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52-24-4 molecular structure
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tris(aziridin-1-yl)-λ5-phosphanethione

ChemBase ID: 4140
Molecular Formular: C6H12N3PS
Molecular Mass: 189.218341
Monoisotopic Mass: 189.04895503
SMILES and InChIs

SMILES:
P(=S)(N1CC1)(N1CC1)N1CC1
Canonical SMILES:
S=P(N1CC1)(N1CC1)N1CC1
InChI:
InChI=1S/C6H12N3PS/c11-10(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2
InChIKey:
FOCVUCIESVLUNU-UHFFFAOYSA-N

Cite this record

CBID:4140 http://www.chembase.cn/molecule-4140.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
tris(aziridin-1-yl)-λ5-phosphanethione
tris(aziridin-1-yl)-$l^{5}-phosphanethione
IUPAC Traditional name
thiophosphamide
ThioTEPA
Synonyms
1,1',1''-Phosphorothioyltriaziridine
N,N′,N″-Triethylenethiophosphoramide
Thio-Tep
Thiofozil
Thiotef
Tio-tef
Tiofozil
Tris(aziridinyl)phosphine sulfide
Thio-TEPA
Thiotepa
Thioplex
Tiofosyl
Tiofosfamid
1,1’,1’’-Phosphinothioylidynetrisaziridine
Tris(1-aziridinyl)phosphine Sulfide
AI 3-24916
CBC 806495
Girostan
N,N’,N’’-Triethylenethiophosphoramide
Oncotepa
Oncothio-tepa
Oncotiotepa
Phosphorothioic Acid Triethylenetriamide
Tespamin
Tespamine
Tris(aziridinyl)phosphine-thioxide
Thio-TEPA
Triethylenethiophosphoramide
CAS Number
52-24-4
EC Number
200-135-7
MDL Number
MFCD00145452
PubChem SID
24900346
160967572
PubChem CID
5453

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) -1.0273812  LogD (pH = 7.4) -1.0273805 
Log P -1.0273805  Molar Refractivity 50.7222 cm3
Polarizability 20.823643 Å3 Polar Surface Area 9.03 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 0.17  LOG S -1.31 
Solubility (Water) 9.27e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Benzene expand Show data source
Apperance
solid expand Show data source
White Solid expand Show data source
Melting Point
52-54°C expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
SZ2975000 expand Show data source
European Hazard Symbols
Highly toxic Highly toxic (T+) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
45-46-28 expand Show data source
Safety Statements
53-22-26-36/37/39-45 expand Show data source
TSCA Listed
false expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H300-H350 expand Show data source
GHS Precautionary statements
P201-P264-P301 + P310-P308 + P313 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 2 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
98% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C6H12N3PS expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB04572 external link
Item Information
Drug Groups approved
Description 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
Humans and other mammals
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]
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]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1775 external link
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 external link
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 external link
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 IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle 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

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INTERNET

INTERNET

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