SODIUM DESOXYCHOLATE

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]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C

InChI

InChIKey=FHHPUSMSKHSNKW-SMOYURAASA-M

InChI=1S/C24H40O4.Na/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3;/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	C24H39O4
Molecular Weight	391.5641
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206333Orig1s000lbl.pdf | https://www.drugbank.ca/drugs/DB03619 | https://www.nature.com/articles/srep17528

Deoxycholic acid is a a bile acid which emulsifies and solubilizes dietary fats in the intestine, and when injected subcutaneously, it disrupts cell membranes in adipocytes and destroys fat cells in that tissue. In April 2015, deoxycholic acid was approved by the FDA for the treatment submental fat to improve aesthetic appearance and reduce facial fullness or convexity. It is marketed under the brand name Kybella by Kythera Biopharma and is the first pharmacological agent available for submental fat reduction, allowing for a safer and less invasive alternative than surgical procedures. As a bile acid, deoxycholic acid emulsifies fat in the gut. Synthetically derived deoxycholic acid, when injected, stimulates a targeted breakdown of adipose cells by disrupting the cell membrane and causing adipocytolysis. This results in an inflammatory reaction and clearing of the adipose tissue remnants by macrophages. Deoxycholic acid's actions are reduced by albumin and tissue-associated proteins, therefore its effect is limited to protein-poor subcutaneous fat tissue. Protein-rich tissues like muscle and skin are unaffected by deoxycholic acid, contributing to its safety profile. Deoxycholic acid is a cytolytic agent. The physiologic effect of deoxycholic acid is by means of decreased cell membrane integrity. Deoxycholic acid inhibits miR-21 expression in primary rat hepatocytes in a dose-dependent manner, and increases miR-21 pro-apoptotic target programmed cell death 4 (PDCD4) and apoptosis. Deoxycholic acid decreases NF-κB activity, shown to represent an upstream mechanism leading to modulation of the miR-21/PDCD4 pathway.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Staphylococcus aureus 70 Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28878747	Inhibitor 8504
Formyl peptide receptor 1 3 Target ID: CHEMBL3359 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11853704 \| http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=biology&ligandId=610	Antagonist 2849	4.0 null [pKi]
G-protein coupled bile acid receptor 1 16 Target ID: CHEMBL5409 Sources: http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=biology&ligandId=610 \| https://www.ncbi.nlm.nih.gov/pubmed/12419312	Agonist 2752	6.2 null [pEC50]
Bile acid receptor FXR 29 Target ID: CHEMBL2047 Sources: http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=biology&ligandId=610 \| https://www.ncbi.nlm.nih.gov/pubmed/10334993 \| https://www.ncbi.nlm.nih.gov/pubmed/10360171	Agonist 2752	4.0 null [pEC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Subcutaneous fat disorders 2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206333Orig1s000lbl.pdf	Primary		Approved 8583	KYBELLA Approved Use KYBELLA™ (deoxycholic acid) injection is indicated for improvement in the appearance of moderate to severe convexity or fullness associated with submental fat in adults Launch Date 2015
Lipoma 2 Sources: https://clinicaltrials.gov/ct2/show/NCT00608842	Primary		Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
249 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25684122/	100 mg single, subcutaneous dose: 100 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		DEOXYCHOLIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
7241 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25684122/	100 mg single, subcutaneous dose: 100 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		DEOXYCHOLIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25684122/	100 mg single, subcutaneous dose: 100 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		DEOXYCHOLIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25684122/	100 mg single, subcutaneous dose: 100 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		DEOXYCHOLIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 BSEP 550 P-gp 1741 OATP1B1 1079 OATP1B3 961 OCT2 779 OAT1 725 OAT3 747 MRP2 499 MRP4 290 BCRP 910	BSEP 63	CYP1A 59 CYP2B6 669 CYP3A 142

Drug as perpetrator

Target	Modality	Activity
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=13 Page: 13.0	no
MRP2 625	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=13 Page: 13.0	no
MRP4 345	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=13 Page: 13.0	no
OAT1 730	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
OAT3 749	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
OATP1B3 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
OCT2 782	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
CYP1A 122	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP3A 317	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
BSEP 554	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	yes [Ki 21.7 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
BSEP 63	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000PharmR.pdf#page=21 Page: 21.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:28834	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28834
ChemicalBook	CB8325514	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8325514
eMolecules	29541141	https://www.emolecules.com/cgi-bin/more?vid=29541141
eMolecules	29549277	https://www.emolecules.com/cgi-bin/more?vid=29549277
eMolecules	496898	https://www.emolecules.com/cgi-bin/more?vid=496898
MolPort	MolPort-002-507-414	https://www.molport.com/shop/molecule-link/MolPort-002-507-414
ZINC	ZINC000003914810	http://zinc15.docking.org/substances/ZINC000003914810

PubMed

Title	Date	PubMed
Role of mitochondrial complexes I and II, reactive oxygen species and arachidonic acid metabolism in deoxycholate-induced apoptosis.	2002-03-28	11825660
Functional alterations of splenocytes in severe acute pancreatitis.	2002-02	11796014
Increased corneal hydration induced by potential ocular penetration enhancers: assessment by differential scanning calorimetry (DSC) and by desiccation.	2002-01-31	11790497
Intestinal absorption and biodistribution of cosalane and its amino acid conjugates: novel anti-HIV agents.	2002-01-14	11755272
Solute-solvent interactions in micellar electrokinetic chromatography. III. Characterization of the selectivity of micellar electrokinetic chromatography systems.	2002-01-04	11822389
Solute-solvent interactions in micellar electrokinetic chromatography: IV. Characterization of electroosmotic flow and micellar markers.	2002-01	11824622
7alpha-OH epimerisation of bile acids via oxido-reduction with Xanthomonas maltophilia.	2002-01	11728521
Conjugation of low-molecular-weight heparin and deoxycholic acid for the development of a new oral anticoagulant agent.	2001-12-18	11748110
Triphasic vascular responses to bradykinin in the mesenteric resistance artery of the rat.	2001-12-14	11755140
Biosynthetic requirements for the repair of membrane damage in pressure-treated Escherichia coli.	2001-12-04	11764887
Establishment of an animal model of chronic atrophic gastritis and a study on the factors inducing atrophy.	2001-12	11793864
Selective involvement of calcium and calcium channels in stimulated mucin secretion from rat colon.	2001-12	11761027
Combined use of Lactobacillus reuteri and soygerm powder as food supplement.	2001-12	11737624
Bile acid metabolism by fresh human colonic contents: a comparison of caecal versus faecal samples.	2001-12	11709519
Effects of cisapride on gall bladder emptying, intestinal transit, and serum deoxycholate: a prospective, randomised, double blind, placebo controlled trial.	2001-12	11709518
Butyrate suppression of colonocyte NF-kappa B activation and cellular proteasome activity.	2001-11-30	11572859
Effect of environmental and chemotactic stimuli on the activity of the Campylobacter jejuni flaA sigma(28) promoter.	2001-11-27	11728714
Structural characteristics of size-controlled self-aggregates of deoxycholic acid-modified chitosan and their application as a DNA delivery carrier.	2001-11-22	11716684
Role of calcium homeostasis in gastric mucosal injury and protection.	2001-11-09	11758834
Indirect evidence that intestinal bile salt absorption in rats and hamsters is under positive feedback control.	2001-11	11778152
Nasal absorption enhancement of insulin by sodium deoxycholate in combination with cyclodextrins.	2001-11	11749800
Lowering of sodium deoxycholate-induced nasal ciliotoxicity with cyclodextrins.	2001-11	11749799
A nifedipine coground mixture with sodium deoxycholate. II. Dissolution characteristics and stability.	2001-10	11763473
A nifedipine coground mixture with sodium deoxycholate. I. Colloidal particle formation and solid-state analysis.	2001-10	11763472
The effect of a functional group in penicillin derivatives on the interaction with bile salt micelles studied by micellar electrokinetic chromatography.	2001-10	11669544
Colonic transit influences deoxycholic acid kinetics.	2001-10	11606495
The structure of truncated recombinant human bile salt-stimulated lipase reveals bile salt-independent conformational flexibility at the active-site loop and provides insights into heparin binding.	2001-09-21	11563913
Summaries for patients. Itraconazole and amphotericin B to treat fungal infections in patients with cancer who are receiving chemotherapy.	2001-09-18	11575279
Intravenous and oral itraconazole versus intravenous amphotericin B deoxycholate as empirical antifungal therapy for persistent fever in neutropenic patients with cancer who are receiving broad-spectrum antibacterial therapy. A randomized, controlled trial.	2001-09-18	11560454
Nephrotoxicity of amphotericin B desoxycholate.	2001-09-15	11512101
Effect of different bile salts on the relative hypoglycemia of witepsol W35 suppositories containing insulin in diabetic Beagle dogs.	2001-09	11699836
Ursodeoxycholic acid and in vitro vasoactivity of hydrophobic bile acids.	2001-09	11575458
External biliary drainage plus bile acid feeding is not equal to internal drainage in preserving the cellular immunity following prolonged obstructive jaundice.	2001-09	11575437
Octreotide increases the proportions of arachidonic acid-rich phospholipids in gall-bladder bile.	2001-09	11552916
Oxygen free radical generating mechanisms in the colon: do the semiquinones of vitamin K play a role in the aetiology of colon cancer?	2001-08-15	11479033
Successful treatment of invasive mould infection affecting lung and brain in an adult suffering from acute leukaemia.	2001-08	11722602
Deoxycholic acid stimulates migration in colon cancer cells.	2001-08	11507360
Hyodeoxycholic acid efficiently suppresses atherosclerosis formation and plasma cholesterol levels in mice.	2001-08	11483626
Quantitative determination of amygdalin epimers by cyclodextrin-modified micellar electrokinetic chromatography.	2001-07-20	11510547
Effect of surfactants and natural detergents on phosphatidylcholine synthesis in photoreceptor membranes.	2001-07	11699863
Fetal bile acid metabolism: analysis of urinary 3beta-monohydroxy-delta(5) bile acid in preterm infants.	2001-07	11474144
Enhancement of endothelial nitric oxide production by chenodeoxycholic acids in patients with hepatobiliary diseases.	2001-05	11605772
The mechanism of bile salt-induced hemolysis.	2001	11753435
Frequency of tuberculous and non-tuberculous mycobacteria in HIV infected patients from Bogota, Colombia.	2001	11722797
The linkage between beta1 integrin and the actin cytoskeleton is differentially regulated by tyrosine and serine/threonine phosphorylation of beta1 integrin in normal and cancerous human breast cells.	2001	11716783
Differential modulation of cellular death and survival pathways by conjugated bile acids.	2001	11707155
Upregulation of nitric oxide synthase in mice with severe hypoxia-induced pulmonary hypertension.	2001	11686901
Bone morphogenetic protein-5 (BMP-5) promotes dendritic growth in cultured sympathetic neurons.	2001	11580864
The inhibitory effects of camptothecin, a topoisomerase I inhibitor, on collagen synthesis in fibroblasts from patients with systemic sclerosis.	2001	11549373
Cholesterol 7alpha-hydroxylase. 2. Biochemical properties and participation of endogenous cholesterol in the assay in vitro.	1975-06-16	1175606

Patents

Sample Use Guides

In Vivo Use Guide

0.2 mL injections spaced 1-cm apart until all sites in the planned treatment area have been injected. (2.1) • Up to 50 injections or 10 mL may be injected in a single treatment. (2.1) • Up to 6 single treatments may be administered at intervals no less than 1 month apart. (2.1) Injection: 10 mg/mL sterile solution, supplied in 2 mL vials. Each vial is for single patient use.

Route of Administration: Other

In Vitro Use Guide

Unconjugated bile salts at their minimum inhibitory concentration (cholic and deoxycholic acid at 20 and 1 mM, respectively) killed S. aureus, and this was associated with increased membrane disruption and leakage of cellular contents.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:24:41 GMT 2025` Edited by `admin` on `Mon Mar 31 18:24:41 GMT 2025`
Record UNII	436LS6U35Y
Record Status	`Validated (UNII)`
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Name

Type

Language

SODIUM DESOXYCHOLATE

Common Name

English

SODIUM DEOXYCHOLATE

Preferred Name

English

ATX-101 (SODIUM DESOXYCHOLATE)

Code

English

SODIUM DEOXYCHOLIC ACID

Common Name

English

NSC-681065

Code

English

3-.ALPHA.,12-.ALPHA.-DIHYDROXY-5-.BETA.-CHOLAN-24-OIC ACID SODIUM SALT

Common Name

English

DEOXYCHOLIC ACID, SODIUM SALT

Common Name

English

SODIUM DESOXYCHOLATE [II]

Common Name

English

Sodium desoxycholate [WHO-DD]

Common Name

English

KYBELLA

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C843