CHC

6-ETHYL-CHENODEOXYCHOLIC ACID

Created:	2003-04-18
Last modified:	2011-06-04

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2 entries where CHC is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	74
Chiral Atom Count	11
Bond Count	77
Aromatic Bond Count	0

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Chemical Component Summary
Name	6-ETHYL-CHENODEOXYCHOLIC ACID
Systematic Name (OpenEye OEToolkits)	(4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
Formula	C₂₆ H₄₄ O₄
Molecular Weight	420.625
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)CCC(C4C3(C(C1C(C2(C(C(CC)C1O)CC(O)CC2)C)CC3)CC4)C)C
SMILES	CACTVS	3.341	CC[CH]1[CH](O)[CH]2[CH]3CC[CH]([CH](C)CCC(O)=O)[C]3(C)CC[CH]2[C]4(C)CC[CH](O)C[CH]14
SMILES	OpenEye OEToolkits	1.5.0	CCC1C2CC(CCC2(C3CCC4(C(C3C1O)CCC4C(C)CCC(=O)O)C)C)O
Canonical SMILES	CACTVS	3.341	CC[C@H]1[C@@H](O)[C@H]2[C@@H]3CC[C@H]([C@H](C)CCC(O)=O)[C@@]3(C)CC[C@@H]2[C@@]4(C)CC[C@@H](O)C[C@@H]14
Canonical SMILES	OpenEye OEToolkits	1.5.0	CC[C@@H]1[C@@H]2C[C@@H](CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3[C@@H]1O)CC[C@@H]4[C@H](C)CCC(=O)O)C)C)O
InChI	InChI	1.03	InChI=1S/C26H44O4/c1-5-17-21-14-16(27)10-12-26(21,4)20-11-13-25(3)18(15(2)6-9-22(28)29)7-8-19(25)23(20)24(17)30/h15-21,23-24,27,30H,5-14H2,1-4H3,(H,28,29)/t15-,16-,17-,18-,19+,20+,21+,23+,24-,25-,26-/m1/s1
InChIKey	InChI	1.03	ZXERDUOLZKYMJM-ZWECCWDJSA-N

Drug Info: DrugBank

DrugBank ID	DB05990
Name	Obeticholic acid
Groups	approved
Description	Primary biliary cirrhosis, or PBC, is a progressive and chronic condition that leads to hepatic injury often resulting in end-stage liver failure that requires liver transplantation.[A192786] Obeticholic acid is a farnesoid-X receptor (FXR) agonist used to treat this condition, possibly allowing for increased survival.[A18696] In 2016, it was granted approval to treat primary biliary cholangitis in combination with [ursodeoxycholic acid], which was previously the mainstay treatment for this condition.[A18696,L12633] In May 2021, the FDA updated its prescribing information to contraindicate the use of obeticholic acid in patients with PBC and advanced cirrhosis (e.g. those with portal hypertension or hepatic decompensation) due to a risk of liver failure, in some cases requiring liver transplantation.[L34650] Obeticholic acid is currently being considered for FDA approval to treat fibrosis caused by non-alcoholic liver steatohepatitis (NASH). The NDA from Intercept Pharmaceuticals was approved in November 2019 and obeticholic acid is expected to be granted full approval for this indication in 2020.[L12636]
Synonyms	6α-ethylchenodeoxycholic acid 6-ECDCA 6-ethylchenodeoxycholic acid (3α,5β,6α,7α)-6-ethyl-3,7-dihydroxycholan-24-oic acid Obeticholic acid 6-alpha-ethylchenodeoxycholic acid 6alpha-Ethyl-chenodeoxycholic acid 6-Ethyl-CDCA
Brand Names	Ocaliva
Indication	Obeticholic acid is indicated for the treatment of primary biliary cholangitis in combination with ursodeoxycholic acid (UDCA) in adults with an inadequate response to UDCA. It is also used as a monotherapy in adults with PBC that are unable to tolerate UDCA.[L12633] Obeticholic acid is currently being considered for FDA approval to treat fibrosis caused by non-alcoholic liver steatohepatitis (NASH), and is likely to be approved for this indication in 2020.[L12636]
Categories	Alimentary Tract and Metabolism Bile Acid Preparations Bile acids and derivatives Bile Acids and Salts Bile and Liver Therapy Bile Therapy BSEP/ABCB11 inducers BSEP/ABCB11 Inhibitors Cholanes Cholic Acids Cytochrome P-450 CYP1A2 Inhibitors Cytochrome P-450 CYP1A2 Inhibitors (strength unknown) Cytochrome P-450 Enzyme Inhibitors Farnesoid X Receptor Agonist Farnesoid X Receptor Agonists Fused-Ring Compounds Miscellaneous GI Drugs
ATC-Code	A05AA04
CAS number	459789-99-2

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Bile acid receptor	MVMQFQGLENPIQISPHCSCTPSGFFMEMMSMKPAKGVLTEQVAGPLGQN...	unknown	agonist
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	inhibitor,downregulator
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	inhibitor,inducer

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682