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Compound Detail

CHEMBL566315

OBETICHOLIC ACID
💊 Approved Drug
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💊 Approved Drug
CC[C@H]1[C@@H](O)[C@@H]2[C@H](CC[C@]3(C)[C@@H]([C@H](C)CCC(=O)O)CC[C@@H]23)[C@@]2(C)CC[C@@H](O)C[C@@H]12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL566315
Name OBETICHOLIC ACID
Phase Approved
Structure Type MOL
InChI Key ZXERDUOLZKYMJM-ZWECCWDJSA-N
Therapeutic ✓ Yes

Known Names

6-ecdca 6-ethylchenodeoxycholic acid Acide obeticholique Acido obeticolico DSP-1747 INT-747 Obeticholic acid Ocaliva
3
Targets
48
Activities
1
Assay Types
10
PK Parameters
20
Publications
8
Known Names
14
Indications
1
Mechanisms

Molecular Properties

420.6
MW (Da)
5.11
ALogP
3
HBA
3
HBD
77.8
PSA (Ų)
0.58
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2016
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Withdrawn Natural Product First in Class
USAN Year 2008

Extended Properties

Molecular Formula C26H44O4
MW 420.63
Aromatic Rings 0
Heavy Atoms 30
NP-Likeness 2.32

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bile acid receptor FXR agonist AGONIST Bile acid receptor ✓ ✓

Indications

Cholangitis Liver Cirrhosis, Biliary Liver Cirrhosis, Biliary Non-alcoholic Fatty Liver Disease Non-alcoholic Fatty Liver Disease Barrett Esophagus Cholangitis, Sclerosing Hepatitis, Alcoholic Lipodystrophy, Familial Partial Adenomatous Polyposis Coli Cholestasis Liver Diseases Obesity Pruritus

ATC Classification

A05AA04
obeticholic acid
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: BILE AND LIVER THERAPY

Drug Warnings

Withdrawn
General Warning
benefits are no longer considered to outweigh its risks
Country: European Union   Year: 2024
Black Box Warning
General Warning
Country: United States

Activity Summary

EC50 48 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bile acid receptor
CHEMBL2047
 EC50 8.0 6.7782 10.0 34
G-protein coupled bile acid receptor 1
CHEMBL5409
 EC50 7.62 5.882 23.7 10
G-protein coupled bile acid receptor 1
CHEMBL1255150
 EC50 5.24 5.24 5740.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 299.91 ng.hr.mL-1 Mus musculus
AUC - - Mus musculus
AUC 7596.58 ng.hr.mL-1 Mus musculus
CL 109.0 mL.min-1.g-1 Mus musculus
Cmax 1543.0 nM Mus musculus
Cmax - - Mus musculus
Cmax 838.0 nM Mus musculus
T1/2 0.35 hr Mus musculus
Tmax 0.25 hr Mus musculus
Tmax 8.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bile acid receptor EC50 = 10.0 nM 8.0 Agonist activity at recombinant human GST-tagged FXR ligand binding domain (193 ... 29148806
G-protein coupled bile acid receptor 1 EC50 = 23.7 nM 7.62 Agonist activity at human TGR5 expressed in HEK293 cells measured after 30 mins ... 32991173
Bile acid receptor EC50 = 42.0 nM 7.38 Agonist activity at human FXR expressed in HEK293T cells assessed as BSEP promot... 29148806
Bile acid receptor EC50 = 75.0 nM 7.12 Coactivation of TR-FRET Farnesoid X Receptor Protein: Purchasing Invitrogen PV48... -
Bile acid receptor EC50 = 85.0 nM 7.07 Agonist activity at FXR (unknown origin) by reporter gene assay 25255039
Bile acid receptor EC50 = 85.0 nM 7.07 Agonist activity at FXR (unknown origin) by cell based assay 31930920
Bile acid receptor EC50 = 85.0 nM 7.07 Agonist activity at full length FXR in human Huh-7 cells 32339855
Bile acid receptor EC50 = 90.0 nM 7.05 Binding affinity for human Farnesoid X receptor in FRET assay 15317466
Bile acid receptor EC50 = 98.0 nM 7.01 Binding affinity to FXR assessed as ligand-dependent SRC1 recruitment by FRET ba... 16821780
Bile acid receptor EC50 = 99.0 nM 7.0 Agonist activity at FXR (unknown origin) by fluorescence resonance energy tranfe... 32339855
G-protein coupled bile acid receptor 1 EC50 = 100.0 nM 7.0 Agonist activity at wild type TGR5 (unknown origin) 24900622
Bile acid receptor EC50 = 99.0 nM 7.0 Binding affinity for Farnesoid X Receptor (FXR) 12749886
Bile acid receptor EC50 = 99.0 nM 7.0 Effective concentration against Farnesoid X receptor (FXR) 12166927
Bile acid receptor EC50 = 99.0 nM 7.0 Activation of human farnesoid X receptor 16107136
Bile acid receptor EC50 = 100.0 nM 7.0 Agonist activity at FXR (unknown origin) assessed as recruitment of SRC1 peptide... 28252961
Bile acid receptor EC50 = 99.0 nM 7.0 Agonist activity at FXR (unknown origin) 31930920
Bile acid receptor EC50 = 99.0 nM 7.0 Agonist activity at FXR (unknown origin) by FRET assay 36155354
Bile acid receptor EC50 = 99.0 nM 7.0 Agonist activity at FXR expressed in COS1 cells by cell-based bioluminescence as... 20014870
Bile acid receptor EC50 = 150.0 nM 6.82 Agonist activity at glutathione transferase-tagged human FXR-LBD using biotinyla... 27652492
Bile acid receptor EC50 = 150.0 nM 6.82 Agonist activity at glutathione transferase-tagged human FXR ligand binding doma... 36049273

Literature References

PubMed DOI Target Context # Activities
38574638 10.1016/j.ejmech.2024.116358 Mus musculus 20
32991173 10.1021/acs.jmedchem.0c01065 Mus musculus 15
29259742 10.1021/acsmedchemlett.7b00318 ADMET 13
21459580 10.1016/j.bmc.2011.03.004 Bile acid receptor 11
29259742 10.1021/acsmedchemlett.7b00318 Mus musculus 11
27652492 10.1021/acs.jmedchem.6b01126 Bile acid receptor 10
36347091 10.1016/j.ejmech.2022.114886 Mus musculus 10
34256254 10.1016/j.bmc.2021.116280 Bile acid receptor 10
27652492 10.1021/acs.jmedchem.6b01126 ADMET 9
- 10.6019/CHEMBL5303304 Fibroblast 8
24900622 10.1021/ml400247k G-protein coupled bile acid receptor 1 8
24900622 10.1021/ml400247k Unchecked 7
37413879 10.1016/j.ejmech.2023.115614 Mus musculus 7
28845983 10.1021/acs.jmedchem.7b00398 Bile acid receptor 5
24387325 10.1021/jm401873d Bile acid receptor 5
37079895 10.1021/acs.jmedchem.2c01918 Mus musculus 5
- 10.6019/CHEMBL5724696 TERT-RPE1 4
- 10.6019/CHEMBL5303304 HEK-293T 4
29148806 10.1021/acs.jmedchem.7b00907 G-protein coupled bile acid receptor 1 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4

Data from ChEMBL 36 via Core Engine