Skip to Content
Merck

S0130

Streptozocin

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

Synonym(s):

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

Sign In to View Organizational & Contract Pricing.

Select a Size


About This Item

Empirical Formula (Hill Notation):
C8H15N3O7
CAS Number:
Molecular Weight:
265.22
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
242-646-8
MDL number:
Beilstein/REAXYS Number:
2060675
Assay:
≥75% α-anomer basis, ≥98% (HPLC)
Form:
powder
Quality level:
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

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

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

≥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

storage temp.

−20°C

Quality Level

Looking for similar products? Visit Product Comparison Guide

General description

Streptozocin (STZ) is an antineoplastic antibiotic. This N-nitroso-containing compound acts as a nitric oxide donor in pancreatic islets. It is a methylnitrosourea attached to a single molecule of glucosamine and has a high affinity for the cell surface glucose transporter glucose transporter type 2 (GLUT2), which is highly expressed on beta cells of the islets of Langerhans. Streptozotocin cannot pass through the blood-brain barrier, but its metabolites are usually seen in the cerebrospinal fluid.

In cell culture medium, it has been shown to have a biological half-life of approximately 19 minutes. It is a strong methylating agent that interacts with DNA in vitro to produce methylated purines. It can impact glucose metabolism because STZ is particularly toxic to the insulin-producing beta cells of the pancreas in mammals and is also an effective antibiotic against Gram-negative bacteria. It inhibits the synthesis of DNA in microorganisms and mammalian cells by alkylation and cross-linking the strands of DNA and affects all stages of the mammalian cell cycle. STZ is considered mutagenic, carcinogenic, and possibly teratogenic in humans. It is cytotoxic to the neuroendocrine tumor cell lines that express the GLUT2 glucose transporter.

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.
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

Mixed anomers

pictograms

FlameHealth hazard

signalword

Danger

Hazard Classifications

Carc. 2 - Flam. Sol. 1 - 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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

S0130-BULK: + S0130-100MG: + S0130-500MG: + S0130-1G: + S0130-50MG: + S0130-5G: + S0130-VAR:

jan


Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Housekeeping proteins: How useful are they in skeletal muscle
diabetes studies and muscle hypertrophy models?
Marco
Analytical Biochemistry, 504, 38-40 (2016)
Streptozocin
Papich MG
Saunders Handbook of Veterinary Drugs, 742-743 (2016)
Review of the mechanism of cell death resulting from streptozotocin challenge in experimental animals, its practical use and potential risk to humans
Chinedum
Journal of diabetes and metabolic disorders, 12, 60-60 (2013)
Cordyceps militaris Treatment Preserves Renal Function in Type 2 Diabetic Nephropathy Mice
Sung-Hsun Yu
PLoS ONE (2016)
Streptozotocin
Abdollahi, M and Hosseini, A
Encyclopedia of Toxicology (2014)

Articles

Nitric oxide (NO) as a signal transporter in neurons, endothelial cells and in the immune system.

DISCOVER Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service