Details of the Drug

General Information of Drug (ID: DM3Q1SM)

Drug Name

Obeticholic acid

Synonyms

INT747; INT-747; 6-ethylchenodeoxycholic acid; 6-ECDCA; OCA; 6-Et CDCA

Indication

Disease Entry	ICD 11	Status	REF
Primary biliary cholangitis	DB96.1	Approved	[1]
Insomnia	7A00-7A0Z	Clinical trial	[2]

Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

420.6

Topological Polar Surface Area (xlogp)

5.7

Rotatable Bond Count (rotbonds)

5

Hydrogen Bond Donor Count (hbonddonor)

3

Hydrogen Bond Acceptor Count (hbondacc)

4

ADMET Property

Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 28.8-53.7 mcg/L [3]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 1.5 h [3]
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 [4]
Half-life: The concentration or amount of drug in body reduced by one-half in 24 hours [5]
Metabolism: The drug is metabolized via the liver [4]
Vd: The volume of distribution (Vd) of drug is 618 L [4]

Chemical Identifiers

Formula: C26H44O4
IUPAC Name: (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
Canonical SMILES: 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=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: ZXERDUOLZKYMJM-ZWECCWDJSA-N

Cross-matching ID

PubChem CID: 447715
ChEBI ID: CHEBI:43602
CAS Number: 459789-99-2
DrugBank ID: DB05990
TTD ID: D0M4WA
INTEDE ID: DR1183
ACDINA ID: D00482

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Farnesoid X-activated receptor (FXR)	TTS4UGC	NR1H4_HUMAN	Modulator	[1]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Bile acid-CoA thioesterase (BAAT)_{Main DME}	DERA3OF	BAAT_HUMAN	Substrate	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Primary biliary cholangitis

ICD Disease Classification

DB96.1

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Farnesoid X-activated receptor (FXR)	DTT	NR1H4	5.72E-01	0.39	1.68
Bile acid-CoA thioesterase (BAAT)	DME	BAAT	9.73E-01	-6.99E-02	-2.12E-01

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Obeticholic acid (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Revefenacin	DMMP5SI	Moderate	Decreased clearance of Obeticholic acid due to the transporter inhibition by Revefenacin.	Chronic obstructive pulmonary disease [CA22]	[17]
Stiripentol	DMMSDOY	Moderate	Decreased metabolism of Obeticholic acid caused by Stiripentol mediated inhibition of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[18]
GS-9857	DMYU6P5	Moderate	Decreased clearance of Obeticholic acid due to the transporter inhibition by GS-9857.	Hepatitis virus infection [1E50-1E51]	[19]
Tasimelteon	DMLOQ1V	Moderate	Decreased metabolism of Obeticholic acid caused by Tasimelteon mediated inhibition of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[20]
Asenapine	DMSQZE2	Moderate	Decreased metabolism of Obeticholic acid caused by Asenapine mediated inhibition of CYP450 enzyme.	Schizophrenia [6A20]	[21]
Pomalidomide	DMTGBAX	Moderate	Decreased metabolism of Obeticholic acid caused by Pomalidomide mediated inhibition of CYP450 enzyme.	Systemic sclerosis [4A42]	[22]
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⏷ Show the Full List of 6 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 3350	E00652	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Obeticholic acid 10 mg tablet	10 mg	Oral Tablet	Oral
Obeticholic acid 5 mg tablet	5 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	2016 FDA drug approvals. Nat Rev Drug Discov. 2017 Feb 2;16(2):73-76.
2	Nuclear receptors and lipid physiology: opening the X-files. Science. 2001 Nov 30;294(5548):1866-70.
3	Product Monograph: Ocaliva (obeticholic acid) oral tablets
4	FDA Approved Products: Ocaliva (obeticholic acid) oral tablets
5	NIH InXight Drugs: Obeticholic acid
6	Glycine and taurine conjugation of bile acids by a single enzyme. Molecular cloning and expression of human liver bile acid CoA:amino acid N-acyltransferase. J Biol Chem. 1994 Jul 29;269(30):19375-9.
7	Bile acid coenzyme A: amino acid N-acyltransferase in the amino acid conjugation of bile acids. Methods Enzymol. 2005;400:374-94.
8	Lithocholic acid decreases expression of bile salt export pump through farnesoid X receptor antagonist activity. J Biol Chem. 2002 Aug 30;277(35):31441-7.
9	Effect of guggulsterone and cembranoids of Commiphora mukul on pancreatic phospholipase A(2): role in hypocholesterolemia. J Nat Prod. 2009 Jan;72(1):24-8.
10	The Nonsteroidal Farnesoid X Receptor Agonist Cilofexor (GS-9674) Improves Markers of Cholestasis and Liver Injury in Patients With Primary Sclerosing Cholangitis. Hepatology. 2019 Sep;70(3):788-801.
11	The nuclear receptors FXR and LXRalpha: potential targets for the development of drugs affecting lipid metabolism and neoplastic diseases. Curr Pharm Des. 2001 Mar;7(4):231-59.
12	FXR modulators for enterohepatic and metabolic diseases.Expert Opin Ther Pat. 2018 Nov;28(11):765-782.
13	Clinical pipeline report, company report or official report of ENYO Pharma.
14	A novel non-bile acid FXR agonist EDP-305 potently suppresses liver injury and fibrosis without worsening of ductular reaction. Liver Int. 2020 Jul;40(7):1655-1669.
15	Nidufexor (LMB763), a Novel FXR Modulator for the Treatment of Nonalcoholic Steatohepatitis. J Med Chem. 2020 Apr 23;63(8):3868-3880.
16	Clinical pipeline report, company report or official report of Metacrine.
17	Product Information. Nexletol (bempedoic acid). Esperion Therapeutics, Ann Arbor, MI.
18	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
19	Product Information. Vosevi (sofosbuvir/velpatasvir/voxilaprevir). Gilead Sciences, Foster City, CA.
20	Product Information. Hetlioz (tasimelteon). Vanda Pharmaceuticals Inc, Rockville, MD.
21	Product Information. Saphris (asenapine). Schering-Plough Corporation, Kenilworth, NJ.
22	Product Information. Ocaliva (obeticholic acid). Intercept Pharmaceuticals, Inc., New York, NY.