DEHYDROCHOLATE SODIUM

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H33O5.Na
Molecular Weight	424.5056
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=FKJIJBSJQSMPTI-CAOXKPNISA-M

InChI=1S/C24H34O5.Na/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);/q;+1/p-1/t13-,14+,16-,17+,18+,22+,23+,24-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C24H33O5
Molecular Weight	401.5158
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.drugs.com/dict/dehydrocholic-acid.htmlhttps://www.ncbi.nlm.nih.gov/pubmed/6620121
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Anionic polypeptide fraction (APF) secretion in bile 2 Target ID: Anionic polypeptide fraction (APF) secretion in bile Sources: https://www.ncbi.nlm.nih.gov/pubmed/1502488	Modulator 846
bile acid secretion 2 Target ID: GO:0032782 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2340963	Inhibitor 8504
Pepsin A 6 Target ID: CHEMBL2714 Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1251031/pdf/annsurg00095-0018.pdf	Inhibitor 8504
Homeobox protein CDX-2 2 Target ID: Q99626 Gene ID: 1045.0 Gene Symbol: CDX2 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1856383/pdf/16.pdf	Activator 1447
Bile secretion 2 Target ID: map04976 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2340963	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2596
Gallstones in the biliary ducts of the liver 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19102397	Diagnostic	Basic research	Unknown Approved Use Unknown
Psoriasis 87 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14643904	Primary	Basic research	Unknown Approved Use Unknown
Congenital hepatic fibrosis with cholestasis 2 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3969982	Primary	Basic research	Unknown Approved Use Unknown
Cholangitis 4 Sources: http://www.medical-enc.ru/5/decholinum.shtml	Primary	Approved 8583	Decholinum Approved Use Unknown

Doses

Dose	Population	Adverse 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: https://www.hpbonline.org/article/S1365-182X(19)30434-4/fulltext	unhealthy, 36-75 Health Status: unhealthy Age Group: 36-75 Sex: M+F Sources: https://www.hpbonline.org/article/S1365-182X(19)30434-4/fulltext	Other AEs: Nausea, Diarrhea... Other AEs: Nausea (1 patient) Diarrhea (1 patient) Weight loss (1 patient) Pain in hand (1 patient) Sources: https://www.hpbonline.org/article/S1365-182X(19)30434-4/fulltext

AEs

AE	Significance	Dose	Population
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: https://www.hpbonline.org/article/S1365-182X(19)30434-4/fulltext	unhealthy, 36-75 Health Status: unhealthy Age Group: 36-75 Sex: M+F Sources: https://www.hpbonline.org/article/S1365-182X(19)30434-4/fulltext
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: https://www.hpbonline.org/article/S1365-182X(19)30434-4/fulltext	unhealthy, 36-75 Health Status: unhealthy Age Group: 36-75 Sex: M+F Sources: https://www.hpbonline.org/article/S1365-182X(19)30434-4/fulltext
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: https://www.hpbonline.org/article/S1365-182X(19)30434-4/fulltext	unhealthy, 36-75 Health Status: unhealthy Age Group: 36-75 Sex: M+F Sources: https://www.hpbonline.org/article/S1365-182X(19)30434-4/fulltext
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: https://www.hpbonline.org/article/S1365-182X(19)30434-4/fulltext	unhealthy, 36-75 Health Status: unhealthy Age Group: 36-75 Sex: M+F Sources: https://www.hpbonline.org/article/S1365-182X(19)30434-4/fulltext

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 1079 OATP1B3 961 ASBT 7 NTCP 39

Drug as perpetrator

Target	Modality	Activity
ASBT 8	inhibitor 4027 Sources: https://archive.hshsl.umaryland.edu/handle/10713/771	no
NTCP 40	inhibitor 4027 Sources: https://archive.hshsl.umaryland.edu/handle/10713/771	weak [Ki 355 uM]
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://transportal.compbio.ucsf.edu/compounds/dehydrocholic-acid/, https://pubmed.ncbi.nlm.nih.gov/19427586/, https://pubmed.ncbi.nlm.nih.gov/19427586/	yes [Ki 29.7 uM]

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1064	http://www.3bsc.com/index/pro_info.php?id=47695
AA Blocks	AA0036EL	https://www.aablocks.com/goods/Goods/detail?id=AA0036EL
Aaron Chemicals	AR00376D	http://www.aaronchem.com/81-23-2
abcr GmbH	AB126539	http://www.abcr.com/shop/en/AB126539
AbMole Bioscience	M5560	http://www.abmole.com/products/dehydrocholic-acid.html
Acadechem	ACDS-065451	http://www.acadechemical.com/product/140150
Achemtek	0104-000842	http://www.achemtek.com/81-23-2
Alfa Chemistry	AP81232	https://reagents.alfa-chemistry.com/product/dehydrocholic-acid-cas-81-23-2-16903.html
Aurora Fine Chemicals LLC	A17.890.971	http://online.aurorafinechemicals.com/info?ID=A17.890.971
BioSynth	W-104212	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-104212.html
BLD Pharm	BD83115	http://www.bldpharm.com/products/81-23-2.html
Chem Scene	CS-4902	http://www.chemscene.com/81-23-2.html
ChemMol	99155734	http://www.chemmol.com/chemmol/99155734.html
Chemspace	CSSB00016989140	https://chem-space.com/CSSB00016989140
Glentham Life Sciences	GE2305	http://www.glentham.com/products/product/GE2305/
Hairui	HR128700	http://www.hairuichem.com/en/product/81-23-2.html
Lab Network	LN01278398	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01278398
MedChem Express	HY-B1393	https://www.medchemexpress.com/Dehydrocholic-acid.html
MuseChem	I004953	https://www.musechem.com/product/I004953.html
Parchem	28668	http://www.parchem.com/chemical-supplier-distributor/Dehydrocholic-Acid-018668.aspx
Sigma-Aldrich	1166502_USP	https://www.sigmaaldrich.com/catalog/product/usp/1166502?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	30830_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/30830?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S049794	http://www.sinfoobiotech.com/product/1053192
Smolecule	S525568	http://www.smolecule.com/products/s525568
Smolecule	S772680	https://www.smolecule.com/products/s772680
THE BioTek	bt-266616	https://www.thebiotek.com/product/inhibitors/bt-266616
THE BioTek	bt-288721	https://www.thebiotek.com/product/others/bt-288721

PubMed

Title	Date	PubMed
Surgical outcome in relation to duct size at the porta hepatis and the use of cholagogues in patients with biliary atresia.	2011-05-13	21560523
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.	2010-07	20622262
Thermodynamic and elastic fluctuation analysis of Langmuir mixed monolayers composed by dehydrocholic acid (HDHC) and didodecyldimethylammonium bromide (DDAB).	2010-01-01	19734023
Study on bioactive compounds of in vitro cultured Calculus Suis and natural Calculus Bovis.	2009-12	20163661
Protective effect of bile acid derivatives in phalloidin-induced rat liver toxicity.	2009-08-15	19409403
Acidic and basic solutions dissolve protein plugs made of lithostathine complicating choledochal cyst/pancreaticobiliary maljunction.	2009-07	18989781
A new approach for diagnosis of hepatolithiasis: magnetic resonance cholangiopancreatography: potential usefulness of dehydrocholic acid (DHCA) administration in the evaluation of hepatolithiasis.	2008-12-24	19102397
Magnetic resonance cholangiopancreatography: potential usefulness of dehydrocholic acid (DHCA) administration in the evaluation of biliary disease.	2008-07-11	18613358
Magnetic resonance cholangiopancreatography: potential usefulness of dehydrocholic acid (DHCA) administration in the evaluation of anastomotic site.	2008-05-30	18507070
Spread mixed monolayers of deoxycholic and dehydrocholic acids at the air-water interface, effect of subphase pH. Characterization by axisymmetric drop shape analysis.	2008-01	17967503
Aqueous sodium dehydrocholate-sodium deoxycholate mixtures at low concentration.	2007-10-15	17612553
Determination of critical micellar concentrations of cholic acid and its keto derivatives.	2007-10-01	17604970
Regio- and stereoselective reductions of dehydrocholic acid.	2006-06	16504228
Bile acids directly augment caudal related homeobox gene Cdx2 expression in oesophageal keratinocytes in Barrett's epithelium.	2006-01	16118348
A novel insulin derivative chemically modified with dehydrocholic acid: synthesis, characterization and biological activity.	2005-08	15612881
Sterol-derived hormone(s) controls entry into diapause in Caenorhabditis elegans by consecutive activation of DAF-12 and DAF-16.	2004-10	15383841
Lasting blood-brain barrier disruption induces epileptic focus in the rat somatosensory cortex.	2004-09-08	15356194
Choleretic activity and biliary elimination of lipids and bile acids induced by an artichoke leaf extract in rats.	2002-12	12587687
Spasmocanulase in irritable bowel syndrome.	2002-09	12370715
Carbonic anhydrase inhibitors. Preparation of potent sulfonamides inhibitors incorporating bile acid tails.	2002-06-17	12039560
Choledocholithiasis in an infant of extremely low birthweight.	2002-04	12031009
Anodic electrochemical oxidation of cholic acid.	2001-02	11146084
Effects of sodium ursodeoxycholate, hyodeoxycholate and dehydrocholate on cholesterol and bile acid metabolism in rats.	1983-05	6620121
Influence of dehydrocholate sodium on the biliary reabsorption of sulfobromophtalein sodium from the rat biliary tree after retrograde intrabilary injection.	1976-08-15	957600

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Mon Mar 31 17:35:58 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:58 GMT 2025`
Record UNII	W4193719XR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SODIUM DEHYDROCHOLATE

Preferred Name

English

DEHYDROCHOLATE SODIUM

Common Name

English

Sodium 3,7,12-trioxo-5?-cholan-24-oate

Systematic Name

English

DEHYDROCHOLIC ACID SODIUM SALT

Common Name

English

CHOLAN-24-OIC ACID, 3,7,12-TRIOXO-, SODIUM SALT, (5.BETA.)-

Common Name

English

sodium dehydrocholate [INN]

Common Name

English

DEHYDROCHOLIC ACID SODIUM SALT [MI]

Common Name

English

Sodium dehydrocholate [WHO-DD]

Common Name

English

DECHOLIN SODIUM

Brand Name

English

NSC-756707

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C66913