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Streptozotocin

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CAS:18883-66-4
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CAS:18883-66-4
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CAS:18883-66-4
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Lastest Price from Streptozotocin manufacturers

  • Streptozocin
  • US $1.00 / KG
  • 2019-07-06
  • CAS:18883-66-4
  • Min. Order: 1KG
  • Purity: 99%
  • Supply Ability: 100
Streptozotocin Basic information
Physical and chemical properties History of discovery Animal diabetes inducer Uses
Product Name:Streptozotocin
Synonyms:STZ;STREPTOZOCIN;STREPTOZOTOCIN;STR;ZANOSAR;U-9889;2-deoxy-2-(((methylnitrosoamino)carbonyl)amino)-d-glucopyranos;2-deoxy-2-(((methylnitrosoamino)carbonyl)amino)-d-glucos
CAS:18883-66-4
MF:C8H15N3O7
MW:265.22
EINECS:242-646-8
Product Categories:Active Pharmaceutical Ingredients;Antibiotic Explorer;Peptide Synthesis/Antibiotics;ZANOSAR;antibiotic
Mol File:18883-66-4.mol
Streptozotocin Structure
Streptozotocin Chemical Properties
Melting point 121 °C (dec.)(lit.)
alpha D25 +39°
Boiling point 408.44°C (rough estimate)
density 1.4410 (rough estimate)
refractive index 1.6500 (estimate)
storage temp. −20°C
pkapKa 1.3 (Uncertain)
form powder
color white to light yellow
Water Solubility soluble
Sensitive Hygroscopic
Merck 13,8912
BRN 2060675
InChIKeyZSJLQEPLLKMAKR-FEQHFJGESA-N
CAS DataBase Reference18883-66-4
EPA Substance Registry SystemStreptozotocin (18883-66-4)
Safety Information
Hazard Codes Xn,T
Risk Statements 40-61-46-45-22-20/21/22
Safety Statements 36/37-53-45-36-22
RIDADR 3249
WGK Germany 3
RTECS LZ5775000
3-10-21
HazardClass 6.1(b)
PackingGroup III
HS Code 29419090
Hazardous Substances Data18883-66-4(Hazardous Substances Data)
ToxicityLD50 in female mice (mg/kg): 360 i.p.; 275 i.v.; in male dogs (mg/kg): 50 i.v. (Iwasaki)
MSDS Information
Streptozotocin Usage And Synthesis
Physical and chemical propertiesLight yellow crystalline powder, soluble in water, but its water solution is very unstable at room temperature,which can be broken down intothe gas evaporates after a half-hour , it takes using now. Dissolved in lower alcohols and ketones degrees, insoluble in polar organic solvents.
History of discoveryStreptozocin is produced by streptococcal bacteria ,it is natural compound which has a specific toxicity on mammalian insulin-producing pancreas islet B cells, it is a nitrosourea antibiotic, it is different from fat-soluble nitrosourea ,in chloroethyl place it is a methyl group at the other end of the molecule it is an amino sugar, Streptozocin can break down reactive methyl positive carbon ions alone, and forms cross-links between the chains with DNA , so that it can lead to the DNA alkylation, but its alkylation is weaker than other nitrosourea drugs, and its metabolite methylsulfinyl nitrosourea’s alkylation is 3 to 4 times stronger than its STZ . STZ can form isocyanates in the body . It can combine with Nucleic acid protein and thereby inhibit DNA polymerase vitality,to make it difficult to repair damaged DNA. In the late 1950s,it was discovered at the beginning considered to be an antibiotic, scientists from the pharmaceutical company Upjohn in Kalamazoo (now a subsidiary of Pfizer) found STZ in the soil Streptomyces strains. In the mid-1960s, it was discovered that Streptozocin has specific toxicity on insulin-producing pancreatic B cells . This discovery makes STZ later used in animal model of diabetes and used to treat pancreatic B cell tumors.from 1860s to the 1870s, the US National Cancer Institute began to study Streptozocin application in chemotherapy. Upjohn Company in November 1976 applied for FDA approval for its treatment of pancreatic cancer, and in July 1982 it was approved. After that ,it has been using the trade name Zanosar. It is used to treat pancreatic islet cell tumors (β cells or non-β cell carcinoma) clinically, it has a certain effect on for carcinoid tumor, Hodgkin's disease, colon cancer and liver cancer . It is used to Establish an animal model of type 1 diabetes in medical research.
Animal diabetes inducerDiabetes is a common metabolic endocrine disease, the main causes are due to relative or absolute lack of insulin, which is characterized by high blood sugar and diabetes. Experimental drugs can be used (such as alloxan and Streptozocin , etc.) to selectively destroy pancreatic β-cells, resulting in elevated blood glucose levels to make experimental diabetic mice.
Streptozocin (referred STZ) is a induced diabetic agent , it has an selectively destructive effect on a certain species of animals islet β cells ,which can induce diabetes in many animals, but they do not include the guinea pigs and humans, the general manufacture of animal models usually uses rats and mice. Foreign scholars reported that the incidence of diabetes in male rats selected manufacturing model is significantly higher than in female rats. Type 1 diabetes and type 2 diabetes animal models preparation is related to STZ injection dose: when bolus injection, as a direct result of the extensive destruction of pancreatic β cells,it can cause type 1 diabetes model; and when a relatively small amount STZ injection, since it just destroys part of the islet β cell function, resulting in peripheral tissues insensitive to insulin , while giving high-calorie diet, the combination will induce a animal model whose pathological, physiological changes are both close to human type 2 diabetes.
The above information is edited by the Chemicalbook of Tian Ye.
UsesIt is a compound containing N-nitroso ,it acts as a nitric oxide donor in pancreatic islets ; it can induce the death of diabetic animal model style of insulin-secreting cells . Efficient DNA methylation agent, can induce chromosome breakage.it has cell toxicity On the neuroendocrine tumor cell lines with the expression of GLUT2 glucose transporter (GLUT2 glucose transporter) . Streptozocin is used for inducing Type 1 diabetes in Medical researches .
Chemical Propertiesoff-white to pale yellow crystalline powder
Usesantineoplastic, alkylating agent
UsesStreptozotocin is used in the treatment metastatic cancer of the pancreatic islet cells. Streptozotocin has a highlrisk of toxicity and is generally limited to cancers that are inoperable.
UsesStreptozotocin is an unusual aminoglycoside containing a nitrosoamino group produced by Streptomyces achromogenes and discovered in 1959 as an antibiotic. The nitrosoamino group enables the metabolite to act as a nitric oxide (NO) donor. NO is an important messenger molecule involved in many physiological and pathological processes in the body. Streptozotocin is also widely used to induce diabetes in rodent models by inhibition of β-cell O-GlcNAcase.
Usessomatostatin octapeptide analog
DefinitionChEBI: An antibiotic that is produced by Streptomyces achromogenes. It is used as an antineoplastic agent and to induce diabetes in experimental animals.
IndicationsStreptozocin (Zanosar), a water-soluble nitrosourea produced by the fungus Streptomyces achromogenes, acts through methylation of nucleic acids and proteins. In addition, it produces rapid and severe depletion of the pyridine nucleotides nicotinamide adenine dinucleotide (NAD) and its reduced form (NADH) in liver and pancreatic islets.
Streptozocin is not well absorbed from the gastrointestinal tract and must be administered intravenously or intraarterially. In preclinical studies, the plasma half-life was 5 to 10 minutes.
Streptozocin produces remission in 50 to 60% of patients with islet cell carcinomas of the pancreas. It is also useful in malignant carcinoid tumors.
Almost all patients have nausea and vomiting. The major toxicity is renal tubular damage, which may be severe in 5 to 10% of patients taking streptozocin. Treatment of metastatic insulinomas may result in the release of insulin from the tumor and subsequent hypoglycemic coma. Less severe toxicities include diarrhea, anemia, and mild alterations in glucose tolerance or liver function tests.
Brand nameZanosar (Sicor).
General DescriptionOff-white powder. Melting point 115°C. Used as an anti-cancer drug. Carcinogenic.
General DescriptionStreptozocin is available in 1-g vials for IV administrationin the treatment of metastatic islet cell carcinoma of the pancreas,colon cancer, and Hodgkin’s disease. Activation resultsin the formation of methyl carbonium ions, which alkylateDNA, but the agent is less effective in alkylating DNAand carbamylating proteins than other nitrosoureas, which isbecause in part of an intramolecular carbamoylation. The internalcarbamate group migration occurs via the hydroxylgroups of the glucose portion of the molecule. There is a reducedeffect on RNA function compared with other nitrosoureasas well. The hydrophilic agent is rapidly clearedfrom the plasma with an elimination half-life of 35 minutes.The presence of the glucose moiety allows for utilization ofglucose transporters, which concentrate the compound inthe -cells of the pancreas. The metabolism of the agent hasnot been well characterized. Renal toxicity is dose limitingand may present initially as proteinuria and azotemia butmay progress to renal failure. Nausea and vomiting may besevere with the agent, whereas myelosuppression is generallymild. Normal glucose metabolism may be altered sothat hypoglycemia or hyperglycemia may be seen. In someanimal species, streptozocin produces diabetes but muchmilder effects are seen in man.
Air & Water ReactionsWater soluble.
Reactivity Profile[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.
Biological ActivityAntibiotic and antitumor agent. Alkylates DNA and induces diabetes mellitus via reduction of nicotinamide adenine dinucleotide in pancreatic β -cells in vivo .
Safety ProfileConfirmed carcinogen with experimental carcinogenic, neoplas tigenic, tumorigenic, and teratogenic data. Experimental poison by intravenous, parenteral, subcutaneous, and intraperitoneal routes. Moderately toxic to humans by intravenous route. Human systemic effects: nausea or vomiting, impaired liver function, kidney changes. Human mutation data reported. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx. See also NITROSAMINES.
Veterinary Drugs and TreatmentsAt present the primary purpose for streptozocin use in veterinary medicine is as a treatment for insulinomas in dogs, particularly those with refractory hypoglycemia and when tumors are nonresectable or have metastasized. Streptozocin potentially could be used for other oncologic conditions as well.
CarcinogenicityStreptozotocin is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.
Purification MethodsRecrystallise streptozotocin from 95% EtOH. It is soluble in H2O, MeOH and Me2CO. It has UV max at 228nm ( 6360) in EtOH. The tetraacetate has m 111-114o(dec), and [] D 25 +41o (c 0.78, 95% EtOH) after recrystallisation from EtOAc. [Herr et al. J Am Chem Soc 89 4808 1967, NMR: Wiley et al. J Org Chem 44 9 1979.] It is a potent methylating agent for DNA [Bennett & Pegg Cancer Res 41 2786 1981].
Streptozotocin Preparation Products And Raw materials
Tag:Streptozotocin(18883-66-4) Related Product Information
Methyl Methyl acetate Kresoxim-methyl 6-Aminocaproic acid PYRAZOPHOS Streptozotocin Glycine CORN SYRUP Ivermectin D-Glucose monohydrate Methyl bromide Centchroman CARBONYL SULFIDE glucopyranose Parathion-methyl Tetrahydro-4H-pyran-4-one Methyl acrylate Thiophanate-methyl