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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 of SODIUM DESOXYCHOLATE

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

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
249 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
7241 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.5 h
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
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

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
yes [Ki 21.7 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Cholesterol 7alpha-hydroxylase. 2. Biochemical properties and participation of endogenous cholesterol in the assay in vitro.
1975 Jun 16
Ursodeoxycholic acid prevents hepatic cytochrome P450 isozyme reduction in rats with deoxycholic acid-induced liver injury.
1999 Aug
Endogenous bile acids are ligands for the nuclear receptor FXR/BAR.
1999 May
Bile acids: natural ligands for an orphan nuclear receptor.
1999 May 21
Identification of a nuclear receptor for bile acids.
1999 May 21
The mechanism of bile salt-induced hemolysis.
2001
Differential modulation of cellular death and survival pathways by conjugated bile acids.
2001
Upregulation of nitric oxide synthase in mice with severe hypoxia-induced pulmonary hypertension.
2001
Bone morphogenetic protein-5 (BMP-5) promotes dendritic growth in cultured sympathetic neurons.
2001
The inhibitory effects of camptothecin, a topoisomerase I inhibitor, on collagen synthesis in fibroblasts from patients with systemic sclerosis.
2001
Osmotic stress-dependent serine phosphorylation of the histidine kinase homologue DokA.
2001
Soybean resistant proteins interrupt an enterohepatic circulation of bile acids and suppress liver tumorigenesis induced by azoxymethane and dietary deoxycholate in rats.
2001 Apr
Non-involvement of the K-ras mutation in colon carcinogenesis promoted by dietary deoxycholate in azoxymethane-treated rats.
2001 Apr
Role of humoral mediators in, and influence of a liposomal formulation on, acute amphotericin B nephrotoxicity.
2001 Apr
The effect of absorption enhancers on the initial degradation kinetics of insulin by alpha-chymotrypsin.
2001 Apr 17
Successful treatment of invasive mould infection affecting lung and brain in an adult suffering from acute leukaemia.
2001 Aug
Influence of pH on the phase distribution of nascent deoxycholic acid in fresh human cecal aspirates.
2001 Aug
Effect of bile acids on formation of azoxymethane-induced aberrant crypt foci in colostomized F344 rat colon.
2001 Aug 28
Effects of cisapride on gall bladder emptying, intestinal transit, and serum deoxycholate: a prospective, randomised, double blind, placebo controlled trial.
2001 Dec
Determination of alkylphenol ethoxylates by micellar electrokinetic chromatography with bile salts.
2001 Feb
Cholesterol solubilization in aqueous micellar solutions of quillaja saponin, bile salts, or nonionic surfactants.
2001 Jan
Empirical antifungal therapy for persistent fever in patients with neutropenia.
2001 Jan 15
Effect of surfactants and natural detergents on phosphatidylcholine synthesis in photoreceptor membranes.
2001 Jul
Bile acid hydrophobicity is correlated with induction of apoptosis and/or growth arrest in HCT116 cells.
2001 Jun 1
Secretion of the virulence-associated Campylobacter invasion antigens from Campylobacter jejuni requires a stimulatory signal.
2001 Jun 1
Complexing of basic pancreatic proteinase inhibitor with soybean phospholipid multilamellar vesicles.
2001 Mar
Influence of butyric and lactic acids on the beta-glucuronidase activity of Clostridium perfringens.
2001 Mar
Bile-induced 'pili' in Campylobacter jejuni are bacteria-independent artifacts of the culture medium.
2001 Mar
Biliary lipid composition in cholesterol microlithiasis.
2001 May
Indirect evidence that intestinal bile salt absorption in rats and hamsters is under positive feedback control.
2001 Nov
Nasal absorption enhancement of insulin by sodium deoxycholate in combination with cyclodextrins.
2001 Nov
Lowering of sodium deoxycholate-induced nasal ciliotoxicity with cyclodextrins.
2001 Nov
Effect of environmental and chemotactic stimuli on the activity of the Campylobacter jejuni flaA sigma(28) promoter.
2001 Nov 27
Butyrate suppression of colonocyte NF-kappa B activation and cellular proteasome activity.
2001 Nov 30
Colonic transit influences deoxycholic acid kinetics.
2001 Oct
Ursodeoxycholic acid and in vitro vasoactivity of hydrophobic bile acids.
2001 Sep
External biliary drainage plus bile acid feeding is not equal to internal drainage in preserving the cellular immunity following prolonged obstructive jaundice.
2001 Sep
Nephrotoxicity of amphotericin B desoxycholate.
2001 Sep 15
Solute-solvent interactions in micellar electrokinetic chromatography: IV. Characterization of electroosmotic flow and micellar markers.
2002 Jan
Solute-solvent interactions in micellar electrokinetic chromatography. III. Characterization of the selectivity of micellar electrokinetic chromatography systems.
2002 Jan 4
Role of mitochondrial complexes I and II, reactive oxygen species and arachidonic acid metabolism in deoxycholate-induced apoptosis.
2002 Mar 28
Patents

Sample Use Guides

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
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
II  
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
INCI  
INCI  
Official Name English
KYBELLA
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C843
Created by admin on Fri Jun 25 21:42:36 UTC 2021 , Edited by admin on Fri Jun 25 21:42:36 UTC 2021
Code System Code Type Description
DRUG BANK
DB05780
Created by admin on Fri Jun 25 21:42:36 UTC 2021 , Edited by admin on Fri Jun 25 21:42:36 UTC 2021
PRIMARY
CAS
302-95-4
Created by admin on Fri Jun 25 21:42:36 UTC 2021 , Edited by admin on Fri Jun 25 21:42:36 UTC 2021
PRIMARY
EPA CompTox
302-95-4
Created by admin on Fri Jun 25 21:42:36 UTC 2021 , Edited by admin on Fri Jun 25 21:42:36 UTC 2021
PRIMARY
EVMPD
SUB15971MIG
Created by admin on Fri Jun 25 21:42:36 UTC 2021 , Edited by admin on Fri Jun 25 21:42:36 UTC 2021
PRIMARY
FDA UNII
436LS6U35Y
Created by admin on Fri Jun 25 21:42:36 UTC 2021 , Edited by admin on Fri Jun 25 21:42:36 UTC 2021
PRIMARY
NCI_THESAURUS
C80912
Created by admin on Fri Jun 25 21:42:36 UTC 2021 , Edited by admin on Fri Jun 25 21:42:36 UTC 2021
PRIMARY
WIKIPEDIA
Sodium deoxycholate
Created by admin on Fri Jun 25 21:42:36 UTC 2021 , Edited by admin on Fri Jun 25 21:42:36 UTC 2021
PRIMARY
ECHA (EC/EINECS)
206-132-7
Created by admin on Fri Jun 25 21:42:36 UTC 2021 , Edited by admin on Fri Jun 25 21:42:36 UTC 2021
PRIMARY
PUBCHEM
23668196
Created by admin on Fri Jun 25 21:42:36 UTC 2021 , Edited by admin on Fri Jun 25 21:42:36 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY