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
Cholesterol 7alpha-hydroxylase. 2. Biochemical properties and participation of endogenous cholesterol in the assay in vitro.
1975 Jun 16
Endogenous bile acids are ligands for the nuclear receptor FXR/BAR.
1999 May
Frequency of tuberculous and non-tuberculous mycobacteria in HIV infected patients from Bogota, Colombia.
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
Expression of ionotropic glutamate receptors in the retina of the rdta transgenic mouse.
2001
Regulation of prostaglandin synthesis and cell adhesion by a tryptophan catabolizing enzyme.
2001
Inhibition of carcinogen induced c-Ha-ras and c-fos proto-oncogenes expression by dietary curcumin.
2001
Bile acid acyl adenylate: a possible intermediate to produce a protein-bound bile acid.
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
Hyodeoxycholic acid efficiently suppresses atherosclerosis formation and plasma cholesterol levels in mice.
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
Establishment of an animal model of chronic atrophic gastritis and a study on the factors inducing atrophy.
2001 Dec
Combined use of Lactobacillus reuteri and soygerm powder as food supplement.
2001 Dec
Conjugation of low-molecular-weight heparin and deoxycholic acid for the development of a new oral anticoagulant agent.
2001 Dec 18
Determination of alkylphenol ethoxylates by micellar electrokinetic chromatography with bile salts.
2001 Feb
Determination of bile acids in biological fluids by liquid chromatography-electrospray tandem mass spectrometry.
2001 Jan
Latent TGF-beta binding protein LTBP-1 contains three potential extracellular matrix interacting domains.
2001 Jan
Effect of surfactants and natural detergents on phosphatidylcholine synthesis in photoreceptor membranes.
2001 Jul
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
Chemical and physical factors affecting the excystation of Cryptosporidium parvum oocysts.
2001 Jun
Comparison of effects of amphotericin B deoxycholate infused over 4 or 24 hours: randomised controlled trial.
2001 Mar 10
[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
Hydrophilic and hydrophobic bile acids exhibit different cytotoxicities through cytolysis, interleukin-8 synthesis and apoptosis in the intestinal epithelial cell lines. IEC-6 and Caco-2 cells.
2001 May
Indirect evidence that intestinal bile salt absorption in rats and hamsters is under positive feedback control.
2001 Nov
Effect of different bile salts on the relative hypoglycemia of witepsol W35 suppositories containing insulin in diabetic Beagle dogs.
2001 Sep
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
Summaries for patients. Itraconazole and amphotericin B to treat fungal infections in patients with cancer who are receiving chemotherapy.
2001 Sep 18
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
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
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.
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