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药品详细

Streptozocin(链脲菌素)

化学结构式图
中文名
链脲菌素
英文名
Streptozocin
分子式
C8H15N3O7
化学名
3-methyl-3-nitroso-1-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea
分子量
Average: 265.2206
Monoisotopic: 265.090999849
CAS号
18883-66-4
ATC分类
L01A 烷化剂
药物类型
small molecule
阶段
approved
商品名
Streptozocin [Usan:Inn];Streptozocine [INN-French];Streptozocinium [Latin];Streptozocinum [INN-Latin];Streptozoticin;STREPTOZOTOCIN;STRZ;STZ;Zanosar;
同义名
基本介绍

An antibiotic that is produced by Stretomyces achromogenes. It is used as an antineoplastic agent and to induce diabetes in experimental animals. [PubChem]

生产厂家
  • Teva parenteral medicines inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Link
  2. 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
  3. 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
  4. 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
  5. VAVRA JJ, DEBOER C, DIETZ A, HANKA LJ, SOKOLSKI WT: Streptozotocin, a new antibacterial antibiotic. Antibiot Annu. 1959-1960;7:230-5. Pubmed
  6. 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
剂型
规格
化合物类型
Type small molecule
Classes
  • Carbohydrates
Substructures
  • Carbohydrates
  • Aminoglycosides
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Pyrans
  • Oxoazaniums
  • Acetals and Derivatives
  • Nitroso Compounds
  • Ethers
  • Ureas and Derivatives
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Semicarbazides
  • Hydrazine Derivatives
  • Amynoglycosides
适应症
Cancer 癌症;
药理
Indication For the treatment of malignant neoplasms of pancreas (metastatic islet cell carcinoma).
Pharmacodynamics 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.
Mechanism of action Although its mechanism of action is not completely clear, streptozocin is known to inhibit DNA synthesis, interfere with biochemical reactions of NAD and NADH, and inhibit some enzymes involved in gluconeogenesis. Its activity appears to occur as a result of formation of methylcarbonium ions, which alkylate or bind with many intracellular molecular structures including nucleic acids. Its cytotoxic action is probably due to cross-linking of strands of DNA, resulting in inhibition of DNA synthesis.
Absorption Poor oral absorption (17-25%)
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Primarily hepatic
Route of elimination As much as 20% of the drug (or metabolites containing an N-nitrosourea group) is metabolized and/or excreted by the kidney.
Half life 5-15 minutes
Clearance Not Available
Toxicity Symptoms of overdose include nausea and vomiting, anorexia, myelosuppression; and nephrotoxicity.
Affected organisms
  • Humans and other mammals
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 115 °C PhysProp
water solubility 5070 mg/L Not Available
logP -1.45 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 3.35e+01 g/l ALOGPS
logP -1.7 ALOGPS
logP -2.7 ChemAxon
logS -0.9 ALOGPS
pKa (strongest acidic) 11.43 ChemAxon
pKa (strongest basic) -3 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 7 ChemAxon
hydrogen donor count 5 ChemAxon
polar surface area 151.92 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 55.96 ChemAxon
polarizability 23.74 ChemAxon
药物相互作用
Drug Interaction
Bendamustine Increases toxicity through pharmacodynamic synergism. Additive myelosuppression.
Trastuzumab Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
食物相互作用
Not Available

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