Details of the Drug

General Information of Drug (ID: DMQ8JIK)

Drug Name

Chenodiol

Synonyms

474-25-9; Chenix; Chenic acid; Chenodeoxycholate; Gallodesoxycholic acid; Chendol; Chenodesoxycholic acid; Cdca; Chenofalk; Anthropodeoxycholic acid; Anthropodesoxycholic acid; Anthropododesoxycholic acid; Chenodesoxycholsaeure; Xenbilox; Henohol; Chenique Acid; Chenodiol [USAN]; 3alpha,7alpha-Dihydroxy-5beta-cholan-24-oic acid; Sodium chenodeoxycholate; Acido chenodeoxicholico; Chenodesoxycholsaeure [German]; Acide chenodeoxycholique; 7-alpha-Hydroxylithocholic acid; Acidum chenodeoxycholicum

Indication

Disease Entry	ICD 11	Status	REF
Cholelithiasis	DC11	Approved	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

392.6

Logarithm of the Partition Coefficient (xlogp)

4.9

Rotatable Bond Count (rotbonds)

4

Hydrogen Bond Donor Count (hbonddonor)

3

Hydrogen Bond Acceptor Count (hbondacc)

4

ADMET Property

Absorption: The drug is well absorbed from the small intestine []
Clearance: The drug present in the plasma can be removed from the body at the rate of 5.7 mL/min/kg [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 1.42 hours [2]
Metabolism: The drug is metabolized via the liver []
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.19 L/kg [2]

Chemical Identifiers

Formula: C24H40O4
IUPAC Name: (4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-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: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
InChI: InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1
InChIKey: RUDATBOHQWOJDD-BSWAIDMHSA-N

Cross-matching ID

PubChem CID: 10133
ChEBI ID: CHEBI:16755
CAS Number: 474-25-9
DrugBank ID: DB06777
TTD ID: D03ZTE
VARIDT ID: DR00524
INTEDE ID: DR0295
ACDINA ID: D00118

Combinatorial Drugs (CBD)

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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	[3]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[4]
UDP-glucuronosyltransferase 1A1 (UGT1A1)	DEYGVN4	UD11_HUMAN	Substrate	[5]
Cytochrome P450 8B1 (CYP8B1)	DETL4WB	CP8B1_HUMAN	Substrate	[6]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
11-beta-hydroxysteroid dehydrogenase 1 (HSD11B1)	OTO7FJA9	DHI1_HUMAN	Gene/Protein Processing	[7]
3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR)	OTRT3F3U	HMDH_HUMAN	Drug Response	[8]
7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase (CYP8B1)	OTRI4UR1	CP8B1_HUMAN	Gene/Protein Processing	[9]
Acetyl-CoA acetyltransferase, mitochondrial (ACAT1)	OTJC60Q7	THIL_HUMAN	Gene/Protein Processing	[10]
Acyl-CoA dehydrogenase family member 11 (ACAD11)	OT3T9HAX	ACD11_HUMAN	Gene/Protein Processing	[10]
Aflatoxin B1 aldehyde reductase member 3 (AKR7A3)	OTW3GO4Y	ARK73_HUMAN	Gene/Protein Processing	[10]
Aldo-keto reductase family 1 member C1 (AKR1C1)	OTQKR4CM	AK1C1_HUMAN	Gene/Protein Processing	[10]
Aldo-keto reductase family 1 member C2 (AKR1C2)	OTQ2XMO3	AK1C2_HUMAN	Gene/Protein Processing	[11]
Aldo-keto reductase family 1 member C4 (AKR1C4)	OTW2MMOF	AK1C4_HUMAN	Gene/Protein Processing	[10]
Angiopoietin-related protein 3 (ANGPTL3)	OTCD5Z9W	ANGL3_HUMAN	Gene/Protein Processing	[10]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Cholelithiasis

ICD Disease Classification

DC11

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
UDP-glucuronosyltransferase 1A1 (UGT1A1)	DME	UGT1A1	5.20E-01	-3.27E-03	-2.84E-02
Cytochrome P450 8B1 (CYP8B1)	DME	CYP8B1	3.12E-02	1.29E-01	1.45E+00
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	2.76E-01	-4.64E-01	-9.16E-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 Chenodiol (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Chenodiol and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[12]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Chenodiol and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[13]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Chenodiol and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[14]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Chenodiol and Cannabidiol.	Epileptic encephalopathy [8A62]	[15]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Chenodiol and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[16]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Chenodiol and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[17]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Chenodiol and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[18]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Chenodiol and Idelalisib.	Mature B-cell leukaemia [2A82]	[19]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Glycerin	E00026	753	Antimicrobial preservative; Emollient; Flavoring agent; Humectant; Lubricant; Plasticizing agent; Solvent; Suppository base; Tonicity agent; Viscosity-controlling agent
Magnesium stearate	E00208	11177	lubricant
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Cellulose microcrystalline	E00698	Not Available	Adsorbent; Suspending agent; Diluent
Pregelatinized starch	E00674	Not Available	Binding agent; Diluent; Disintegrant
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Chenodeoxycholic acid 250 mg tablet	250 mg	Oral Tablet	Oral
Chenodiol 250mg tablet	250mg	Tablet	Oral

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References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3	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.
4	Identification of human hepatic cytochrome p450 enzymes involved in the biotransformation of cholic and chenodeoxycholic acid. Drug Metab Dispos. 2008 Oct;36(10):1983-91.
5	Human UDP-glucuronosyltransferase (UGT)1A3 enzyme conjugates chenodeoxycholic acid in the liver. Hepatology. 2006 Nov;44(5):1158-70.
6	Conversion of chenodeoxycholic acid to cholic acid by human CYP8B1. Biol Chem. 2019 Apr 24;400(5):625-628.
7	In the search for specific inhibitors of human 11beta-hydroxysteroid-dehydrogenases (11beta-HSDs): chenodeoxycholic acid selectively inhibits 11beta-HSD-I. Eur J Endocrinol. 2000 Feb;142(2):200-7.
8	Lack of response to chenodeoxycholic acid in obese and non-obese patients. Role of cholesterol synthesis and possible response to ursodeoxycholic acid. Gut. 1980 Dec;21(12):1082-6. doi: 10.1136/gut.21.12.1082.
9	Potency of individual bile acids to regulate bile acid synthesis and transport genes in primary human hepatocyte cultures. Toxicol Sci. 2014 Oct;141(2):538-46. doi: 10.1093/toxsci/kfu151. Epub 2014 Jul 23.
10	Chenodeoxycholic acid significantly impacts the expression of miRNAs and genes involved in lipid, bile acid and drug metabolism in human hepatocytes. Life Sci. 2016 Jul 1;156:47-56.
11	Relationship of human liver dihydrodiol dehydrogenases to hepatic bile-acid-binding protein and an oxidoreductase of human colon cells. Biochem J. 1996 Jan 15;313 ( Pt 2)(Pt 2):373-6.
12	Cerner Multum, Inc. "Australian Product Information.".
13	Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
14	Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
15	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
16	Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
17	Canadian Pharmacists Association.
18	Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
19	Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.