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
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
DrugBank ID
DB05990
TTD ID
D0M4WA
INTEDE ID
DR1183
ACDINA ID
D00482
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Bile acid-CoA thioesterase (BAAT)
Main DME 		DERA3OF BAAT_HUMAN Substrate [6]

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]
Molecular Interaction Atlas (MIA) 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) 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] [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]
⏷ 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
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.