Tìm theo
Capecitabine
Các tên gọi khác (7 ) :
  • (1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamic acid pentyl ester
  • Capecitabin
  • Capecitabina
  • Capecitabinum
  • Pentyl [1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl]carbamate
  • Pentyl 1-(5-deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinecarbamate
  • Xeloda
Thuốc điều trị ung thư
Thuốc Gốc
Small Molecule
CAS: 154361-50-9
ATC: L01BC06
ĐG : Dept Health Central Pharmacy
CTHH: C15H22FN3O6
PTK: 359.3501
Capecitabine is an orally-administered chemotherapeutic agent used in the treatment of metastatic breast and colorectal cancers. Capecitabine is a prodrug, that is enzymatically converted to fluorouracil (antimetabolite) in the tumor, where it inhibits DNA synthesis and slows growth of tumor tissue.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C15H22FN3O6
Phân tử khối
359.3501
Monoisotopic mass
359.149263656
InChI
InChI=1S/C15H22FN3O6/c1-3-4-5-6-24-15(23)18-12-9(16)7-19(14(22)17-12)13-11(21)10(20)8(2)25-13/h7-8,10-11,13,20-21H,3-6H2,1-2H3,(H,17,18,22,23)/t8-,10-,11-,13-/m1/s1
InChI Key
InChIKey=GAGWJHPBXLXJQN-UORFTKCHSA-N
IUPAC Name
pentyl N-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl}carbamate
Traditional IUPAC Name
capecitabine
SMILES
CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@@H]1O[C@H](C)[C@@H](O)[C@H]1O
Độ tan chảy
110-121 °C
Độ hòa tan
26 mg/mL
logP
0.4
logS
-3.2
pKa (strongest acidic)
8.23
pKa (Strongest Basic)
-3.6
PSA
120.69 Å2
Refractivity
82.75 m3·mol-1
Polarizability
35.81 Å3
Rotatable Bond Count
7
H Bond Acceptor Count
6
H Bond Donor Count
3
Physiological Charge
0
Number of Rings
2
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Capecitabine is a fluoropyrimidine carbamate with antineoplastic activity indicated for the treatment of metastatic breast cancer and colon cancer. It is an orally administered systemic prodrug that has little pharmacologic activity until it is converted to fluorouracil by enzymes that are expressed in higher concentrations in many tumors. Fluorouracil it then metabolized both normal and tumor cells to 5-fluoro-2′-deoxyuridine 5′-monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP).
Cơ Chế Tác Dụng : Capecitabine is an orally-administered chemotherapeutic agent used in the treatment of metastatic breast and colorectal cancers. Capecitabine is a prodrug, that is enzymatically converted to fluorouracil (antimetabolite) in the tumor, where it inhibits DNA synthesis and slows growth of tumor tissue. Capecitabine is a prodrug that is selectively tumour-activated to its cytotoxic moiety, fluorouracil, by thymidine phosphorylase, an enzyme found in higher concentrations in many tumors compared to normal tissues or plasma. Fluorouracil is further metabolized to two active metabolites, 5-fluoro-2'-deoxyuridine 5'-monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP), within normal and tumour cells. These metabolites cause cell injury by two different mechanisms. First, FdUMP and the folate cofactor, N5-10-methylenetetrahydrofolate, bind to thymidylate synthase (TS) to form a covalently bound ternary complex. This binding inhibits the formation of thymidylate from 2'-deaxyuridylate. Thymidylate is the necessary precursor of thymidine triphosphate, which is essential for the synthesis of DNA, therefore a deficiency of this compound can inhibit cell division. Secondly, nuclear transcriptional enzymes can mistakenly incorporate FUTP in place of uridine triphosphate (UTP) during the synthesis of RNA. This metabolic error can interfere with RNA processing and protein synthesis through the production of fraudulent RNA.
Dược Động Học :
▧ Absorption :
Readily absorbed through the GI tract (~70%)
▧ Protein binding :
< 60% (mainly albumin)
▧ Metabolism :
Metabolized by thymidine phosphorylase to fluoruracil.
▧ Route of Elimination :
Capecitabine and its metabolites are predominantly excreted in urine; 95.5% of administered capecitabine dose is recovered in urine. Fecal excretion is minimal (2.6%). The major metabolite excreted in urine is FBAL which represents 57% of the administered dose.About 3% of the administered dose is excreted in urine as unchanged drug.
▧ Half Life :
45-60 minutes for capecitabine and its metabolites.
Chỉ Định : For the treatment of patients with metastatic breast cancer resistant to both paclitaxel and an anthracycline-containing chemotherapy regimen. May also be used in combination with docetaxel for the treatment of metastatic breast cancer in patients who have failed to respond to, or recurred or relasped during or following anthracycline-containing chemotherapy. Capecitabine is used alone as an adjuvant therapy following the complete resection of primary tumor in patients with stage III colon cancer when monotherapy with fluroprymidine is preferred. The use or capecitabine in combination regimens for advanced gastric cancer is currently being investigated.
Tương Tác Thuốc :
  • Acenocoumarol Capecitabine may increase the anticoagulant effect of acenocoumarol by increasing its serum concentration.
  • Anisindione Capecitabine may increase the anticoagulant effect of anisindione by increasing its serum concentration.
  • Dicoumarol Capecitabine may increase the anticoagulant effect of dicumarol by increasing its serum concentration.
  • Ethotoin Capecitabine increases the effect of hydantoin
  • Fosphenytoin Capecitabine increases the effect of hydantoin
  • Mephenytoin Capecitabine increases the effect of hydantoin
  • Phenytoin Capecitabine increases the effect of hydantoin
  • Tamoxifen Capecitabine may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Capecitabine is initiated, discontinued or dose changed.
  • Tolbutamide Capecitabine, 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 Capecitabine is initiated, discontinued or dose changed.
  • Torasemide Capecitabine, 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 Capecitabine 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, Capecitabine, 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 Capecitabine is initiated, discontinued or dose changed.
  • Voriconazole Capecitabine, 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 capecitabine is initiated, discontinued or dose changed.
  • Warfarin Capecitabine may increase the serum concentration of warfarin by decreasing its metabolism. Monitor for changes in prothrombin time and therapeutic effects of warfarin if capecitabine is initiated or discontinued. Subsequent cycles of capecitabine may increase this effect.
  • Zafirlukast Capecitabine, 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 capecitabine is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Xeloda 150 mg tablet
    Giá bán buôn : USD >8.69
    Đơn vị tính : tablet
  • Biệt dược thương mại : Xeloda 500 mg tablet
    Giá bán buôn : USD >28.97
    Đơn vị tính : tablet
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Xeloda
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01101
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=60953
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508686
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C12650
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D01223
ChemSpider
http://www.chemspider.com/Chemical-Structure.54916.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0004-1100-20
PharmGKB
http://www.pharmgkb.org/drug/PA448771
Wikipedia
http://en.wikipedia.org/wiki/Capecitabine
RxList
http://www.rxlist.com/cgi/generic3/capecitabine.htm
Drugs.com
http://www.drugs.com/cdi/capecitabine.html
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