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Streptozocin

Catalog No. DB00428 Name DrugBank
CAS Number 18883-66-4 Website http://www.ualberta.ca/
M. F. C8H15N3O7 Telephone (780) 492-3111
M. W. 265.2206 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 311

SYNONYMS

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
STZ
Streptozocinum [INN-Latin]
Streptozoticin
Streptozocine [INN-French]
Zanosar
STREPTOZOTOCIN
STRZ
Streptozocin [Usan:Inn]
Streptozocinium [Latin]

DATABASE IDS

PubChem CID 29327
PubChem SID 46508872
CAS Number 18883-66-4

PROPERTIES

Hydrophobicity(logP) -1.7
Solubility 5070 mg/L

DETAILS

Description (English)
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
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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