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CHEBI:175901 - gemcitabine

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ChEBI Name gemcitabine
ChEBI ID CHEBI:175901
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42752, CHEBI:5295
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Formula C9H11F2N3O4
Net Charge 0
Average Mass 263.19810
Monoisotopic Mass 263.072
InChI InChI=1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6-,7-/m1/s1
InChIKey SDUQYLNIPVEERB-QPPQHZFASA-N
SMILES Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)C2(F)F)c(=O)n1
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor
An EC 1.17.* (oxidoreductase acting on CH or CH2) inhibitor that inhibits the action of ribonucleoside-diphosphate reductase (EC 1.17.4.1).
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
antimetabolite
A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
Application(s): photosensitizing agent
A chemical compound that can be excited by light of a specific wavelength and subsequently transfer energy to a chosen reactant. This is commonly molecular oxygen within a cancer tissue, which is converted to (highly rective) singlet state oxygen. This rapidly reacts with any nearby biomolecules, ultimately killing the cancer cells.
radiosensitizing agent
A drug that makes increases the sensitivity of tumour cells to radiation therapy.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing gemcitabine (CHEBI:175901) has role antimetabolite (CHEBI:35221)
gemcitabine (CHEBI:175901) has role antineoplastic agent (CHEBI:35610)
gemcitabine (CHEBI:175901) has role antiviral drug (CHEBI:36044)
gemcitabine (CHEBI:175901) has role DNA synthesis inhibitor (CHEBI:59517)
gemcitabine (CHEBI:175901) has role EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor (CHEBI:74213)
gemcitabine (CHEBI:175901) has role environmental contaminant (CHEBI:78298)
gemcitabine (CHEBI:175901) has role immunosuppressive agent (CHEBI:35705)
gemcitabine (CHEBI:175901) has role photosensitizing agent (CHEBI:47868)
gemcitabine (CHEBI:175901) has role prodrug (CHEBI:50266)
gemcitabine (CHEBI:175901) has role radiosensitizing agent (CHEBI:132992)
gemcitabine (CHEBI:175901) has role xenobiotic (CHEBI:35703)
gemcitabine (CHEBI:175901) is a organofluorine compound (CHEBI:37143)
gemcitabine (CHEBI:175901) is a pyrimidine 2'-deoxyribonucleoside (CHEBI:19255)
Incoming gemcitabine hydrochloride (CHEBI:31647) has part gemcitabine (CHEBI:175901)
IUPAC Name
2'-deoxy-2',2'-difluorocytidine
INNs Sources
gemcitabina DrugBank
gemcitabine KEGG DRUG
gemcitabinum DrugBank
Synonyms Sources
2',2'-Difluorodeoxycytidine ChemIDplus
2'-Deoxy-2',2'-difluorocytidine ChemIDplus
4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one ChEMBL
Database Links Databases
C07650 KEGG COMPOUND
D02368 KEGG DRUG
DB00441 DrugBank
EP1939198 Patent
EP2108368 Patent
EP2275135 Patent
GB2136425 Patent
Gemcitabine Wikipedia
GEO PDBeChem
LSM-5333 LINCS
US2009124797 Patent
US2010111852 Patent
US4808614 Patent
View more database links
Registry Numbers Types Sources
5382060 Beilstein Registry Number Beilstein
5382060 Reaxys Registry Number Reaxys
95058-81-4 CAS Registry Number KEGG COMPOUND
95058-81-4 CAS Registry Number ChemIDplus
95058-81-4 CAS Registry Number DrugBank
95058-81-4 CAS Registry Number KEGG DRUG
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Last Modified
11 August 2016
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag