Streptozocin
[CAS# 18883-66-4]

Identification

• Classification: API >> Antibiotics >> Other antibiotics
• Name: Streptozocin
• Synonyms: 2-Desoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose; 2-Deoxy-2-[[(methylnitrosoamino)carbonyl]amino]-D-glucose
• Molecular Formula: C₈H₁₅N₃O₇
• Molecular Weight: 265.22
• CAS Registry Number: 18883-66-4
• EC Number: 242-646-8
• SMILES: CN(C(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O)CO)O)O)N=O

Properties

• Density: 1.9±0.1 g/cm³ Calc.^*
• Melting point: 121 °C (Decomposes) (Expl.)
• Solubility: 10 mM in DMSO (Expl.)
• Index of refraction: 1.67 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H312-H332-H340-H350-H360
• Safety Statements: P203-P261-P271-P280-P302+P352-P304+P340-P317-P318-P321-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Carcinogenicity	Carc.	1B	H350
Reproductive toxicity	Repr.	1A	H360
Germ cell mutagenicity	Muta.	1A	H340
Carcinogenicity	Carc.	1A	H350
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Germ cell mutagenicity	Muta.	2	H341
Flammable solids	Flam. Sol.	2	H228
Carcinogenicity	Carc.	2	H351

Discovery and Applications

Streptozocin is a naturally occurring nitrosourea compound isolated from the bacterium Streptomyces achromogenes. It was first discovered in the 1950s during the search for novel antitumor antibiotics. The compound gained attention for its unique chemical structure, which combines a glucose moiety with a nitrosourea functional group, enabling it to target specific cells selectively.

Streptozocin has been primarily developed and applied as a chemotherapeutic agent. Its mechanism of action involves alkylation and DNA strand breakage, leading to cytotoxic effects, particularly in cells with high glucose uptake. This selectivity allows streptozocin to preferentially target pancreatic beta cells, which absorb glucose at a high rate. Consequently, streptozocin has been widely used in oncology for the treatment of pancreatic islet cell tumors, also known as pancreatic neuroendocrine tumors.

Beyond its clinical application in oncology, streptozocin has been employed in experimental research as a diabetogenic agent. Due to its selective toxicity to pancreatic beta cells, administration of streptozocin in laboratory animals induces insulin-dependent diabetes mellitus. This model is extensively utilized in studies of diabetes pathophysiology and in the evaluation of antidiabetic drugs.

Clinically, streptozocin is often administered in combination with other chemotherapeutic agents to enhance antitumor efficacy. It is given intravenously, and its pharmacological profile includes rapid uptake into target cells, metabolic activation, and generation of DNA-damaging species. Its use is accompanied by monitoring for side effects such as nephrotoxicity, hepatotoxicity, and nausea.

Streptozocin’s discovery provided a valuable tool both for cancer therapy and for diabetes research, contributing to advances in understanding pancreatic function and disease. Its dual role highlights the importance of natural products in drug discovery and biomedical research.

The chemical’s stability and solubility characteristics have allowed for various formulation developments, improving its clinical usability. Ongoing research explores analogues and derivatives of streptozocin aiming to optimize therapeutic indices and reduce adverse effects.

Overall, streptozocin remains an important compound in both clinical and research settings due to its unique biological activity and specificity for pancreatic beta cells.

References

1994. Comparison of the effects of various vanadium salts on glucose homeostasis in streptozotocin-diabetic rats. European Journal of Pharmacology, 261(1-2).
DOI: 10.1016/0014-2999(94)90334-4

1998. Streptozotocin may provide protection against subsequent oxidative stress of endotoxin or streptozotocin in rats. Journal of Biochemical and Molecular Toxicology, 12(3).
DOI: 10.1002/(sici)1099-0461(1998)12:3<143::aid-jbt2>3.0.co;2-l

2024. Antihyperglycemic and hypolipidemic effect of yellow-fleshed cassava/wheat flour composite bread in high fat/streptozotocin induced diabetic rats. Journal of Food Measurement and Characterization.
DOI: 10.1007/s11694-024-02622-7