Streptozocin - Moligand™, ≥75%, α-anomer basis , CAS No.18883-66-4

CAS: 18883-66-4 Cat. No.: S766968 Formula: C₈H₁₅N₃O₇ Molecular Weight: 265.22 Beilstein Registry Number: 2060675 EC Number: 242-646-8

GRADE & PURITY Moligand™, ≥75%, α-anomer basis

Synonyms

N-(Methylnitrosocarbamoyl)-α-D-glucosamine | Streptozotocin | 2-Desoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose | STZ | NSC-85998 | U-9889

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

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.
An NO donor and DNA methylating agent; Streptozotocin is used in medicine as a drug against certain cancers of the Langerhans Islets. It is cytotoxic to neuroendocrine tumor cell lines that express the GLUT2 glucose transporter; Streptozocin is used to induce Type 1 diabetes for medical research.

Specifications

Synonyms

N-(Methylnitrosocarbamoyl)-α-D-glucosamine | Streptozotocin | 2-Desoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose | STZ | NSC-85998 | U-9889

Specifications & Purity

Moligand™, ≥75%, α-anomer basis

Biochemical and Physiological Mechanisms

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 neuroend

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥75%

Names and Identifiers

Pubchem Sid

528776204

Canonical Smiles

CN(C(=O)NC1C(C(C(OC1O)CO)O)O)N=O

IUPAC Name

1-methyl-1-nitroso-3-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea

InChIKey

ZSJLQEPLLKMAKR-GKHCUFPYSA-N

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

Isomeric SMILES

CN(C(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O)CO)O)O)N=O

WGK Germany

3

RTECS

LZ5775000

UN Number

3077

Packing Group

III

Molecular Weight

265.22

Beilstein

2060675

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Monosaccharides
          • Level6 Hexoses

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Monosaccharides
• Direct Parent: Hexoses
• Alternative Parents: N-methylnitrosoureas Oxanes Semicarbazides Nitrosamides Secondary alcohols Hemiacetals Polyols Oxacyclic compounds Primary alcohols Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Hexose monosaccharide - N-methylnitrosourea - Nitrosourea - Oxane - Nitrosamide - Semicarbazide - Organic n-nitroso compound - Hemiacetal - Carbonic acid derivative - Secondary alcohol - Organic nitroso compound - Oxacycle - Polyol - Organoheterocyclic compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic nitrogen compound - Carbonyl group - Primary alcohol - Alcohol - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
• External Descriptors: N-nitrosoureas - N-acylglucosamine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in water (≥53 mg/ml), ethanol ( ≥3 mg/ml), and DMSO (≥53 mg/ml).
• Sensitivity: Moisture sensitive；Light sensitive
• Melt Point(°C): 115°C
• Molecular Weight: 265.220 g/mol
• XLogP3: -1.400
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 265.091 Da
• Monoisotopic Mass: 265.091 Da
• Topological Polar Surface Area: 152.000 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 315.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1