U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H15N3O7
Molecular Weight 265.2209
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of STREPTOZOCIN

SMILES

CN(C(=N[C@@]([H])(C=O)[C@]([H])([C@@]([H])([C@@]([H])(CO)O)O)O)O)N=O

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

HIDE SMILES / InChI

Description
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

Curator's Comment:: It does not cross the blood-brain barrier, but its metabolites are found in cerebral spinal fluid

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P36897
Gene ID: 7046.0
Gene Symbol: TGFBR1
Target Organism: Homo sapiens (Human)
38.0 nM [Ki]
Target ID: P37173
Gene ID: 7048.0
Gene Symbol: TGFBR2
Target Organism: Homo sapiens (Human)
300.0 nM [Ki]
Target ID: CHEMBL2311221
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZANOSAR

Approved Use

ZANOSAR is indicated in the treatment of metastatic islet cell carcinoma of the pancreas.

Launch Date

3.94675192E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.03 mM
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

AUC

ValueDoseCo-administeredAnalytePopulation
5.3 mM × min
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

Doses

DosePopulationAdverse 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%)
Acute tubular necrosis (grade 5, 2%)
Sources: Page: p.608
AEs

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
Relative importance of transport and alkylation for pancreatic beta-cell toxicity of streptozotocin.
2000 Dec
Polymorphisms in the Mn-SOD and EC-SOD genes and their relationship to diabetic neuropathy in type 1 diabetes mellitus.
2001
Photomechanical transdermal delivery of insulin in vivo.
2001
Effects of coenzyme Q10 treatment on antioxidant pathways in normal and streptozotocin-induced diabetic rats.
2001
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
Streptozotocin-Induced diabetes mellitus is associated with increased pancreatic tissue levels of noradrenaline and adrenaline in the rat.
2001 Apr
A hydroxyl radical-like species oxidizes cynomolgus monkey artery wall proteins in early diabetic vascular disease.
2001 Apr
Gene expression profile in streptozotocin-induced diabetic mice kidneys undergoing glomerulosclerosis.
2001 Apr
Insulin deprivation leads to deficiency of Sp1 transcription factor in H-411E hepatoma cells and in streptozotocin-induced diabetic ketoacidosis in the rat.
2001 Apr
Compensatory increase in AQP2, p-AQP2, and AQP3 expression in rats with diabetes mellitus.
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
Perineurium inflammation and altered connexin isoform expression in a rat model of diabetes related peripheral neuropathy.
2001 Apr 27
The impact of glycaemic control on autoregulation of glomerular filtration rate in patients with non-insulin dependent diabetes.
2001 Feb
A new halogenated antidiabetic vanadyl complex, bis(5-iodopicolinato)oxovanadium(IV): in vitro and in vivo insulinomimetic evaluations and metallokinetic analysis.
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
Early streptozotocin-diabetes mellitus downregulates rat kidney AT2 receptors.
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
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
Reduced Na-K pump but increased Na-K-2Cl cotransporter in aorta of streptozotocin-induced diabetic rat.
2001 Feb
Spinal and supraspinal components of opioid antinociception in streptozotocin induced diabetic neuropathy in rats.
2001 Feb 1
Low dose streptozotocin-induced diabetes in rat insulin promoter-mCD80-transgenic mice is T cell autoantigen-specific and CD28 dependent.
2001 Feb 15
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
In vivo effects of vanadium on GLUT4 translocation in cardiac tissue of STZ-diabetic rats.
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
Influence of long-term diabetes on renal glycogen metabolism in the rat.
2001 Jan
Synergistic antidiabetic activities of zinc, cyclo (his-pro), and arachidonic acid.
2001 Jan
GDNF rescues nonpeptidergic unmyelinated primary afferents in streptozotocin-treated diabetic mice.
2001 Jan
Ornithine decarboxylase, kidney size, and the tubular hypothesis of glomerular hyperfiltration in experimental diabetes.
2001 Jan
Intracerebroventricular injection of streptozotocin in rats produces both oxidative stress in the brain and cognitive impairment.
2001 Jan 19
Treatment of diabetes with vanadium salts: general overview and amelioration of nutritionally induced diabetes in the Psammomys obesus gerbil.
2001 Jan-Feb
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
Lack of antidiabetic effect of a Eugenia jambolana leaf decoction on rat streptozotocin diabetes.
2001 Mar
Advanced glycation end-products are responsible for the impairment of corpus cavernosal smooth muscle relaxation seen in diabetes.
2001 Mar
Effect of NGF and neurotrophin-3 treatment on experimental diabetic autonomic neuropathy.
2001 Mar
Contractile and electrical properties of sternohyoid muscle in streptozotocin diabetic rats.
2001 Mar
Changes in paw oedema triggered via bradykinin B(1) and B(2) receptors in streptozotocin-diabetic rats.
2001 Mar 23
Cisplatin pharmacokinetics and its nephrotoxicity in diabetic rabbits.
2001 Mar-Apr
The MEF2A and MEF2D isoforms are differentially regulated in muscle and adipose tissue during states of insulin deficiency.
2001 May
K cells: a novel target for insulin gene therapy for the prevention of diabetes.
2001 May-Jun
Patents

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
STREPTOZOCIN (STZ) (30 mM) caused urine pancreatic beta cell line, INS-1 to undergo necrosis (22%) as well as apoptosis (17%)
Name Type Language
STREPTOZOCIN
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
STREPTOZOCIN [ORANGE BOOK]
Common Name English
STREPTOZOTOCIN
Common Name English
U-9889
Code English
STREPTOZOCIN [MART.]
Common Name English
STREPTOZOCIN [INN]
Common Name English
STREPTOZOCIN [WHO-DD]
Common Name English
1-METHYL-1-NITROSO-3-((3R,4R,5S,6R)-2,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-3-YL)UREA
Systematic Name English
NSC-37917
Code English
STREPTOZOCIN [USAN]
Common Name English
STREPTOZOCIN [MI]
Common Name English
2-DEOXY-2-(3-METHYL-3-NITROSOUREIDO)-.ALPHA.(AND .BETA.)-D-GLUCOPYRANOSE
Common Name English
1-METHYL-1-NITROSO-3-((2R,3R,4S,5R)-3,4,5,6-TETRAHYDROXY-1-OXOHEXAN-2-YL)UREA
Systematic Name English
D-GLUCOPYRANOSE, 2-DEOXY-2-(((METHYLNITROSOAMINO)CARBONYL)AMINO)-
Systematic Name English
STREPTOZOCIN [VANDF]
Common Name English
ZANOSAR
Brand Name English
STREPTOZOTOCIN [IARC]
Common Name English
STREPTOZOCIN [JAN]
Common Name English
2-DEOXY-2-(3-METHYL-3-NITROSOUREIDO)-D-GLUCOPYRANOSE
Systematic Name English
STREPTOZOCIN [HSDB]
Common Name English
NSC-85998
Code English
Classification Tree Code System Code
NDF-RT N0000175558
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
LIVERTOX 901
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
WHO-ATC L01AD04
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
WHO-VATC QL01AD04
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
NCI_THESAURUS C699
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
NDF-RT N0000000236
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
242-646-8
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
PRIMARY
NCI_THESAURUS
C845
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
PRIMARY
DRUG BANK
DB00428
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
PRIMARY
EVMPD
SUB10658MIG
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
PRIMARY
WIKIPEDIA
STREPTOZOTOCIN
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
PRIMARY
CAS
72521-89-2
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
ALTERNATIVE
INN
3824
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
PRIMARY
EPA CompTox
18883-66-4
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
PRIMARY
CAS
18883-66-4
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
PRIMARY
PUBCHEM
23615975
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
PRIMARY
MESH
D013311
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
PRIMARY
FDA UNII
5W494URQ81
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
PRIMARY
DRUG CENTRAL
2483
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
PRIMARY
RXCUI
10114
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL1651906
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
PRIMARY
HSDB
5119
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
PRIMARY
MERCK INDEX
M10232
Created by admin on Sat Jun 26 16:31:21 UTC 2021 , Edited by admin on Sat Jun 26 16:31:21 UTC 2021
PRIMARY Merck Index