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18883-66-4 molecular structure
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3-methyl-3-nitroso-1-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea

ChemBase ID: 311
Molecular Formular: C8H15N3O7
Molecular Mass: 265.2206
Monoisotopic Mass: 265.09099984
SMILES and InChIs

SMILES:
O1[C@@H]([C@@H](O)[C@H](O)[C@@H](NC(=O)N(N=O)C)[C@H]1O)CO
Canonical SMILES:
OC[C@H]1O[C@H](O)[C@@H]([C@H]([C@@H]1O)O)NC(=O)N(N=O)C
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

Cite this record

CBID:311 http://www.chembase.cn/molecule-311.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
3-methyl-3-nitroso-1-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea
IUPAC Traditional name
streptozocin
Brand Name
STREPTOZOTOCIN
STRZ
STZ
Streptozocin [Usan:Inn]
Streptozocine [INN-French]
Streptozocinium [Latin]
Streptozocinum [INN-Latin]
Streptozoticin
Zanosar
Synonyms
Streptozocin
N-(Methylnitrosocarbamoyl)-α-D-glucosamine
Streptozotocin
Streptozocin
Streptozocin
Zanosar
STZ
CAS Number
18883-66-4
EC Number
242-646-8
MDL Number
MFCD00006607
Beilstein Number
2060675
PubChem SID
24899428
46508872
160963774
PubChem CID
29327

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 11.425146  H Acceptors
H Donor LogD (pH = 5.5) -2.7202861 
LogD (pH = 7.4) -2.7203243  Log P -2.7202857 
Molar Refractivity 55.9552 cm3 Polarizability 21.796125 Å3
Polar Surface Area 151.92 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -1.71  LOG S -0.9 
Solubility (Water) 3.35e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
5070 mg/L expand Show data source
Apperance
white to off-white powder expand Show data source
Melting Point
121 °C (dec.)(lit.) expand Show data source
Hydrophobicity(logP)
-1.7 expand Show data source
Storage Condition
-20°C expand Show data source
RTECS
LZ5775000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
45 expand Show data source
Safety Statements
53-45 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H350 expand Show data source
GHS Precautionary statements
P201-P308 + P313 expand Show data source
Personal Protective Equipment
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥75% α-anomer basis expand Show data source
≥98% (HPLC) expand Show data source
≥98.0% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Empirical Formula (Hill Notation)
C8H15N3O7 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
DrugBank - DB00428 external link
Item Information
Drug Groups approved
Description An antibiotic that is produced by Stretomyces achromogenes. It is used as an antineoplastic agent and to induce diabetes in experimental animals. [PubChem]
Indication For the treatment of malignant neoplasms of pancreas (metastatic islet cell carcinoma).
Pharmacology Streptozocin is an antitumour antibiotic consisting of a nitrosourea moiety interposed between a methyl group and a glucosamine. Streptozocin is indicated in the treatment of metastatic islet cell carcinoma of the pancreas. 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.
Toxicity Symptoms of overdose include nausea and vomiting, anorexia, myelosuppression; and nephrotoxicity.
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic
Absorption Poor oral absorption (17-25%)
Half Life 5-15 minutes
Elimination As much as 20% of the drug (or metabolites containing an N-nitrosourea group) is metabolized and/or excreted by the kidney.
References
[Link]
Brentjens R, Saltz L: Islet cell tumors of the pancreas: the medical oncologist's perspective. Surg Clin North Am. 2001 Jun;81(3):527-42. [Pubmed]
Wang Z, Gleichmann H: GLUT2 in pancreatic islets: crucial target molecule in diabetes induced with multiple low doses of streptozotocin in mice. Diabetes. 1998 Jan;47(1):50-6. [Pubmed]
Schnedl WJ, Ferber S, Johnson JH, Newgard CB: STZ transport and cytotoxicity. Specific enhancement in GLUT2-expressing cells. Diabetes. 1994 Nov;43(11):1326-33. [Pubmed]
VAVRA JJ, DEBOER C, DIETZ A, HANKA LJ, SOKOLSKI WT: Streptozotocin, a new antibacterial antibiotic. Antibiot Annu. 1959-1960;7:230-5. [Pubmed]
Mansford KR, Opie L: Comparison of metabolic abnormalities in diabetes mellitus induced by streptozotocin or by alloxan. Lancet. 1968 Mar 30;1(7544):670-1. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1312 external link
Research Area: Cancer
Biological Activity:
Streptozotocin 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 Type 1 diabetes. Streptozocin is also a synthetic antineoplastic agent that is chemically related to other nitrosoureas used in cancer chemotherapy. [1]
Sigma Aldrich - S0130 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Streptozocin is used to induce Type 1 diabetes for medical research.
General description
Streptozotocin, a glucosamine-nitrosourea, is a DNA alkylating agent that enters cells exclusively via the GLUT2 glucose transport protein. Streptozocin, a diabetagen, is especially toxic to pancreatic islet insulin-producing β-cells. It is toxic to GLUT2 positive neuroendocrine tumor cells.
Other Notes
Mixed anomers
包装
1, 5 g in glass bottle
100, 500 mg in glass bottle
50 mg in poly bottle
Biochem/physiol Actions
An N-nitroso-containing compound that acts as a nitric oxide donor in pancreatic islets; induces death of insulin-secreting cells, producing an animal model of diabetes. Potent DNA methylating agent that induces chromosomal breakage.1 Cytotoxic to neuroendocrine tumor cell lines that express the GLUT2 glucose transporter.
Sigma Aldrich - 85882 external link
Biochem/physiol Actions
An N-nitroso-containing compound that acts as a nitric oxide donor in pancreatic islets; induces death of insulin-secreting cells, producing an animal model of diabetes. Potent DNA methylating agent that induces chromosomal breakage.1 Cytotoxic to neuroendocrine tumor cell lines that express the GLUT2 glucose transporter.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Brentjens R, Saltz L: Islet cell tumors of the pancreas: the medical oncologist's perspective. Surg Clin North Am. 2001 Jun;81(3):527-42. Pubmed
  • • Wang Z, Gleichmann H: GLUT2 in pancreatic islets: crucial target molecule in diabetes induced with multiple low doses of streptozotocin in mice. Diabetes. 1998 Jan;47(1):50-6. Pubmed
  • • Schnedl WJ, Ferber S, Johnson JH, Newgard CB: STZ transport and cytotoxicity. Specific enhancement in GLUT2-expressing cells. Diabetes. 1994 Nov;43(11):1326-33. Pubmed
  • • VAVRA JJ, DEBOER C, DIETZ A, HANKA LJ, SOKOLSKI WT: Streptozotocin, a new antibacterial antibiotic. Antibiot Annu. 1959-1960;7:230-5. Pubmed
  • • Mansford KR, Opie L: Comparison of metabolic abnormalities in diabetes mellitus induced by streptozotocin or by alloxan. Lancet. 1968 Mar 30;1(7544):670-1. Pubmed
  • •  Link
  • • http://www.rxlist.com/zanosar-drug.htm
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PATENTS

PATENTS

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INTERNET

INTERNET

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