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18883-66-4

18883-66-4 structure
18883-66-4 structure
  • Name: Streptozotocin
  • Chemical Name: streptozocin
  • CAS Number: 18883-66-4
  • Molecular Formula: C8H15N3O7
  • Molecular Weight: 265.221
  • Catalog: API Antibiotics Other antibiotics
  • Create Date: 2018-07-07 19:58:33
  • Modify Date: 2024-01-02 07:11:36
  • Streptozocin is a potent DNA-methylating agent, with IC50s of 11.7, 904 and 1024 μg/mL in HL60, K562 and C1498 cells respectively.
Name streptozocin
Synonyms Streptozocin
Zanosar
1-methyl-1-nitroso-3-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]urea
2-Deoxy-2-{[methyl(nitroso)carbamoyl]amino}-α-D-glucopyranose
MFCD00006607
α-D-Glucopyranose, 2-deoxy-2-[[(methylnitrosoamino)carbonyl]amino]-
2-deoxy-2-({[methyl(nitroso)amino]carbonyl}amino)-α-D-glucopyranose
Streptozotocin (STZ)
STR
N-(Methylnitrosocarbamoyl)-α-D-glucosamine
EINECS 242-646-8
2-deoxy-2-{[methyl(nitroso)carbamoyl]amino}-a-D-glucopyranose
STZ
U-9889
a-D-glucopyranose, 2-deoxy-2-[[(methylnitrosoamino)carbonyl]amino]-
Streptozotocin
strz
Description Streptozocin is a potent DNA-methylating agent, with IC50s of 11.7, 904 and 1024 μg/mL in HL60, K562 and C1498 cells respectively.
Related Catalog
Target

DNA alkylator[1]
In Vitro Streptozocin (STZ) shows higher cytotoxic effect in vitro on hematological cell lines compared to Alloxan (ALX). ALX appeares not to be toxic for the studied cell lines with estimated IC50 values of 2809, 3679 or over 4000 μg/mL for HL60, K562 and C1498 cells, respectively. Streptozocin is more toxic, especially for the human myeloid leukemia cell line, HL60. The IC50 values of Streptozocin are 11.7, 904 and 1024 μg/mL for HL60, K562 and C1498 cells, respectively. Results also show that the murine leukemic cells are more resistant to Streptozocin and ALX cytotoxicity than human leukemic cells[2].
In Vivo Streptozocin (STZ)-injected mice show tendency to have lower body weight than that observed in animals injected with ALX. Streptozocin -injected mice have significantly fewer splenocytes (22.2±3.2×106; n=10) compared to mice injected with ALX (60.7±4.3×106; n=15; p=0.01)[2].
Cell Assay Human and murine cell lines are cultured in triplicate in 96-well plates at a density of 2×104 cells/well in the absence (untreated control) or presence of various concentrations of ALX (20-3000 μg/mL) or STZ (1-3000 μg/mL) for 48 h at 37°C under a humidified atmosphere containing 5% CO2. Cells incubated in complete media including dH2O in a final concentration of 0.1% served as control for solvent toxicity and cells incubated in complete medium are used as a control for the experiments. The effects of the tested drugs on tumor cell growth or viability are determined employing the MTT assay in accordance with the manufacturer's instructions. The IC50values (drug concentration that induces 50% inhibition of the cell growth) are calculated using the GraphPad Prism 4 program[2].
Animal Admin Mice[2] Male C57BL/6 mice (10-16 weeks) are used.The age group distribution in the mouse group treated with Streptozocin and ALX as well as controls is as follows: Streptozocin xenograft (n=7, median age 14 weeks), ALX xenograft (n=11, median age 15 weeks), Streptozocin non-transplanted (n=7, median age 14 weeks), ALX non-transplanted (n=15, median age 15 weeks).Male C57BL/6 mice are under inhalation anesthesia injected via the penile vein with ALX (75 mg/mL) or Streptozocin (180 mg/kg). Control group contain male C57BL/6 mice. Blood glucose levels and body weight are measured before injection, after 6 h, then daily after drug injection. Rats[3] Thirty rats underwent oophorectomy to induce menopausal status. Oophorectomy is performed under sterile conditions via a midline incision after anesthetization using intraperitoneal injection of ketamine hydrochloride (90 mg/kg) and xylazine (10 mg/kg). The incisions are closed with 3.0 polyglactin sutures. The remaining 10 rats formed the control group (Group 1). Ten of the 30 rats that underwent oophorectomy constituted the menopause control group (Group 2). Beginning 1 week after the operation, methylprednisolone (1 mg/kg) is injected daily until the end of the study to mimic steroid treatment for rheumatologic diseases in 10 rats (Group 3). Group 4 consisted of rats that received intraperitoneal administration of Streptozocin (50 mg/kg) to induce diabetes mellitus (DM) 1 week after the oophorectomy. Blood glucose level is checked 3 days after Streptozocin administration, and values >250 mg/dL are considered as positive for DM.
References

[1]. Bennett RA, et al. Alkylation of DNA in rat tissues following administration of streptozotocin. Cancer Res. 1981 Jul;41(7):2786-90

[2]. Diab RA, et al. Immunotoxicological effects of streptozotocin and alloxan: in vitro and in vivo studies. Immunol Lett. 2015 Feb;163(2):193-8

[3]. Acer S, et al. Oxidative stress of crystalline lens in rat menopausal model. Arq Bras Oftalmol. 2016 Jul-Aug;79(4):222-5.
Density 1.9±0.1 g/cm3
Melting Point 121 °C (dec.)(lit.)
Molecular Formula C8H15N3O7
Molecular Weight 265.221
Exact Mass 265.091003
PSA 151.92000
LogP -1.33
Index of Refraction 1.670
Storage condition −20°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
LZ5775000
CHEMICAL NAME :
Glucopyranose, 2-deoxy-2-(3-methyl-3-nitrosoureido)-, D-
CAS REGISTRY NUMBER :
18883-66-4
LAST UPDATED :
199706
DATA ITEMS CITED :
92
MOLECULAR FORMULA :
C8-H15-N3-O7
MOLECULAR WEIGHT :
265.26
WISWESSER LINE NOTATION :
T6OTJ BQ CMVN1&NO DQ EQ F1Q -D,GLU

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
13513 ug/kg
TOXIC EFFECTS :
Behavioral - toxic psychosis Vascular - BP lowering not characterized in autonomic section Nutritional and Gross Metabolic - body temperature increase
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
440 mg/kg/65W-I
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from duodenum Kidney, Ureter, Bladder - urine volume increased Nutritional and Gross Metabolic - changes in potassium
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human
DOSE/DURATION :
1044 mg/kg/5D
TOXIC EFFECTS :
Gastrointestinal - nausea or vomiting Liver - liver function tests impaired Kidney, Ureter, Bladder - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
138 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 :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
360 mg/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
335 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 - mouse
DOSE/DURATION :
275 mg/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
264 mg/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
80 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
125 mg/kg/5D-I
TOXIC EFFECTS :
Gastrointestinal - changes in structure or function of endocrine pancreas Kidney, Ureter, Bladder - other changes Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
200 mg/kg/5D-I
TOXIC EFFECTS :
Gastrointestinal - changes in structure or function of endocrine pancreas Blood - changes in bone marrow (not otherwise specified) Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
470 mg/kg/26W-I
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Liver - tumors Kidney, Ureter, Bladder - Kidney tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
25 mg/kg
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Kidney, Ureter, Bladder - Kidney tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
470 mg/kg/26W-I
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors Kidney, Ureter, Bladder - Kidney tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
250 mg/kg
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Kidney, Ureter, Bladder - Kidney tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
100 mg/kg/I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors Kidney, Ureter, Bladder - Kidney tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
65 mg/kg
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors Kidney, Ureter, Bladder - Kidney tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Kidney, Ureter, Bladder - Kidney tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
30 mg/kg
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Gastrointestinal - tumors Kidney, Ureter, Bladder - Kidney tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
65 mg/kg
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors Kidney, Ureter, Bladder - Kidney tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Kidney, Ureter, Bladder - Kidney tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
65 mg/kg
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Kidney, Ureter, Bladder - Kidney tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
30 mg/kg
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Gastrointestinal - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
65 mg/kg
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
50 mg/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
50 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
50 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
50 mg/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
70 mg/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
35 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
30 mg/kg
SEX/DURATION :
female 5 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
40 mg/kg
SEX/DURATION :
female 5 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - endocrine system Reproductive - Effects on Newborn - biochemical and metabolic
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
40 mg/kg
SEX/DURATION :
female 1 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
60 mg/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
40 mg/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
65 mg/kg
SEX/DURATION :
female 5 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 :
150 mg/kg
SEX/DURATION :
female 3 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
100 mg/kg
SEX/DURATION :
female 85-95 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Endocrine - diabetes mellitus
TYPE OF TEST :
DNA damage
TYPE OF TEST :
Unscheduled DNA synthesis
TYPE OF TEST :
DNA adduct

MUTATION DATA

TYPE OF TEST :
Mutation in mammalian somatic cells
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
500 umol/L
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 40,2719,1980 *** 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: 17,337,1978 IARC Cancer Review:Human No Adequate Data 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: 17,337,1978 IARC Cancer Review:Group 2B IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 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: 1(1),93,1971 TOXICOLOGY REVIEW ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,830,1972 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5492 No. of Facilities: 87 (estimated) No. of Industries: 1 No. of Occupations: 4 No. of Employees: 2074 (estimated) No. of Female Employees: 1713 (estimated)
Symbol GHS08
GHS08
Signal Word Danger
Hazard Statements H350
Precautionary Statements P201-P308 + P313
Personal Protective Equipment Eyeshields;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:Toxic
Risk Phrases R22;R45;R46;R61
Safety Phrases 36/37-53-45-36-22
RIDADR 3249
WGK Germany 3
RTECS LZ5775000
Packaging Group III
Hazard Class 6.1(b)
HS Code 2932999099
HS Code 2932999099
Summary 2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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