thiotepa   Click here for help

GtoPdb Ligand ID: 7622

Synonyms: Tepadina® | Thioplex®
Approved drug
thiotepa is an approved drug (FDA (1959), EMA (2010))
Compound class: Synthetic organic
Comment: Thiotepa is an organophosphorus DNA alkylating anti-cancer chemotherapeutic [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 50.93
Molecular weight 189.05
XLogP 0.76
No. Lipinski's rules broken 0
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Canonical SMILES S=P(N1CC1)(N1CC1)N1CC1
Isomeric 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
No information available.
Summary of Clinical Use Click here for help
Thiotepa was originally used as an antineoplastic agent for various malignancies, including breast and ovarian adenocarcinoma and papillary carcinoma of the urinary bladder. Additionally, it is designated as an orphan drug by both the European Medicines Agency (EMA) and US FDA (both in 2007) for use as a preparative treatment prior to allogeneic or autologous haematopoietic progenitor cell transplantation.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Thiotepa is an organophosphorus compound that acts as a DNA alkylating agent. Alkylating agents inhibit tumour growth by cross-linking nucleotide bases in DNA double-helix strands. Drug treatment irreversibly interferes with DNA replication, RNA transcription and general disruption of nucleic acid function. This action causes cell death. A major side effect of most alkylating agents is bone marrow depression and myelosuppression. With thiotepa, this complication is utilised to clinical benefit to destroy haematopoietic progenitor cells in the bone marrow of patients requiring bone-marrow transplant.
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