Record Information |
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Version | 2.0 |
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Creation Date | 2014-09-11 02:06:13 UTC |
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Update Date | 2014-12-24 20:26:56 UTC |
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Accession Number | T3D4716 |
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Identification |
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Common Name | Thiotepa |
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Class | Small Molecule |
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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. |
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Compound Type | - Drug
- Metabolite
- Organic Compound
- Synthetic Compound
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Chemical Structure | |
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Synonyms | |
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Chemical Formula | C6H12N3PS |
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Average Molecular Mass | 189.218 g/mol |
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Monoisotopic Mass | 189.049 g/mol |
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CAS Registry Number | 52-24-4 |
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IUPAC Name | tris(aziridin-1-yl)-λ⁵-phosphanethione |
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Traditional Name | thiophosphamide |
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SMILES | S=P(N1CC1)(N1CC1)N1CC1 |
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InChI Identifier | InChI=1S/C6H12N3PS/c11-10(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2 |
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InChI Key | InChIKey=FOCVUCIESVLUNU-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as organic thiophosphoric acids and derivatives. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure RP(R')(R'')=S, where R,R',R'' = O,N, halogen residue. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Organic thiophosphoric acids and derivatives |
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Sub Class | Not Available |
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Direct Parent | Organic thiophosphoric acids and derivatives |
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Alternative Parents | |
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Substituents | - Organic thiophosphoric acid or derivatives
- Azacycle
- Organoheterocyclic compound
- Aziridine
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 51.5°C | Boiling Point | Not Available | Solubility | 1.9E+005 mg/L (at 25°C) | LogP | 0.53 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0007-9700000000-870c297591c0a9b9707c | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0udj-2910000000-ba7d9f76d09c90907cd5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0udj-2910000000-ba7d9f76d09c90907cd5 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0900000000-0cd73bb1e3f4935cf116 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0005-3900000000-5c3374f9826ed342ca4e | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-8dc6d03ec98f9c80f9d2 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-2900000000-bb1e4366af9868c15a01 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-074s-0900000000-dc8c896ef045e2852518 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9100000000-7251e3acc37a1500dc98 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0900000000-1123ba8976a8239bb663 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-0900000000-103f3980559601ae7672 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f6x-9700000000-b8be72202a635e78e521 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-460ca1d15e5d5215d31f | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0900000000-acd27824890aefdaae3f | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9700000000-601e44410bd7bac39398 | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-00kn-6900000000-6d6b7c109663ea65ad79 | JSpectraViewer | MoNA | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | 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. |
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Metabolism | 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 |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | 1, carcinogenic to humans. (2) |
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Uses/Sources | 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. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB04572 |
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HMDB ID | HMDB15576 |
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PubChem Compound ID | 5453 |
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ChEMBL ID | CHEMBL671 |
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ChemSpider ID | 5254 |
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KEGG ID | C07641 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 128310 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Thiotepa |
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References |
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Synthesis Reference | John Kazan, “Process for producing thiotepa.” U.S. Patent US4918199, issued February, 1954. |
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MSDS | T3D4716.pdf |
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General 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. [10913381 ]
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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