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Streptozotocin

CAT: 0804-HY-13753-01Size: 100 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-13753-01Size:100 mg
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Description
Streptozotocin (Streptozocin; STZ) is an antibiotic widely used in experimental animal models of induced diabetes. Streptozotocin enters B cells via the glucose transporter (GLUT2) and causes the alkylation of DNA (DNA-methylating) . Streptozotocin can induce the apoptosis of β cells[1][2][3].
CAS Number
18883-66-4
Product Name Alternative
Streptozocin; NSC-85998; U 9889
UNSPSC
12352005
Hazard Statement
H228, H341, H351
Target
Antibiotic; Apoptosis; Autophagy; Bacterial; DNA Alkylator/Crosslinker; DNA/RNA Synthesis
Type
Natural Products
Related Pathways
Anti-infection; Apoptosis; Autophagy; Cell Cycle/DNA Damage
Applications
Cancer-programmed cell death
Field of Research
Cancer; Infection
Assay Protocol
https://www.medchemexpress.com/streptozotocin.html
Purity
99.20
Solubility
DMSO : 100 mg/mL (ultrasonic) |H2O : 100 mg/mL (ultrasonic)
Smiles
O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](NC(N(C)N=O)=O)[C@H]1O
Molecular Formula
C8H15N3O7
Molecular Weight
265.22
Precautions
H228, H341, H351
References & Citations
[1]Furman BL. Streptozotocin-Induced Diabetic Models in Mice and Rats. Curr Protoc Pharmacol. 2015 Sep 1;70:5.47.1-5.47.20.|[2]Bennett RA, et al. Alkylation of DNA in rat tissues following administration of streptozotocin. Cancer Res. 1981 Jul;41 (7) :2786-90.|[3]Kim B, et al. Outbred Mice with Streptozotocin-Induced Diabetes Show Sex Differences in Glucose Metabolism. Int J Mol Sci. 2023 Mar 8;24 (6) :5210.|[4]Gurley SB, et al. Impact of genetic background on nephropathy in diabetic mice. Am J Physiol Renal Physiol. 2006 Jan;290 (1) :F214-22.|[5]Huang F, et al. Antidiabetic effect of a new peptide from Squalus mitsukurii liver (S-8300) in streptozocin-induced diabetic mice. J Pharm Pharmacol. 2005 Dec;57 (12) :1575-80.|[6]Diab RA, et al. Immunotoxicological effects of streptozotocin and alloxan: in vitro and in vivo studies. Immunol Lett. 2015 Feb;163 (2) :193-8.|[7]Raza H, et al. Streptozotocin-induced cytotoxicity, oxidative stress and mitochondrial dysfunction in human hepatoma HepG2 cells. Int J Mol Sci. 2012;13 (5) :5751-5767.|[8]Schnedl WJ, et al. STZ transport and cytotoxicity. Specific enhancement in GLUT2-expressing cells. Diabetes. 1994 Nov;43 (11) :1326-33.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C (Powder, sealed storage, away from moisture and light)
Scientific Category
Natural Products
Clinical Information
Launched

Chemical Information

Streptozocin

Streptozotocin (Streptozocin) can cause cancer according to an independent committee of scientific and health experts. It can cause developmental toxicity, female reproductive toxicity and male reproductive toxicity according to state or federal government labeling requirements.

CAS Number18883-66-4
PubChem CID29327
IUPAC Name1-methyl-1-nitroso-3-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea
Molecular FormulaC8H15N3O7
Molecular Weight265.22
XLogP-1.4
Topological Polar Surface Area152
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count8
Rotatable Bond Count2
Heavy Atom Count18
Formal Charge0
Complexity315
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
InChIKey
ZSJLQEPLLKMAKR-GKHCUFPYSA-N
Chemical Structure
2D Structure
2D structure of Streptozocin
CAS: 18883-66-4
CID: 29327
Formula: C8H15N3O7
MW: 265.22
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight265.22
XLogP3-1.4
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count8
Rotatable Bond Count2
Exact Mass265.09099983
Monoisotopic Mass265.09099983
Topological Polar Surface Area152 Ų
Heavy Atom Count18
Formal Charge0
Complexity315
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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