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]
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ATC Code

A05AA04: obeticholic acid

A05AA: Bile acids and derivatives

A05A: BILE THERAPY

A05: BILE AND LIVER THERAPY

A: ALIMENTARY TRACT AND METABOLISM

Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

420.6

Logarithm of the Partition Coefficient (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
UNII: 0462Z4S4OZ
DrugBank ID: DB05990
TTD ID: D0M4WA
INTEDE ID: DR1183
ACDINA ID: D00482

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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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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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
1-acyl-sn-glycerol-3-phosphate acyltransferase beta (AGPAT2)	OT5I4Y9K	PLCB_HUMAN	Gene/Protein Processing	[7]
1-acyl-sn-glycerol-3-phosphate acyltransferase epsilon (AGPAT5)	OTNY3VMD	PLCE_HUMAN	Gene/Protein Processing	[7]
14-3-3 protein sigma (SFN)	OTLJCZ1U	1433S_HUMAN	Gene/Protein Processing	[7]
24-hydroxycholesterol 7-alpha-hydroxylase (CYP39A1)	OTBAJT4I	CP39A_HUMAN	Gene/Protein Processing	[7]
3 beta-hydroxysteroid dehydrogenase type 7 (HSD3B7)	OT2Y9IW4	3BHS7_HUMAN	Gene/Protein Processing	[7]
3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR)	OTRT3F3U	HMDH_HUMAN	Gene/Protein Processing	[7]
3-keto-steroid reductase/17-beta-hydroxysteroid dehydrogenase 7 (HSD17B7)	OTV7VOV3	DHB7_HUMAN	Gene/Protein Processing	[7]
3-ketoacyl-CoA thiolase, mitochondrial (ACAA2)	OTGLVWOP	THIM_HUMAN	Gene/Protein Processing	[7]
3-ketoacyl-CoA thiolase, peroxisomal (ACAA1)	OTVKRET0	THIK_HUMAN	Gene/Protein Processing	[7]
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1 (PFKFB1)	OTTHX4NB	F261_HUMAN	Gene/Protein Processing	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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

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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]	[8]
Stiripentol	DMMSDOY	Moderate	Decreased metabolism of Obeticholic acid caused by Stiripentol mediated inhibition of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[9]
GS-9857	DMYU6P5	Moderate	Decreased clearance of Obeticholic acid due to the transporter inhibition by GS-9857.	Hepatitis virus infection [1E50-1E51]	[10]
Tasimelteon	DMLOQ1V	Moderate	Decreased metabolism of Obeticholic acid caused by Tasimelteon mediated inhibition of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[11]
Asenapine	DMSQZE2	Moderate	Decreased metabolism of Obeticholic acid caused by Asenapine mediated inhibition of CYP450 enzyme.	Schizophrenia [6A20]	[12]
Pomalidomide	DMTGBAX	Moderate	Decreased metabolism of Obeticholic acid caused by Pomalidomide mediated inhibition of CYP450 enzyme.	Systemic sclerosis [4A42]	[13]
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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	Pharmacotoxicology of clinically-relevant concentrations of obeticholic acid in an organotypic human hepatocyte system. Toxicol In Vitro. 2017 Mar;39:93-103.
8	Product Information. Nexletol (bempedoic acid). Esperion Therapeutics, Ann Arbor, MI.
9	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
10	Product Information. Vosevi (sofosbuvir/velpatasvir/voxilaprevir). Gilead Sciences, Foster City, CA.
11	Product Information. Hetlioz (tasimelteon). Vanda Pharmaceuticals Inc, Rockville, MD.
12	Product Information. Saphris (asenapine). Schering-Plough Corporation, Kenilworth, NJ.
13	Product Information. Ocaliva (obeticholic acid). Intercept Pharmaceuticals, Inc., New York, NY.