NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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tris(aziridin-1-yl)-λ5-phosphanethione
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tris(aziridin-1-yl)-$l^{5}-phosphanethione
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IUPAC Traditional name
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Synonyms
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1,1',1''-Phosphorothioyltriaziridine
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N,N′,N″-Triethylenethiophosphoramide
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Thio-Tep
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Thiofozil
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Thiotef
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Tio-tef
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Tiofozil
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Tris(aziridinyl)phosphine sulfide
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Thio-TEPA
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Thiotepa
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Thioplex
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Tiofosyl
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Tiofosfamid
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1,1’,1’’-Phosphinothioylidynetrisaziridine
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Tris(1-aziridinyl)phosphine Sulfide
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AI 3-24916
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CBC 806495
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Girostan
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N,N’,N’’-Triethylenethiophosphoramide
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Oncotepa
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Oncothio-tepa
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Oncotiotepa
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Phosphorothioic Acid Triethylenetriamide
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Tespamin
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Tespamine
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Tris(aziridinyl)phosphine-thioxide
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Thio-TEPA
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Triethylenethiophosphoramide
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CAS Number
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EC Number
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MDL Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
ALOGPS 2.1
H Acceptors
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3
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H Donor
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0
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LogD (pH = 5.5)
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-1.0273812
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LogD (pH = 7.4)
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-1.0273805
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Log P
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-1.0273805
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Molar Refractivity
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50.7222 cm3
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Polarizability
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20.823643 Å3
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Polar Surface Area
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9.03 Å2
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Rotatable Bonds
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3
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Lipinski's Rule of Five
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true
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Log P
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0.17
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LOG S
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-1.31
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Solubility (Water)
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9.27e+00 g/l
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DETAILS
DETAILS
DrugBank
Selleck Chemicals
Sigma Aldrich
TRC
DrugBank -
DB04572
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Item |
Information |
Drug Groups
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approved |
Description
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N,N'N'-triethylenethiophosphoramide (ThioTEPA) is a cancer chemotherapeutic member of the alkylating agent group, now in use for over 50 years. It is a stable derivative of N,N',N''- triethylenephosphoramide (TEPA). It is mostly used to treat breast cancer, ovarian cancer and bladder cancer. It is also used as conditioning for Bone marrow transplantation. Its main toxicity is myelosuppression. |
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 nonspecifically. |
Affected Organisms |
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Humans and other mammals |
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Half Life |
1.5 to 4.1 hours |
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%. |
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] |
References |
• |
Maanen MJ, Smeets CJ, Beijnen JH: Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA). Cancer Treat Rev. 2000 Aug;26(4):257-68.
[Pubmed]
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• |
Maanen MJ, Smeets CJ, Beijnen JH: Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA). Cancer Treat Rev. 2000 Aug;26(4):257-68.
[Pubmed]
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External Links |
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Selleck Chemicals -
S1775
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Research Area: Cancer Biological Activity: Thiotepa(Thioplex) is an alkylating agent used to treat cancer.. It is an analogue of N,N’,N’’- triethylenephosphoramide (TEPA). This molecule features tetrahedral phosphorus and is structurally akin to phosphate. It is derived from aziridine and thiophosphoryl chloride. Thiotepa has been previously used in the palliation of a wide variety of neoplastic diseases. The more consistent results have been seen in: adenocarcinoma of the breast, adenocarcinoma of the ovary, superficial papillary carcinoma of the urinary bladder and for controlling intracavitary effusions secondary to diffuse or localized neoplastic diseases of various serosal cavities. [1] |
Sigma Aldrich -
T6069
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Application Thio-TEPA (N,N’N’-triethylenethiophosphoramide) is used as a cancer chemotherapeutic, alkylating agent. It is used to treat various kinds of cancer such as breast, ovarian and bladder cancer. It is also used as conditioning treatment prior to haematopoietic progenitor cell transplantation (HPCT)1,2. Biochem/physiol Actions The unstable nitrogen-carbon groups alkylate with DNA which causes irreversible DNA damage. They stop tumor growth by crosslinking guanine nucleobases in DNA double-helix strands, directly attacking DNA. The DNA strands are unable to uncoil and separate which halts cell division1. |
Toronto Research Chemicals -
T776650
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This substance is listed as a known human carcinogen. It is useful for the treatment of cancers, especially cancers resistant to chemotherapy. Antineoplastic. |
REFERENCES
REFERENCES
From Suppliers
Google Scholar
PubMed
Google Books
- • Maanen MJ, Smeets CJ, Beijnen JH: Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA). Cancer Treat Rev. 2000 Aug;26(4):257-68. Pubmed
- • Maanen MJ, Smeets CJ, Beijnen JH: Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA). Cancer Treat Rev. 2000 Aug;26(4):257-68. Pubmed
- • http://en.wikipedia.org/wiki/Thiotepa
- • Kyriakou, C., et al.: J. Clin. Oncol., 27, 3262 (2009)
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PATENTS
PATENTS
PubChem Patent
Google Patent