U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H40O4
Molecular Weight 392.5729
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEOXYCHOLIC ACID

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

InChI

InChIKey=KXGVEGMKQFWNSR-LLQZFEROSA-N
InChI=1S/C24H40O4/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)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1

HIDE SMILES / InChI
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
Ursodeoxycholic acid prevents hepatic cytochrome P450 isozyme reduction in rats with deoxycholic acid-induced liver injury.
1999 Aug
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
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
The inhibitory effects of camptothecin, a topoisomerase I inhibitor, on collagen synthesis in fibroblasts from patients with systemic sclerosis.
2001
Expression of ionotropic glutamate receptors in the retina of the rdta transgenic mouse.
2001
Inhibition of carcinogen induced c-Ha-ras and c-fos proto-oncogenes expression by dietary curcumin.
2001
20beta-Hydroxysteroid dehydrogenase of the Japanese eel ovary: its cellular localization and changes in the enzymatic activity during sexual maturation.
2001 Apr
Role of humoral mediators in, and influence of a liposomal formulation on, acute amphotericin B nephrotoxicity.
2001 Apr
Modulation of steady-state messenger RNA levels in the regenerating rat liver with bile acid feeding.
2001 Apr
The effect of absorption enhancers on the initial degradation kinetics of insulin by alpha-chymotrypsin.
2001 Apr 17
Deoxycholic acid stimulates migration in colon cancer cells.
2001 Aug
Hyodeoxycholic acid efficiently suppresses atherosclerosis formation and plasma cholesterol levels in mice.
2001 Aug
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
Effect of bile acids on formation of azoxymethane-induced aberrant crypt foci in colostomized F344 rat colon.
2001 Aug 28
Bile acid metabolism by fresh human colonic contents: a comparison of caecal versus faecal samples.
2001 Dec
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
Deoxycholate induces DNA damage and apoptosis in human colon epithelial cells expressing either mutant or wild-type p53.
2001 Feb
Colonic luminal contents induce cyclooxygenase 2 transcription in human colon carcinoma cells.
2001 Feb
Determination of bile acids in biological fluids by liquid chromatography-electrospray tandem mass spectrometry.
2001 Jan
Activation and role of mitogen-activated protein kinases in deoxycholic acid-induced apoptosis.
2001 Jan
Latent TGF-beta binding protein LTBP-1 contains three potential extracellular matrix interacting domains.
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
Efficacy of aerosolized amphotericin B desoxycholate and liposomal amphotericin B in the treatment of invasive pulmonary aspergillosis in severely immunocompromised rats.
2001 Jul
Quantitative determination of amygdalin epimers by cyclodextrin-modified micellar electrokinetic chromatography.
2001 Jul 20
Combined effect of dietary calcium and iron on colonic aberrant crypt foci, cell proliferation and apoptosis, and fecal bile acids in 1,2-dimethylhydrazine-treated rats.
2001 Jul-Aug
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
The puzzle of zmpB and extensive chain formation, autolysis defect and non-translocation of choline-binding proteins in Streptococcus pneumoniae.
2001 Mar
Comparison of effects of amphotericin B deoxycholate infused over 4 or 24 hours: randomised controlled trial.
2001 Mar 10
Enhancement of endothelial nitric oxide production by chenodeoxycholic acids in patients with hepatobiliary diseases.
2001 May
Effects of deoxycholic acid and its epimers on lipid peroxidation in isolated rat hepatocytes.
2001 May
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
Role of calcium homeostasis in gastric mucosal injury and protection.
2001 Nov 9
Structural characteristics of size-controlled self-aggregates of deoxycholic acid-modified chitosan and their application as a DNA delivery carrier.
2001 Nov-Dec
Colonic transit influences deoxycholic acid kinetics.
2001 Oct
Effect of different bile salts on the relative hypoglycemia of witepsol W35 suppositories containing insulin in diabetic Beagle dogs.
2001 Sep
Octreotide increases the proportions of arachidonic acid-rich phospholipids in gall-bladder bile.
2001 Sep
Nephrotoxicity of amphotericin B desoxycholate.
2001 Sep 15
Summaries for patients. Itraconazole and amphotericin B to treat fungal infections in patients with cancer who are receiving chemotherapy.
2001 Sep 18
Functional alterations of splenocytes in severe acute pancreatitis.
2002 Feb
Solute-solvent interactions in micellar electrokinetic chromatography: IV. Characterization of electroosmotic flow and micellar markers.
2002 Jan
7alpha-OH epimerisation of bile acids via oxido-reduction with Xanthomonas maltophilia.
2002 Jan
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.
Name Type Language
DEOXYCHOLIC ACID
DASH   HSDB   II   INN   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
DEOXYCHOLIC ACID [ORANGE BOOK]
Common Name English
DEOXYCHOLIC ACID [INN]
Common Name English
DEOXYCHOLIC ACID [WHO-DD]
Common Name English
DEOXYCHOLATE
Common Name English
DEOXYCHOLIC ACID [USP-RS]
Common Name English
DEOXYCHOLIC ACID [INCI]
Common Name English
DESOXYCHOLIC ACID [FCC]
Common Name English
DEOXYCHOLIC ACID [II]
Common Name English
3.ALPHA.,12.ALPHA.-DIHYDROXYCHOLANIC ACID
Systematic Name English
URSODEOXYCHOLIC ACID IMPURITY E [EP]
Common Name English
DEOXYCHOLIC ACID [MI]
Common Name English
DESOXYCHOLIC ACID
FCC   NF   VANDF  
Common Name English
DESOXYCHOLIC ACID [NF]
Common Name English
DWJ211
Code English
DESOXYCHOLIC ACID [VANDF]
Common Name English
DEOXYCHOLIC ACID [HSDB]
Common Name English
DEOXYCHOLIC ACID [USAN]
Common Name English
DWJ-211
Code English
DEOXYCHOLIC ACID [EP]
Common Name English
NSC-8797
Code English
Classification Tree Code System Code
LOINC 2201-2
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
NDF-RT N0000191548
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
NCI_THESAURUS C66913
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
WHO-ATC D11AX24
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
LOINC 30520-1
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
Code System Code Type Description
EVMPD
SUB13541MIG
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY
CAS
83-44-3
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY
INN
9540
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL406393
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY
RXCUI
3194
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY
USP_CATALOG
1171273
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY USP-RS
FDA UNII
005990WHZZ
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY
WIKIPEDIA
DEOXYCHOLIC ACID
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY
IUPHAR
610
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY
EPA CompTox
83-44-3
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY
NDF-RT
N0000008476
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY Decreased Cell Membrane Integrity [PE]
RXCUI
42627
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
ALTERNATIVE
HSDB
293
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY
PUBCHEM
222528
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-478-5
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY
MERCK INDEX
M4171
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB03619
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY
MESH
D003840
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY
DRUG CENTRAL
4988
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY
NCI_THESAURUS
C81042
Created by admin on Sat Jun 26 09:15:45 UTC 2021 , Edited by admin on Sat Jun 26 09:15:45 UTC 2021
PRIMARY