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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H34O5
Molecular Weight 402.5247
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEHYDROCHOLIC ACID

SMILES

C[C@]([H])(CCC(=O)O)[C@@]1([H])CC[C@@]2([H])[C@@]3([H])[C@]([H])(CC(=O)[C@]12C)[C@@]4(C)CCC(=O)C[C@@]4([H])CC3=O

InChI

InChIKey=OHXPGWPVLFPUSM-KLRNGDHRSA-N
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

HIDE SMILES / InChI

Molecular Formula C24H34O5
Molecular Weight 402.5247
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including http://patft.uspto.gov/netacgi/nph-Parser?Sect2=PTO1&Sect2=HITOFF&p=1&u=/netahtml/PTO/search-bool.html&r=1&f=G&l=50&d=PALL&RefSrch=yes&Query=PN/5935948

Sodium dehydrocholate is a hydrocholeretic and is used to study biliary excretion.

CNS Activity

Curator's Comment:: In rats, sodium dehydrocholate disrupts the blood-brain barrier for a period of over 3 days.

Originator

Curator's Comment:: Hammarsten in 1881 succeeded in converting cholic acid into dehydrocholic acid

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Anionic polypeptide fraction (APF) secretion in bile
Target ID: Q99626
Gene ID: 1045.0
Gene Symbol: CDX2
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Decholinum

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
250 mg 3 times / day multiple, oral
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, 36-75
n = 11
Health Status: unhealthy
Condition: recurrent acute cholangitis
Age Group: 36-75
Sex: M+F
Population Size: 11
Sources:
Other AEs: Nausea, Diarrhea...
Other AEs:
Nausea (1 patient)
Diarrhea (1 patient)
Weight loss (1 patient)
Pain in hand (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhea 1 patient
250 mg 3 times / day multiple, oral
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, 36-75
n = 11
Health Status: unhealthy
Condition: recurrent acute cholangitis
Age Group: 36-75
Sex: M+F
Population Size: 11
Sources:
Nausea 1 patient
250 mg 3 times / day multiple, oral
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, 36-75
n = 11
Health Status: unhealthy
Condition: recurrent acute cholangitis
Age Group: 36-75
Sex: M+F
Population Size: 11
Sources:
Pain in hand 1 patient
250 mg 3 times / day multiple, oral
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, 36-75
n = 11
Health Status: unhealthy
Condition: recurrent acute cholangitis
Age Group: 36-75
Sex: M+F
Population Size: 11
Sources:
Weight loss 1 patient
250 mg 3 times / day multiple, oral
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, 36-75
n = 11
Health Status: unhealthy
Condition: recurrent acute cholangitis
Age Group: 36-75
Sex: M+F
Population Size: 11
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Influence of dehydrocholate sodium on the biliary reabsorption of sulfobromophtalein sodium from the rat biliary tree after retrograde intrabilary injection.
1976 Aug 15
Effects of sodium ursodeoxycholate, hyodeoxycholate and dehydrocholate on cholesterol and bile acid metabolism in rats.
1983 May
Anodic electrochemical oxidation of cholic acid.
2001 Feb
Choledocholithiasis in an infant of extremely low birthweight.
2002 Apr
Choleretic activity and biliary elimination of lipids and bile acids induced by an artichoke leaf extract in rats.
2002 Dec
Carbonic anhydrase inhibitors. Preparation of potent sulfonamides inhibitors incorporating bile acid tails.
2002 Jun 17
Spasmocanulase in irritable bowel syndrome.
2002 Sep
Sterol-derived hormone(s) controls entry into diapause in Caenorhabditis elegans by consecutive activation of DAF-12 and DAF-16.
2004 Oct
Lasting blood-brain barrier disruption induces epileptic focus in the rat somatosensory cortex.
2004 Sep 8
A novel insulin derivative chemically modified with dehydrocholic acid: synthesis, characterization and biological activity.
2005 Aug
Aqueous sodium dehydrocholate-sodium deoxycholate mixtures at low concentration.
2007 Oct 15
Spread mixed monolayers of deoxycholic and dehydrocholic acids at the air-water interface, effect of subphase pH. Characterization by axisymmetric drop shape analysis.
2008 Jan
Magnetic resonance cholangiopancreatography: potential usefulness of dehydrocholic acid (DHCA) administration in the evaluation of anastomotic site.
2008 Jan-Feb
Magnetic resonance cholangiopancreatography: potential usefulness of dehydrocholic acid (DHCA) administration in the evaluation of biliary disease.
2008 Mar-Apr
A new approach for diagnosis of hepatolithiasis: magnetic resonance cholangiopancreatography: potential usefulness of dehydrocholic acid (DHCA) administration in the evaluation of hepatolithiasis.
2008 Sep-Oct
Protective effect of bile acid derivatives in phalloidin-induced rat liver toxicity.
2009 Aug 15
Study on bioactive compounds of in vitro cultured Calculus Suis and natural Calculus Bovis.
2009 Dec
Acidic and basic solutions dissolve protein plugs made of lithostathine complicating choledochal cyst/pancreaticobiliary maljunction.
2009 Jul
Thermodynamic and elastic fluctuation analysis of Langmuir mixed monolayers composed by dehydrocholic acid (HDHC) and didodecyldimethylammonium bromide (DDAB).
2010 Jan 1
Chemical genetic screen identifies lithocholic acid as an anti-aging compound that extends yeast chronological life span in a TOR-independent manner, by modulating housekeeping longevity assurance processes.
2010 Jul
Surgical outcome in relation to duct size at the porta hepatis and the use of cholagogues in patients with biliary atresia.
2010 Jul-Sep
Patents

Sample Use Guides

The usual daily dose of dehydrocholic acid may be 250-750 mg per day, dehydrocholic acid may be administered in doses of 250 mg ingested once or twice per day, usually before meals or, for persons with sensitive gastrointestinal tracts, 125 mg two or three times per day before meals.
Route of Administration: Oral
Dehydrocholic acid (DHCA) was added to CV-1, monkey kidney cell line, TT (a human oesophageal squamous carcinoma), HT-29 (a human colon carcinoma) at 100 uM to afford a ~4-fold increase in CDX2 expression.
Substance Class Chemical
Created
by admin
on Sat Jun 26 06:41:43 UTC 2021
Edited
by admin
on Sat Jun 26 06:41:43 UTC 2021
Record UNII
NH5000009I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEHYDROCHOLIC ACID
INN   MART.   MI   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
DECHOLIN
Brand Name English
DEHYDROCHOLIC ACID [WHO-DD]
Common Name English
PROCHOLON
Brand Name English
DEHYDROCHOLIC ACID [MART.]
Common Name English
DEHYDROCHOLIC ACID [INN]
Common Name English
DEHYDROCHOLIC ACID [USP]
Common Name English
DEHYDROCHOLIC ACID [VANDF]
Common Name English
DEHYDROCHOLIC ACID [USP-RS]
Common Name English
NSC-8796
Code English
3,7,12-TRIOXO-5.BETA.-CHOLAN-24-OIC ACID
Systematic Name English
DILABIL
Brand Name English
CHOLAN-24-OIC ACID, 3,7,12-TRIOXO-, (5.BETA.)-
Common Name English
DEHYDROCHOLIC ACID [JAN]
Common Name English
DEHYDROCHOLIC ACID [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66913
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
Code System Code Type Description
INN
157
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY
ChEMBL
CHEMBL514446
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY
NCI_THESAURUS
C76605
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY
MESH
D003685
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY
FDA UNII
NH5000009I
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY
EPA CompTox
81-23-2
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY
RXCUI
42625
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY
PUBCHEM
6674
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY
EVMPD
SUB06945MIG
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY
WIKIPEDIA
DEHYDROCHOLIC ACID
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY
USP_CATALOG
1166502
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY USP-RS
RXCUI
3141
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M4142
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
201-335-7
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY
DRUG BANK
DB11622
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY
CAS
81-23-2
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY
DRUG CENTRAL
794
Created by admin on Sat Jun 26 06:41:43 UTC 2021 , Edited by admin on Sat Jun 26 06:41:43 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY