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Merck
CN

85882

Streptozocin

≥98.0% (HPLC)

Synonym(s):

N-(Methylnitrosocarbamoyl)-α-D-glucosamine, Streptozotocin

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About This Item

Empirical Formula (Hill Notation):
C8H15N3O7
CAS Number:
18883-66-4
Molecular Weight:
265.22
EC Number:
242-646-8
UNSPSC Code:
12352200
PubChem Substance ID:
329769421
Beilstein/REAXYS Number:
2060675
MDL number:
MFCD00006607

Key Documents

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InChI key

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

SMILES string

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

assay

≥98.0% (HPLC)

mp

121 °C (dec.) (lit.)

mode of action

DNA synthesis | interferes

storage temp.

−20°C

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General description

Chemical structure: aminoglycoside

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.
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.

Other Notes

This product has been replaced by S0130-SIGMA | Streptozocin ≥75% α-anomer basis, ≥98% (HPLC), powder

pictograms

FlameHealth hazard
GHS02,GHS08

signalword

Warning

Hazard Classifications

Carc. 2 - Flam. Sol. 2 - Muta. 2

Storage Class

4.1B - Flammable solid hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Bas Brouwers et al.
The Journal of biological chemistry, 288(38), 27200-27207 (2013-08-14)
Streptozotocin (STZ) is widely used as diabetogenic agent in animal models for diabetic nephropathy (DN). However, it is also directly cytotoxic to kidneys, making it difficult to distinguish between DN-related and STZ-induced nephropathy. Therefore, an improved protocol to generate mice
Keith Al-Hasani et al.
Developmental cell, 26(1), 86-100 (2013-07-03)
It was recently demonstrated that embryonic glucagon-producing cells in the pancreas can regenerate and convert into insulin-producing β-like cells through the constitutive/ectopic expression of the Pax4 gene. However, whether α cells in adult mice display the same plasticity is unknown.
Jayasankar Kosaraju et al.
Neuropharmacology, 72, 291-300 (2013-04-23)
Type 2 diabetes (T2D) is one of the major risk factors associated with Alzheimer's disease (AD). Recent studies have found similarities in molecular mechanisms that underlie the respective degenerative developments in the two diseases. Pharmacological agents, such as dipeptidyl peptidase-4
Mouse models of insulin dependent diabetes: low-dose streptozocin-induced diabetes and nonobese diabetic (NOD) mice.
H Kolb
Diabetes/metabolism reviews, 3(3), 751-778 (1987-07-01)
Greg Tesch et al.
Diabetologia, 57(9), 1977-1985 (2014-06-25)
The AGEs and the receptor for AGEs (RAGE) are known contributors to diabetic complications. RAGE also has a physiological role in innate and adaptive immunity and is expressed on immune cells. The aim of this study was to determine whether
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