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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 18883-66-4
• EC Number: 242-646-8
• MDL Number: MFCD00006607
• Beilstein Number: 2060675
• PubChem SID: 46508872; 24899428; 160963774
• PubChem CID: 29327

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.425146
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -2.7202861
• LogD (pH = 7.4): -2.7203243
• Log P: -2.7202857
• Molar Refractivity: 55.9552 cm^3
• Polarizability: 21.796125 Å^3
• Polar Surface Area: 151.92 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.71
• LOG S: -0.9
• Solubility (Water): 3.35e+01 g/l

PROPERTIES

Physical Property

• Solubility: 5070 mg/L
• Apperance: white to off-white powder
• Melting Point: 121 °C (dec.)(lit.)
• Hydrophobicity(logP): -1.7

Safety Information

• Storage Condition: -20°C
• RTECS: LZ5775000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45
• Safety Statements: 53-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H350
• GHS Precautionary statements: P201-P308 + P313
• 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
• Storage Temperature: -20°C

Product Information

• Purity: ≥75% α-anomer basis; ≥98% (HPLC); ≥98.0% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C8H15N3O7

DETAILS

DrugBank - DB00428

• 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

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

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

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

• 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