THIOTEPA

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H12N3PS
Molecular Weight	189.218
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

S=P(N1CC1)(N2CC2)N3CC3

InChI

InChIKey=FOCVUCIESVLUNU-UHFFFAOYSA-N

InChI=1S/C6H12N3PS/c11-10(7-1-2-7,8-3-4-8)9-5-6-9/h1-6H2

HIDE SMILES / InChI

Molecular Formula	C6H12N3PS
Molecular Weight	189.218
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/075547Orig1s006lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/10913381
Curator's Comment: Description was created based on several sources, including http://www.drugbank.ca/drugs/DB04572

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). The radiomimetic action of thiotepa is believed to occur through the release of ethylenimine radicals which, like irradiation, disrupt the bonds of DNA. One of the principal bond disruptions is initiated by alkylation of guanine at the N-7 position, which severs the linkage between the purine base and the sugar and liberates alkylated guanines. Thiotepa has been 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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 278 Target ID: CHEMBL2311221 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/075547Orig1s006lbl.pdf \| http://www.drugbank.ca/drugs/DB04572	Crosslinking Agent 81

Conditions

Condition	Modality	Highest Phase	Product
Breast adenocarcinoma 7 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/2001/75-547_Thiotepa_prntlbl.pdf	Primary	Approved 8429	THIOTEPA Approved Use Adenocarcinoma of the breast. Launch Date 1959
Adenocarcinoma of the ovary 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/075547Orig1s006lbl.pdf	Primary	Approved 8429	THIOTEPA Approved Use Adenocarcinoma of the ovary. Launch Date 1959
Superficial papillary carcinoma of the urinary bladder 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/2001/75-547_Thiotepa_prntlbl.pdf	Primary	Approved 8429	THIOTEPA Approved Use For the treatment of superficial papillary carcinoma of the urinary bladder Launch Date 1959

C_max

Value	Dose	Co-administered	Analyte	Population
8.91 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11249051	200 mg/m² single, intravenous dose: 200 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		THIOTEPA plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
28.24 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11249051	200 mg/m² single, intravenous dose: 200 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		THIOTEPA plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.15 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11249051	200 mg/m² single, intravenous dose: 200 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		THIOTEPA plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
2.55 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf	20 mg/m² unknown, intravenous dose: 20 mg/m² route of administration: Intravenous experiment type: UNKNOWN co-administered:		THIOTEPA unknown	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
85% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf	20 mg/m² unknown, intravenous dose: 20 mg/m² route of administration: Intravenous experiment type: UNKNOWN co-administered:		THIOTEPA unknown	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
65 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 65 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 65 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/1710167 Page: p.3172	unhealthy, 25-74 n = 8 Health Status: unhealthy Condition: Cancer Age Group: 25-74 Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/1710167 Page: p.3172	Other AEs: Leukopenia, Thrombocytopenia... Other AEs: Leukopenia (grade 3, 25%) Thrombocytopenia (grade 4, 12.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/1710167 Page: p.3172
75 mg/m2 1 times / 3 weeks multiple, intravenous Studied dose Dose: 75 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 75 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/1710167 Page: p.3172	unhealthy, 25-74 n = 7 Health Status: unhealthy Condition: Cancer Age Group: 25-74 Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/1710167 Page: p.3172	DLT: Leukopenia, Thrombocytopenia... Dose limiting toxicities: Leukopenia (grade 3, 28.6%) Thrombocytopenia (grade 3, 28.6%) Thrombocytopenia (grade 4, 28.6%) Sources: https://pubmed.ncbi.nlm.nih.gov/1710167 Page: p.3172
750 mg/m2 2 times / day multiple, intravenous (total) MTD Dose: 750 mg/m2, 2 times / day Route: intravenous Route: multiple Dose: 750 mg/m2, 2 times / day Co-administed with:: Busulfan, p.o(30 mg/m(2); 4 times/day; 4 days) Etoposide. i.v.(800 mg/m(2); q.d; 3 days) Sources: https://pubmed.ncbi.nlm.nih.gov/10531568 Page: p.453	unhealthy, 2–16 n = 6 Health Status: unhealthy Condition: Disseminated solid tumors Age Group: 2–16 Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/10531568 Page: p.453	Other AEs: Mucositis, Gastrointestinal toxicity... Other AEs: Mucositis (grade 3, 33.3%) Gastrointestinal toxicity (grade 3, 33.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/10531568 Page: p.453
60 mg/m2 1 times / month multiple, intravenous MTD Dose: 60 mg/m2, 1 times / month Route: intravenous Route: multiple Dose: 60 mg/m2, 1 times / month Co-administed with:: pentoxifylline, p.o(1600 mg; t.i.d; 4 doses) Sources: https://pubmed.ncbi.nlm.nih.gov/9816047 Page: p.793	unhealthy, 30-76 n = 25 Health Status: unhealthy Condition: Breast cancer Age Group: 30-76 Sex: F Population Size: 25 Sources: https://pubmed.ncbi.nlm.nih.gov/9816047 Page: p.793	Other AEs: Leukopenia, Leukopenia... Other AEs: Leukopenia (grade 3, 16%) Leukopenia (grade 4, 8%) Thrombocytopenia (grade 3, 16%) Thrombocytopenia (grade 4, 12%) Sources: https://pubmed.ncbi.nlm.nih.gov/9816047 Page: p.793
5 mg/kg 2 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 2 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 2 times / day Co-administed with:: Busulfan, I.V(weight-based dose) Cyclophosphamide, I.V(40 mg/kg/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Class 3 Beta-Thalassemia Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf Page: p.1	Disc. AE: Myelosuppression, Bone marrow failure... AEs leading to discontinuation/dose reduction: Myelosuppression (severe) Bone marrow failure (severe) Disorder fetal Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf Page: p.1

AEs

AE	Significance	Dose	Population
Leukopenia	grade 3, 25%	65 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 65 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 65 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/1710167 Page: p.3172	unhealthy, 25-74 n = 8 Health Status: unhealthy Condition: Cancer Age Group: 25-74 Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/1710167 Page: p.3172
Thrombocytopenia	grade 4, 12.5%	65 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 65 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 65 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/1710167 Page: p.3172	unhealthy, 25-74 n = 8 Health Status: unhealthy Condition: Cancer Age Group: 25-74 Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/1710167 Page: p.3172
Leukopenia	grade 3, 28.6% DLT	75 mg/m2 1 times / 3 weeks multiple, intravenous Studied dose Dose: 75 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 75 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/1710167 Page: p.3172	unhealthy, 25-74 n = 7 Health Status: unhealthy Condition: Cancer Age Group: 25-74 Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/1710167 Page: p.3172
Thrombocytopenia	grade 3, 28.6% DLT	75 mg/m2 1 times / 3 weeks multiple, intravenous Studied dose Dose: 75 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 75 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/1710167 Page: p.3172	unhealthy, 25-74 n = 7 Health Status: unhealthy Condition: Cancer Age Group: 25-74 Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/1710167 Page: p.3172
Thrombocytopenia	grade 4, 28.6% DLT	75 mg/m2 1 times / 3 weeks multiple, intravenous Studied dose Dose: 75 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 75 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/1710167 Page: p.3172	unhealthy, 25-74 n = 7 Health Status: unhealthy Condition: Cancer Age Group: 25-74 Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/1710167 Page: p.3172
Gastrointestinal toxicity	grade 3, 33.3%	750 mg/m2 2 times / day multiple, intravenous (total) MTD Dose: 750 mg/m2, 2 times / day Route: intravenous Route: multiple Dose: 750 mg/m2, 2 times / day Co-administed with:: Busulfan, p.o(30 mg/m(2); 4 times/day; 4 days) Etoposide. i.v.(800 mg/m(2); q.d; 3 days) Sources: https://pubmed.ncbi.nlm.nih.gov/10531568 Page: p.453	unhealthy, 2–16 n = 6 Health Status: unhealthy Condition: Disseminated solid tumors Age Group: 2–16 Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/10531568 Page: p.453
Mucositis	grade 3, 33.3%	750 mg/m2 2 times / day multiple, intravenous (total) MTD Dose: 750 mg/m2, 2 times / day Route: intravenous Route: multiple Dose: 750 mg/m2, 2 times / day Co-administed with:: Busulfan, p.o(30 mg/m(2); 4 times/day; 4 days) Etoposide. i.v.(800 mg/m(2); q.d; 3 days) Sources: https://pubmed.ncbi.nlm.nih.gov/10531568 Page: p.453	unhealthy, 2–16 n = 6 Health Status: unhealthy Condition: Disseminated solid tumors Age Group: 2–16 Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/10531568 Page: p.453
Leukopenia	grade 3, 16%	60 mg/m2 1 times / month multiple, intravenous MTD Dose: 60 mg/m2, 1 times / month Route: intravenous Route: multiple Dose: 60 mg/m2, 1 times / month Co-administed with:: pentoxifylline, p.o(1600 mg; t.i.d; 4 doses) Sources: https://pubmed.ncbi.nlm.nih.gov/9816047 Page: p.793	unhealthy, 30-76 n = 25 Health Status: unhealthy Condition: Breast cancer Age Group: 30-76 Sex: F Population Size: 25 Sources: https://pubmed.ncbi.nlm.nih.gov/9816047 Page: p.793
Thrombocytopenia	grade 3, 16%	60 mg/m2 1 times / month multiple, intravenous MTD Dose: 60 mg/m2, 1 times / month Route: intravenous Route: multiple Dose: 60 mg/m2, 1 times / month Co-administed with:: pentoxifylline, p.o(1600 mg; t.i.d; 4 doses) Sources: https://pubmed.ncbi.nlm.nih.gov/9816047 Page: p.793	unhealthy, 30-76 n = 25 Health Status: unhealthy Condition: Breast cancer Age Group: 30-76 Sex: F Population Size: 25 Sources: https://pubmed.ncbi.nlm.nih.gov/9816047 Page: p.793
Thrombocytopenia	grade 4, 12%	60 mg/m2 1 times / month multiple, intravenous MTD Dose: 60 mg/m2, 1 times / month Route: intravenous Route: multiple Dose: 60 mg/m2, 1 times / month Co-administed with:: pentoxifylline, p.o(1600 mg; t.i.d; 4 doses) Sources: https://pubmed.ncbi.nlm.nih.gov/9816047 Page: p.793	unhealthy, 30-76 n = 25 Health Status: unhealthy Condition: Breast cancer Age Group: 30-76 Sex: F Population Size: 25 Sources: https://pubmed.ncbi.nlm.nih.gov/9816047 Page: p.793
Leukopenia	grade 4, 8%	60 mg/m2 1 times / month multiple, intravenous MTD Dose: 60 mg/m2, 1 times / month Route: intravenous Route: multiple Dose: 60 mg/m2, 1 times / month Co-administed with:: pentoxifylline, p.o(1600 mg; t.i.d; 4 doses) Sources: https://pubmed.ncbi.nlm.nih.gov/9816047 Page: p.793	unhealthy, 30-76 n = 25 Health Status: unhealthy Condition: Breast cancer Age Group: 30-76 Sex: F Population Size: 25 Sources: https://pubmed.ncbi.nlm.nih.gov/9816047 Page: p.793
Disorder fetal	Disc. AE	5 mg/kg 2 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 2 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 2 times / day Co-administed with:: Busulfan, I.V(weight-based dose) Cyclophosphamide, I.V(40 mg/kg/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Class 3 Beta-Thalassemia Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf Page: p.1
Bone marrow failure	severe Disc. AE	5 mg/kg 2 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 2 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 2 times / day Co-administed with:: Busulfan, I.V(weight-based dose) Cyclophosphamide, I.V(40 mg/kg/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Class 3 Beta-Thalassemia Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf Page: p.1
Myelosuppression	severe Disc. AE	5 mg/kg 2 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 2 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 2 times / day Co-administed with:: Busulfan, I.V(weight-based dose) Cyclophosphamide, I.V(40 mg/kg/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Class 3 Beta-Thalassemia Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf Page: p.1

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2B6 810 CYP2C8 911 CYP2C19 1478 CYP2E1 882	CYP2B6 664

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11950782/	no
CYP2C19 1553	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11950782/	no
CYP2C8 965	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11950782/	no
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11950782/	no
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11950782/	no
CYP2E1 970	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11950782/	no
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11950782/	no
CYP2B6 1001	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11950782/	strong [Ki 4.8 uM]	likely (co-administration study) Comment: noncompetitive inhibition. Ki value obtained using HLM; may increase the exposure of drugs that are substrates of CYP2B6 in patients; however, the clinical relevance of this in vitro interaction is unknown Sources: https://pubmed.ncbi.nlm.nih.gov/11950782/

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf#page=10; https://link.springer.com/article/10.1007/s00280-004-0922-y Page: 10.0	yes		likely (co-administration study) Comment: Avoid coadministration of strong CYP3A4 inhibitors (e.g., itraconazole, clarithromycin, ritonavir) and strong CYP3A4 inducers (e.g., rifampin, phenytoin); exposure to thiotepa was significantly reduced (29%) when coadministered with phenytoin (CYP inducer) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf#page=10; https://link.springer.com/article/10.1007/s00280-004-0922-y Page: 10.0
CYP2B6 664	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf#page=10; https://link.springer.com/article/10.1007/s00280-004-0922-y Page: 10.0	yes		weak (co-administration study) Comment: exposure to thiotepa was significantly reduced (29%) when coadministered with phenytoin (CYP inducer); Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf#page=10; https://link.springer.com/article/10.1007/s00280-004-0922-y Page: 10.0

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY558133	https://www.001chemical.com/chem/52-24-4
3B Scientific (Wuhan) Corp	3B3-059218	http://www.3bsc.com/index/pro_info.php?id=98039
AA Blocks	AA006VEM	https://www.aablocks.com/goods/Goods/detail?id=AA006VEM
AHH Chemical co.,ltd	MT-00905	http://www.ahhchemical.com/product/MT-00905.html
AK Scientific, Inc. (AKSCI)	Y0223	http://www.aksci.com/item_detail.php?cat=Y0223
Aaron Chemicals	AR006W6E	http://www.aaronchem.com/52-24-4
AbMole Bioscience	M6008	http://www.abmole.com/products/thio-tepa.html
Acadechem	ACDR-018556	http://acadechemical.com/product/31135
Acorn PharmaTech	ACN-034979	http://www.acornpharmatech.com/
Alfa Aesar	H61778	https://www.alfa.com/en/catalog/H61778/
Alfa Chemistry	AP52244	https://reagents.alfa-chemistry.com/product/thiotepa-cas-52-24-4-12480.html
Alfa Chemistry	ACM52244	https://www.alfa-chemistry.com/product/triethylenethiophosphoramide-cas-52-24-4-284757.html
Alfa Chemistry	52-24-4	https://www.alfa-chemistry.com/triethylenethiophosphoramide-product-52-24-4-284757.htm
Alinda	ALBB-034802	http://alinda.ru/finechem_en_.html?i=ALBB-034802
Allbio Pharm Co., Ltd	AB00387	http://www.allbiopharm.com/product/n/AB00387
Alsachim	4087	http://www.alsachim.com/product-C5393-glo.bal-view.html
Ambeed	A496771	https://www.ambeed.com/products/52-24-4.html
Angene	AGN-PC-0SCGN6	http://www.angenechemical.com/productshow/AGN-PC-0SCGN6.html
Anward	ANW-58232	http://www.anward.com/pro_result/44683
ApexBio Technology	B3742	http://www.apexbt.com/thio-tepa.html
Aronis	ARONIS24177	http://www.aronis.ru/store/index.php?main_page=product_info&cPath=1&products_id=1313
Aurora Fine Chemicals LLC	K02.103.785	http://online.aurorafinechemicals.com/info?ID=K02.103.785
Aurum Pharmatech LLC	Z-0841	http://www.Aurumpharmatech.com/Product/ProductDetails/Z_0841
BLD Pharm	BD153994	http://www.bldpharm.com/products/52-24-4.html
BOC Sciences	52-24-4	https://www.bocsci.com/thiotepa-cas-52-24-4-item-84-465345.html
BioChemPartner	BCP04110	http://www.biochempartner.com/52-24-4-BCP04110
BioCrick	BCC5354	http://www.biocrick.com/Thio-TEPA-BCC5354.html
BioSynth	Q-201826	https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/Q-201826.html
CSNpharm	CSN12081	https://www.csnpharm.com/products/thio-tepa.html
Chem Scene	CS-3119	http://www.chemscene.com/52-24-4.html
ChemMol	44024343	http://www.chemmol.com/chemmol/44024343.html
ChemMol	49417196	http://www.chemmol.com/chemmol/49417196.html
ChemMol	80101321	http://www.chemmol.com/chemmol/80101321.html
ChemShuttle	153574	http://www.chemshuttle.com/catalogsearch/result/?q=52-24-4&cat=
Chemspace	CSSB00015194678	https://chem-space.com/CSSB00015194678
Clearsynth	CS-T-62309	https://www.clearsynth.com/en/CST62309.html
DC Chemicals	DC9298	http://www.dcchemicals.com/product_show-thiotepa.html
Enamine	Z2574360269	https://www.enaminestore.com/catalog/Z2574360269
Finetech	FT-0600281	http://www.finetechnology-ind.com/prod/detail/pub/52-24-4.html
Glentham Life Sciences	GP6020	http://www.glentham.com/products/product/GP6020/
Hairui	HR126340	http://www.hairuichem.com/en/product/52-24-4.html
Matrix Scientific	58443	https://www.matrixscientific.com/058443.html
MedChem Express	HY-17574	https://www.medchemexpress.com/Thio-TEPA.html
MolPort	MolPort-001-783-551	https://www.molport.com/shop/molecule-link/MolPort-001-783-551
Molcore	MC558133	https://www.molcore.com/product/52-24-4
MuseChem	I003904	https://www.musechem.com/product/I003904.html
OChem	6481	http://www.ocheminc.com/index.php?act=psearch&pid=145T452
Oakwood	223000	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=103999&ExtHyperLink=1
Renno Tech	RL03925	http://www.rennotech.com/product_show.asp?id=4245
Selleck Chemicals	S1775	http://www.selleckchem.com/products/thiotepa-thioplex.html
Shangyu Catsyn Co., Ltd.	GC10080	http://www.catsyn.com/product/52-24-4.html
Sigma-Aldrich	T6069_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/t6069?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1664000_USP	https://www.sigmaaldrich.com/catalog/product/usp/1664000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S545258	http://www.smolecule.com/products/s545258
THE BioTek	bt-284642	https://www.thebiotek.com/product/inhibitors/bt-284642
abcr GmbH	AB425425	http://www.abcr.com/shop/en/AB425425
iChemical	EBD4234	http://www.ichemical.com/chemicals/cas-52-24-4
mcule	MCULE-5478761622	https://mcule.com/MCULE-5478761622/

PubMed

Title	Date	PubMed
Pancytopenia and generalized sepsis following treatment of cancer of the bladder with instillations of triethylene thiophosphoramide.	1967 Mar	4960046
Prolonged apnea after succinylcholine in a case treated with cytostatics for cancer.	1972 Sep-Oct	4672170
The morphologic effects of mitomycin C in mammalian urinary bladder.	1981 Jun 1	6790156
Single and sequential combination intravesical chemotherapy of murine bladder cancer.	1982 Feb	6800090
A phase I-II study of high-dose cyclophosphamide, thiotepa and escalating doses of mitoxantrone with autologous stem cell rescue in patients with refractory malignancies.	1990 Dec	1982927
Biotransformation of N,N',N''-triethylenethiophosphoramide: oxidative desulfuration to yield N,N',N''-triethylenephosphoramide associated with suicide inactivation of a phenobarbital-inducible hepatic P-450 monooxygenase.	1990 Feb 1	2105156
Severe polyneuropathy and motor loss after intrathecal thiotepa combination chemotherapy: description of two cases.	1990 Oct	2131034
The role of human glutathione S-transferase isoenzymes in the formation of glutathione conjugates of the alkylating cytostatic drug thiotepa.	1995 Apr 15	7712478
A phase II trial of vinorelbine and thiotepa in metastatic breast cancer.	1995 Feb	7786825
Multiple myeloma after treatment of essential thrombocythemia.	1995 Jan	7817232
Inhibitory effects of combinations of HER-2/neu antibody and chemotherapeutic agents used for treatment of human breast cancers.	1999 Apr 1	10327070
Hprt mutant frequency and molecular analysis of Hprt mutations in Fischer 344 rats treated with thiotepa.	1999 Feb	10069464
Pilot trial of cytoprotection with amifostine given with high-dose chemotherapy and autologous peripheral blood stem cell transplantation.	2000 Aug	10955873
Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA).	2000 Aug	10913381
[Establishment of MRP-overexpression subline of bladder carcinoma and its MDR phenotype].	2000 Jul	11778547
High-dose carmustine, thiotepa and etoposide followed by autologous bone marrow rescue for the treatment of high risk central nervous system tumors.	2000 Jul	10918425
Retrovirus-mediated expression of the base excision repair proteins, formamidopyrimidine DNA glycosylase or human oxoguanine DNA glycosylase, protects hematopoietic cells from N,N',N"-triethylenethiophosphoramide (thioTEPA)-induced toxicity in vitro and in vivo.	2001 Jul 1	11431349
Thiotepa and fludarabine (TT-FLUDA) as conditioning regimen in poor candidates for conventional allogeneic hemopoietic stem cell transplant.	2001 Sep	11669300
Sensitivity of p53-deficient cells to oxaliplatin and thio-TEPA (N, N', N" triethylenethiophosphoramide).	2002 Apr	12058967
Factors affecting progression-free survival in hormone-dependent metastatic breast cancer patients receiving high-dose chemotherapy and hematopoietic progenitor cell transplantation: role of maintenance endocrine therapy.	2002 May	12058236
High-dose thiotepa and etoposide in children with poor-prognosis brain tumors.	2004 May 15	15139067
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Contribution of CYP2C9, CYP2A6, and CYP2B6 to valproic acid metabolism in hepatic microsomes from individuals with the CYP2C91/1 genotype.	2006 Dec	16945988
Risk factors for hepatic veno-occlusive disease: a retrospective unicentric study in 116 children autografted after a high-dose BU-thiotepa regimen.	2008 Oct	18587430
Breast cancer management: the road to today.	2008 Oct 1	18798545
Excessive toxicity of once daily i.v. BU, melphalan and thiotepa followed by auto SCT on patients with non-Hodgkin's lymphoma.	2010 Apr	19767780
Zebrafish (Danio rerio) embryos as a model for testing proteratogens.	2011 Mar 15	21237239
Efficient monitoring of in vivo pig-a gene mutation and chromosomal damage: summary of 7 published studies and results from 11 new reference compounds.	2012 Dec	22923490

Patents

Sample Use Guides

In Vivo Use Guide

Thiotepa may be given by rapid intravenous administration in doses of 0.3 to 0.4 ug/kg. Doses should be given at 1 to 4 week intervals.

Route of Administration: Intravenous

In Vitro Use Guide

The cytotoxicity of thiotepa toward MCF-7 cells was markedly dependent on the presence of oxygen during the period of drug exposure, with a 3-log greater cell kill at 500 umol with cells that were normally oxygenated compared with hypoxic cells.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:12:13 GMT 2023` Edited by `admin` on `Fri Dec 15 15:12:13 GMT 2023`
Record UNII	905Z5W3GKH
Record Status	`Validated (UNII)`
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Name

Type

Language

THIOTEPA

Official Name

English

thiotepa [INN]

Common Name

English

TRIS(1-AZIRIDINYL)PHOSPHINE SULFIDE

Systematic Name

English

THIOTEPA [USP MONOGRAPH]

Common Name

English

1,1',1''-PHOSPHOROTHIOYLTRIAZIRIDINE

Systematic Name

English

NSC-6396

Code

English

THIOTEPA [ORANGE BOOK]

Common Name

English

AZIRIDINE,1,1',1''-PHOSPHINOTHIOYLIDYNETRIS-

Common Name

English

THIOTEPA [MART.]

Common Name

English

Thiotepa [WHO-DD]

Common Name

English

1,1',1''-PHOSPHINOTHIOYLIDYNETRIS(AZIRIDINE)

Common Name

English

THIOTEPA [MI]

Common Name

English

THIOTEPA [JAN]

Common Name

English

TEPADINA

Brand Name

English

THIOPLEX

Brand Name

English

THIOTEPA [HSDB]

Common Name

English

THIOTEPA [IARC]

Common Name

English

THIOTEPA [EMA EPAR]

Common Name

English

THIOTEPA [VANDF]

Common Name

English

THIOTEPA [USP-RS]

Common Name

English

PHOSPHOROTHIOIC TRI(ETHYLENEAMIDE)

Common Name

English

Classification Tree Code System Code

IARC

Thiotepa

WHO-ATC

L01AC01