylenethiophosphorotriamide; CBC 806495; N,N', N''-Triethylenethiophosphamide; Spectrum_001689; HSDB 3258; DivK1c_000817; N,N',N''-Tri-1,2-ethanediylthiophosphoramide; SPBio_001434; KBioGR_000815; Thiophosphamide; Oncotepa; Phosphorothioic acid triethylenetriamide; Thiotef; D00583; Tris(1-aziridinyl)phosphine sulphide; Spectrum2_001557; N,N',N''-Triethylenephosphorothioic triamide; N,N', N''-Triethylenethiophosphoramide; Tiotepa [INN-Spanish]; Tiofozil; NCI-C01649; Tiofosfamid; N, N',N''-Tri-1,2-ethanediylthiophosphoramide; KBioSS_002169 show less «

DrugBank

Identification

Name:	Thiotepa
Name (isomeric):	DB04572
Drug Type:	small molecule
Description:	A very toxic alkylating antineoplastic agent also used as an insect sterilant. It causes skin, gastrointestinal, CNS, and bone marrow damage. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), thiotepa may reasonably be anticipated to be a carcinogen (Merck Index, 11th ed).
Category:	Antineoplastic Agents, Alkylating, Alkylating Agents
CAS number:	52-24-4

Pharmacology

Indication:	ThioTEPA is used a as conditioning treatment prior to allogeneic or autologous haematopoietic progenitor cell transplantation (HPCT) in haematological diseases in adult and paediatric patients. Also, when high dose chemotherapy with HPCT support it is appropriate for the treatment of solid tumours in adult and paediatric patients.
Pharmacology:	The unstable nitrogen-carbon groups alkylate with DNA causing irrepairable DNA damage. They stop tumor growth by crosslinking guanine nucleobases in DNA double-helix strands, directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. These drugs act nonspeci... show more » The unstable nitrogen-carbon groups alkylate with DNA causing irrepairable DNA damage. They stop tumor growth by crosslinking guanine nucleobases in DNA double-helix strands, directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. These drugs act nonspecifically. show less «
Mechanism of Action:	The alkyl group is attached to the guanine base of DNA, at the number 7 nitrogen atom of the imidazole ring. They stop tumor growth by crosslinking guanine nucleobases in DNA double-helix strands, directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. Th... show more » The alkyl group is attached to the guanine base of DNA, at the number 7 nitrogen atom of the imidazole ring. They stop tumor growth by crosslinking guanine nucleobases in DNA double-helix strands, directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. These drugs act nonspecifically. show less «
Route of elimination:	Urinary excretion of 14C-labeled thiotepa and metabolites in a 34-year old patient with metastatic carcinoma of the cecum who received a dose of 0.3 mg/kg intravenously was 63%.
Half Life:	1.5 to 4.1 hours
Clearance:	446 +/- 63 mL/min [female patients (45 to 84 years) with advanced stage ovarian cancer receiving 60 mg and 80 mg thiotepa by intravenous infusion on subsequent courses given at 4-week intervals]
Affected organisms:	Humans and other mammals

Interactions

Drug interaction:

Selegiline	Thiotepa, a strong CYP2B6 inhibitor, may decrease the metabolism and clearance of Selegiline, a CYP2B6 substrate. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Selegiline if Thiotepa is initiated, discontinued or dose changed.
Natalizumab	The immunosuppressant, Thiotepa, may increase the adverse effects of Natalizumab. Increased risk of Progressive Multifocal Leukoencephalopathy (PML) and other infections. Concurrent therapy should be avoided.
Trastuzumab	Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
Fosphenytoin	Possible increase in thiotepa levels
Bupropion	Thiotepa, a strong CYP2B6 inhibitor, may decrease the metabolism and clearance of Bupropion, a CYP2B6 substrate. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Bupropion if Thiotepa is initiated, discontinued or dose changed.

Selegiline	Thiotepa, a strong CYP2B6 inhibitor, may decrease the metabolism and clearance of Selegiline, a CYP2B6 substrate. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Selegiline if Thiotepa is initiated, discontinued or dose changed.
Natalizumab	The immunosuppressant, Thiotepa, may increase the adverse effects of Natalizumab. Increased risk of Progressive Multifocal Leukoencephalopathy (PML) and other infections. Concurrent therapy should be avoided.
Trastuzumab	Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
Fosphenytoin	Possible increase in thiotepa levels
Bupropion	Thiotepa, a strong CYP2B6 inhibitor, may decrease the metabolism and clearance of Bupropion, a CYP2B6 substrate. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Bupropion if Thiotepa is initiated, discontinued or dose changed.
Promethazine	Thiotepa, a strong CYP2B6 inhibitor, may decrease the metabolism and clearance of Promethazine, a CYP2B6 substrate. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Promethazine if Thiotepa is initiated, discontinued or dose changed.
Phenytoin	Possible increase in thiotepa levels
Ketamine	Thiotepa, a strong CYP2B6 inhibitor, may decrease the metabolism and clearance of Ketamine, a CYP2B6 substrate. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Ketamine if Thiotepa is initiated, discontinued or dose changed.
Irinotecan	Thiotepa, a strong CYP2B6 inhibitor, may decrease the metabolism and clearance of Irinotecan, a CYP2B6 substrate. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Irinotecan if Thiotepa is initiated, discontinued or dose changed.
Cyclophosphamide	Thiotepa, a strong CYP2B6 inhibitor, may decrease the metabolism and clearance of Cyclophosphamide, a CYP2B6 substrate. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Cyclophosphamide if Thiotepa is initiated, discontinued or dose changed.

Targets

Enzymes

Cytochrome P450 2B6

Cytochrome P450 3A4