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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
Bile acids: natural ligands for an orphan nuclear receptor.
1999 May 21
Identification of a nuclear receptor for bile acids.
1999 May 21
Ursodeoxycholic acid prevents cytochrome c release in apoptosis by inhibiting mitochondrial membrane depolarization and channel formation.
1999 Sep
In vitro anti-HIV-1 virucidal activity of tyrosine-conjugated tri- and dihydroxy bile salt derivatives.
2000 May
Frequency of tuberculous and non-tuberculous mycobacteria in HIV infected patients from Bogota, Colombia.
2001
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
Bone morphogenetic protein-5 (BMP-5) promotes dendritic growth in cultured sympathetic neurons.
2001
Role of humoral mediators in, and influence of a liposomal formulation on, acute amphotericin B nephrotoxicity.
2001 Apr
Oxygen free radical generating mechanisms in the colon: do the semiquinones of vitamin K play a role in the aetiology of colon cancer?
2001 Aug 15
Establishment of an animal model of chronic atrophic gastritis and a study on the factors inducing atrophy.
2001 Dec
Selective involvement of calcium and calcium channels in stimulated mucin secretion from rat colon.
2001 Dec
Conjugation of low-molecular-weight heparin and deoxycholic acid for the development of a new oral anticoagulant agent.
2001 Dec 18
Colonic luminal contents induce cyclooxygenase 2 transcription in human colon carcinoma cells.
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
[Perioperative nutritional management for patients with obstructive jaundice caused by biliary tract disease].
2001 May
Surface behaviour of bile salts and tetrahydrolipstatin at air/water and oil/water interfaces.
2001 May
Design and synthesis of novel chiral dendritic species derived from bile acids.
2001 May 4
Effect of environmental and chemotactic stimuli on the activity of the Campylobacter jejuni flaA sigma(28) promoter.
2001 Nov 27
Octreotide increases the proportions of arachidonic acid-rich phospholipids in gall-bladder bile.
2001 Sep
Nephrotoxicity of amphotericin B desoxycholate.
2001 Sep 15
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 Sep 18
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 Sep 21
7alpha-OH epimerisation of bile acids via oxido-reduction with Xanthomonas maltophilia.
2002 Jan
Solute-solvent interactions in micellar electrokinetic chromatography. III. Characterization of the selectivity of micellar electrokinetic chromatography systems.
2002 Jan 4
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
  • Download
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