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+].[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=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	Na
Molecular Weight	22.9898
Charge	1
Count

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

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

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

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 828
bile acid secretion 2 Target ID: GO:0032782 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2340963	Inhibitor 8297
Pepsin A 6 Target ID: CHEMBL2714 Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1251031/pdf/annsurg00095-0018.pdf	Inhibitor 8297
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 1430
Bile secretion 2 Target ID: map04976 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2340963	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2578
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 84 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 8429	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 n = 11 Health Status: unhealthy Condition: recurrent acute cholangitis Age Group: 36-75 Sex: M+F Population Size: 11 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 n = 11 Health Status: unhealthy Condition: recurrent acute cholangitis Age Group: 36-75 Sex: M+F Population Size: 11 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 n = 11 Health Status: unhealthy Condition: recurrent acute cholangitis Age Group: 36-75 Sex: M+F Population Size: 11 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 n = 11 Health Status: unhealthy Condition: recurrent acute cholangitis Age Group: 36-75 Sex: M+F Population Size: 11 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 n = 11 Health Status: unhealthy Condition: recurrent acute cholangitis Age Group: 36-75 Sex: M+F Population Size: 11 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 788 OATP1B3 706 ASBT 5 NTCP 34

Drug as perpetrator

Target	Modality	Activity
ASBT 6	inhibitor 3277 Sources: https://archive.hshsl.umaryland.edu/handle/10713/771	no
NTCP 35	inhibitor 3277 Sources: https://archive.hshsl.umaryland.edu/handle/10713/771	weak [Ki 355 uM]
OATP1B3 715	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]
OATP1B1 803	inhibitor 3277 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
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
BLD Pharm	BD83115	http://www.bldpharm.com/products/81-23-2.html
BioSynth	W-104212	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-104212.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	30830_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/30830?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1166502_USP	https://www.sigmaaldrich.com/catalog/product/usp/1166502?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
abcr GmbH	AB126539	http://www.abcr.com/shop/en/AB126539

PubMed

Title	Date	PubMed
Influence of dehydrocholate sodium on the biliary reabsorption of sulfobromophtalein sodium from the rat biliary tree after retrograde intrabilary injection.	1976 Aug 15	957600
Effects of sodium ursodeoxycholate, hyodeoxycholate and dehydrocholate on cholesterol and bile acid metabolism in rats.	1983 May	6620121
Choledocholithiasis in an infant of extremely low birthweight.	2002 Apr	12031009
Choleretic activity and biliary elimination of lipids and bile acids induced by an artichoke leaf extract in rats.	2002 Dec	12587687
Carbonic anhydrase inhibitors. Preparation of potent sulfonamides inhibitors incorporating bile acid tails.	2002 Jun 17	12039560
Spasmocanulase in irritable bowel syndrome.	2002 Sep	12370715
Sterol-derived hormone(s) controls entry into diapause in Caenorhabditis elegans by consecutive activation of DAF-12 and DAF-16.	2004 Oct	15383841
Lasting blood-brain barrier disruption induces epileptic focus in the rat somatosensory cortex.	2004 Sep 8	15356194
Study on bioactive compounds of in vitro cultured Calculus Suis and natural Calculus Bovis.	2009 Dec	20163661
Thermodynamic and elastic fluctuation analysis of Langmuir mixed monolayers composed by dehydrocholic acid (HDHC) and didodecyldimethylammonium bromide (DDAB).	2010 Jan 1	19734023
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	20622262
Surgical outcome in relation to duct size at the porta hepatis and the use of cholagogues in patients with biliary atresia.	2010 Jul-Sep	21560523

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 `Fri Dec 15 15:01:55 GMT 2023` Edited by `admin` on `Fri Dec 15 15:01:55 GMT 2023`
Record UNII	W4193719XR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEHYDROCHOLATE SODIUM

Common Name

English

Sodium 3,7,12-trioxo-5β-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

Official 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