FB2026_03 , released September 17, 2026
Chemical: gemcitabine
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General Information
Name
gemcitabine
FlyBase ID
FBch0000434
ChEBI Name
gemcitabine
ChEBI ID
PubChem Name
Gemcitabine
PubChem ID
Chemical Structure
Chemical structure of gemcitabine
gemcitabine
InChIKey

SDUQYLNIPVEERB-QPPQHZFASA-N

Definition (ChEBI)

ChEBI: Gemcitabine is a 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer. It has a role as a photosensitizing agent, a DNA synthesis inhibitor, a prodrug, an EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor, an environmental contaminant, a xenobiotic, a radiosensitizing agent, an antineoplastic agent, an antimetabolite, an antiviral drug and an immunosuppressive agent. It is an organofluorine compound and a pyrimidine 2'-deoxyribonucleoside.NCI Thesaurus (NCIt): Gemcitabine is a broad-spectrum antimetabolite and deoxycytidine analogue with antineoplastic activity. Upon administration, gemcitabine is converted into the active metabolites difluorodeoxycytidine diphosphate (dFdCDP) and difluorodeoxycytidine triphosphate (dFdCTP) by deoxycytidine kinase. dFdCTP competes with deoxycytidine triphosphate (dCTP) and is incorporated into DNA. This locks DNA polymerase thereby resulting in masked termination during DNA replication. On the other hand, dFdCDP inhibits ribonucleotide reductase, thereby decreasing the deoxynucleotide pool available for DNA synthesis. The reduction in the intracellular concentration of dCTP potentiates the incorporation of dFdCTP into DNA.

Roles Classification (ChEBI)
Comment
Synonyms and Secondary IDs (23)
Synonyms
2',2'-Difluorodeoxycytidine
2',2'-difluorodeoxycytidine
2'-Deoxy-2',2'-difluorocytidine
2'-deoxy-2',2'-difluorocytidine
4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
95058-81-4
Cytidine, 2'-deoxy-2',2'-difluoro-
GEMCITABINE HYDROCHLORIDE
Gemcitabine HCl
Gemcitabine free base
PubChem:60750
UNII-B76N6SBZ8R
cytidine, 2'-deoxy-2',2'-difluoro-
gemcitabina
gemcitabine free base
gemcitabine hcl
gemcitabine hydrochloride
gemcitabinum
pubchem:60750
unii-b76n6sbz8r
Secondary FlyBase IDs
    References (8)