Identification
- Generic Name
- Dehydrocholic acid
- DrugBank Accession Number
- DB11622
- Background
Dehydrocholic acid is a synthetic bile acid that was prepared from the oxidation of cholic acid with chromic acid 1. It has been used for stimulation of biliary lipid secretion. The use of dehydrocholic acid in over-the-counter products has been discontinued by Health Canada.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Dehydrocholic acid (DB11622)
- Weight
- Average: 402.531
Monoisotopic: 402.240624195 - Chemical Formula
- C24H34O5
- Synonyms
- 3,7,12-Triketo-5beta-cholanoic acid
- 3,7,12-triketocholanic acid
- 3,7,12-trioxo-5beta-cholanic acid
- 3,7,12-trioxo-5β-cholanic acid
- 3,7,12-trioxocholanic acid
- Decholin
- Dehydrocholate
- Dehydrocholic acid
Pharmacology
- Indication
No approved therapeutic indications.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Dyspepsia Combination Product in combination with: Dimethicone (DB11074), Metoclopramide (DB01233), Bromelains (DB13281), Pancrelipase (DB00085) •••••••••••• ••••••• •••••• - Contraindications & Blackbox Warnings
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Following infusion of dehydrocholic acid (DHCA) in rats, the secretions of all the endogenous biliary bile acids were decreased within 30-60 minutes of infusion 2,4. Phospholipid secretion as well as cholesterol levels were also declined. The bile flow was increased after administration of dehydrocholic acid 1.
- Mechanism of action
It is proposed that dehydrocholic acid induces choleresis, which is associated with biliary lipid secretion and reduced secretion of endogenous and/or exogenous biliary components 2. Dehydrocholic acid may decrease bile phospholipid secretion due to a lack of micelle formation by dehydrocholic acid-produced bile 3. A study suggests that due to enhanced permeability of tight junctions in the canalicular membranes, dehydrocholic acid facilitates direct exchange between bile and plasma 3.
- Absorption
The duodenal experiment indicates that dehydrocholic acid is absorbed from the proximal small intestine 1.
- Volume of distribution
No pharmacokinetic data available.
- Protein binding
No pharmacokinetic data available.
- Metabolism
The major site of metabolism is proposed to be the liver. The major metabolite accounting for 70% of total detectable metabolites is dihydroxymonoketo bile acid (3α,7α-dihydroxy-12-keto-5β-cholanoic acid). About 20% of metabolites is monohydroxydiketoacid (3α-hydroxy-7,12-keto-5β-cholanoic acid) and about 10% is cholic acid 1.
- Route of elimination
Administered dehydrocholic acid is excreted rapidly in bile as glycine- and taurine-conjugated bile acids 1.
- Half-life
No pharmacokinetic data available.
- Clearance
No pharmacokinetic data available.
- Adverse Effects
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Oral LD50, intravenous LD50, and intramuscular LD50 in rat is 4000 mg/kg, 750 mg/kg, and 1500 mg/kg, respectively MSDS. Oral LD50, subcutaneous LD50, and intravenous LD50 in mouse is 3100 mg/kg, 1620 mg/kg, and 1492 mg/kg, respectively MSDS. There have been no reports of overdose with dehydrocholic acid.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab The risk or severity of adverse effects can be increased when Abciximab is combined with Dehydrocholic acid. Acenocoumarol The risk or severity of bleeding and bruising can be increased when Acenocoumarol is combined with Dehydrocholic acid. Acetazolamide The risk or severity of dehydration can be increased when Acetazolamide is combined with Dehydrocholic acid. Acetylsalicylic acid The risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Dehydrocholic acid. Aclidinium The therapeutic efficacy of Dehydrocholic acid can be decreased when used in combination with Aclidinium. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Dehydrocholate sodium W4193719XR 145-41-5 FKJIJBSJQSMPTI-CAOXKPNISA-M - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dycholium Tablet 300mg Tablet 300 mg Oral Rhone Poulenc Rorer 1992-12-31 1997-08-13 Canada 
Dycholium Tablet 300mg Tablet 300 mg Oral Novartis 1996-09-06 2016-08-02 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Acidobyl Dehydrocholic acid (120 mg) + Docusate sodium (60 mg) + Homatropine methylbromide (0.5 mg) + Sodium taurocholate (120 mg) Tablet Oral Desbergers LtÉe, Division Of Technilab Inc. 1951-12-31 1999-09-17 Canada Duchol Ect Dehydrocholic acid (30 mg) + Deoxycholic acid (30 mg) + Pancrelipase (200 mg) + Pepsin (200 mg) + Sodium taurocholate (100 mg) Tablet, delayed release Oral Duchesnay Inc. 1977-12-31 2003-07-18 Canada Medichol Dehydrocholic acid (30 mg) + Deoxycholic acid (30 mg) + Pancrelipase (200 mg) + Pepsin (200 mg) + Sodium taurocholate (100 mg) Tablet Oral Medic Laboratory LtÉe 1959-12-31 2007-10-22 Canada Regubil Dehydrocholic acid (30 mg) + Deoxycholic acid (30 mg) + Sodium taurocholate (150 mg) Tablet Oral Laboratoire Riva Inc 1983-12-31 Not applicable Canada
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Bile acids, alcohols and derivatives
- Direct Parent
- Bile acids, alcohols and derivatives
- Alternative Parents
- 7-oxosteroids / 3-oxo-5-beta-steroids / Cyclic ketones / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
- Substituents
- 12-oxosteroid / 3-oxo-5-beta-steroid / 3-oxosteroid / 7-oxosteroid / Aliphatic homopolycyclic compound / Bile acid, alcohol, or derivatives / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclic ketone
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- oxo-5beta-cholanic acid (CHEBI:31459) / C24 bile acids, alcohols, and derivatives, Cholane and derivatives (C13154) / C24 bile acids, alcohols, and derivatives (LMST04010106)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- NH5000009I
- CAS number
- 81-23-2
- InChI Key
- OHXPGWPVLFPUSM-KLRNGDHRSA-N
- InChI
- InChI=1S/C24H34O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-18,22H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,22+,23+,24-/m1/s1
- IUPAC Name
- (4R)-4-[(1R,3aS,3bR,5aS,9aS,9bS,11aR)-9a,11a-dimethyl-4,7,11-trioxo-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid
- SMILES
- [H][C@@]1(CC[C@@]2([H])[C@]3([H])C(=O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC(=O)[C@]12C)[C@H](C)CCC(O)=O
References
- General References
- Soloway RD, Hofmann AF, Thomas PJ, Schoenfield LJ, Klein PD: Triketocholanoic (dehydrocholic) acid. Hepatic metabolism and effect on bile flow and biliary lipid secretion in man. J Clin Invest. 1973 Mar;52(3):715-24. doi: 10.1172/JCI107233. [Article]
- Yousef IM, Mignault D, Weber AM, Tuchweber B: Influence of dehydrocholic acid on the secretion of bile acids and biliary lipids in rats. Digestion. 1990;45(1):40-51. doi: 10.1159/000200223. [Article]
- Chanussot F, Domingo N, Tuchweber B, Lafont H, Yousef I: Influence of dehydrocholic and cholic acids on the biliary secretion of anionic polypeptide fraction, the major apoprotein of the biliary lipoprotein complex. Scand J Gastroenterol. 1992;27(3):238-42. [Article]
- Chanussot F, Lafont H, Hauton J, Tuchweber B, Yousef I: Studies on the origin of biliary phospholipid. Effect of dehydrocholic acid and cholic acid infusions on hepatic and biliary phospholipids. Biochem J. 1990 Sep 15;270(3):691-5. [Article]
- External Links
- KEGG Drug
- D01693
- KEGG Compound
- C13154
- PubChem Compound
- 6674
- PubChem Substance
- 347828014
- ChemSpider
- 6422
- 42625
- ChEBI
- 31459
- ChEMBL
- CHEMBL514446
- ZINC
- ZINC000003860869
- Wikipedia
- Dehydrocholic_acid
- MSDS
- Download (286 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral Tablet, delayed release Oral Tablet Oral 300 mg Tablet, coated Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 237-240 MSDS water solubility Insoluble MSDS - Predicted Properties
Property Value Source Water Solubility 0.00705 mg/mL ALOGPS logP 3.37 ALOGPS logP 3.64 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 4.35 Chemaxon pKa (Strongest Basic) -6.9 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 88.51 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 108.01 m3·mol-1 Chemaxon Polarizability 44.81 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 214.0772577 predictedDarkChem Lite v0.1.0 [M-H]- 187.1712 predictedDeepCCS 1.0 (2019) [M+H]+ 215.9877577 predictedDarkChem Lite v0.1.0 [M+H]+ 188.9961 predictedDeepCCS 1.0 (2019) [M+Na]+ 214.2308577 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.7569 predictedDeepCCS 1.0 (2019)
Drug created at September 06, 2016 21:01 / Updated at April 24, 2024 14:30