Tìm theo
Ixabepilone
Các tên gọi khác (2) :
  • Aza-epothilone B
  • Azaepothilone B
Thuốc Gốc
Small Molecule
CAS: 219989-84-1
ATC: L01DC04
CTHH: C27H42N2O5S
PTK: 506.698
Ixabepilone is an epothilone B analog developed by Bristol-Myers Squibb as a cancer drug. On October 16, 2007, the U.S. Food and Drug Administration approved ixabepilone for the treatment of aggressive metastatic or locally advanced breast cancer no longer responding to currently available chemotherapies. Ixabepilone is administered through injection, and will be marketed under the trade name Ixempra. [Wikipedia] Ixabepilone is a semisynthetic analogue of epothilone B. It has a lactone–lactam modification that minimizes susceptibility to esterase degradation.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C27H42N2O5S
Phân tử khối
506.698
Monoisotopic mass
506.281443154
InChI
InChI=1S/C27H42N2O5S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)29-23(31)13-21(30)26(5,6)25(33)17(3)24(15)32/h11,14-15,17,20-22,24,30,32H,8-10,12-13H2,1-7H3,(H,29,31)/b16-11+/t15-,17-,20-,21+,22-,24-,27+/m0/s1
InChI Key
InChIKey=FABUFPQFXZVHFB-CFWQTKTJSA-N
IUPAC Name
(1S,3S,7R,10S,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione
Traditional IUPAC Name
(1S,3S,7R,10S,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione
SMILES
C[C@H]1CCC[C@@]2(C)O[C@@]2([H])C[C@H](NC(=O)C[C@@H](O)C(C)(C)C(=O)[C@@H](C)[C@H]1O)C(\C)=C\C1=CSC(C)=N1
Độ hòa tan
3.52e-03 g/l
logP
3.39
logS
-5.2
pKa (strongest acidic)
13.85
pKa (Strongest Basic)
2.73
PSA
112.05 Å2
Refractivity
136.71 m3·mol-1
Polarizability
57.06 Å3
Rotatable Bond Count
2
H Bond Acceptor Count
6
H Bond Donor Count
3
Physiological Charge
0
Number of Rings
3
Bioavailability
1
Cơ Chế Tác Dụng : Ixabepilone is an epothilone B analog developed by Bristol-Myers Squibb as a cancer drug. On October 16, 2007, the U.S. Food and Drug Administration approved ixabepilone for the treatment of aggressive metastatic or locally advanced breast cancer no longer responding to currently available chemotherapies. Ixabepilone is administered through injection, and will be marketed under the trade name Ixempra. [Wikipedia] Ixabepilone is a semisynthetic analogue of epothilone B. It has a lactone–lactam modification that minimizes susceptibility to esterase degradation. Binding of Ixabepilone to beta-tubulins (e.g. beta-III tubulin) stabilizes microtubules. Microtubules are essential to cell division, and epothilones therefore stop cells from properly dividing. Like taxol, Ixabepilone binds to the αβ-tubulin heterodimer subunit. Once bound, the rate of αβ-tubulin dissociation decreases, thus stabilizing the microtubules.
Dược Động Học :

▧ Protein binding :
67-77%
▧ Route of Elimination :
Mostly fecal and some renal.
▧ Half Life :
52 hours
Chỉ Định : Investigated for use/treatment in breast cancer, head and neck cancer, melanoma, lung cancer, lymphoma (non-hodgkin's), prostate cancer, renal cell carcinoma, and cancer/tumors (unspecified).
Tương Tác Thuốc :
  • Conivaptan CYP3A4 Inhibitors (Strong) may increase the serum concentration of Ixabepilone. The dose of ixabepilone must be reduced when used with strong inhibitors of CYP3A.1 In one published abstract, ixabepilone 20mg/m2 was the maximum tolerated dose in patients who were also receiving the CYP3A-inhibitor ketoconazole (400mg).
  • Telithromycin Telithromycin may reduce clearance of Ixabepilone. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Ixabepilone if Telithromycin is initiated, discontinued or dose changed.
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of ixabepilone by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of ixabepilone if voriconazole is initiated, discontinued or dose changed.
Dữ Kiện Thương Mại
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Ixempra
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB04845
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=23305354
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=99443224
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D04645
ChemSpider
http://www.chemspider.com/Chemical-Structure.4949236.html
PharmGKB
http://www.pharmgkb.org/drug/PA165958343
Wikipedia
http://en.wikipedia.org/wiki/Ixabepilone
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