API reference

Fluorouracil

CAS number
51-21-8
Molecular formula
C4H3FN2O2
Molecular weight
130.08 g/mol
Fluorouracil — 2D structure
2D structure (PubChem)

About this molecule

Fluorouracil is an antimetabolite fluoropyrimidine analog of the nucleoside pyrimidine with antineoplastic activity. Fluorouracil and its metabolites possess a number of different mechanisms of action. In vivo, fluoruracil is converted to the active metabolite 5-fluoroxyuridine monophosphate (F-UMP); replacing uracil, F-UMP incorporates into RNA and inhibits RNA processing, thereby inhibiting cell growth. Another active metabolite, 5-5-fluoro-2'-deoxyuridine-5'-O-monophosphate (F-dUMP), inhibits thymidylate synthase, resulting in the depletion of thymidine triphosphate (TTP), one of the four nucleotide triphosphates used in the in vivo synthesis of DNA. Other fluorouracil metabolites incorporate into both RNA and DNA; incorporation into RNA results in major effects on both RNA processing and functions.

Source: NCI Thesaurus (NCIt), via PubChem.

Identifiers

IUPAC name
5-fluoro-1H-pyrimidine-2,4-dione
InChIKey
GHASVSINZRGABV-UHFFFAOYSA-N
SMILES
C1=C(C(=O)NC(=O)N1)F
Other CAS numbers recorded
191047-65-1 · 191047-64-0 · 191115-88-5 · 1004-03-1
PubChem CID
3385

Also known as

5-Fluorouracil · fluorouracil · Efudex · Fluracil · Fluoroblastin · Queroplex · Carzonal · Fluril

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