Thiotepa

Base Information Edit

Chemical Name:Thiotepa
CAS No.:52-24-4
Deprecated CAS:639-23-6,85177-92-0,1631739-26-8,1631739-26-8,85177-92-0
Molecular Formula:C6H12N3PS
Molecular Weight:189.221
Hs Code.:2933999552
European Community (EC) Number:200-135-7
NSC Number:758455,6396
UN Number:2811
UNII:905Z5W3GKH
DSSTox Substance ID:DTXSID0021339
Nikkaji Number:J2.307H
Wikipedia:Thiotepa
Wikidata:Q416507
NCI Thesaurus Code:C875
RXCUI:10473
Pharos Ligand ID:UR3FXJZP9BKM
Metabolomics Workbench ID:43621
ChEMBL ID:CHEMBL671
Mol file:52-24-4.mol

Synonyms:AI3 24916;AI3-24916;AI324916;Girostan;NSC 6396;NSC-6396;NSC6396;Tespa;Tespamin;Thio Tepa;Thio-Tepa;Thiophosphamide;Thiotepa;Triethylenethiophosphoramide;Tris(1-aziridinyl)phosphine Sulfide

Suppliers and Price of Thiotepa

Supply Marketing:Edit

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
Triethylenethiophosphoramide
500mg
$ 275.00

Sigma-Aldrich
Thio-TEPA 98%, solid
1g
$ 216.00

Sigma-Aldrich
Thio-TEPA United States Pharmacopeia (USP) Reference Standard
500mg
$ 366.00

Medical Isotopes, Inc.
Thiotepa
50 mg
$ 560.00

DC Chemicals
thiotepa >98%
250 mg
$ 500.00

DC Chemicals
thiotepa >98%
100 mg
$ 250.00

CSNpharm
Thio-TEPA
25mg
$ 35.00

CSNpharm
Thio-TEPA
100mg
$ 48.00

Cayman Chemical
Thio-TEPA ≥98%
500mg
$ 81.00

Cayman Chemical
Thio-TEPA ≥98%
250mg
$ 43.00

Total 138 raw suppliers

Chemical Property of Thiotepa Edit

Chemical Property:

Appearance/Colour:white crystals or powder
Vapor Pressure:0.00695mmHg at 25°C
Melting Point:54-57 °C
Refractive Index:1.708
Boiling Point:270.2 °C at 760 mmHg
PKA:2.74±0.20(Predicted)
Flash Point:117.2 °C
PSA：50.93000
Density:1.5 g/cm³
LogP:0.62200
Storage Temp.:2-8°C
Solubility.:Soluble in benzene, acetone and methanol.
Water Solubility.:19 g/100 mL (25 ºC)
XLogP3:0.5
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:189.04895557
Heavy Atom Count:11
Complexity:194
Transport DOT Label:Poison

Purity/Quality:

99% ^*data from raw suppliers

Triethylenethiophosphoramide ^*data from reagent suppliers

Safty Information:

Pictogram(s): T+
Hazard Codes:T+
Statements: 45-46-28
Safety Statements: 53-22-26-36/37/39-45-36/37-28

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Chemical Classes:Pesticides -> Insect Sterilants
Drug Classes:Antineoplastic Agents, Alkylating Agents
Canonical SMILES:C1CN1P(=S)(N2CC2)N3CC3
Recent ClinicalTrials:Graft Versus Host Disease-Reduction Strategies for Donor Blood Stem Cell Transplant Patients With Acute Leukemia or Myelodysplastic Syndrome (MDS)
Recent EU Clinical Trials:Optimizing MATRix as remission induction in PCNSL:
Recent NIPH Clinical Trials:A single center Phase II study for the safety and efficacy of upfront high dose chemotherapy with thiotepa and busulfan followed by autologous peripheral blood stem cell transplantation for primary central nervous system lymphoma.
Description Thiotepa, a tertiary aziridine, is less reactive than quaternary aziridinium compounds and is classified as a weak alkylator. It is possible for the nitrogen atoms to be protonate before reacting with DNA (a positively charged aziridine is more reactive than the un-ionized aziridine), but the electron-withdrawing effect of the sulfur atom decreases the pKa to approximately six, which keeps the percentage ionized at pH 7.4 relatively low. Thiotepa undergoes oxidative desulfuration, forming an active cytotoxic metabolite known as TEPA (triethylenephosphoramide).
Uses Tri(1-aziridinyl)phosphine sulfide is useful for the treatment of cancers, especially cancers resistant to chemotherapy. Antineoplastic. 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 hematopoietic progenitor cell transplantation (HPCT) This substance is listed as a known human carcinogen. It is useful for the treatment of cancers, especially cancers resistant to chemotherapy. Antineoplastic. suzuki reaction antiseborrheic, antipruritic Insect sterilant.
Indications Although thiotepa is chemically less reactive than the nitrogen mustards, it is thought to act by similar mechanisms. Its oral absorption is erratic. After intravenous injection, the plasma half-life is less than 2 hours. Urinary excretion accounts for 60 to 80% of eliminated drug. Thiotepa has antitumor activity against ovarian and breast cancers and lymphomas. However, it has been largely supplanted by cyclophosphamide and other nitrogen mustards for treatment of these diseases. It is used by direct instillation into the bladder for multifocal local bladder carcinoma. Nausea and myelosuppression are the major toxicities of thiotepa. It is not a local vesicant and has been safely injected intramuscularly and even intrathecally.
Therapeutic Function Antineoplastic
Clinical Use This antineoplastic agent is most commonly employed in the treatment of ovarian and breast cancers, as well as papillary carcinoma of the bladder.
Drug interactions Potentially hazardous interactions with other drugs Antipsychotics: avoid concomitant use with clozapine. Avoid concomitant use with other myelosuppressive agents. Administration

Technology Process of Thiotepa

There total 2 articles about Thiotepa which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.7%