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 282 Target ID: CHEMBL2311221 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/075547Orig1s006lbl.pdf \| http://www.drugbank.ca/drugs/DB04572	Crosslinking Agent 83

Conditions

Condition	Modality	Highest Phase	Product
Breast adenocarcinoma 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/2001/75-547_Thiotepa_prntlbl.pdf	Primary	Approved 8583	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 8583	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 8583	THIOTEPA Approved Use For the treatment of superficial papillary carcinoma of the urinary bladder Launch Date 1959

C_max

Value	Dose	Analyte	Population
1828 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/075547Orig1s006lbl.pdf	80 mg 1 times / 4 weeks multiple, intravenous dose: 80 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	THIOTEPA serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
1331 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/075547Orig1s006lbl.pdf	60 mg 1 times / 4 weeks multiple, intravenous dose: 60 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	THIOTEPA serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
0.098 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8603453/	60 mg single, intravesical dose: 60 mg route of administration: Intravesical experiment type: SINGLE co-administered:	THIOTEPA urine	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED
0.129 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8603453/	60 mg single, intravesical dose: 60 mg route of administration: Intravesical experiment type: SINGLE co-administered:	THIOTEPA urine	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED
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	Analyte	Population
4127 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/075547Orig1s006lbl.pdf	80 mg 1 times / 4 weeks multiple, intravenous dose: 80 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	THIOTEPA serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
2832 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/075547Orig1s006lbl.pdf	60 mg 1 times / 4 weeks multiple, intravenous dose: 60 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	THIOTEPA serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
22.4 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8603453/	60 mg single, intravesical dose: 60 mg route of administration: Intravesical experiment type: SINGLE co-administered:	THIOTEPA urine	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED
24.8 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8603453/	60 mg single, intravesical dose: 60 mg route of administration: Intravesical experiment type: SINGLE co-administered:	THIOTEPA urine	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED
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	Analyte	Population
2.3 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/075547Orig1s006lbl.pdf	80 mg 1 times / 4 weeks multiple, intravenous dose: 80 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	THIOTEPA serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
2.4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/075547Orig1s006lbl.pdf	60 mg 1 times / 4 weeks multiple, intravenous dose: 60 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	THIOTEPA serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
91 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8603453/	60 mg single, intravesical dose: 60 mg route of administration: Intravesical experiment type: SINGLE co-administered:	THIOTEPA urine	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED
89 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8603453/	60 mg single, intravesical dose: 60 mg route of administration: Intravesical experiment type: SINGLE co-administered:	THIOTEPA urine	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED
2.55 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf	20 mg/m² single, intravenous dose: 20 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	THIOTEPA plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
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

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 single, intravenous dose: 20 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		THIOTEPA plasma	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	unhealthy, 25-74 Health Status: unhealthy Age Group: 25-74 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1710167	Other AEs: Leukopenia, Thrombocytopenia... Other AEs: Leukopenia (grade 3, 25%) Thrombocytopenia (grade 4, 12.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/1710167
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	unhealthy, 25-74 Health Status: unhealthy Age Group: 25-74 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1710167	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
750 mg/m2 2 times / day multiple, intravenous MTD Dose: 750 mg/m2, 2 times / day Route: intravenous Route: multiple Dose: 750 mg/m2, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10531568	unhealthy, 2–16 Health Status: unhealthy Age Group: 2–16 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10531568	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
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 Sources: https://pubmed.ncbi.nlm.nih.gov/9816047	unhealthy, 30-76 Health Status: unhealthy Age Group: 30-76 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9816047	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
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf	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

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	unhealthy, 25-74 Health Status: unhealthy Age Group: 25-74 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1710167
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	unhealthy, 25-74 Health Status: unhealthy Age Group: 25-74 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1710167
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	unhealthy, 25-74 Health Status: unhealthy Age Group: 25-74 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1710167
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	unhealthy, 25-74 Health Status: unhealthy Age Group: 25-74 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1710167
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	unhealthy, 25-74 Health Status: unhealthy Age Group: 25-74 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1710167
Gastrointestinal toxicity	grade 3, 33.3%	750 mg/m2 2 times / day multiple, intravenous MTD Dose: 750 mg/m2, 2 times / day Route: intravenous Route: multiple Dose: 750 mg/m2, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10531568	unhealthy, 2–16 Health Status: unhealthy Age Group: 2–16 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10531568
Mucositis	grade 3, 33.3%	750 mg/m2 2 times / day multiple, intravenous MTD Dose: 750 mg/m2, 2 times / day Route: intravenous Route: multiple Dose: 750 mg/m2, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10531568	unhealthy, 2–16 Health Status: unhealthy Age Group: 2–16 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10531568
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 Sources: https://pubmed.ncbi.nlm.nih.gov/9816047	unhealthy, 30-76 Health Status: unhealthy Age Group: 30-76 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9816047
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 Sources: https://pubmed.ncbi.nlm.nih.gov/9816047	unhealthy, 30-76 Health Status: unhealthy Age Group: 30-76 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9816047
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 Sources: https://pubmed.ncbi.nlm.nih.gov/9816047	unhealthy, 30-76 Health Status: unhealthy Age Group: 30-76 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9816047
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 Sources: https://pubmed.ncbi.nlm.nih.gov/9816047	unhealthy, 30-76 Health Status: unhealthy Age Group: 30-76 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9816047
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf
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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208264s000lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 CYP2E1 1060	CYP2B6 776

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11950782/	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11950782/	no
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11950782/	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11950782/	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11950782/	no
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11950782/	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11950782/	no
CYP2B6 1160	inhibitor 4027 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 1946	substrate 4014 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 776	substrate 4014 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
Aaron Chemicals	AR006W6E	http://www.aaronchem.com/52-24-4
abcr GmbH	AB425425	http://www.abcr.com/shop/en/AB425425
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/
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
Alfa Aesar	H61778	https://www.alfa.com/en/catalog/H61778/
Alfa Chemistry	52-24-4	https://www.alfa-chemistry.com/triethylenethiophosphoramide-product-52-24-4-284757.htm
Alfa Chemistry	ACM52244	https://www.alfa-chemistry.com/product/triethylenethiophosphoramide-cas-52-24-4-284757.html
Alfa Chemistry	AP52244	https://reagents.alfa-chemistry.com/product/thiotepa-cas-52-24-4-12480.html
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
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
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
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
CSNpharm	CSN12081	https://www.csnpharm.com/products/thio-tepa.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
iChemical	EBD4234	http://www.ichemical.com/chemicals/cas-52-24-4
Matrix Scientific	58443	https://www.matrixscientific.com/058443.html
mcule	MCULE-5478761622	https://mcule.com/MCULE-5478761622/
MedChem Express	HY-17574	https://www.medchemexpress.com/Thio-TEPA.html
Molcore	MC558133	https://www.molcore.com/product/52-24-4
MolPort	MolPort-001-783-551	https://www.molport.com/shop/molecule-link/MolPort-001-783-551
MuseChem	I003904	https://www.musechem.com/product/I003904.html
Oakwood	223000	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=103999&ExtHyperLink=1
OChem	6481	http://www.ocheminc.com/index.php?act=psearch&pid=145T452
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	1664000_USP	https://www.sigmaaldrich.com/catalog/product/usp/1664000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	T6069_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/t6069?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

PubMed

Title	Date	PubMed
Potent inhibition of cytochrome P450 2B6 by sibutramine in human liver microsomes.	2013-09-05	23777987
Efficient monitoring of in vivo pig-a gene mutation and chromosomal damage: summary of 7 published studies and results from 11 new reference compounds.	2012-12	22923490
Zebrafish (Danio rerio) embryos as a model for testing proteratogens.	2011-03-15	21237239
Nicotinamide inhibits alkylating agent-induced apoptotic neurodegeneration in the developing rat brain.	2011	22164206
The chemotherapy agent, thioTEPA, yields long-term impairment of hippocampal cell proliferation and memory deficits but not depression-related behaviors in mice.	2010-05-01	20096731
Excessive toxicity of once daily i.v. BU, melphalan and thiotepa followed by auto SCT on patients with non-Hodgkin's lymphoma.	2010-04	19767780
Cytochrome P(450)-dependent toxic effects of primaquine on human erythrocytes.	2009-11-15	19616568
Impairment of APE1 function enhances cellular sensitivity to clinically relevant alkylators and antimetabolites.	2009-06	19470598
Polymorphisms of drug-metabolizing enzymes (GST, CYP2B6 and CYP3A) affect the pharmacokinetics of thiotepa and tepa.	2009-01	19076156
Relations between polymorphisms in drug-metabolising enzymes and toxicity of chemotherapy with cyclophosphamide, thiotepa and carboplatin.	2008-11	18854779
Breast cancer management: the road to today.	2008-10-01	18798545
Risk factors for hepatic veno-occlusive disease: a retrospective unicentric study in 116 children autografted after a high-dose BU-thiotepa regimen.	2008-10	18587430
The monoterpenoids citral and geraniol are moderate inhibitors of CYP2B6 hydroxylase activity.	2008-08-11	18611395
Brain magnetic resonance imaging after high-dose chemotherapy and radiotherapy for childhood brain tumors.	2008-03-15	17904307
Wound healing in patients with cancer.	2008-01-11	18264518
Contribution of CYP2C9, CYP2A6, and CYP2B6 to valproic acid metabolism in hepatic microsomes from individuals with the CYP2C91/1 genotype.	2006-12	16945988
High-dose chemotherapy with autologous stem-cell transplantation and hyperfractionated radiotherapy as first-line treatment of primary CNS lymphoma.	2006-08-20	16864853
Efficacy of high-dose alkylating chemotherapy in HER2/neu-negative breast cancer.	2006-04	16446318
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
The naturally occurring cytochrome P450 (P450) 2B6 K262R mutant of P450 2B6 exhibits alterations in substrate metabolism and inactivation.	2005-06	15769884
Cardiac toxicity observed in association with high-dose cyclophosphamide-based chemotherapy for metastatic breast cancer.	2004-08	15325671
Selective inhibition of CYP2B6-catalyzed bupropion hydroxylation in human liver microsomes in vitro.	2004-06	15155554
Phase I trial of sequential high-dose chemotherapy with escalating dose paclitaxel, melphalan, and cyclophosphamide, thiotepa, and carboplatin with peripheral blood progenitor support in women with responding metastatic breast cancer.	1998-07	9676843
Transforming growth factor-beta 1 overexpression produces drug resistance in vivo: reversal by decorin.	1998-03-24	9509296
[A comparative study of thio-tepa and mitomycin C in the treatment of pterygium. Preliminary results].	1998-02	9759389
Therapeutic activity of CPT-11, a DNA-topoisomerase I inhibitor, against peripheral primitive neuroectodermal tumour and neuroblastoma xenografts.	1996-08	8761367
[Paraplegia following intrathecal chemotherapy].	1996-06-22	8711459
Intravesical thiotepa-induced eosinophilic cystitis.	1995-11	7495132
Bladder tumours following chemotherapy and radiotherapy for ovarian cancer: a case-control study.	1995-09-27	7558434
The role of human glutathione S-transferase isoenzymes in the formation of glutathione conjugates of the alkylating cytostatic drug thiotepa.	1995-04-15	7712478
A phase II trial of vinorelbine and thiotepa in metastatic breast cancer.	1995-02	7786825
Multiple myeloma after treatment of essential thrombocythemia.	1995-01	7817232
Acquired episodic complete heart block after high-dose chemotherapy with cyclophosphamide and thiotepa.	1994-03	8122625
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.	1990-12	1982927
Phase I evaluation of thio-TEPA in combination with cisplatin for advanced gynecologic malignancies.	1990-11	2121628
Severe polyneuropathy and motor loss after intrathecal thiotepa combination chemotherapy: description of two cases.	1990-10	2131034
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.	1990-02-01	2105156
Nephrogenic adenoma in a patient with chronic renal failure associated with intravesical treatment with thiotepa.	1990	2107082
Systemic influence of intravesical chemotherapy with verapamil.	1985	3922100
[Arsenic trioxide inhibition of the thiophosphamide induction of mutations in mouse germ and somatic cells].	1984-02	6423448
Single and sequential combination intravesical chemotherapy of murine bladder cancer.	1982-02	6800090
The morphologic effects of mitomycin C in mammalian urinary bladder.	1981-06-01	6790156
Hematologic effects of intravesicular thiotepa therapy for bladder carcinoma.	1980-11-07	6776297
The prophylactic use of thio-tepa and urokinase in transitional cell carcinoma of the bladder: a preliminary report.	1975-09	806708
[Fatal bone marrow aplasia due to endovesical thio-tepa].	1973-12	4216649
[Spontaneously cured pancytopenia due to intravesical thio-tepa, apropos of one case].	1973-12	4216648
Renal failure associated with the use of thio-tepa.	1973-11	4201562
Prolonged apnea after succinylcholine in a case treated with cytostatics for cancer.	1972-09-01	4672170
Severe pancytopenia associated with the use of intravesical thio-TEPA.	1967-10	4964489
Pancytopenia and generalized sepsis following treatment of cancer of the bladder with instillations of triethylene thiophosphoramide.	1967-03	4960046

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 `Mon Mar 31 17:50:01 GMT 2025` Edited by `admin` on `Mon Mar 31 17:50:01 GMT 2025`
Record UNII	905Z5W3GKH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TEPADINA

Preferred Name

English

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

TEPYLUTE

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