U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H34O5
Molecular Weight 402.5238
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEHYDROCHOLIC 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

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 402.5238
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

Dehydrocholic acid is manufactured from cholic acid by oxidation. The main use of dehydrocholic acid is as a digestive aid in the dietary supplement industry. It is typically formulated with enzymes like papain and pancreatin. It has a stimulating effect on the secretion of bile by the liver (choleretic); improves absorption of essential food materials in states associated with deficient bile formation.

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
Choleretic activity and biliary elimination of lipids and bile acids induced by an artichoke leaf extract in rats.
2002 Dec
Lasting blood-brain barrier disruption induces epileptic focus in the rat somatosensory cortex.
2004 Sep 8
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
Patents

Sample Use Guides

In Vivo Use Guide
in rats: intravenously as a constant infusion (3.1 mumol/min/kg body weight) or as a bolus injection (24.8 mumol/rat)
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:01:10 GMT 2023
Edited
by admin
on Sat Dec 16 17:01:10 GMT 2023
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 [VANDF]
Common Name English
DEHYDROCHOLIC ACID [USP-RS]
Common Name English
NSC-8796
Code English
3,7,12-Trioxo-5β-cholan-24-oic acid
Systematic Name English
DEHYDROCHOLIC ACID [USP MONOGRAPH]
Common 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 Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
Code System Code Type Description
INN
157
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
ChEMBL
CHEMBL514446
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
NSC
8796
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
NCI_THESAURUS
C76605
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
MESH
D003685
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
FDA UNII
NH5000009I
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
CHEBI
137881
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
EPA CompTox
DTXSID2022888
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
CHEBI
31459
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
RXCUI
42625
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
PUBCHEM
6674
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
EVMPD
SUB06945MIG
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
WIKIPEDIA
DEHYDROCHOLIC ACID
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
RXCUI
3141
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m4142
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
201-335-7
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
DRUG BANK
DB11622
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
SMS_ID
100000083477
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
RS_ITEM_NUM
1166502
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
CAS
81-23-2
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
DRUG CENTRAL
794
Created by admin on Sat Dec 16 17:01:11 GMT 2023 , Edited by admin on Sat Dec 16 17:01:11 GMT 2023
PRIMARY
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