Dehydrocholic acid

Identification

Name
Dehydrocholic acid
Accession Number
DB11622
Type
Small Molecule
Groups
Approved, Investigational
Description

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.

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Dehydrocholate sodiumW4193719XR145-41-5FKJIJBSJQSMPTI-CAOXKPNISA-M
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dycholium Tablet 300mgTabletOralNovartis1996-09-062016-08-02Canada
Dycholium Tablet 300mgTabletOralRhone Poulenc Rorer1992-12-311997-08-13Canada
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AcidobylDehydrocholic acid (120 mg) + Docusate sodium (60 mg) + Homatropine methylbromide (0.5 mg) + Sodium taurocholate (120 mg)TabletOralDesbergers LtÉe, Division Of Technilab Inc.1951-12-311999-09-17Canada
Duchol EctDehydrocholic acid (30 mg) + Deoxycholic acid (30 mg) + Pancrelipase (200 mg) + Pepsin (200 mg) + Sodium taurocholate (100 mg)Tablet, delayed releaseOralDuchesnay Inc.1977-12-312003-07-18Canada
MedicholDehydrocholic acid (30 mg) + Deoxycholic acid (30 mg) + Pancrelipase (200 mg) + Pepsin (200 mg) + Sodium taurocholate (100 mg)TabletOralMedic Laboratory LtÉe1959-12-312007-10-22Canada
RegubilDehydrocholic acid (30 mg) + Deoxycholic acid (30 mg) + Sodium taurocholate (150 mg)TabletOralLaboratoire Riva Inc1983-12-31Not applicableCanada
Categories
UNII
NH5000009I
CAS number
81-23-2
Weight
Average: 402.531
Monoisotopic: 402.240624195
Chemical Formula
C24H34O5
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

Pharmacology

Indication

No approved therapeutic indications.

Pharmacodynamics

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.

Additional Data Available
Adverse Effects

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Additional Data Available
Contraindications

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Additional Data Available
Blackbox Warnings

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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.

Toxicity

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.

Affected organisms
Not Available
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.
DrugInteraction
(R)-warfarinThe risk or severity of bleeding and bruising can be increased when (R)-warfarin is combined with Dehydrocholic acid.
(S)-WarfarinThe risk or severity of bleeding and bruising can be increased when (S)-Warfarin is combined with Dehydrocholic acid.
4-hydroxycoumarinThe risk or severity of bleeding and bruising can be increased when 4-hydroxycoumarin is combined with Dehydrocholic acid.
AbciximabThe risk or severity of adverse effects can be increased when Abciximab is combined with Dehydrocholic acid.
AcenocoumarolThe risk or severity of bleeding and bruising can be increased when Acenocoumarol is combined with Dehydrocholic acid.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Dehydrocholic acid.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Dehydrocholic acid.
AclidiniumThe therapeutic efficacy of Dehydrocholic acid can be decreased when used in combination with Aclidinium.
AgmatineThe therapeutic efficacy of Dehydrocholic acid can be decreased when used in combination with Agmatine.
AlcuroniumThe therapeutic efficacy of Dehydrocholic acid can be decreased when used in combination with Alcuronium.
Additional Data Available
  • Extended Description
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  • Severity
    Severity

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Food Interactions
Not Available

References

General References
  1. 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. [PubMed:4685091]
  2. 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. [PubMed:2340963]
  3. 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. [PubMed:1502488]
  4. 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. [PubMed:2241901]
External Links
KEGG Drug
D01693
KEGG Compound
C13154
PubChem Compound
6674
PubChem Substance
347828014
ChemSpider
6422
RxNav
42625
ChEBI
31459
ChEMBL
CHEMBL514446
ZINC
ZINC000003860869
Wikipedia
Dehydrocholic_acid
AHFS Codes
  • 56:12.00 — Cathartics and Laxatives
  • 56:16.01* — Choleretic
MSDS
Download (286 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral
Tablet, delayed releaseOral
TabletOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)237-240MSDS
water solubilityInsolubleMSDS
Predicted Properties
PropertyValueSource
Water Solubility0.00705 mg/mLALOGPS
logP3.37ALOGPS
logP3.64ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area88.51 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity108.01 m3·mol-1ChemAxon
Polarizability44.81 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-001i-0019100000-fa5bf60a4d1599fa3b77
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-001i-0029000000-f9c226fc3f0811dc78ef
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-001i-0029000000-3dfad07549f72814be6c
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0009000000-eb22bdb679d22824f879
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00kr-0459000000-435f87bc1a58a855a0ce
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-3962000000-2dfafa7266e72ac813b0

Taxonomy

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
Bile acid, alcohol, or derivatives / 3-oxosteroid / 3-oxo-5-beta-steroid / 7-oxosteroid / Oxosteroid / 12-oxosteroid / Ketone / Cyclic ketone / Carboxylic acid derivative / Carboxylic acid
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)

Drug created on September 06, 2016 15:01 / Updated on March 28, 2020 16:15

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