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3-methyl-3-nitroso-1-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea
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ChemBase ID:
311
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Molecular Formular:
C8H15N3O7
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Molecular Mass:
265.2206
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Monoisotopic Mass:
265.09099984
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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
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Cite this record
CBID:311 http://www.chembase.cn/molecule-311.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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3-methyl-3-nitroso-1-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea
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IUPAC Traditional name
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Brand Name
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STREPTOZOTOCIN
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STRZ
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STZ
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Streptozocin [Usan:Inn]
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Streptozocine [INN-French]
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Streptozocinium [Latin]
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Streptozocinum [INN-Latin]
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Streptozoticin
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Zanosar
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Synonyms
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Streptozocin
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N-(Methylnitrosocarbamoyl)-α-D-glucosamine
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Streptozotocin
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Streptozocin
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Streptozocin
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Zanosar
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STZ
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CAS Number
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EC Number
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MDL Number
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Beilstein Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
ALOGPS 2.1
Acid pKa
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11.425146
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H Acceptors
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7
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H Donor
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5
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LogD (pH = 5.5)
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-2.7202861
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LogD (pH = 7.4)
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-2.7203243
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Log P
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-2.7202857
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Molar Refractivity
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55.9552 cm3
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Polarizability
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21.796125 Å3
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Polar Surface Area
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151.92 Å2
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Rotatable Bonds
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3
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Lipinski's Rule of Five
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true
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Log P
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-1.71
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LOG S
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-0.9
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Solubility (Water)
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3.35e+01 g/l
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DETAILS
DETAILS
DrugBank
Selleck Chemicals
Sigma Aldrich
DrugBank -
DB00428
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Item |
Information |
Drug Groups
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approved |
Description
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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 |
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Humans and other mammals |
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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 |
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[Link]
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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]
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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]
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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]
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VAVRA JJ, DEBOER C, DIETZ A, HANKA LJ, SOKOLSKI WT: Streptozotocin, a new antibacterial antibiotic. Antibiot Annu. 1959-1960;7:230-5.
[Pubmed]
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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]
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External Links |
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Selleck Chemicals -
S1312
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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
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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
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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
PubMed
Google 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
PubChem Patent
Google Patent