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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 of SODIUM DESOXYCHOLATE

SMILES

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

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

Description

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 TargetPharmacologyConditionPotency
4.0 null [pKi]
6.2 null [pEC50]
4.0 null [pEC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
KYBELLA
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
249 ng/mL
100 mg single, subcutaneous
DEOXYCHOLIC ACID plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
7241 ng × h/mL
100 mg single, subcutaneous
DEOXYCHOLIC ACID plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
6.5 h
100 mg single, subcutaneous
DEOXYCHOLIC ACID plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
100 mg single, subcutaneous
DEOXYCHOLIC ACID plasma
Homo sapiens

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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.