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药品详细

Fluorouracil (氟尿嘧啶 )

化学结构式图
中文名
氟尿嘧啶
英文名
Fluorouracil
分子式
Not Available
化学名
5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione
分子量
Average: 130.0772
Monoisotopic: 130.017855555
CAS号
51-21-8
ATC分类
L01B 抗代谢药
药物类型
small molecule
阶段
商品名
5 Fluorouracil;Adrucil;Arumel;Carac;Carzonal;Effluderm;Efudex;Efudix;Efurix;Fluoroblastin;Fluoroplex;Fluracil;Fluracilum;Fluri;Fluril;Fluro Uracil;Ftoruracil;FU;Kecimeton;Phthoruracil;Phtoruracil;Queroplex;Timazin;Ulup;URF;
同义名
基本介绍

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. [PubChem]

生产厂家
  • Abic ltd
  • Abraxis pharmaceutical products
  • Allergan herbert skin care div allergan inc
  • App pharmaceuticals llc
  • Bedford laboratories div ben venue laboratories inc
  • Bioniche pharma usa llc
  • Ebewe pharma ges mbh nfg kg
  • Elorac inc
  • Marchar laboratories inc ltd
  • Pharmacia and upjohn co
  • Sanofi aventis us llc
  • Smith and nephew solopak div smith and nephew
  • Spear pharmaceuticals inc
  • Taro pharmaceutical industries ltd
  • Taro pharmaceuticals usa inc
  • Teva parenteral medicines inc
  • Valeant pharmaceuticals international
  • Watson laboratories inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8. Pubmed
  2. Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204. Pubmed
剂型
Form Route Strength
Cream Topical
Solution Intravenous
规格
Unit description Cost Unit
Efudex 5% Cream 40 gm Tube 478.39 USD tube
Fluoroplex 1% Cream 30 gm Tube 268.61 USD tube
Fluorouracil 5% Cream 40 gm Tube 249.98 USD tube
Carac 0.5% Cream 30 gm Tube 209.77 USD tube
Efudex 5% Solution 10ml Bottle 136.51 USD bottle
Fluorouracil 5% Solution 10ml Bottle 115.78 USD bottle
Fluorouracil 2% Solution 10ml Bottle 78.63 USD bottle
Efudex 5% cream 10.28 USD g
Fluorouracil 5% cream 9.62 USD g
Fluorouracil powder 8.45 USD g
Fluoroplex 1% cream 7.85 USD g
Carac cream 6.43 USD g
Efudex 50 mg/g Cream 0.9 USD g
Fluorouracil 50 mg/ml Solution 0.52 USD ml
Adrucil 50 mg/ml vial 0.4 USD ml
Fluorouracil 5000 mg/100 ml 0.28 USD ml
化合物类型
Type small molecule
Classes
  • Pyrimidines and Derivatives
Substructures
  • Pyrimidines and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • Cyanamides
  • Aryl Halides
适应症
Cancer 癌症;
药理
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.
Pharmacodynamics 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.
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 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.
Absorption 28-100%
Volume of distribution Not Available
Protein binding 8-12%
Metabolism

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
Clearance Not Available
Toxicity LD50=230mg/kg (orally in mice)
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00469 Capecitabine Pathway SMP00469
Smp00470 Fluorouracil Pathway SMP00470
理化性质
Properties
State solid
Melting point 280-282oC
Experimental Properties
Property Value Source
water solubility < 0.1 g/100 mL at 19 °C PhysProp
logP -0.8 PhysProp
logS -1.07 [ADME Research, USCD] PhysProp
pKa 8.02 Various sources
Predicted Properties
Property Value Source
water solubility 5.86e+00 g/l ALOGPS
logP -0.58 ALOGPS
logP -0.66 ChemAxon Molconvert
logS -1.35 ALOGPS
pKa 12.02 ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 58.20 ChemAxon Molconvert
rotatable bond count 0 ChemAxon Molconvert
refractivity 26.17 ChemAxon Molconvert
polarizability 9.46 ChemAxon Molconvert
药物相互作用
Drug Interaction
Acenocoumarol The antineoplasic agent, fluorouracil, may increase the anticoagulant effect of acenocoumarol.
Anisindione The antineoplasic agent, fluorouracil, may increase the anticoagulant effect of anisindione.
Dicumarol The antineoplasic agent, fluorouracil, may increase the anticoagulant effect of dicumarol.
Ethotoin Fluorouracil increases the effect of hydantoin
Fosphenytoin Fluorouracil increases the effect of hydantoin
Mephenytoin Fluorouracil increases the effect of hydantoin
Metronidazole Risk of 5-FU toxicity when associated with metronidazole
Phenytoin Fluorouracil increases the effect of hydantoin
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.
Temsirolimus Co-administration of Temsirolimus and Fluorouracil may result in serious adverse drug reactions.
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.
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.
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.
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.
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.
食物相互作用
  • Vitamin B1 needs increased with long term use.

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