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| CAS No.: | 18883-66-4 |
|---|---|
| Name: | Streptozocin |
| Molecular Structure: | |
|
|
|
| Formula: | C8H15N3O7 |
| Molecular Weight: | 265.22 . |
| Synonyms: | Glucopyranose,2-deoxy-2-(3-methyl-3-nitrosoureido)-, D- (8CI);Estreptozocin;NSC 37917;NSC85998;STRZ;STZ;Streptozoticin;Streptozotocin;U 9889;Zanosar; |
| EINECS: | 242-646-8 |
| Density: | 1.86 g/cm3 |
| Melting Point: | 121 °C (dec.)(lit.) |
| Boiling Point: | 408.44°C (rough estimate) |
| Solubility: | soluble in water |
| Appearance: | off-white to pale yellow crystalline powder |
| Hazard Symbols: |
 Xn, T
|
| Risk Codes: | 40-61-46-45-22-20/21/22 |
| Safety: | 36/37-53-45-36-22 |
| PSA: | 151.92000 |
| LogP: | -2.50000 |
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Chemistry
IUPAC name: 1-Methyl-1-nitroso-3-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea
Molecular Formula: C8H15N3O7
Molecular Weight: 265.22 g/mol
EINECS: 242-646-8
Melting point: 115 °C (dec.)
Water solubility: soluble
Index of Refraction: 1.67
Storage temp.: −20 °C
Merck: 13,8912
Density: 1.86 g/cm3
Surface Tension: 81.1 dyne/cm
Vapour Pressure: mmHg at 25 °C
Appearance: off-white to pale yellow crystalline powde
Product Categories: Active Pharmaceutical Ingredients;Antibiotic Explorer;Peptide Synthesis/Antibiotics
Following is the structure of Streptozoticin (18883-66-4):
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History
Streptozocin (CAS NO.18883-66-4) was originally identified in the late 1950s as an antibiotic. The drug was discovered in a strain of the soil microbe Streptomyces achromogenes by scientists at the drug company Upjohn (now part of Pfizer) in Kalamazoo, Michigan. The soil sample in which the microbe turned up had been taken from Blue Rapids, Kansas, which can therefore be considered the birthplace of streptozotocin. Upjohn filed for patent protection for the drug in August 1958 and U.S. Patent 3,027,300 was granted in March 1962.
In the mid-1960s streptozotocin was found to be selectively toxic to the beta cells of the pancreatic islets, the cells that normally regulate blood glucose levels by producing the hormone insulin. This suggested the drug's use as an animal model of diabetes, and as a medical treatment for cancers of the beta cells. In the 1960s and 1970s the National Cancer Institute investigated streptozotocin's use in cancer chemotherapy. Upjohn filed for FDA approval of streptozotocin as a treatment for pancreatic islet cell cancer in November 1976, and approval was granted in July 1982. The drug was subsequently marketed as Zanosar. Streptozotocin is now marketed by the generic drug company Sicor (Teva).
Uses
Streptozocin (CAS NO.18883-66-4) is used in medicine for treating certain cancers of the Islets of Langerhans and used in medical research to produce an animal model for Type 1 diabetes.
Streptozotocin is approved by the U.S. Food and Drug Administration (FDA) for treating metastatic cancer of the pancreatic islet cells. Since it carries a substantial risk of toxicity and rarely cures the cancer, its use is generally limited to patients whose cancer cannot be removed by surgery. In these patients, streptozotocin can reduce the tumor size and reduce symptoms (especially hypoglycemia due to excessive insulin secretion by insulinomas).
Toxicity Data With Reference
Streptozoticin (18883-66-4) has been listed as a carcinogen by NTP: Suspect carcinogen and IARC: Group 2B carcinogen. Its result of Ames-test is positive. And the toxicological properties have not been fully investigated. You can see actual entry in RTECS for complete information.
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LD50 | intravenous | 50mg/kg (50mg/kg) | Journal of Medicinal Chemistry. Vol. 19, Pg. 918, 1976. | |
| human | TDLo | intravenous | 1044mg/kg/5D (1044mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING LIVER: LIVER FUNCTION TESTS IMPAIRED KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Cancer Vol. 34, Pg. 993, 1974. |
| monkey | LDLo | intravenous | 80mg/kg (80mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Drug and Chemical Toxicology. Vol. 3, Pg. 201, 1980. |
| mouse | LD50 | intraperitoneal | 360mg/kg (360mg/kg) | Journal of Medicinal Chemistry. Vol. 19, Pg. 918, 1976. | |
| mouse | LD50 | intravenous | 275mg/kg (275mg/kg) | Journal of Medicinal Chemistry. Vol. 19, Pg. 918, 1976. | |
| mouse | LD50 | parenteral | 264mg/kg (264mg/kg) | Cancer Chemotherapy Reports. Vol. 48, Pg. 1, 1965. | |
| mouse | LD50 | subcutaneous | 335mg/kg (335mg/kg) | National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986, | |
| rat | LD50 | intravenous | 138mg/kg (138mg/kg) | Cancer Chemotherapy Reports. Vol. 29, Pg. 91, 1963. | |
| women | LDLo | intravenous | 440mg/kg/65W- (440mg/kg) | GASTROINTESTINAL: ULCERATION OR BLEEDING FROM DUODENUM KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED | Gut. Vol. 12, Pg. 717, 1971. |
| women | TDLo | intravenous | 13513ug/kg (13.513mg/kg) | BEHAVIORAL: TOXIC PSYCHOSIS VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | New England Journal of Medicine. Vol. 311, Pg. 798, 1984. |
Safety Profile
Hazard Codes:
Xn,
T
Risk Statements: 40-61-46-45-22-20/21/22
R40:Limited evidence of a carcinogenic effect.
R61:May cause harm to the unborn child.
R46:May cause heritable genetic damage.
R45:May cause cancer.
R22:Harmful if swallowed.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 36/37-53-45-36-22
S36/37:Wear suitable protective clothing and gloves.
S53:Avoid exposure - obtain special instructions before use.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36:Wear suitable protective clothing.
S22:Do not breathe dust.
RIDADR: 3249
WGK Germany: 3
RTECS: LZ5775000
F: 3-10-21
HazardClass: 6.1(b)
PackingGroup: III
Specification
Streptozocin , its cas register number is 18883-66-4. It also can be called 2-Desoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose ; and 2-Deoxy-2-[[(methylnitrosoamino)carbonyl]amino]-D-glucose .
Streptozotocin (Streptozocin, STZ, Zanosar) is a naturally occurring chemical that is particularly toxic to the insulin-producing beta cells of the pancreas in mammals.
[D-Glucose, 2-deoxy-2-[[(methylnitrosoamino)-carbonyl]amino] is weakly basic. Reacts exothermically with acids. Reacts with both strong oxidizing agents and strong reducing agents.
Streptozoticin (18883-66-4) is unstable. It should avoid the condition of incompatible materials, exposure to moist air or water. It is not compatible with strong oxidizing agents,strong acids, strong bases, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: carbon monoxide, oxides of nitrogen, carbon dioxide. Its hazardous polymerization will not occur.