S0130

Streptozocin

≥75% α-anomer basis, ≥98% (HPLC), powder

• Synonym(s): N-(Methylnitrosocarbamoyl)-α-D-glucosamine, Streptozotocin
• Empirical Formula (Hill Notation): C₈H₁₅N₃O₇
• CAS Number: 18883-66-4
• Molecular Weight: 265.22
• Beilstein: 2060675
• EC Number: 242-646-8
• MDL number: MFCD00006607
• PubChem Substance ID: 57654595
• NACRES: NA.77

Properties

• Quality Level: 200
• Assay: ≥75% α-anomer basis; ≥98% (HPLC)
• form: powder
• color: white to light yellow
• mp: 121 °C (dec.) (lit.)
• antibiotic activity spectrum: neoplastics
• Mode of action: DNA synthesis | interferes
• originator: Pfizer
• storage temp.: −20°C
• SMILES string: CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O
• InChI: 1S/C8H15N3O7/c1-11(10-17)8(16)9-4-6(14)5(13)3(2-12)18-7(4)15/h3-7,12-15H,2H2,1H3,(H,9,16)/t3-,4-,5-,6-,7+/m1/s1
• InChI key: ZSJLQEPLLKMAKR-GKHCUFPYSA-N

Description

General description

Streptozocin or streptozotocin, is obtained from Streptomyces achromogenes. Streptozotocin, a glucosamine-nitrosourea, is a DNA alkylating agent that enters cells exclusively via the GLUT2 glucose transport protein. Streptozocin, a diabetagen, is especially toxic to pancreatic islet insulin-producing β-cells. It is toxic to GLUT2 positive neuroendocrine tumor cells.

Application

Streptozocin or streptozotocin is used to induce type 1 diabetes for medical research.

Biochem/physiol Actions

An N-nitroso-containing compound that acts as a nitric oxide donor in pancreatic islets; induces death of insulin-secreting cells, producing an animal model of diabetes. Potent DNA methylating agent that induces chromosomal breakage. Cytotoxic to neuroendocrine tumor cell lines that express the GLUT2 glucose transporter.

Clinically, the chemical is used for the treatment of pancreatic β cell carcinoma.

Features and Benefits

This compound was developed by Pfizer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Other Notes

Mixed anomers

Safety Information

• Pictograms: GHS02,GHS08
• Signal Word: Warning
• Hazard Statements: H228 - H341 - H351
• Precautionary Statements: P201 - P202 - P210 - P240 - P241 - P308 + P313
• Hazard Classifications: Carc. 2 - Flam. Sol. 2 - Muta. 2
• Storage Class Code: 4.1B - Flammable solid hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves