Tìm theo
Chenodeoxycholic acid
Các tên gọi khác (12 ) :
  • 3alpha,7alpha-Dihydroxy-5beta-cholanic acid
  • 7alpha-Hydroxylithocholic acid
  • Anthropodeoxycholic acid
  • Anthropodesoxycholic acid
  • CDCA
  • Chenic acid
  • Chenix
  • Chenocholic acid
  • Chenodeoxycholic acid
  • Chenodesoxycholic acid
  • Chenodiol
  • Gallodesoxycholic acid
gastrointestinal agents, cathartics
Thuốc Gốc
Small Molecule
CAS: 474-25-9
ATC: A05AA01
CTHH: C24H40O4
PTK: 392.572
Chenodeoxycholic acid (or Chenodiol) is an epimer of ursodeoxycholic acid (DB01586). Chenodeoxycholic acid is a bile acid naturally found in the body. It works by dissolving the cholesterol that makes gallstones and inhibiting production of cholesterol in the liver and absorption in the intestines, which helps to decrease the formation of gallstones. It can also reduce the amount of other bile acids that can be harmful to liver cells when levels are elevated.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C24H40O4
Phân tử khối
392.572
Monoisotopic mass
392.292659768
InChI
InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1
InChI Key
InChIKey=RUDATBOHQWOJDD-BSWAIDMHSA-N
IUPAC Name
(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional IUPAC Name
chenodeoxycholic acid
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O
Độ tan chảy
168-171
Độ hòa tan
89.9 mg/L (at 20 °C)
logP
4.15
logS
-4.3
pKa (strongest acidic)
4.6
pKa (Strongest Basic)
-0.54
PSA
77.76 Å2
Refractivity
109.27 m3·mol-1
Polarizability
46.39 Å3
Rotatable Bond Count
4
H Bond Acceptor Count
4
H Bond Donor Count
3
Physiological Charge
-1
Number of Rings
4
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : It acts by reducing levels of cholesterol in the bile, helping gallstones that are made predominantly of cholesterol to dissolve. Chenodeoxycholic acid is ineffective with stones of a high calcium or bile acid content.
Cơ Chế Tác Dụng : Chenodeoxycholic acid (or Chenodiol) is an epimer of ursodeoxycholic acid (DB01586). Chenodeoxycholic acid is a bile acid naturally found in the body. It works by dissolving the cholesterol that makes gallstones and inhibiting production of cholesterol in the liver and absorption in the intestines, which helps to decrease the formation of gallstones. It can also reduce the amount of other bile acids that can be harmful to liver cells when levels are elevated. Chenodiol suppresses hepatic synthesis of both cholesterol and cholic acid, gradually replacing the latter and its metabolite, deoxycholic acid in an expanded bile acid pool. These actions contribute to biliary cholesterol desaturation and gradual dissolution of radiolucent cholesterol gallstones in the presence of a gall-bladder visualized by oral cholecystography. Bile acids may also bind the the bile acid receptor (FXR) which regulates the synthesis and transport of bile acids.
Dược Động Học :
▧ Absorption :
Chenodiol is well absorbed from the small intestine.
▧ Metabolism :
Chenodiol is well absorbed from the small intestine and taken up by the liver where it is converted to its taurine and glycine conjugates and secreted in bile. At steady-state, an amount of chenodiol near the daily dose escapes to the colon and is converted by bacterial action to lithocholic acid. About 80% of the lithocholate is excreted in the feces; the remainder is absorbed and converted in the liver to its poorly absorbed sulfolithocholyl conjugates. During chenodiol therapy there is only a minor increase in biliary lithocholate, while fecal bile acids are increased three- to fourfold.
▧ Route of Elimination :
About 80% of its bacterial metabolite lithocholate is excreted in the feces.
Độc Tính : Hepatotoxic.
Chỉ Định : Chenodiol is indicated for patients with radiolucent stones in well-opacifying gallbladders, in whom selective surgery would be undertaken except for the presence of increased surgical risk due to systemic disease or age. Chenodiol will not dissolve calcified (radiopaque) or radiolucent bile pigment stones.
Tương Tác Thuốc :
  • Colesevelam Bile Acid Sequestrants may decrease the serum concentration of Chenodiol. Consider administration of chenodiol 5 hours or more after bile acid sequestrants to reduce chenodiol adsorption in the gastrointestinal tract. Monitor for decreased therapeutic effects of chenodiol in patients receiving bile acid sequestrants.
Liều Lượng & Cách Dùng : Tablet, film coated - Oral - 250 mg
Dữ Kiện Thương Mại
Nhà Sản Xuất
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB06777
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=10133
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=99443291
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C02528
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00163
ChemSpider
http://www.chemspider.com/Chemical-Structure.9728.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0722-7121-01
PharmGKB
http://www.pharmgkb.org/drug/PA165958403
Wikipedia
http://en.wikipedia.org/wiki/Chenodeoxycholic_acid
Drugs.com
http://www.drugs.com/cdi/chenodiol.html
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