SODIUM DESOXYCHOLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H39O4.Na
Molecular Weight	414.5547
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

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	391.565
Charge	-1
Count

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

Molecular Formula	Na
Molecular Weight	22.9898
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 30 Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28878747	Inhibitor 3315
Formyl peptide receptor 1 1 Target ID: CHEMBL3359 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11853704 \| http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=biology&ligandId=610	Antagonist 1131	4.0 null [pKi]
G-protein coupled bile acid receptor 1 5 Target ID: CHEMBL5409 Sources: http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=biology&ligandId=610 \| https://www.ncbi.nlm.nih.gov/pubmed/12419312	Agonist 1109	6.2 null [pEC50]
Bile acid receptor FXR 13 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 1109	4.0 null [pEC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Subcutaneous fat disorders 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206333Orig1s000lbl.pdf	Primary		Approved 4033	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 1.43026566E12
Lipoma 1 Sources: https://clinicaltrials.gov/ct2/show/NCT00608842	Primary		Phase II 394	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 753	inhibitor 825	inhibitor 894	inhibitor 775

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 725 CYP2B6 371 CYP2C8 417 CYP2C19 700 BSEP 185 P-gp 666 OATP1B1 369 OATP1B3 319 OCT2 297 OAT1 279 OAT3 290 MRP2 184 MRP4 107 BCRP 303	BSEP 15	CYP1A 31 CYP2B6 243 CYP3A 60

Drug as perpetrator

Target	Modality	Activity
BCRP 346	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=13 Page: 13.0	no
MRP2 239	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=13 Page: 13.0	no
MRP4 124	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=13 Page: 13.0	no
OAT1 280	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
OAT3 291	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
OATP1B1 379	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
OATP1B3 326	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
OCT2 298	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
P-gp 754	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
CYP1A 63	inducer 772 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP1A2 805	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2B6 465	inducer 772 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2B6 465	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2C19 738	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2C8 448	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2C9 851	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2D6 908	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP3A 146	inducer 772 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP3A4 920	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
BSEP 186	inhibitor 1612 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 15	substrate 1689 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 796	inhibitor 786 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
MolPort	MolPort-002-507-414	https://www.molport.com/shop/molecule-link/MolPort-002-507-414
ZINC	ZINC000003914810	http://zinc15.docking.org/substances/ZINC000003914810
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

PubMed

Title	Date	PubMed
Cholesterol 7alpha-hydroxylase. 2. Biochemical properties and participation of endogenous cholesterol in the assay in vitro.	1975 Jun 16	1175606
Ursodeoxycholic acid prevents hepatic cytochrome P450 isozyme reduction in rats with deoxycholic acid-induced liver injury.	1999 Aug	10453939
Endogenous bile acids are ligands for the nuclear receptor FXR/BAR.	1999 May	10360171
Bile acids: natural ligands for an orphan nuclear receptor.	1999 May 21	10334993
Identification of a nuclear receptor for bile acids.	1999 May 21	10334992
The mechanism of bile salt-induced hemolysis.	2001	11753435
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
Osmotic stress-dependent serine phosphorylation of the histidine kinase homologue DokA.	2001	11299049
Soybean resistant proteins interrupt an enterohepatic circulation of bile acids and suppress liver tumorigenesis induced by azoxymethane and dietary deoxycholate in rats.	2001 Apr	11388492
Non-involvement of the K-ras mutation in colon carcinogenesis promoted by dietary deoxycholate in azoxymethane-treated rats.	2001 Apr	11388463
Role of humoral mediators in, and influence of a liposomal formulation on, acute amphotericin B nephrotoxicity.	2001 Apr	11322173
The effect of absorption enhancers on the initial degradation kinetics of insulin by alpha-chymotrypsin.	2001 Apr 17	11292547
Successful treatment of invasive mould infection affecting lung and brain in an adult suffering from acute leukaemia.	2001 Aug	11722602
Influence of pH on the phase distribution of nascent deoxycholic acid in fresh human cecal aspirates.	2001 Aug	11447017
Effect of bile acids on formation of azoxymethane-induced aberrant crypt foci in colostomized F344 rat colon.	2001 Aug 28	11431100
Effects of cisapride on gall bladder emptying, intestinal transit, and serum deoxycholate: a prospective, randomised, double blind, placebo controlled trial.	2001 Dec	11709518
Determination of alkylphenol ethoxylates by micellar electrokinetic chromatography with bile salts.	2001 Feb	11258765
Cholesterol solubilization in aqueous micellar solutions of quillaja saponin, bile salts, or nonionic surfactants.	2001 Jan	11170603
Empirical antifungal therapy for persistent fever in patients with neutropenia.	2001 Jan 15	11170928
Effect of surfactants and natural detergents on phosphatidylcholine synthesis in photoreceptor membranes.	2001 Jul	11699863
Bile acid hydrophobicity is correlated with induction of apoptosis and/or growth arrest in HCT116 cells.	2001 Jun 1	11368775
Secretion of the virulence-associated Campylobacter invasion antigens from Campylobacter jejuni requires a stimulatory signal.	2001 Jun 1	11343209
Complexing of basic pancreatic proteinase inhibitor with soybean phospholipid multilamellar vesicles.	2001 Mar	11333161
Influence of butyric and lactic acids on the beta-glucuronidase activity of Clostridium perfringens.	2001 Mar	11264737
Bile-induced 'pili' in Campylobacter jejuni are bacteria-independent artifacts of the culture medium.	2001 Mar	11260471
Biliary lipid composition in cholesterol microlithiasis.	2001 May	11302972
Indirect evidence that intestinal bile salt absorption in rats and hamsters is under positive feedback control.	2001 Nov	11778152
Nasal absorption enhancement of insulin by sodium deoxycholate in combination with cyclodextrins.	2001 Nov	11749800
Lowering of sodium deoxycholate-induced nasal ciliotoxicity with cyclodextrins.	2001 Nov	11749799
Effect of environmental and chemotactic stimuli on the activity of the Campylobacter jejuni flaA sigma(28) promoter.	2001 Nov 27	11728714
Butyrate suppression of colonocyte NF-kappa B activation and cellular proteasome activity.	2001 Nov 30	11572859
Colonic transit influences deoxycholic acid kinetics.	2001 Oct	11606495
Ursodeoxycholic acid and in vitro vasoactivity of hydrophobic bile acids.	2001 Sep	11575458
External biliary drainage plus bile acid feeding is not equal to internal drainage in preserving the cellular immunity following prolonged obstructive jaundice.	2001 Sep	11575437
Nephrotoxicity of amphotericin B desoxycholate.	2001 Sep 15	11512101
Solute-solvent interactions in micellar electrokinetic chromatography: IV. Characterization of electroosmotic flow and micellar markers.	2002 Jan	11824622
Solute-solvent interactions in micellar electrokinetic chromatography. III. Characterization of the selectivity of micellar electrokinetic chromatography systems.	2002 Jan 4	11822389
Role of mitochondrial complexes I and II, reactive oxygen species and arachidonic acid metabolism in deoxycholate-induced apoptosis.	2002 Mar 28	11825660

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 `Fri Jun 25 21:42:36 UTC 2021` Edited by `admin` on `Fri Jun 25 21:42:36 UTC 2021`
Record UNII	436LS6U35Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SODIUM DESOXYCHOLATE

Common 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

SODIUM DEOXYCHOLATE [INCI]

Common Name

English

DEOXYCHOLIC ACID, SODIUM SALT

Common Name

English

SODIUM DESOXYCHOLATE [II]

Common Name

English

SODIUM DEOXYCHOLATE

Official Name

English

KYBELLA

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C843