SODIUM HYODEOXYCHOLATE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H39O4.Na
Molecular Weight	414.5538
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
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]3C[C@H](O)[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI

InChIKey=DUYSCILLIVEITB-ADQIWYCWSA-M

InChI=1S/C24H40O4.Na/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2;/h14-21,25-26H,4-13H2,1-3H3,(H,27,28);/q;+1/p-1/t14-,15-,16+,17-,18+,19+,20+,21+,23-,24-;/m1./s1

HIDE SMILES / InChI

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

Molecular Formula	C24H39O4
Molecular Weight	391.5641
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://cdn2.hubspot.net/hub/150154/file-473189780-pdf/docs/AtheroNova-AHRO-Executive-Informational-Overview2-01-22-2014.pdf
Curator's Comment: description was created based on several sources, including: https://en.wikipedia.org/wiki/Hyodeoxycholic_acid | https://cdn2.hubspot.net/hub/150154/file-27656828-pdf/docs/atheronova-ahro-quarterly-update-04-05-2013.pdf | https://www.ncbi.nlm.nih.gov/pubmed/10936612

Hyodeoxycholic acid, also known as HDCA, is a secondary bile acid. Natural 6alpha-hydroxylated bile acids are receptor-specific activators of nuclear liver X receptor alpha (LXRalpha), a nuclear receptor regulating the expression of the cholesterol 7alpha-hydroxylase gene. AHRO-001 (Hyodeoxycholic acid) is in phase I clinical trials for the treatment of atherosclerosis. Through a complex signaling processes utilizing LXR receptors, the compound is designed to increase the efficiency of cholesterol efflux using the HDL cells, which act on all cholesterol in the arterial circulation as well as in the lipid core of plaque deposits in the artery walls. Use of AHRO-001 has shown no adverse effects on morbidity, mortality or toxicity and has been well tolerated at high doses.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
LXR-alpha 10 Target ID: CHEMBL2808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10936612	Agonist 2752
UDP-glucuronosyltransferase 2B7 4 Target ID: CHEMBL4370 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12527334	Substrate 661
UDP-glucuronosyltransferase 2B4 3 Target ID: CHEMBL6196 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8244999	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atherosclerosis 76 Sources: http://adisinsight.springer.com/drugs/800038244 https://www.ncbi.nlm.nih.gov/pubmed/23752203	Primary		Phase I 438	Unknown Approved Use Unknown
Hypercholesterolemia 51 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7619860 http://adisinsight.springer.com/trials/700206192	Primary		Phase I 438	Unknown Approved Use Unknown

AUC

Value	Dose	Co-administered	Analyte	Population
3344 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16750434	3.44 mg/kg single, intraperitoneal dose: 3.44 mg/kg route of administration: Intraperitoneal experiment type: SINGLE co-administered: GENIPOSIDE\|Isoniazid\|Cholic acid	GENIPOSIDE\|Isoniazid\|Cholic acid	HYODEOXYCHOLIC ACID plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.121 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16750434	3.44 mg/kg single, intraperitoneal dose: 3.44 mg/kg route of administration: Intraperitoneal experiment type: SINGLE co-administered: GENIPOSIDE\|Isoniazid\|Cholic acid	GENIPOSIDE\|Isoniazid\|Cholic acid	HYODEOXYCHOLIC ACID plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	UGT1A10 331 UGT2B4 278 UGT2A2 49 UGT2A1 39 UGT8 2 UGT2B7 456 UGT1A8 323 UGT1A1 479 UGT2A3 49 UGT 219 UGT1A3 470 UGT2B28 65 UGT1A7 249 UGT2B10 131 UGT2B15 236 UGT2B17 237 P-gp 2052

Drug as victim

Target	Modality	Activity
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12527334/	likely
UGT2A3 49	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23756265/	likely
UGT2B28 65	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12527334/	likely
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=363680132	no
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10836148/	no
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10836148/	no
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10836148/	no
UGT2B10 131	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10836148/	no
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10836148/	no
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10836148/	no
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12527334/ \| https://pubmed.ncbi.nlm.nih.gov/23756265/	weak
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12527334/ \| https://pubmed.ncbi.nlm.nih.gov/23756265/	yes [Km 11.6 uM]
UGT 219	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/1909626/	yes [Km 12 uM]
UGT2A2 49	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23756265/	yes [Km 150.4 uM]
UGT2A1 39	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23756265/	yes [Km 178.5 uM]
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12527334/ \| https://pubmed.ncbi.nlm.nih.gov/23756265/	yes
UGT8 2	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25519837/	yes

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P003RFW	https://www.1pchem.com/search?query=1P003RFW
A2B Chem	AB74732	http://a2bchem.com/prod/AB74732
AK Scientific	0003TG	https://aksci.com/item_detail.php?cat=0003TG
AK Scientific	H106	https://aksci.com/item_detail.php?cat=H106
AK Scientific	J91554	https://aksci.com/item_detail.php?cat=J91554
AK Scientific	J92519	https://aksci.com/item_detail.php?cat=J92519
AK Scientific	K489	https://aksci.com/item_detail.php?cat=K489
AstaTech	43086	http://astatechinc.com/CPSResult.php?CRNO=43086
BioSynth	W-104141	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-104141
BOC Sciences	10421-49-5	http://www.bocsci.com/description.asp?cas=10421-49-5
Cayman Chemical	20294	http://www.caymanchem.com/app/template/Product.vm/catalog/20294
Chem-Impex International	29962	http://www.chemimpex.com/category/search/29962/2?filter=&search=29962&type=q&keywordoption=ANY&cid=2&fltrdesc=
Chem-Impex International	31890	http://www.chemimpex.com/category/search/31890/2?filter=&search=31890&type=q&keywordoption=ANY&cid=2&fltrdesc=
Chem Scene	CS-0007886	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0007886
ChemShuttle	112189	https://www.chemshuttle.com/catalogsearch/result/?q=112189
Combi-Blocks	QA-8913	http://www.combi-blocks.com/cgi-bin/find.cgi?QA-8913
eMolecules	300679078	https://orderbb.emolecules.com/search/#?query=300679078
eMolecules	30151939	https://orderbb.emolecules.com/search/#?query=30151939
eMolecules	43470322	https://orderbb.emolecules.com/search/#?query=43470322
eMolecules	50505823	https://orderbb.emolecules.com/search/#?query=50505823
eNovation Chemicals	D659533	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D659533&searchbtn.x=0&searchbtn.y=0
Fluorochem	516405	http://www.fluorochem.co.uk/Products/Product?code=516405
KeyOrganics	AS-14254	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-14254
KeyOrganics	AS-60591	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-60591
Lab Network	LN01285032	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01285032
Lab Network	LN01352348	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01352348
Matrix Scientific	98473	http://www.matrixscientific.com/098473.html
mcule	MCULE-6151721743	https://mcule.com/MCULE-6151721743/
mcule	MCULE-6751073161	https://mcule.com/MCULE-6751073161/
mcule	MCULE-7294774452	https://mcule.com/MCULE-7294774452/
MedChem Express	HY-N0169	https://www.medchemexpress.com/search.html?q=HY-N0169&ft=&fa=&fp=
Molnova	M19159	https://www.molnova.com/en/serch-list.html?keywords=M19159
MolPort	MolPort-016-633-329	https://www.molport.com/shop/molecule-link/MolPort-016-633-329
MolPort	MolPort-023-220-260	https://www.molport.com/shop/molecule-link/MolPort-023-220-260
Selleck Chemicals	S2311	http://www.selleckchem.com/search.html?searchDTO.searchParam=S2311
TargetMol	83-49-8	https://www.targetmol.com/search?keyword=83-49-8
TargetMol	HMDB0000733	https://www.targetmol.com/search?keyword=HMDB0000733
TargetMol	T2968	https://www.targetmol.com/search?keyword=T2968
Tetrahedron	TS09187	http://www.thsci.com/search.do?q=TS09187
Tetrahedron	TS69717	http://www.thsci.com/search.do?q=TS69717
Toronto Research Chemicals	H998100	https://www.trc-canada.com/product-detail/?CatNum=H998100
W&J PharmaChem	50A573126	http://wjpharmachem.com/new/searcht.php?keyword=50A573126
W&J PharmaChem	50C163273	http://wjpharmachem.com/new/searcht.php?keyword=50C163273

PubMed

Title	Date	PubMed
Inhibition of human UGT2B7 gene expression in transgenic mice by the constitutive androstane receptor.	2011-06	21415305
Voluntary wheel running exercise and dietary lactose concomitantly reduce proportion of secondary bile acids in rat feces.	2010-09	20616226
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
Regulation of bile acid synthesis by fat-soluble vitamins A and D.	2010-05-07	20233723
Identification of human UGT2B7 as the major isoform involved in the O-glucuronidation of chloramphenicol.	2010-03	20008037
Liver X receptor agonist methyl-3β-hydroxy-5α,6α-epoxycholanate attenuates atherosclerosis in apolipoprotein E knockout mice without increasing plasma triglyceride.	2010	21071998
Challenges predicting ligand-receptor interactions of promiscuous proteins: the nuclear receptor PXR.	2009-12	20011107
Consumption of some polyphenols reduces fecal deoxycholic acid and lithocholic acid, the secondary bile acids of risk factors of colon cancer.	2009-09-23	19711910
3-ketocholanoic acid is the major in vitro human hepatic microsomal metabolite of lithocholic acid.	2009-09	19487251
Serum bile acid profiling reflects enterohepatic detoxification state and intestinal barrier function in inflammatory bowel disease.	2009-07-07	19575493
Bear bile: dilemma of traditional medicinal use and animal protection.	2009-01-12	19138420
Improved analysis of bile acids in tissues and intestinal contents of rats using LC/ESI-MS.	2009-01	18772484
The inhibitory effects of cholalic acid and hyodeoxycholalic acid on the expression of TNFalpha and IL-1beta after cerebral ischemia in rats.	2009-01	19183878
Regulation of sulfotransferase and UDP-glucuronosyltransferase gene expression by the PPARs.	2009	19680455
Novel polymorphic human UDP-glucuronosyltransferase 2A3: cloning, functional characterization of enzyme variants, comparative tissue expression, and gene induction.	2008-09	18523138
Biotransformation of lithocholic acid by rat hepatic microsomes: metabolite analysis by liquid chromatography/mass spectrometry.	2008-02	18039809
Use of selected chemical markers in combination with a multiple regression model to assess the contribution of domesticated animal sources of fecal pollution in the environment.	2007-11	17590407
[Determination of chyodeoxycholic acid in Bile Arisaema by HPLC-ELSD].	2007-08	18027654
Comparative study on major bioactive components in natural, artificial and in-vitro cultured Calculus Bovis.	2007-01	17202716
Isolation and determination of bile acids.	2006-12-02	17136860
Simultaneous determination of geniposide, baicalin, cholic acid and hyodeoxycholic acid in rat serum for the pharmacokinetic investigations by high performance liquid chromatography-tandem mass spectrometry.	2006-09-14	16750434
Resistance to ursodeoxycholic acid-induced growth arrest can also result in resistance to deoxycholic acid-induced apoptosis and increased tumorgenicity.	2006-09-01	16948850
3alpha-6alpha-Dihydroxy-7alpha-fluoro-5beta-cholanoate (UPF-680), physicochemical and physiological properties of a new fluorinated bile acid that prevents 17alpha-ethynyl-estradiol-induced cholestasis in rats.	2006-07-15	16487557
Role for enhanced faecal excretion of bile acid in hydroxysteroid sulfotransferase-mediated protection against lithocholic acid-induced liver toxicity.	2006-07	16864508
Determination of three bile acids in artificial Calculus Bovis and its medicinal preparations by micellar electrokinetic capillary electrophoresis.	2006-06-06	16651035
Enzymatic production of bile Acid glucuronides used as analytical standards for liquid chromatography-mass spectrometry analyses.	2006-06-06	16749861
Mice lacking Mrp3 (Abcc3) have normal bile salt transport, but altered hepatic transport of endogenous glucuronides.	2006-04	16225954
Simultaneous determination of nine components in Qingkailing injection by HPLC/ELSD/DAD and its application to the quality control.	2006-03-03	16257167
Simultaneous determination of major bioactive components in Qingkailing injection by high-performance liquid chromatography with evaporative light scattering detection.	2005-11	16272719
[Simultaneous determination of five groups of components in qingkailing injection by high performance liquid chromatography with photo diode array detector and evaporative light scattering detector].	2005-09	16350790
Interfacial properties of most monofluorinated bile acids deviate markedly from the natural congeners: studies with the Langmuir-Pockels surface balance.	2005-03	15604514
Effect of dried plums on colon cancer risk factors in rats.	2005	16351514
Identification of UGT2B9*2 and UGT2B33 isolated from female rhesus monkey liver.	2004-06-01	15130782
[Study on extraction technique of HDCA].	2004-05	15706890
Effects of ileo-rectal anastomosis on cholesterol metabolism in pigs fed either casein or extruded soya beans.	2004-05	15137920
UDP-glucuronosyltransferase and sulfotransferase polymorphisms, sex hormone concentrations, and tumor receptor status in breast cancer patients.	2004	15318931
Steroids in the intestinal tract of rats are affected by dietary-fibre-rich barley-based diets.	2003-11	14667183
Substrate specificities of rat oatp1 and ntcp: implications for hepatic organic anion uptake.	2003-11	12842829
The cytotoxicity of hydrophobic bile acids is ameliorated by more hydrophilic bile acids in intestinal cell lines IEC-6 and Caco-2.	2003-10-10	14534721
Peroxisome proliferator-activated receptor alpha induces hepatic expression of the human bile acid glucuronidating UDP-glucuronosyltransferase 2B4 enzyme.	2003-08-29	12810707
Glucosidation of hyodeoxycholic acid by UDP-glucuronosyltransferase 2B7.	2003-02-01	12527334
Dietary bile acids inhibit potentially elemental diet-induced small intestinal atrophy in rats.	2002-11	12373304
[Study on effect of qingkailing injection and its active principle in inducing cell apoptosis in human acute promyelocytic leukemia].	2001-11	12575380
Hyodeoxycholic acid efficiently suppresses atherosclerosis formation and plasma cholesterol levels in mice.	2001-08	11483626
Effect of bile salts on colonic mucus secretion in isolated vascularly perfused rat colon.	2001-06	11414298
Hydrophilic and hydrophobic bile acids exhibit different cytotoxicities through cytolysis, interleukin-8 synthesis and apoptosis in the intestinal epithelial cell lines. IEC-6 and Caco-2 cells.	2001-05	11346209
UGT2B23, a novel uridine diphosphate-glucuronosyltransferase enzyme expressed in steroid target tissues that conjugates androgen and estrogen metabolites.	1999-12	10579317
Reinduction of the hypnotic effects of thiopental with NSAIDs by decreasing thiopental plasma protein binding in humans.	1993-04	8517101
Complementary deoxyribonucleic acid cloning and expression of a human liver uridine diphosphate-glucuronosyltransferase glucuronidating carboxylic acid-containing drugs.	1993-01	8423545
Isolation and characterization of hyodeoxycholic-acid: UDP-glucuronosyltransferase from human liver.	1991-09-01	1909626

Patents

Sample Use Guides

In Vivo Use Guide

Cohort 1: 500 mg/dose, given as a single dose then as bid x7days and tid x 7days Cohort 2: 750 mg/dose, given as a single dose then as bid x7days and tid x 7days Cohort 3: 1000 mg/dose, given as a single dose then as bid x7days and tid x7days Cohort 4: 21 days dosing given at best tolerated dose determined by cohorts 1-3 Cohort 5: 12 wks dosing given at best tolerated dose determined by cohorts 1-4

Route of Administration: Oral

In Vitro Use Guide

HDCA treatment (50 and 100 uM) significantly increased the expression of ATP-binding cassette subfamily A member 1 (Abca1), ATP-binding cassette subfamily G member 1 (Abcg1), and apolipoprotein E (Apoe) in RAW cells in a dose-response way.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:56:22 GMT 2025` Edited by `admin` on `Mon Mar 31 17:56:22 GMT 2025`
Record UNII	HBY71R8HO2
Record Status	`Validated (UNII)`
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Name

Type

Language

SODIUM HYODEOXYCHOLATE

Common Name

English

SODIUM HYODESOXYCHOLATE

Preferred Name

English

CHOLAN-24-OIC ACID, 3,6-DIHYDROXY-, SODIUM SALT (1:1), (3.ALPHA.,5.BETA.,6.ALPHA.)-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID60908871