Chemical Component Summary

Name5-FLUOROURACIL
Identifiers5-fluoro-1H-pyrimidine-2,4-dione
FormulaC4 H3 F N2 O2
Molecular Weight130.077
TypeNON-POLYMER
Isomeric SMILESC1=C(C(=O)NC(=O)N1)F
InChIInChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
InChIKeyGHASVSINZRGABV-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count12
Chiral Atom Count0
Bond Count12
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB00544 
NameFluorouracil
Groups approved
DescriptionA pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the thymidylate synthetase conversion of deoxyuridylic acid to thymidylic acid.
Synonyms
  • Fluorouracilo
  • Fluoro Uracil
  • Fluorouracilum
  • 5-FU
  • 5-Fluorouracil
Brand Names
  • Fluorouracil Injection
  • Efudex
  • Adrucil
  • Fluorouracil Cream
  • Fluorac
IndicationFor the topical treatment of multiple actinic or solar keratoses. In the 5% strength it is also useful in the treatment of superficial basal cell carcinomas when conventional methods are impractical, such as with multiple lesions or difficult treatment sites. Fluorouracil injection is indicated in the palliative management of some types of cancer, including colon, esophageal, gastric, rectum, breast, biliary tract, stomach, head and neck, cervical, pancreas, renal cell, and carcinoid.
Categories
  • Antimetabolites
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • BCRP/ABCG2 Substrates
  • Cardiotoxic antineoplastic agents
ATC-Code
  • L01BC52
  • L01BC02
CAS number51-21-8

Drug Targets

NameTarget SequencePharmacological ActionActions
DNA-unknownincorporation into and destabilization
RNA-unknownincorporation into and destabilization
Thymidylate synthaseMPVAGSELPRRPLPPAAQERDAEPRPPHGELQYLGQIQHILRCGVRKDDR...unknownother/unknown
Dihydropyrimidine dehydrogenase [NADP(+)]MAPVLSKDSADIESILALNPRTQTHATLCSTSAKKLDKKHWKRNPDKNCF...unknownsubstrate
Uridine phosphorylase 1MAATGANAEKAESHNDCPVRLLNPNIAKMKEDILYHFNLTTSRHNFPALF...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL185
PubChem 5281053, 3385
ChEMBL CHEMBL185
ChEBI CHEBI:46345
CCDC/CSD BIKHIN01, CAWKAP, FURACL14, WEWTAU, HOZPIX, GUXNEV, QACBAA, FEPKES, UDOVIV, CATGOV, IQILEB, BOLLUK, OPOVAS, QABZOL, DUQXOF, ZOYXAP, IQILAX, DUQXUL, BOLMAR, OPOTUK, OXODOW02, IHISIE, SOBNEE, KUTGIS, IQIKUQ, SANBER, PAHHUC, FEPKIW, RIPVIY, RUXVUD01, FURACL01, FURACL15, CADLUR, PAHHOW, RIPVOE, FURACL03, FUREHX, ZAYLOA, SOBNEE01, SANBIV, FURACL02, DUQXIZ, FURACL, FURMCY, FEPKIW01, NAGTAU, EROBEV, KAGZOL, CAGXER, HAHDED
COD 2020808, 2207359, 4506049, 7052012, 2204298, 4134117