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

• ChemBase编号: 311
• 分子式: C8H15N3O7
• 平均质量: 265.2206
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 3-methyl-3-nitroso-1-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea
• IUPAC传统名: streptozocin
• 商标名: STREPTOZOTOCIN; STRZ; STZ; Streptozocin [Usan:Inn]; Streptozocine [INN-French]; Streptozocinium [Latin]; Streptozocinum [INN-Latin]; Streptozoticin; Zanosar
• 别名: Streptozocin; N-(Methylnitrosocarbamoyl)-α-D-glucosamine; Streptozotocin; Streptozocin; Streptozocin; Zanosar; STZ

登记号

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

理论计算性质

JChem

• Acid pKa: 11.425146
• 质子受体: 7
• 质子供体: 5
• LogD (pH = 5.5): -2.7202861
• LogD (pH = 7.4): -2.7203243
• Log P: -2.7202857
• 摩尔折射率: 55.9552 cm^3
• 极化性: 21.796125 Å^3
• 极化表面积: 151.92 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.71
• LOG S: -0.9
• 溶解度: 3.35e+01 g/l

分子性质

理化性质

• 溶解度: 5070 mg/L
• 外观: white to off-white powder
• 熔点: 121 °C (dec.)(lit.)
• 疏水性(logP): -1.7

安全信息

• 保存条件: -20°C
• RTECS编号: LZ5775000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 45
• 安全公开号: 53-45
• GHS危险品标识: GHS08
• GHS警示词: Danger
• GHS危险声明: H350
• GHS警示性声明: P201-P308 + P313
• 个人保护装置: 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
• 保存温度: -20°C

产品相关信息

• 纯度: ≥75% α-anomer basis; ≥98% (HPLC); ≥98.0% (HPLC)
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C8H15N3O7

详细说明

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.

参考文献

• 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