Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C8H15N3O7 |
Molecular Weight | 265.2206 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O
InChI
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
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=15d161ed-9e7b-4c92-ba45-0556d2423e67Curator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Streptozotocin
http://www.drugs.com/ppa/streptozocin.html
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=15d161ed-9e7b-4c92-ba45-0556d2423e67
Curator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Streptozotocin
http://www.drugs.com/ppa/streptozocin.html
Streptozotocin (Streptozocin, STZ, Zanosar) 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 1 diabetes with multiple low doses. Streptozocin inhibits DNA synthesis in bacterial and mammalian cells. In bacterial cells, a specific interaction with cytosine moieties leads to degradation of DNA. The biochemical mechanism leading to mammalian cell death has not been definitely established; streptozocin inhibits cell proliferation at a considerably lower level than that needed to inhibit precursor incorporation into DNA or to inhibit several of the enzymes involved in DNA synthesis. Although streptozocin inhibits the progression of cells into mitosis, no specific phase of the cell cycle is particularly sensitive to its lethal effects. Streptozocin is active in the L1210 leukemic mouse over a fairly wide range of parenteral dosage schedules. In experiments in many animal species, streptozocin induced a diabetes that resembles human hyperglycemic nonketotic diabetes mellitus. This phenomenon, which has been extensively studied, appears to be mediated through a lowering of beta cell nicotinamide adenine dinucleotide (NAD) and consequent histopathologic alteration of pancreatic islet beta cells. The metabolism and the chemical dissociation of streptozocin that occurs under physiologic conditions has not been extensively studied. When administered intravenously to a variety of experimental animals, streptozocin disappears from the blood very rapidly. In all species tested, it was found to concentrate in the liver and kidney. As much as 20% of the drug (or metabolites containing an N-nitrosourea group) is metabolized and/or excreted by the kidney. Metabolic products have not yet been identified.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4282704
Curator's Comment: It does not cross the blood-brain barrier, but its metabolites are found in cerebral spinal fluid
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P36897 Gene ID: 7046.0 Gene Symbol: TGFBR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18413796 |
38.0 nM [Ki] | ||
Target ID: P37173 Gene ID: 7048.0 Gene Symbol: TGFBR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18413796 |
300.0 nM [Ki] | ||
Target ID: CHEMBL2311221 Sources: http://www.drugbank.ca/drugs/DB00428 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ZANOSAR Approved UseZANOSAR is indicated in the treatment of metastatic islet cell carcinoma of the pancreas. Launch Date1982 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.03 mM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1458714 |
1 g single, intraperitoneal dose: 1 g route of administration: Intraperitoneal experiment type: SINGLE co-administered: |
STREPTOZOCIN plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.3 mM × min EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1458714 |
1 g single, intraperitoneal dose: 1 g route of administration: Intraperitoneal experiment type: SINGLE co-administered: |
STREPTOZOCIN plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2 g/m2 1 times / 6 weeks multiple, intravenous MTD Dose: 2 g/m2, 1 times / 6 weeks Route: intravenous Route: multiple Dose: 2 g/m2, 1 times / 6 weeks Co-administed with:: carmustine, i.v(125 mg/m2; 1/6wk) Sources: Page: p.258 |
unhealthy, 31-79 n = 24 Health Status: unhealthy Condition: Cancer Age Group: 31-79 Sex: M+F Population Size: 24 Sources: Page: p.258 |
|
500 mg/m2 1 times / day multiple, intravenous Recommended Dose: 500 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 500 mg/m2, 1 times / day Co-administed with:: Cyclophosphamide, i.v.(1000 mg/m2 given on day 1 and 21) Sources: Page: p.608 |
unhealthy n = 51 Health Status: unhealthy Condition: Adenocarcinoma of the pancreas Sex: M+F Population Size: 51 Sources: Page: p.608 |
Disc. AE: Leukopenia, Acute tubular necrosis... AEs leading to discontinuation/dose reduction: Leukopenia (grade 5, 2%) Sources: Page: p.608Acute tubular necrosis (grade 5, 2%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Acute tubular necrosis | grade 5, 2% Disc. AE |
500 mg/m2 1 times / day multiple, intravenous Recommended Dose: 500 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 500 mg/m2, 1 times / day Co-administed with:: Cyclophosphamide, i.v.(1000 mg/m2 given on day 1 and 21) Sources: Page: p.608 |
unhealthy n = 51 Health Status: unhealthy Condition: Adenocarcinoma of the pancreas Sex: M+F Population Size: 51 Sources: Page: p.608 |
Leukopenia | grade 5, 2% Disc. AE |
500 mg/m2 1 times / day multiple, intravenous Recommended Dose: 500 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 500 mg/m2, 1 times / day Co-administed with:: Cyclophosphamide, i.v.(1000 mg/m2 given on day 1 and 21) Sources: Page: p.608 |
unhealthy n = 51 Health Status: unhealthy Condition: Adenocarcinoma of the pancreas Sex: M+F Population Size: 51 Sources: Page: p.608 |
PubMed
Title | Date | PubMed |
---|---|---|
Inhibition of the neuronal insulin receptor causes Alzheimer-like disturbances in oxidative/energy brain metabolism and in behavior in adult rats. | 1999 |
|
Suppression subtractive hybridization identifies high glucose levels as a stimulus for expression of connective tissue growth factor and other genes in human mesangial cells. | 1999 Feb 26 |
|
Role of sympathetic nervous system in experimental hypertension and diabetes mellitus. | 1999 Jan-Feb |
|
Diabetes and hypertension: experimental models for pharmacological studies. | 1999 Jan-Feb |
|
KRH-594, a new angiotensin AT1 receptor antagonist, ameliorates nephropathy and hyperlipidaemia in diabetic spontaneously hypertensive rats. | 2000 Apr |
|
Gabapentin inhibits excitatory synaptic transmission in the hyperalgesic spinal cord. | 2000 Aug |
|
Opposite regulation of brain and C-type natriuretic peptides in the streptozotocin-diabetic cardiopathy. | 2000 Jun |
|
NaCl-induced hypertensive rat model of non-insulin-dependent diabetes: role of sympathetic modulation. | 2000 May |
|
Lower faecal egg excretion in chemically-induced diabetic mice infected with Schistosoma mansoni due to impaired egg maturation. | 2001 Apr |
|
Mechanisms underlying increased release of endothelin-1 from aorta in diabetic rats. | 2001 Apr |
|
A hydroxyl radical-like species oxidizes cynomolgus monkey artery wall proteins in early diabetic vascular disease. | 2001 Apr |
|
12-lipoxygenase is increased in glucose-stimulated mesangial cells and in experimental diabetic nephropathy. | 2001 Apr |
|
Defective glucose-dependent cytosolic Ca2+ handling in islets of GK and nSTZ rat models of type 2 diabetes. | 2001 Apr |
|
Agouti-related protein is a mediator of diabetic hyperphagia. | 2001 Apr 2 |
|
Gene therapy for streptozotocin-induced diabetic mice by electroporational transfer of naked human insulin precursor DNA into skeletal muscle in vivo. | 2001 Apr 20 |
|
Metabolic and functional studies on isolated islets in a new rat model of type 2 diabetes. | 2001 Apr 25 |
|
The effect of streptozotocin-induced experimental diabetes mellitus on calvarial defect healing and bone turnover in the rat. | 2001 Feb |
|
Insulin-like growth factor-I and over-expression of Bcl-xL prevent glucose-mediated apoptosis in Schwann cells. | 2001 Feb |
|
Ramipril and aminoguanidine restore renal lysosomal processing in streptozotocin diabetic rats. | 2001 Feb |
|
Experimental hypoxia of STZ-diabetic rat myocardium and protective effects of Ginkgo biloba extract. II. Ultrastructural investigation of microvascular endothelium. | 2001 Feb |
|
The effect of streptozotocin-induced diabetes on the release of excitotoxic and other amino acids from the ischemic rat cerebral cortex. | 2001 Feb |
|
Localization of extracellular matrix and mitogen-activated protein kinase (MAPK) in aorta of streptozotocin treated Mongolian gerbils. | 2001 Feb |
|
Excessive matrix metalloproteinase activity in diabetes: inhibition by tetracycline analogues with zinc reactivity. | 2001 Feb |
|
Hypoglycemic effect of the water extract of Smallantus sonchifolius (yacon) leaves in normal and diabetic rats. | 2001 Feb |
|
The effect of bradykinin on the oxidative state of rats with acute hyperglycaemia. | 2001 Feb |
|
Spinal and supraspinal components of opioid antinociception in streptozotocin induced diabetic neuropathy in rats. | 2001 Feb 1 |
|
Mechanisms underlying endothelial dysfunction in diabetes mellitus. | 2001 Feb 2 |
|
Recovery of microvascular responses during streptozotocin-induced diabetes. | 2001 Feb 23 |
|
Isolation of antidiabetic components from white-skinned sweet potato (Ipomoea batatas L.). | 2001 Jan |
|
In vivo effects of vanadium on GLUT4 translocation in cardiac tissue of STZ-diabetic rats. | 2001 Jan |
|
Ornithine decarboxylase, kidney size, and the tubular hypothesis of glomerular hyperfiltration in experimental diabetes. | 2001 Jan |
|
Hypotriglyceridemic and hypocholesterolemic effects of anti-diabetic Momordica charantia (karela) fruit extract in streptozotocin-induced diabetic rats. | 2001 Mar |
|
Progressive cortical atrophy after forebrain ischemia in diabetic rats. | 2001 Mar |
|
Changes in paw oedema triggered via bradykinin B(1) and B(2) receptors in streptozotocin-diabetic rats. | 2001 Mar 23 |
Sample Use Guides
daily intravenous administration is 500 mg/m2 of body surface area for five consecutive days every six weeks until maximum benefit or until treatment-limiting toxicity is observed
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=8876977
STREPTOZOCIN (STZ) (30 mM) caused urine pancreatic beta cell line, INS-1 to undergo necrosis (22%) as well as apoptosis (17%)
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SUBSTANCE RECORD