NAV

Obeticholic acid

Identification

Summary

Obeticholic acid is a bile acid analog and farnesoid X receptor agonist used to treat primary biliary cholangitis in adult patients with inadequate clinical response or intolerance to UDCA.

Brand Names
Ocaliva
Generic Name
Obeticholic acid
DrugBank Accession Number
DB05990
Background

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.3

Obeticholic acid is a farnesoid-X receptor (FXR) agonist used to treat this condition, possibly allowing for increased survival.1 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.1,9 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.14

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 2020.10

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 420.6252
Monoisotopic: 420.323959896
Chemical Formula
C26H44O4
Synonyms
  • (3α,5β,6α,7α)-6-ethyl-3,7-dihydroxycholan-24-oic acid
  • 6-alpha-ethylchenodeoxycholic acid
  • 6-ECDCA
  • 6-Ethyl-CDCA
  • 6-ethylchenodeoxycholic acid
  • 6alpha-Ethyl-chenodeoxycholic acid
  • 6α-ethylchenodeoxycholic acid
  • Obeticholic acid
External IDs
  • DSP-1747
  • INT 747
  • INT-747
  • INT747
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Pharmacology

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.9

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 2020.10

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatPrimary biliary cholangitisRegimen in combination with: Ursodeoxycholic acid (DB01586)•••••••••••••••••••••• •••••••• •• •••• •••••••••••••••• •••••••••••
Treatment ofPrimary biliary cholangitis•••••••••••••••••• •• •••••••• ••••••••••••••• •••• ••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

The activation of the FXR by obeticholic acid acts to reduce the synthesis of bile acids, inflammation, and the resulting hepatic fibrosis. This may increase the survival of patients with PBC, but to date, an association between obeticholic acid and survival in PBC has not been established.3,9

Mechanism of action

Primary biliary cirrhosis is an autoimmune process by which the bile ducts and liver are damaged progressively, leading to fibrosis and cirrhosis. Bile acids increase the risk of damage and fibrosis to the damaged bile ducts.3,5

Obeticholic acid is a potent agonist of the farnesoid X receptor, which serves to regulate the hepatic metabolism of bile and cholesterol. This drug acts by binding to the farnesoid X receptor (FXR), found in the nucleus of liver and intestinal cells, which in turn increases liver bile flow, suppressing its production and decreasing hepatocyte exposure to excess levels of bile with cholestasis. Cholestasis is a process that normally causes inflammation and cirrhosis of the liver.4,9

TargetActionsOrganism
ABile acid receptor
agonist
Humans
Absorption

Obeticholic acid is absorbed in the gastrointestinal tract. The Cmax of obeticholic acid occurs at approximately 1.5 hours after an oral dose and ranges from 28.8-53.7 ng/mL at doses of 5-10mg.12 The median Tmax for both the conjugates of obeticholic acid is about 10 hours.9 One product monograph reports a Tmax of 4.5h for both 5 and 10mg doses. The AUC ranged from 236.6-568.1 ng/h/mL with 5mg to 10 mg doses.12

Volume of distribution

The volume of distribution of obeticholic acid is 618 L.9,11

Protein binding

Obeticholic acid and its metabolic conjugates are >99% plasma protein-bound.9,11

Metabolism

The metabolism of obeticholic acid occurs in the liver. Obeticholic acid is conjugated with glycine or taurine, followed by secretion into bile. The conjugates are then absorbed in the small intestine and then re-enter the liver via enterohepatic circulation. The intestinal microbiota in the ileum converts conjugated obeticholic acid in a deconjugated form that may be either reabsorbed or eliminated. Glycine conjugates account for 13.8% of the metabolites and taurine conjugates account for 12.3%. Another metabolite, 3-glucuronide, may also be formed, but displays little pharmacological activity.9

Route of elimination

About 87% of an orally administered dose is accounted for in the feces. Less than 3% of the dose can be recovered in the urine.9,11

Half-life

The biological half-life of obeticholic acid is reported to be 24 hours.13

Clearance

Clearance information for obeticholic acid is not readily available in the literature.9,11

Adverse Effects
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Toxicity

LD50 information for obeticholic acid is not readily available in the literature.9

The maximum documented exposure to obeticholic acid was 500 mg in healthy research volunteers. Doses of 250 mg have been administered to healthy volunteers for 12 consecutive days. Pruritus and reversible transaminase liver elevations were observed. In PBC patients who received 25mg daily to 50mg daily (2.5 to 5 times the maximum recommended dose), dose-dependent transaminase and bilirubin elevations, ascites, primary biliary cholangitis aggravation, and new-onset jaundice were reported.11

In the case of an overdose with obeticholic acid, clinical monitoring and supportive care should be offered as they are required.11

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AbciximabThe risk or severity of adverse effects can be increased when Abciximab is combined with Obeticholic acid.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Obeticholic acid.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Obeticholic acid.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Obeticholic acid.
AcyclovirThe metabolism of Acyclovir can be decreased when combined with Obeticholic acid.
Food Interactions
  • Take with or without food.

Products

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International/Other Brands
Ocaliva
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
OcalivaTablet10 mgOralAdvanz Pharma Canada Inc.2017-05-26Not applicableCanada flag
OcalivaTablet, film coated5 mg/1OralIntercept Pharmaceuticals Inc2016-05-27Not applicableUS flag
OcalivaTablet, film coated10 mgOralAdvanz Pharma Limited2020-12-16Not applicableEU flag
OcalivaTablet5 mgOralAdvanz Pharma Canada Inc.2017-05-26Not applicableCanada flag
OcalivaTablet, film coated10 mgOralAdvanz Pharma Limited2020-12-16Not applicableEU flag

Categories

ATC Codes
A05AA04 — Obeticholic acid
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. These are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Bile acids, alcohols and derivatives
Direct Parent
Dihydroxy bile acids, alcohols and derivatives
Alternative Parents
7-hydroxysteroids / 3-alpha-hydroxysteroids / Secondary alcohols / Cyclic alcohols and derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
3-alpha-hydroxysteroid / 3-hydroxysteroid / 7-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclic alcohol / Dihydroxy bile acid, alcohol, or derivatives
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
cholanoid (CHEBI:43602)
Affected organisms
Not Available

Chemical Identifiers

UNII
0462Z4S4OZ
CAS number
459789-99-2
InChI Key
ZXERDUOLZKYMJM-ZWECCWDJSA-N
InChI
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
IUPAC Name
(4R)-4-[(1R,3aS,3bS,4R,5R,5aS,7R,9aS,9bS,11aR)-5-ethyl-4,7-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)[C@H](CC)[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O

References

Synthesis Reference

He XL, Wang LT, Gu XZ, Xiao JX, Qiu WW. A facile synthesis of ursodeoxycholic acid and obeticholic acid from cholic acid.J.steroids.2018.10.009. Epub 2018 Oct 31.

General References
  1. Markham A, Keam SJ: Obeticholic Acid: First Global Approval. Drugs. 2016 Aug;76(12):1221-6. doi: 10.1007/s40265-016-0616-x. [Article]
  2. Eslam M, Alvani R, Shiha G: Obeticholic acid: towards first approval for NASH. Lancet. 2019 Dec 14;394(10215):2131-2133. doi: 10.1016/S0140-6736(19)32963-0. Epub 2019 Dec 5. [Article]
  3. Manne V, Kowdley KV: Obeticholic acid in primary biliary cholangitis: where we stand. Curr Opin Gastroenterol. 2019 May;35(3):191-196. doi: 10.1097/MOG.0000000000000525. [Article]
  4. Jones DE: Pathogenesis of primary biliary cirrhosis. Gut. 2007 Nov;56(11):1615-24. doi: 10.1136/gut.2007.122150. Epub 2007 Jul 19. [Article]
  5. Onofrio FQ, Hirschfield GM, Gulamhusein AF: A Practical Review of Primary Biliary Cholangitis for the Gastroenterologist. Gastroenterol Hepatol (N Y). 2019 Mar;15(3):145-154. [Article]
  6. Bowlus CL: Obeticholic acid for the treatment of primary biliary cholangitis in adult patients: clinical utility and patient selection. Hepat Med. 2016 Sep 1;8:89-95. doi: 10.2147/HMER.S91709. eCollection 2016. [Article]
  7. Edwards JE, LaCerte C, Peyret T, Gosselin NH, Marier JF, Hofmann AF, Shapiro D: Modeling and Experimental Studies of Obeticholic Acid Exposure and the Impact of Cirrhosis Stage. Clin Transl Sci. 2016 Dec;9(6):328-336. doi: 10.1111/cts.12421. Epub 2016 Oct 15. [Article]
  8. MSDS [Link]
  9. FDA Approved Products: Ocaliva (obeticholic acid) oral tablets [Link]
  10. FDA Accepts Intercept’s NDA for OCA for the Treatment of Liver Fibrosis Due to NASH and Grants Priority Review [Link]
  11. EMA Summary of product characteristics, Ocaliva (obeticholic acid) 5 and 10 mg oral tablets [Link]
  12. Product Monograph: Ocaliva (obeticholic acid) oral tablets [Link]
  13. NIH InXight Drugs: Obeticholic acid [Link]
  14. FDA Drug Safety Communication: Due to risk of serious liver injury, FDA restricts use of Ocaliva (obeticholic acid) in primary biliary cholangitis (PBC) patients with advanced cirrhosis [Link]
KEGG Drug
D09360
KEGG Compound
C15636
PubChem Compound
447715
PubChem Substance
347827752
ChemSpider
394730
BindingDB
21675
RxNav
1798288
ChEBI
43602
ChEMBL
CHEMBL566315
ZINC
ZINC000014164617
PDBe Ligand
CHC
Wikipedia
Obeticholic_acid
PDB Entries
1osv / 1ot7
FDA label
Download (5.07 MB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4TerminatedTreatmentPrimary Bilary Cirrhosis (PBC)2
3CompletedTreatmentCompensated liver disease / Non Alcoholic Steatohepatitis (NASH)1
3CompletedTreatmentPrimary Biliary Cholangitis1
3RecruitingTreatmentPrimary Biliary Cholangitis2
3TerminatedTreatmentNon Alcoholic Steatohepatitis (NASH)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral10 mg
TabletOral5 mg
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral10 MG
Tablet, film coatedOral5 MG
Tablet, film coatedOral5 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7138390No2006-11-212022-11-16US flag
US9238673No2016-01-192033-06-17US flag
US8058267No2011-11-152022-02-21US flag
US8377916No2013-02-192022-02-21US flag
US10052337No2018-08-212036-04-26US flag
US10047117No2018-08-142033-09-06US flag
US10174073No2019-01-082033-06-17US flag
US10751349No2020-08-252036-04-26US flag
US10758549No2020-09-012036-04-26US flag
USRE48286No2020-10-272027-11-16US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)108-110https://www.chemicalbook.com/ChemicalProductProperty_EN_CB92484652.htm
boiling point (°C)562.9±25https://www.chemicalbook.com/ChemicalProductProperty_EN_CB92484652.htm
logP5.11https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL566315/
pKa4.76±0.10https://www.chemicalbook.com/ChemicalProductProperty_EN_CB92484652.htm
Predicted Properties
PropertyValueSource
Water Solubility0.011 mg/mLALOGPS
logP3.5ALOGPS
logP4.52Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.6Chemaxon
pKa (Strongest Basic)-0.16Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area77.76 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity118.35 m3·mol-1Chemaxon
Polarizability49.74 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uk9-0008900000-c33af5291860a90600ad
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0000900000-079fa53b8b7590d7c953
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kmj-7809500000-34757919f4f805c78ffc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0001900000-69eba84235e21d830b4b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0q2a-2009300000-5b035fe6b704112a5010
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ab9-3940100000-8d1aea3963492d9954f8
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-211.4223965
predicted
DarkChem Lite v0.1.0
[M-H]-182.05605
predicted
DeepCCS 1.0 (2019)
[M+H]+210.1519965
predicted
DarkChem Lite v0.1.0
[M+H]+183.77975
predicted
DeepCCS 1.0 (2019)
[M+Na]+208.3682965
predicted
DarkChem Lite v0.1.0
[M+Na]+190.06117
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Learn more
Details1. Bile acid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
Curator comments
Also known as FXR receptor.
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxyla...
Gene Name
NR1H4
Uniprot ID
Q96RI1
Uniprot Name
Bile acid receptor
Molecular Weight
55913.915 Da
References
  1. Pellicciari R, Fiorucci S, Camaioni E, Clerici C, Costantino G, Maloney PR, Morelli A, Parks DJ, Willson TM: 6alpha-ethyl-chenodeoxycholic acid (6-ECDCA), a potent and selective FXR agonist endowed with anticholestatic activity. J Med Chem. 2002 Aug 15;45(17):3569-72. [Article]
  2. Eslam M, Alvani R, Shiha G: Obeticholic acid: towards first approval for NASH. Lancet. 2019 Dec 14;394(10215):2131-2133. doi: 10.1016/S0140-6736(19)32963-0. Epub 2019 Dec 5. [Article]
  3. Manne V, Kowdley KV: Obeticholic acid in primary biliary cholangitis: where we stand. Curr Opin Gastroenterol. 2019 May;35(3):191-196. doi: 10.1097/MOG.0000000000000525. [Article]
  4. Chianelli D, Rucker PV, Roland J, Tully DC, Nelson J, Liu X, Bursulaya B, Hernandez ED, Wu J, Prashad M, Schlama T, Liu Y, Chu A, Schmeits J, Huang DJ, Hill R, Bao D, Zoll J, Kim Y, Groessl T, McNamara P, Liu B, Richmond W, Sancho-Martinez I, Phimister A, Seidel HM, Badman MK, Joseph SB, Laffitte B, Molteni V: Nidufexor (LMB763), a Novel FXR Modulator for the Treatment of Nonalcoholic Steatohepatitis. J Med Chem. 2020 Apr 23;63(8):3868-3880. doi: 10.1021/acs.jmedchem.9b01621. Epub 2020 Feb 5. [Article]
  5. Luo G, Lin X, Li Z, Xiao M, Li X, Zhang D, Xiang H: Structure-guided modification of isoxazole-type FXR agonists: Identification of a potent and orally bioavailable FXR modulator. Eur J Med Chem. 2021 Jan 1;209:112910. doi: 10.1016/j.ejmech.2020.112910. Epub 2020 Oct 7. [Article]
  6. Hernandez ED, Zheng L, Kim Y, Fang B, Liu B, Valdez RA, Dietrich WF, Rucker PV, Chianelli D, Schmeits J, Bao D, Zoll J, Dubois C, Federe GC, Chen L, Joseph SB, Klickstein LB, Walker J, Molteni V, McNamara P, Meeusen S, Tully DC, Badman MK, Xu J, Laffitte B: Tropifexor-Mediated Abrogation of Steatohepatitis and Fibrosis Is Associated With the Antioxidative Gene Expression Profile in Rodents. Hepatol Commun. 2019 May 17;3(8):1085-1097. doi: 10.1002/hep4.1368. eCollection 2019 Aug. [Article]
  7. FDA Accepts Intercept’s NDA for OCA for the Treatment of Liver Fibrosis Due to NASH and Grants Priority Review [Link]

Enzymes

Details1. Cytochrome P450 1A2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Downregulator
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Edwards JE, Eliot L, Parkinson A, Karan S, MacConell L: Assessment of Pharmacokinetic Interactions Between Obeticholic Acid and Caffeine, Midazolam, Warfarin, Dextromethorphan, Omeprazole, Rosuvastatin, and Digoxin in Phase 1 Studies in Healthy Subjects. Adv Ther. 2017 Sep;34(9):2120-2138. doi: 10.1007/s12325-017-0601-0. Epub 2017 Aug 14. [Article]
  2. Ishida C, Sanoh S, Kotake Y: CYP1A2 Downregulation by Obeticholic Acid: Usefulness as a Positive Control for the In Vitro Evaluation of Drug-Drug Interactions. J Pharm Sci. 2019 Dec;108(12):3903-3910. doi: 10.1016/j.xphs.2019.08.021. Epub 2019 Aug 28. [Article]
  3. FDA Approved Products: Ocaliva (obeticholic acid) oral tablets [Link]

Transporters

Details1. Bile salt export pump
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
Curator comments
This transporter action is not expected to result in clinically significant outcomes with obeticholic acid administered at a normal recommended dose.
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. FDA Approved Products: Ocaliva (obeticholic acid) oral tablets [Link]

Drug created at November 18, 2007 18:29 / Updated at September 12, 2023 18:32