Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C8H15N3O7 |
Molecular Weight | 265.2206 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(N=O)C(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO
InChI
InChIKey=AGRCPNMCOXLKFO-BDVNFPICSA-N
InChI=1S/C8H15N3O7/c1-11(10-18)8(17)9-4(2-12)6(15)7(16)5(14)3-13/h2,4-7,13-16H,3H2,1H3,(H,9,17)/t4-,5+,6+,7+/m0/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 Date3.94675192E11 |
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 |
---|---|---|
Modifications in the metabolic pathways of benzene in streptozotocin-induced diabetic rat. | 1999 Aug |
|
Structure, evolution, and liver-specific expression of sterol 12alpha-hydroxylase P450 (CYP8B). | 1999 Jul |
|
Effects of the antihypertensive drug nifedipine on albuminuria and renal histopathology in young spontaneously hypertensive rats with diabetes. | 1999 Nov |
|
Effects of Scutellarein on diabetic rat aorta. | 2000 Apr |
|
Relative importance of transport and alkylation for pancreatic beta-cell toxicity of streptozotocin. | 2000 Dec |
|
Cilostazol prevents impairment of slow axonal transport in streptozotocin-diabetic rats. | 2000 Dec 1 |
|
Gene expression of antioxidant enzymes in experimental diabetic neuropathy. | 2000 Mar |
|
Renal-protective effect of nondepressor dose of cicletanine in diabetic rats with hypertension. | 2000 Mar |
|
Effects of coenzyme Q10 treatment on antioxidant pathways in normal and streptozotocin-induced diabetic rats. | 2001 |
|
Melatonin protects against streptozotocin, but not interleukin-1beta-induced damage of rodent pancreatic beta-cells. | 2001 Apr |
|
Streptozotocin-induced diabetes decreases rat sarcolemmal lactate transport. | 2001 Apr |
|
A hydroxyl radical-like species oxidizes cynomolgus monkey artery wall proteins in early diabetic vascular disease. | 2001 Apr |
|
Selenium-deficient diet induces renal oxidative stress and injury via TGF-beta1 in normal and diabetic rats. | 2001 Apr |
|
Depletion of taurine in experimental diabetic neuropathy: implications for nerve metabolic, vascular, and functional deficits. | 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 |
|
Perineurium inflammation and altered connexin isoform expression in a rat model of diabetes related peripheral neuropathy. | 2001 Apr 27 |
|
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 |
|
Short-term streptozotocin-induced diabetes induces blood pressure decrease associated with reduced aortic (45)Ca(2+) uptake and selective depression of the sustained noradrenergic contraction. | 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 |
|
Effect of KAD-1229, a nonsulfonylurea hypoglycemic agent, on plasma glucose and insulin in streptozotocin-induced diabetic dogs. | 2001 Feb |
|
Excessive matrix metalloproteinase activity in diabetes: inhibition by tetracycline analogues with zinc reactivity. | 2001 Feb |
|
The effect of bradykinin on the oxidative state of rats with acute hyperglycaemia. | 2001 Feb |
|
Reduced Na-K pump but increased Na-K-2Cl cotransporter in aorta of streptozotocin-induced diabetic rat. | 2001 Feb |
|
Involvement of 1,2-diacylglycerol in improvement of heart function by etomoxir in diabetic rats. | 2001 Feb 16 |
|
Mechanisms underlying endothelial dysfunction in diabetes mellitus. | 2001 Feb 2 |
|
Influence of hepatic cells on allogeneic islet transplantation in rats without immunosuppressive drugs. | 2001 Jan |
|
Isolation of antidiabetic components from white-skinned sweet potato (Ipomoea batatas L.). | 2001 Jan |
|
Anticancer drug-induced kidney disorders. | 2001 Jan |
|
Short-term gemfibrozil treatment reverses lipid profile and peroxidation but does not alter blood glucose and tissue antioxidant enzymes in chronically diabetic rats. | 2001 Jan |
|
Distribution of vasoactive intestinal polypeptide, neuropeptide-Y and substance P and their effects on insulin secretion from the in vitro pancreas of normal and diabetic rats. | 2001 Jan |
|
Synergistic antidiabetic activities of zinc, cyclo (his-pro), and arachidonic acid. | 2001 Jan |
|
Ornithine decarboxylase, kidney size, and the tubular hypothesis of glomerular hyperfiltration in experimental diabetes. | 2001 Jan |
|
Quantitative study of the myenteric plexus of the stomach of rats with streptozotocin-induced diabetes. | 2001 Mar |
|
Microscopic analysis of anastomotic healing in the intestine of normal and diabetic rats. | 2001 Mar |
|
Alteration of antioxidants during the progression of heart disease in streptozotocin-induced diabetic rats. | 2001 Mar |
|
Advanced glycation end-products are responsible for the impairment of corpus cavernosal smooth muscle relaxation seen in diabetes. | 2001 Mar |
|
Effect of ligustrum fruit extract on reproduction in experimental diabetic rats. | 2001 Mar |
|
Progressive cortical atrophy after forebrain ischemia in diabetic rats. | 2001 Mar |
|
Effect of NGF and neurotrophin-3 treatment on experimental diabetic autonomic neuropathy. | 2001 Mar |
|
Insulin reverses impaired acetylcholine-induced dilatation of the rat basilar artery during diabetes mellitus. | 2001 Mar 2 |
|
Changes in paw oedema triggered via bradykinin B(1) and B(2) receptors in streptozotocin-diabetic rats. | 2001 Mar 23 |
|
Increase in beta-cell mass in transplanted porcine neonatal pancreatic cell clusters is due to proliferation of beta-cells and differentiation of duct cells. | 2001 May |
|
The MEF2A and MEF2D isoforms are differentially regulated in muscle and adipose tissue during states of insulin deficiency. | 2001 May |
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%)
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NDF-RT |
N0000175558
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
||
|
LIVERTOX |
NBK548344
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
||
|
WHO-ATC |
L01AD04
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
||
|
WHO-VATC |
QL01AD04
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
||
|
NCI_THESAURUS |
C699
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
||
|
NDF-RT |
N0000000236
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
242-646-8
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
C845
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
DB00428
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
SUB10658MIG
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
STREPTOZOTOCIN
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
5W494URQ81
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
72521-89-2
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
ALTERNATIVE | |||
|
3824
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
DTXSID2021282
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
18883-66-4
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
100000083504
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
23615975
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
85998
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
D013311
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
5W494URQ81
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
2483
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
10114
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | RxNorm | ||
|
9288
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
CHEMBL1651906
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
5119
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
37917
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | |||
|
M10232
Created by
admin on Thu Jul 06 00:00:47 UTC 2023 , Edited by admin on Thu Jul 06 00:00:47 UTC 2023
|
PRIMARY | Merck Index |
ACTIVE MOIETY