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QuickView for Fluorouracil (compound)

Summary
General Info

PubChem

PubChem Compound 3385

PubChem Compound 3385

Name:	Fluorouracil
PubChem Compound ID:	3385
Description:	A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.
Molecular formula:	C₄H₃FN₂O₂
Molecular weight:	130.077 g/mol
Synonyms:	EINECS 200-085-6; 5-Faracil; Carzonal; NSC-19893; Kecimeton; DRG-0161; AIDS-008287; Ro 2-9757; Lopac-F-6627; NCGC00091349-01. show more » EINECS 200-085-6; 5-Faracil; Carzonal; NSC-19893; Kecimeton; DRG-0161; AIDS-008287; Ro 2-9757; Lopac-F-6627; NCGC00091349-01; Fluorouracil [USAN:BAN:INN:JAN]; Ftoruracil; SPBio_000291; 2,4-Dioxo-5-fluoropryimidine; Fluro uracil; NSC 19893; 2,4 (1H, 3H)-Pyrimidinedione, 5-fluoro-; Effluderm (free base); KBioGR_001253; pyrimidine antimetabolite: inhibits nucleic acid replication; tetratogen; Uracil, 5-fluoro-; ZINC00897110; HSDB 3228; EU-0100536; NINDS_000054; URF; Uracil, 5-fluoro- (VAN 8CI); KBio2_003889; 5-Fluor-2,4(1H,3H)-pyrimidindion [Czech]; 5-Fluoro-2,4(1H,3H)-pyrimidinedione; 5-Fluoruracil [German]; KBio3_001268; Efudex; 5-Ftouracyl; NSC129417; NCI60_001652; Efurix; 51-21-8; C07649; 5-Fluoropyrimidine-2,4-dione; Fluroblastin; 5-Fluoro-2,4-pyrimidinedione; inhibits thymilidate synthetase; 5-Fluor-2,4-pyrimidindiol [Czech]; Fluracilum; Timazin; nchembio809-comp6; Queroplex; Fluorouracilum [INN-Latin]; Fluorouracile [DCIT]; InChI=1/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9; Phtoruracil; 5-FU (TN); Fluorouracilum; U-8953; 29648-12-2; Arumel; Fluoroblastin; AI3-25297; 5-FU; 5-Fluoracyl; 5-Fluorouracil; Fluracil; Ro-2-9757; 5-fluoropyrimidine-2,4(1H,3H)-dione; Spectrum3_000434; 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-, monothallium(1+) salt; KBio2_001321; 5-Fluoro-2,4(1H, 3H)-pyrimidinedione; Spectrum4_000557; KBio2_006457; UPCMLD-DP130:001; KBioSS_001321; SMR000038082; 5 Fluorouracil; U 8953; DivK1c_000054; Efudix; NSC19893; Fluoro-uracile; NSC168664; Spectrum_000841; AIDS008287; Adrucil (TN); Ulup; Fluorouracilo [INN-Spanish]; Fluoro-uracilo; 79871-89-9; MLS000069498; 5FU; Fluri; 5-Fluor-2,4-dihydroxypyrimidin [Czech]; FU; KBio1_000054; Phthoruracil; Adrucil; 1004-03-1; 4921-97-5; Fluorouracil; Fluorouracil (JP15/USP); Cinco FU; 5-Fluoropyrimidin-2,4-diol; CCRIS 2582; Fluoroplex; 2,4-Dioxo-5-fluoropyrimidine; 5-Fluoracil [German]; D00584; Spectrum2_000076; 79108-01-3; NCGC00015442-01; 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-; Fluril show less «

DrugBank

Identification

Name:	Fluorouracil
Name (isomeric):	DB00544
Drug Type:	small molecule
Description:	A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.
Brand:	5 Fluorouracil, Ulup, Carac, Efudex, FU, Fluoroplex, Efurix, Fluril, Phthoruracil, Timazin, Adrucil, URF, Effluderm, Efudix, Queroplex, Carzonal, Fluri, Fluracilum, Fluro Uracil, Ftoruracil, Fluoroblastin, Arumel, Kecimeton, Phtoruracil, Fluracil
Category:	Antimetabolites, Antimetabolites, Antineoplastic, Antineoplastic Agents, Immunosuppressive Agents
CAS number:	51-21-8

Pharmacology

Indication:	For 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.
Pharmacology:	Fluorouracil is an antineoplastic anti-metabolite. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances from becoming incorporated into DNA during the "S" phase (of the cell cycle), stopping normal development and division. Fluorouracil blocks an enzyme which converts the cytos... show more » Fluorouracil is an antineoplastic anti-metabolite. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances from becoming incorporated into DNA during the "S" phase (of the cell cycle), stopping normal development and division. Fluorouracil blocks an enzyme which converts the cytosine nucleotide into the deoxy derivative. In addition, DNA synthesis is further inhibited because Fluorouracil blocks the incorporation of the thymidine nucleotide into the DNA strand. show less «
Mechanism of Action:	The precise mechanism of action has not been fully determined, but the main mechanism of fluorouracil is thought to be the binding of the deoxyribonucleotide of the drug (FdUMP) and the folate cofactor, N5–10-methylenetetrahydrofolate, to thymidylate synthase (TS) to form a covalently bound ternary complex. This results in the inhibition of the for... show more » The precise mechanism of action has not been fully determined, but the main mechanism of fluorouracil is thought to be the binding of the deoxyribonucleotide of the drug (FdUMP) and the folate cofactor, N5–10-methylenetetrahydrofolate, to thymidylate synthase (TS) to form a covalently bound ternary complex. This results in the inhibition of the formation of thymidylate from uracil, which leads to the inhibition of DNA and RNA synthesis and cell death. Fluorouracil can also be incorporated into RNA in place of uridine triphosphate (UTP), producing a fraudulent RNA and interfering with RNA processing and protein synthesis. show less «
Absorption:	28-100%
Protein binding:	8-12%
Biotransformation:	Hepatic
Route of elimination:	Seven percent to 20% of the parent drug is excreted unchanged in the urine in 6 hours; of this over 90% is excreted in the first hour. The remaining percentage of the administered dose is metabolized, primarily in the liver.
Half Life:	10-20 minutes
Toxicity:	LD₅₀=230mg/kg (orally in mice)
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Vitamin B1 needs increased with long term use.

Drug interaction:

Dicumarol	The antineoplasic agent, fluorouracil, may increase the anticoagulant effect of dicumarol.
Phenytoin	Fluorouracil increases the effect of hydantoin
Zafirlukast	Fluorouracil, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of zafirlukast. Consider alternate therapy or monitor for changes in zafirlukast therapeutic and adverse effects if fluorouracil is initiated, discontinued or dose changed.
Trastuzumab	Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
Trimethoprim	The strong CYP2C9 inhibitor, Fluorouracil, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Fluorouracil is initiated, discontinued or dose changed.

Dicumarol	The antineoplasic agent, fluorouracil, may increase the anticoagulant effect of dicumarol.
Phenytoin	Fluorouracil increases the effect of hydantoin
Zafirlukast	Fluorouracil, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of zafirlukast. Consider alternate therapy or monitor for changes in zafirlukast therapeutic and adverse effects if fluorouracil is initiated, discontinued or dose changed.
Trastuzumab	Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
Trimethoprim	The strong CYP2C9 inhibitor, Fluorouracil, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Fluorouracil is initiated, discontinued or dose changed.
Metronidazole	Risk of 5-FU toxicity when associated with metronidazole
Warfarin	Fluorouracil, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if fluorouracil is initiated, discontinued or dose changed.
Fosphenytoin	Fluorouracil increases the effect of hydantoin
Temsirolimus	Co-administration of Temsirolimus and Fluorouracil may result in serious adverse drug reactions.
Tamoxifen	Fluorouracil may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Fluorouracil is initiated, discontinued or dose changed.
Tolbutamide	Fluorouracil, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Fluorouracil is initiated, discontinued or dose changed.
Torasemide	Fluorouracil, a strong CYP2C9 inhibitor, may increase the serum concentration of Torasemide, a CYP2C9 substrate, by decreasing Torasemide metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Torasemide if Fluorouracil is initiated, discontinued or dose changed.
Voriconazole	Fluorouracil, a strong CYP2C9 inhibitor, may increase the serum concentration of voriconazole by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of voriconazole if fluorouracil is initiated, discontinued or dose changed.
Mephenytoin	Fluorouracil increases the effect of hydantoin
Acenocoumarol	The antineoplasic agent, fluorouracil, may increase the anticoagulant effect of acenocoumarol.
Anisindione	The antineoplasic agent, fluorouracil, may increase the anticoagulant effect of anisindione.
Ethotoin	Fluorouracil increases the effect of hydantoin

Targets

Thymidylate synthase

Enzymes

Cytochrome P450 2C9

Cytochrome P450 1A2

Thymidine phosphorylase

Dihydropyrimidine dehydrogenase [NADP+]

Uridine phosphorylase 1

Uridine phosphorylase 2

Cytochrome P450 2A6

Cytochrome P450 2C8

Methylenetetrahydrofolate reductase

Thymidylate synthase

Carriers