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Substance Name: Thiotepa [USP:INN:BAN:JAN]
RN: 52-24-4
UNII: 905Z5W3GKH
InChIKey: FOCVUCIESVLUNU-UHFFFAOYSA-N

Note

  • A very toxic alkylating antineoplastic agent also used as an insect sterilant. It causes skin, gastrointestinal, CNS, and bone marrow damage. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), thiotepa may reasonably be anticipated to be a carcinogen (Merck Index, 11th ed).

Molecular Formula

  • C6-H12-N3-P-S

Molecular Weight

  • 189.2218
 

Classification Codes

Classification Codes

  • Alkylating Agents
  • Antineoplastic
  • Antineoplastic Agents
  • Antineoplastic Agents, Alkylating
  • Drug / Therapeutic Agent
  • Human Data
  • Immunologic Factors
  • Immunosuppressive Agents
  • Mutation Data
  • Myeloablative Agonists
  • Noxae
  • Reproductive Effect
  • Skin / Eye Irritant
  • Tumor Data

Superlist Classification Codes

  • Known to be a Carcinogen
  • Overall Carcinogenic Evaluation: Group 1

Names and Synonyms

Name of Substance

  • Thiotepa
  • Thiotepa [USP:INN:BAN:JAN]

MeSH Heading

  • Thiotepa

Synonyms

  • 1,1',1''-Phosphinothioylidynetrisaziridine
  • 4-20-00-00052 (Beilstein Handbook Reference)
  • AI 3-24916
  • AI3-24916
  • Aziridine,1,1',1''-phosphinothioylidynetris-
  • BRN 0145978
  • CBC 806495
  • CCRIS 586
  • EINECS 200-135-7
  • Girostan
  • HSDB 3258
  • Ledertepa
  • N,N',N''-Tri-1,2-ethanediylphosphorothioic triamide
  • N,N',N''-Tri-1,2-ethanediylthiophosphoramide
  • N,N',N''-Triethylenephosphorothioic triamide
  • N,N',N''-Triethylenethiophosphamide
  • N,N',N''-Triethylenethiophosphoramide
  • N,N',N''-Triethylenethiophosphortriamide
  • NCI-C01649
  • NSC 6396
  • NSC-6396
  • Oncotepa
  • Oncothio-tepa
  • Oncotiotepa
  • Phosphine sulfide, tris(1-aziridinyl)-
  • Phosphoric tri(ethyleneamide)
  • Phosphorothioic acid triethylenetriamide
  • Phosphorothioic triamide, N,N',N''-tri-1,2-ethanediyl-
  • Phosphorothioic triamide, N,N',N''-triethylene-
  • SK 6882
  • Stepa
  • Tespa
  • Tespamin
  • Tespamine
  • Thio-tep
  • Thio-tepa
  • Thio-tepa S
  • Thiofozil
  • Thiophosphamide
  • Thiophosphamidum
  • Thiophosphoramide, N,N',N''-tri-1,2-ethanediyl-
  • Thiophosphoramide, N,N',N''-triethylene-
  • Thioplex
  • Thiotef
  • Thiotepa
  • Thiotepum
  • Thiotepum [INN-Latin]
  • Thiotriethylenephosphoramide
  • Tifosyl
  • Tio TEF
  • Tio-tef
  • Tiofosfamid
  • Tiofosyl
  • Tiofozil
  • Tiotepa
  • Tiotepa [INN-Spanish]
  • Tri(ethyleneimino)thiophosphoramide
  • Tri-1-aziridinylphosphine sulfide
  • Triaziridinylphosphine sulfide
  • Triethylene thiophosphoramide
  • Triethylenethiophosphoramide
  • Triethylenethiophosphorotriamide
  • Tris(1-aziridinyl)phosphine sulfide
  • Tris(1-aziridinyl)phosphine sulphide
  • Tris(ethylenimino)thiophosphate
  • TSPA
  • UNII-905Z5W3GKH
  • WR 45312
  • WR-45312

Systematic Names

  • Aziridine, 1,1',1''-phosphinothioylidynetris-
  • Phosphine sulfide, tris(1-aziridinyl)-
  • Thiotepa

Superlist Names

  • Aziridine, 1,1',1''-phosphinothioylidynetris-
  • Thio-tepa
  • Thiotepa
  • Tris(1-aziridinyl)phosphine sulfide
  • Tris(aziridinyl)phosphine sulfide

Registry Numbers

CAS Registry Number

  • 52-24-4

FDA UNII

  • 905Z5W3GKH

Other Registry Numbers

  • 1631739-26-8
  • 639-23-6
  • 85177-92-0

System Generated Number

  • 0000052244

Structure Descriptors

InChI

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

InChIKey

FOCVUCIESVLUNU-UHFFFAOYSA-N

Smiles

C1CN1P(=S)(N2CC2)N3CC3

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 5620ug/kg (5.62mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
dog LDLo intravenous 760ug/kg (0.76mg/kg) BLOOD: OTHER CHANGES

BLOOD: AGRANULOCYTOSIS

BLOOD: LEUKOPENIA
Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 203, 1965.
man TDLo parenteral 631ug/kg (0.631mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE

PERIPHERAL NERVE AND SENSATION: PARESTHESIS
Cancer Vol. 38, Pg. 1471, 1976.
monkey LDLo intravenous 1500ug/kg (1.5mg/kg) BLOOD: LEUKOPENIA

BLOOD: OTHER CHANGES

BLOOD: AGRANULOCYTOSIS
Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 203, 1965.
mouse LD50 intramuscular 11500ug/kg (11.5mg/kg)   Pharmaceutical Chemistry Journal Vol. 17, Pg. 353, 1983.
mouse LD50 intraperitoneal 11mg/kg (11mg/kg)   Fiziologicheski Aktivnye Veshchestva. Physiologically Active Substances. Vol. 22, Pg. 36, 1990.
mouse LD50 intravenous 14500ug/kg (14.5mg/kg)   Journal of Antibiotics, Series A. Vol. 13, Pg. 19, 1960.
mouse LD50 oral 38mg/kg (38mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
"Imifos," Giller, S.A., ed., Izd, Riga, USSR, 1968Vol. -, Pg. 129, 1968.
mouse LD50 subcutaneous 16500ug/kg (16.5mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

BLOOD: CHANGES IN SPLEEN
Farmakologiya i Toksikologiya Vol. 8, Pg. 73, 1973.
quail LD50 oral 237mg/kg (237mg/kg)   Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.
rabbit LD50 intravenous 5500ug/kg (5.5mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

BLOOD: CHANGES IN SPLEEN
Farmakologiya i Toksikologiya Vol. 8, Pg. 73, 1973.
rat LD50 intraarterial 8750ug/kg (8.75mg/kg)   Toxicology and Applied Pharmacology. Vol. 4, Pg. 344, 1962.
rat LD50 intraperitoneal 8mg/kg (8mg/kg)   Clinical Proceedings of the Children's Hospital of the District of Columbia. Vol. 18, Pg. 307, 1962.
rat LD50 intravenous 9400ug/kg (9.4mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 1, 1958.
rat LD50 oral 23mg/kg (23mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
rat LD50 subcutaneous 7800ug/kg (7.8mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 51.5 deg C   EXP
log P (octanol-water) 0.53 (none)   EXP
Water Solubility 1.90E+05 mg/L 25 EXP
Vapor Pressure 8.45E-03 mm Hg 25 EST
Henry's Law Constant 2.83E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.23E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.