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QuickView for gemcitabine (compound)

Name: gemcitabine
PubChem Compound ID: 11054511
Molecular formula: C9H11F2N3O4
Molecular weight: 263.198 g/mol
Name: gemcitabine
Name (isomeric): DB00441
Drug Type: small molecule
Brand: Gemcitabinum [INN-Latin], Gemtro, GEO, Gemcitabine hydrochloride, Gemcin, DFDC, Gemcitabine HCl, Gemcitabina [INN-Spanish], DDFC, Gemzar
Category: Antimetabolites, Antimetabolites, Antineoplastic, Radiation-Sensitizing Agents, Antineoplastic Agents, Enzyme Inhibitors, Immunosuppressive Agents, Antiviral Agents
CAS number: 95058-81-4
Indication: For the first-line treatment of patients with metastatic breast cancer, locally advanced (Stage IIIA or IIIB), or metastatic (Stage IV) non-small cell lung cancer and as first-line treatment for patients with adenocarcinoma of the pancreas.
Gemcitabine is an antineoplastic anti-metabolite. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (or DNA synthesis phase of the cell cycle), stopping normal development and division. Gemcitabine blocks an enzyme which c...
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Mechanism of Action:
Gemcitabine inhibits thymidylate synthetase, leading to inhibition of DNA synthesis and cell death. Gemcitabine is a prodrug so activity occurs as a result of intracellular conversion to two active metabolites, gemcitabine diphosphate and gemcitabine triphosphate by deoxycitidine kinase. Gemcitabine diphosphate also inhibits ribonucleotide reductas...
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Absorption: 100%
Protein binding: Plasma protein binding is negligible (<10%)
Biotransformation: Transformed via nucleoside kinases to two active metabolites, gemcitabine diphosphate and gemcitabine triphosphate. Can also undergo deamination via cytidine deaminase to an inactive uracil metabolite (dFdU).
Half Life: Short infusions ranged from 32 to 94 minutes, and the value for long infusions vary from 245 to 638 minutes, depending on age and gender.
Clearance: 92.2 L/hr/m2 [Men 29 yrs] 75.7 L/hr/m2 [Men 45 yrs] 55.1 L/hr/m2 [Men 65 yrs] 40.7 L/hr/m2 [Men 79 yrs] 69.4 L/hr/m2 [Women 29 yrs] 57 L/hr/m2 [Women 45 yrs] 41.5 L/hr/m2 [Women 65 yrs] 30.7 L/hr/m2 [Women 79 yrs]
Toxicity: Myelosuppression, paresthesias, and severe rash were the principal toxicities, LD50=500 mg/kg (orally in mice and rats)
Affected organisms: Humans and other mammals
Drug interaction:
TrastuzumabTrastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
AnisindioneGemcitabine may increase the anticoagulant effect of anisindione.
DicumarolGemcitabine may increase the anticoagulant effect of dicumarol.
AcenocoumarolGemcitabine may increase the anticoagulant effect of acenocoumarol.
TemsirolimusCo-administration of Temsirolimus and Gemcitabine may result in serious adverse drug reactions.
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