Streptozocin

Streptozotocin

Clinical data
Trade names	Zanosar
MedlinePlus	a684053
Pregnancy category	US: D (Evidence of risk)
Routes of administration	Intravenous
ATC code	L01AD04 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	17–25% (100% if IV)
Metabolism	Liver, kidney
Biological half-life	35–40 minutes
Identifiers
IUPAC name 2-Deoxy-2-({[methyl(nitroso)amino]carbonyl}amino)-β-D-glucopyranose
CAS Number	18883-66-4 Y
PubChem CID	29327
DrugBank	DB00428 Y
ChemSpider	27273 Y
UNII	5W494URQ81
KEGG	C07313 N
ChEBI	CHEBI:9288 Y
ChEMBL	CHEMBL450214 N
ECHA InfoCard	100.038.754
Chemical and physical data
Formula	C8H15N3O7
Molar mass	265.221 g/mol
3D model (Jmol)	Interactive image
SMILES CN(C(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O)CO)O)O)N=O
InChI 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 Y Key:ZSJLQEPLLKMAKR-GKHCUFPYSA-N Y
NY (what is this?)

Streptozotocin or streptozocin (INN, USP) (STZ) is a naturally occurring chemical that is particularly toxic to the insulin-producing beta cells of the pancreas in mammals. It is used in medicine for treating certain cancers of the Islets of Langerhans and used in medical research to produce an animal model for hyperglycemia in a large dose as well as Type 2 diabetes or Type 1 Diabetes with multiple low doses.

Streptozotocin is approved by the U.S. Food and Drug Administration (FDA) for treating metastatic cancer of the pancreatic islet cells. Since it carries a substantial risk of toxicity and rarely cures the cancer, its use is generally limited to patients whose cancer cannot be removed by surgery. In these patients, streptozotocin can reduce the tumor size and reduce symptoms (especially hypoglycemia due to excessive insulin secretion by insulinomas). A typical dose is 500 mg/m²/day by intravenous injection, for 5 days, repeated every 4–6 weeks.

Due to its high toxicity to beta cells, in scientific researches, streptozotocin has also been long used for inducing insulitis and diabetes on experimental animals.

Streptozotocin is a glucosamine-nitrosourea compound. As with other alkylating agents in the nitrosourea class, it is toxic to cells by causing damage to the DNA, though other mechanisms may also contribute. DNA damage induces activation of poly ADP-ribosylation, which is likely more important for diabetes induction than DNA damage itself. Streptozotocin is similar enough to glucose to be transported into the cell by the glucose transport protein GLUT2, but is not recognized by the other glucose transporters. This explains its relative toxicity to beta cells, since these cells have relatively high levels of GLUT2.