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Catalog Number | PR18883664 |
CAS | 18883-66-4 |
Structure | ![]() |
Description | An antibiotic that is produced by Stretomyces achromogenes. It is used as an antineoplastic agent and to induce diabetes in experimental animals. |
Synonyms | Estreptozocina; Streptozocine; Streptozocinium; Streptozocinum |
IUPAC Name | 1-methyl-1-nitroso-3-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea |
Molecular Weight | 265.22 |
Molecular Formula | C8H15N3O7 |
InChI | ZSJLQEPLLKMAKR-GKHCUFPYSA-N |
InChI Key | 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 |
Drug Categories | Alkylating Activity; Alkylating Drugs; Amides; Antibiotics, Antineoplastic; Antineoplastic Agents; Antineoplastic Agents, Alkylating; Antineoplastic and Immunomodulating Agents; Carbohydrates; Cytochrome P-450 CYP1A2 Inducers; Cytochrome P-450 CYP1A2 Inducers (strength unknown); Cytochrome P-450 CYP2E1 Inducers; Cytochrome P-450 CYP2E1 Inducers (strength unknown); Cytochrome P-450 Enzyme Inducers; Glycosides; Immunosuppressive Agents; Myelosuppressive Agents; Narrow Therapeutic Index Drugs; Nitroso Compounds; Nitrosourea Compounds; Nitrosoureas; P-glycoprotein inducers |
Drug Interactions | Abatacept-The risk or severity of adverse effects can be increased when Streptozocin is combined with Abatacept. Abciximab-The risk or severity of bleeding can be increased when Abciximab is combined with Streptozocin. Acenocoumarol-The risk or severity of bleeding can be increased when Acenocoumarol is combined with Streptozocin. Acetaminophen-Streptozocin may increase the hepatotoxic activities of Acetaminophen. Acetylsalicylic acid-The risk or severity of bleeding can be increased when Acetylsalicylic acid is combined with Streptozocin. |
Half-Life | 5-15 minutes |
Isomeric SMILES | CN(C(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O)CO)O)O)N=O |
Type | Small Molecule |
Therapeutic Category | Oncology |
Indications
Streptozocin is primarily indicated for the treatment of malignant neoplasms of the pancreas, specifically targeting metastatic islet cell carcinoma. This pancreatic cancer treatment is tailored to address the unique aspects of this particular type of tumor.
Absorption
Streptozocin exhibits poor oral absorption, with rates ranging from 17% to 25%. This limited bioavailability necessitates careful consideration of administration routes to ensure therapeutic effectiveness.
Metabolism
The metabolism of streptozocin occurs primarily in the liver. As the principal site for its metabolic processing, the hepatic system plays a critical role in the drug's breakdown and subsequent elimination.
Mechanism of Action
Streptozocin's mechanism of action, while not entirely elucidated, primarily involves the inhibition of DNA synthesis. It disrupts various biochemical processes, particularly affecting NAD and NADH, and hinders certain enzymes crucial for gluconeogenesis. This compound exerts its effects through the formation of methylcarbonium ions, which have the ability to alkylate or bind to numerous intracellular molecular structures, including nucleic acids. The resulting cytotoxicity is likely attributable to the cross-linking of DNA strands, effectively inhibiting DNA synthesis.
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