D-Glucose, 2-deoxy-2-[[(methylnitrosoamino)-carbonyl]amino]-

Base Information

• Chemical Name: D-Glucose, 2-deoxy-2-[[(methylnitrosoamino)-carbonyl]amino]-
• CAS No.: 18883-66-4
• Molecular Formula: C8H15N3O7
• Molecular Weight: 265.22 .
• Hs Code.: 29419090
• European Community (EC) Number: 242-646-8
• NSC Number: 236997
• UN Number: 3077
• DSSTox Substance ID: DTXSID50860232
• Wikipedia: Streptozotocin
• NCI Thesaurus Code: C845
• RXCUI: 10114
• Metabolomics Workbench ID: 123766
• ChEMBL ID: CHEMBL163484
• Mol file: 18883-66-4.mol

Synonyms:2-Deoxy-2-((methylnitrosoamino)carbonyl)amino-D-glucose;Streptozocin;Streptozotocin;Streptozotocine;Zanosar

Chemical Property of D-Glucose, 2-deoxy-2-[[(methylnitrosoamino)-carbonyl]amino]-

Chemical Property:

• Appearance/Colour: off-white to pale yellow crystalline powder
• Melting Point: 121 °C (dec.)(lit.)
• Refractive Index: 1.67
• Boiling Point: 408.44°C (rough estimate)
• PKA: pKa 1.3 (Uncertain)
• PSA: 151.92000
• Density: 1.86 g/cm³
• LogP: -2.50000
• Storage Temp.: −20°C
• Sensitive.: Hygroscopic
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Water (up to 25 mg/ml)
• Water Solubility.: soluble
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 265.09099983
• Heavy Atom Count: 18
• Complexity: 315
• Transport DOT Label: Class 9

Purity/Quality:

98%min ^*data from raw suppliers

Streptozotocin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T
• Statements: 40-61-46-45-22-20/21/22
• Safety Statements: 36/37-53-45-36-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Bacterial Toxins
• Drug Classes: Antineoplastic Agents
• Canonical SMILES: CN(C(=O)NC1C(C(C(OC1O)CO)O)O)N=O
• Recent ClinicalTrials: Two Chemotherapy Regimens Plus or Minus Bevacizumab
• Recent EU Clinical Trials: Randomized open label study to compare the efficacy and safety of everolimus followed by chemotherapy with STZ-5FU upon progression or the reverse sequence, chemotherapy with STZ-5FU followed by everolimus upon progression, in advanced progressive pNETs (SEQTOR study)
• Uses: It 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 . antineoplastic, alkylating agent Streptozotocin 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. Streptozotocin 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. somatostatin octapeptide analog
• Description: Streptozotocin (STZ) was originally identified in the late 1950s as an antibiotic and was discovered in a strain of the soil microbe Streptomyces achromogenes. In the mid-1960s, STZ was found to be selectively toxic to the beta cells of the pancreatic islets and thus it is used in animal model of diabetes and as a medical treatment for cancers of the beta cells. STZ’s use in cancer chemotherapy received Food and Drug Administration approval in July 1982 and the drug was subsequently marketed as Zanosar.
• Indications: Streptozocin (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.
• Therapeutic Function: Antineoplastic
• Clinical Use: The glucopyranose moiety of streptozocin confers both islet cell specificity and high water solubility to this nitrosourea-based antineoplastic. As a result, it is used exclusively in metastatic islet cell carcinoma of the pancreas and is administered IV in D5W or normal saline.