Tìm theo
Fluorouracil
Các tên gọi khác (11 ) :
  • 5-Fluoracil
  • 5-Fluoropyrimidine-2,4-dione
  • 5-Fluorouracil
  • 5-Fluracil
  • 5-FU
  • Fluoro Uracil
  • Fluorouracil
  • Fluorouracilo
  • Fluorouracilum
  • Fluouracil
  • FU
Thuốc chống ung thư và tác động vào hệ thống miễn dịch
Thuốc Gốc
Small Molecule
CAS: 51-21-8
ATC: L01BC02
ĐG : Allergan Inc. , http://www.allergan.com
CTHH: C4H3FN2O2
PTK: 130.0772
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]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C4H3FN2O2
Phân tử khối
130.0772
Monoisotopic mass
130.017855555
InChI
InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
InChI Key
InChIKey=GHASVSINZRGABV-UHFFFAOYSA-N
IUPAC Name
5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional IUPAC Name
fluorouracil
SMILES
FC1=CNC(=O)NC1=O
Độ tan chảy
282-283
Độ hòa tan
1.11E+004 mg/L (at 22 °C)
logP
-0.89
logS
-1.07
pKa (strongest acidic)
7.76
pKa (Strongest Basic)
-8
PSA
58.2 Å2
Refractivity
26.17 m3·mol-1
Polarizability
9.46 Å3
Rotatable Bond Count
0
H Bond Acceptor Count
2
H Bond Donor Count
2
Physiological Charge
0
Number of Rings
1
Bioavailability
1
Rule of Five
true
pKa
8.02
Dược Lực Học : 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.
Cơ Chế Tác Dụng : 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] 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.
Dược Động Học :
▧ Absorption :
28-100%
▧ Protein binding :
8-12%
▧ Metabolism :
Hepatic. The catabolic metabolism of fluorouracil results in degradation products ( e.g., CO2, urea and α-fluoro-ß-alanine) which are inactive.
▧ 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
Độc Tính : LD50=230mg/kg (orally in mice)
Chỉ Định : 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.
Tương Tác Thuốc :
  • Acenocoumarol The antineoplasic agent, fluorouracil, may increase the anticoagulant effect of acenocoumarol.
  • Anisindione The antineoplasic agent, fluorouracil, may increase the anticoagulant effect of anisindione.
  • Dicoumarol 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.
Liều Lượng & Cách Dùng : Cream - Topical - 0.5%, 1%, 2%, 5%
Injection, solution - Intravenous - 500 mg/10 mL; 500 mg/10 mL; 1 g/20 mL; 2.5 g/50 mL; 5 g/100 mL
Solution - Topical - 2%, 5%
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Adria
    Sản phẩm biệt dược : Adrucil
  • Công ty : Sanofi
    Sản phẩm biệt dược : Carac
  • Công ty : Tobishi
    Sản phẩm biệt dược : Carzonal
  • Công ty : Valeant
    Sản phẩm biệt dược : Efudex
  • Công ty : Meda
    Sản phẩm biệt dược : Efudix
  • Công ty : Valeant
    Sản phẩm biệt dược : Efurix
  • Công ty : Aqua
    Sản phẩm biệt dược : Fluoroplex
  • Công ty : Verofarm
    Sản phẩm biệt dược : Ftoruracil
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00544
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=3385
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508557
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07649
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00584
ChemSpider
http://www.chemspider.com/Chemical-Structure.3268.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0703-3015-13
PharmGKB
http://www.pharmgkb.org/drug/PA128406956
Wikipedia
http://en.wikipedia.org/wiki/Fluorouracil
RxList
http://www.rxlist.com/cgi/generic3/carac.htm
Drugs.com
http://www.drugs.com/cdi/fluorouracil.html
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