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52-24-4

52-24-4 structure
52-24-4 structure
Name thiotepa
Synonyms N,N‘,N’‘-Triethylenethiophosphoramide
Triethylenethiophosphoramide
EINECS 200-135-7
Tri(1-aziridinyl)phosphine sulfide
1,1’,1″-phosphinothioylidynetris[aziridine]
Phosphorothioic tri(ethyleneamide)
N,N',N''-Triethylenethiophosphoramide
MFCD00145452
Tris(aziridinyl)phosphine sulfide
Tri(aziridin-1-yl)phosphine sulfide
thiotepa
1,1’,1″-phosphorothioyltris(aziridine)
tris(1-aziridinyl)phosphine sulfide
1,1',1''-phosphinothioylidynetrisaziridine
Aziridine, 1,1',1''-phosphinothioylidynetris-
1,1',1''-Phosphorothioyltriaziridine
1,1',1"-phosphinothioylidynetrisaziridine
Aziridine, 1-[bis(1-aziridinyl)phosphinothioyl]-
T3NTJ APS&- AT3NTJ&- AT3NTJ
Thio-TEPA
Description Thio-TEPA is a DNA alkylating agent, with antitumor activity.
Related Catalog
Target

DNA Alkylator[1]

In Vitro Thio-TEPA exhibits alkylating activity in rat liver slice incubation. Thio-TEPA does not affect the viability of rat liver slices, and is not accumulated in the slices at all doses of 2, 5, 10 mM[1].
In Vivo Thio-TEPA (20 mg/kg, i.p.) with total body irradiation (TBI) enhances donor-type blood chimerism during the first 10 weeks but is not dramatically higher than that of TBI group alone. Thio-TEPA alone improves both short- and long-term engraftment in mice[2].
Cell Assay The effect of Thio-TEPA on slice viability is studied by the determination of intracellular potassium (K+) leakage. Intracellular K+ is measured by flame photometry and is expressed in relation to the DNA content as measured using fluorometry. Thio-TEPA is added at concentrations of 1, 2, 5, and 10 mM and slices are incubated for 6, 12, and 24 h. The results are compared with the values found for drug-free controls. Thio-TEPA in medium and slices is measured following 3, 6, and 9 h incubation at the three highest concentrations. Krebs-HEPES buffer is used as the slicing buffer and Waymouth's MB 752/1 medium supplemented with 10 μg gentamycin is used as the incubation medium[1].
Animal Admin Mice[2] Male C57BL/6JIco mice, 19 weeks old, 25 to 30 g, are used as recipients. Congenic C57BL/6J-Gpi-1a/Gpi-1a (B6-Gpi-1a) and BALB.B10LiLa (Gpi-1a) mice are used as a source of syngeneic and allogeneic donor bone marrow, respectively. The latter combination is H-2-compatible (both H-2b), but mismatched on a number of minor histocompatibility loci. Thio-TEPA is dissolved in PBS and injected i.p. at a single bolus of 20 mg/kg. Preliminary pilot experiments have established that this approximated to the maximal tolerated dose when higher doses result in lethal gastrointestinal toxicity. Cyclophosphamide (CY) is dissolved in PBS and administered i.p. at a single dose of 200 mg/kg. Total body irradiation is delivered using a 137Cs γ-irradiation unit at a dose rate of 87 cGy/min to a dose of 5 Gy. After Thio-TEPA treatment the mice are maintained on neomycin (3.5 g/L sterile drinking water) for 2 weeks to minimize the possible problems of endotoxemia via gut toxicity[2].
References

[1]. Hagen B, et al. Metabolism and alkylating activity of thio-TEPA in rat liver slice incubation. Cancer Chemother Pharmacol. 1991;28(6):441-7.

[2]. Down JD, et al. Thiotepa improves allogeneic bone marrow engraftment without enhancing stem cell depletion in irradiated mice. Bone Marrow Transplant. 1998 Feb;21(4):327-30.
Density 1.5±0.1 g/cm3
Boiling Point 270.2±23.0 °C at 760 mmHg
Melting Point 54-57 °C
Molecular Formula C6H12N3PS
Molecular Weight 189.218
Flash Point 117.2±22.6 °C
Exact Mass 189.048950
PSA 50.93000
LogP 0.52
Vapour Pressure 0.0±0.6 mmHg at 25°C
Index of Refraction 1.709
Storage condition 2-8°C
Stability Stable. Incompatible with strong oxidizing agents.
Water Solubility 19 G/100 ML (25 ºC)

CHEMICAL IDENTIFICATION

RTECS NUMBER :
SZ2975000
CHEMICAL NAME :
Phosphine sulfide, tris(1-aziridinyl)-
CAS REGISTRY NUMBER :
52-24-4
BEILSTEIN REFERENCE NO. :
0145978
LAST UPDATED :
199612
DATA ITEMS CITED :
116
MOLECULAR FORMULA :
C6-H12-N3-P-S
MOLECULAR WEIGHT :
189.24
WISWESSER LINE NOTATION :
T3NTJ APS&- AT3NTJ&- AT3NTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Human
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
631 ug/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - paresthesis Blood - changes in bone marrow (not otherwise specified)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
8 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
9400 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraarterial
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
8750 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
38 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - somnolence (general depressed activity) Behavioral - ataxia
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
11 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
16500 ug/kg
TOXIC EFFECTS :
Liver - hepatitis (hepatocellular necrosis), zonal Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Blood - changes in spleen
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
14500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
11500 ug/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
760 ug/kg
TOXIC EFFECTS :
Blood - leukopenia Blood - agranulocytosis Blood - other changes
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
1500 ug/kg
TOXIC EFFECTS :
Blood - leukopenia Blood - agranulocytosis Blood - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
5500 ug/kg
TOXIC EFFECTS :
Liver - hepatitis (hepatocellular necrosis), zonal Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Blood - changes in spleen
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - quail
DOSE/DURATION :
237 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - wild bird species
DOSE/DURATION :
5620 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
33 mg/kg/3Y-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
17 mg/kg/56W-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
218 mg/kg/1Y-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Sense Organs and Special Senses (Ear) - effect, not otherwise specified Skin and Appendages - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
52 mg/kg/1Y-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors Blood - lymphoma, including Hodgkin's disease
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
10 gm/kg/17W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Skin and Appendages - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
47 mg/kg/8W-I
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
360 mg/kg/1Y-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia Blood - lymphoma, including Hodgkin's disease
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
218 mg/kg/1Y-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Sense Organs and Special Senses (Ear) - effect, not otherwise specified Skin and Appendages - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
2 mg/kg
SEX/DURATION :
male 5 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
5 mg/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - Central Nervous System
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
7500 ug/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
2500 ug/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
500 ug/kg
SEX/DURATION :
female 13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intratesticular
DOSE :
8 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
25 mg/kg
SEX/DURATION :
male 5 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
625 ug/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1250 ug/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
5 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
7500 ug/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - body wall
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
3 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
5 mg/kg
SEX/DURATION :
male 5 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1 mg/kg
SEX/DURATION :
male 5 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intratesticular
DOSE :
16 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
Sex chromosome loss and nondisjunction
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
DNA inhibition
TYPE OF TEST :
Mutation test systems - not otherwise specified
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
DNA damage
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Sister chromatid exchange
TYPE OF TEST :
Dominant lethal test
TYPE OF TEST :
Dominant lethal test
TYPE OF TEST :
Sperm Morphology
TYPE OF TEST :
Heritable translocation test
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Sister chromatid exchange
TYPE OF TEST :
Sister chromatid exchange
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Sister chromatid exchange

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Rodent - rabbit Kidney
DOSE/DURATION :
15 mg/L
REFERENCE :
ECREAL Experimental Cell Research. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.10- 1950- Volume(issue)/page/year: 36,92,1964 *** REVIEWS *** IARC Cancer Review:Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 9,85,1975 IARC Cancer Review:Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,123,1990 IARC Cancer Review:Human Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,123,1990 IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 9,85,1975 IARC Cancer Review:Group 1 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,123,1990 TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 TOXICOLOGY REVIEW ANPIAM Arquivos de Neuro-Psiquiatria. (Caixa Postal 30.657, 01051 Sao Paulo, Brazil) V.1- 1943- Volume(issue)/page/year: 5,447,1965 TOXICOLOGY REVIEW CRTXB2 CRC Critical Reviews in Toxicology. (CRC Press, Inc., 2000 Corporate Blvd., NW, Boca Raton, FL 33431) V.1- 1971- Volume(issue)/page/year: 2,159,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4618 No. of Facilities: 142 (estimated) No. of Industries: 1 No. of Occupations: 6 No. of Employees: 11452 (estimated) No. of Female Employees: 8724 (estimated)
Symbol GHS06 GHS08
GHS06, GHS08
Signal Word Danger
Hazard Statements H300-H350
Precautionary Statements P201-P264-P301 + P310-P308 + P313
Personal Protective Equipment Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes T+:Verytoxic;
Risk Phrases R28;R45;R46
Safety Phrases 53-22-26-36/37/39-45-36/37-28
RIDADR UN 2811 6.1/PG 2
WGK Germany 3
RTECS SZ2975000
Packaging Group II
Hazard Class 6.1(a)
HS Code 2933990090
151-56-4 structure

151-56-4

~%

52-24-4 structure

52-24-4

Literature: Am. Cyanamid Co. Patent: US2670347 , 1952 ; Full Text Show Details Lidaks et al. Latvijas PSR Zinatnu Akademijas Vestis, 1959 , # 1 p. 87,88 Chem.Abstr., 1959 , p. 17991
HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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