Thiotepa

Thiotepa
Clinical data
Trade names	Tepadina
Other names	N,N',N''(-triethylenethiophosphoramide, INN, Thiotepa, Tepadina, Tepylute
AHFS/Drugs.com	Monograph
MedlinePlus	a682821
License data	US DailyMed: Thiotepa;
Pregnancy; category	AU: D;
Routes of; administration	Intravenous, intracavitary, intravesical
ATC code	L01AC01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Metabolism	Liver (CYP2B6, CYP3A)
Metabolites	Phase 1: Tetraethylenepentamine (tepa) ; Phase 2: Thiotepa-mercapturate
Elimination half-life	1.5–4.1 hours
Excretion	Kidney; 6 hours for thiotepa; 8 hours for TEPA
Identifiers
	IUPAC name 1,1′,1″-Phosphorothioyltriaziridine;
CAS Number	52-24-4 ;
PubChem CID	5453;
IUPHAR/BPS	7622;
DrugBank	DB04572 ;
ChemSpider	5254 ;
UNII	905Z5W3GKH;
KEGG	D00583 ;
ChEMBL	ChEMBL671 ;
CompTox Dashboard (EPA)	DTXSID0021339 ;
ECHA InfoCard	100.000.124
Chemical and physical data
Formula	C6H12N3PS
Molar mass	189.22 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	51.5 °C (124.7 °F)
Solubility in water	0.19 g/mL (water, 25 °C) ; Freely soluble in alcohol, diethyl ether and chloroform mg/mL (20 °C)
	SMILES S=P(N1CC1)(N2CC2)N3CC3;
	InChI InChI=1S/C6H12N3PS/c11-10(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2 ; Key:FOCVUCIESVLUNU-UHFFFAOYSA-N ;
	(what is this?) (verify)

Thiotepa (N,N',N''(-triethylenethiophosphoramide, INN^[7]), sold under the brand name Tepadina among others, is an anti-cancer medication.^[4]^[6]^[8]

Thiotepa is an organophosphorus compound with the formula (C₂H₄N)₃PS.^[9]

^ "Tepadina (Link Medical Products Pty Ltd T/A Link Pharmaceuticals)". Therapeutic Goods Administration (TGA). 28 September 2022. Archived from the original on 18 March 2023. Retrieved 29 April 2023.
^ "Cancer therapies". Health Canada. 8 May 2018. Retrieved 13 April 2024.
^ "Thiotepa 100 mg powder for concentrate for solution for infusion". (emc). 27 October 2022. Retrieved 14 August 2024.
^ ^a ^b "Tepadina- thiotepa injection, powder, for solution". DailyMed. Archived from the original on 12 August 2021. Retrieved 11 August 2021.
^ "Highlights of prescribing information" (PDF). www.accessdata.fda.gov.
^ ^a ^b "Tepadina EPAR". European Medicines Agency (EMA). 17 September 2018. Archived from the original on 6 March 2021. Retrieved 30 April 2021.
^ "International Non-Proprietary Names for Pharmaceutical Preparations. Recommended International Non-Proprietary Names (Rec. I.N.N.): List 4" (PDF). World Health Organization. March 1962. p. 111. Archived from the original (PDF) on 18 May 2016. Retrieved 27 November 2016.
^ Cite error: The named reference FDA was invoked but never defined (see the help page).
^ Maanen MJ, Smeets CJ, Beijnen JH (August 2000). "Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA)". Cancer Treatment Reviews. 26 (4): 257–268. doi:10.1053/ctrv.2000.0170. PMID 10913381.

[1] "Tepadina (Link Medical Products Pty Ltd T/A Link Pharmaceuticals)". Therapeutic Goods Administration (TGA). 28 September 2022. Archived from the original on 18 March 2023. Retrieved 29 April 2023.

[2] "Cancer therapies". Health Canada. 8 May 2018. Retrieved 13 April 2024.

[3] "Thiotepa 100 mg powder for concentrate for solution for infusion". (emc). 27 October 2022. Retrieved 14 August 2024.

[Tepadina_FDA_label-4] "Tepadina- thiotepa injection, powder, for solution". DailyMed. Archived from the original on 12 August 2021. Retrieved 11 August 2021.

[Tepylute_FDA_label-5] "Highlights of prescribing information" (PDF). www.accessdata.fda.gov.

[Tepadina_EPAR-6] "Tepadina EPAR". European Medicines Agency (EMA). 17 September 2018. Archived from the original on 6 March 2021. Retrieved 30 April 2021.

[INN-7] "International Non-Proprietary Names for Pharmaceutical Preparations. Recommended International Non-Proprietary Names (Rec. I.N.N.): List 4" (PDF). World Health Organization. March 1962. p. 111. Archived from the original (PDF) on 18 May 2016. Retrieved 27 November 2016.

[FDA-8] Cite error: The named reference FDA was invoked but never defined (see the help page).

[Maanen2000-9] Maanen MJ, Smeets CJ, Beijnen JH (August 2000). "Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA)". Cancer Treatment Reviews. 26 (4): 257–268. doi:10.1053/ctrv.2000.0170. PMID 10913381.

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