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

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H40O4
Molecular Weight 392.572
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEOXYCHOLIC ACID

SMILES

[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=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

Molecular Formula C24H40O4
Molecular Weight 392.572
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Increased formation of ursodeoxycholic acid in patients treated with chenodeoxycholic acid.
1974 Feb
Cholesterol 7alpha-hydroxylase. 2. Biochemical properties and participation of endogenous cholesterol in the assay in vitro.
1975 Jun 16
Bile acids: natural ligands for an orphan nuclear receptor.
1999 May 21
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
Differential modulation of cellular death and survival pathways by conjugated bile acids.
2001
Expression of ionotropic glutamate receptors in the retina of the rdta transgenic mouse.
2001
Osmotic stress-dependent serine phosphorylation of the histidine kinase homologue DokA.
2001
In vitro dephosphorylation of alpha-crystallin is dependent on the state of oligomerization.
2001 Apr 7
Successful treatment of invasive mould infection affecting lung and brain in an adult suffering from acute leukaemia.
2001 Aug
Hyodeoxycholic acid efficiently suppresses atherosclerosis formation and plasma cholesterol levels in mice.
2001 Aug
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
Triphasic vascular responses to bradykinin in the mesenteric resistance artery of the rat.
2001 Dec 14
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
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
Bile acid hydrophobicity is correlated with induction of apoptosis and/or growth arrest in HCT116 cells.
2001 Jun 1
Influence of butyric and lactic acids on the beta-glucuronidase activity of Clostridium perfringens.
2001 Mar
Comparison of effects of amphotericin B deoxycholate infused over 4 or 24 hours: randomised controlled trial.
2001 Mar 10
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
Effects of treatment with deoxycholic acid and chenodeoxycholic acid on the hepatic synthesis of cholesterol and bile acids in healthy subjects.
2001 May
Indirect evidence that intestinal bile salt absorption in rats and hamsters is under positive feedback control.
2001 Nov
Effect of environmental and chemotactic stimuli on the activity of the Campylobacter jejuni flaA sigma(28) promoter.
2001 Nov 27
Structural characteristics of size-controlled self-aggregates of deoxycholic acid-modified chitosan and their application as a DNA delivery carrier.
2001 Nov-Dec
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
Intestinal absorption and biodistribution of cosalane and its amino acid conjugates: novel anti-HIV agents.
2002 Jan 14
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 Sat Dec 16 16:15:28 UTC 2023
Edited
by admin
on Sat Dec 16 16:15:28 UTC 2023
Record UNII
005990WHZZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEOXYCHOLIC ACID
DASH   HSDB   II   INN   MI   USAN   WHO-DD  
INN   USAN   INCI  
Official Name English
DEOXYCHOLIC ACID [EP IMPURITY]
Common Name English
DEOXYCHOLIC ACID [ORANGE BOOK]
Common Name English
ATX-101 (DEOXYCHOLIC ACID)
Code English
deoxycholic acid [INN]
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
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
Deoxycholic acid [WHO-DD]
Common Name English
DWJ-211
Code English
DEOXYCHOLIC ACID [USP MONOGRAPH]
Common Name English
NSC-8797
Code English
URSODEOXYCHOLIC ACID IMPURITY E [EP IMPURITY]
Common Name English
Classification Tree Code System Code
LOINC 2201-2
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
NDF-RT N0000191548
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
NCI_THESAURUS C66913
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
WHO-ATC D11AX24
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
LOINC 30520-1
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
Code System Code Type Description
EVMPD
SUB13541MIG
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
CAS
83-44-3
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
INN
9540
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
NSC
8797
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
ChEMBL
CHEMBL406393
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
RXCUI
3194
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
FDA UNII
005990WHZZ
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
RS_ITEM_NUM
1171273
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
USAN
BC-35
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
WIKIPEDIA
DEOXYCHOLIC ACID
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
IUPHAR
610
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
EPA CompTox
DTXSID0042662
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
DAILYMED
005990WHZZ
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
NDF-RT
N0000008476
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY Decreased Cell Membrane Integrity [PE]
RXCUI
42627
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
ALTERNATIVE
HSDB
293
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
PUBCHEM
222528
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
ECHA (EC/EINECS)
201-478-5
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
MERCK INDEX
m4171
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB03619
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
MESH
D003840
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
DRUG CENTRAL
4988
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
NCI_THESAURUS
C81042
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
SMS_ID
100000079520
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
CHEBI
28834
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
CHEBI
23614
Created by admin on Sat Dec 16 16:15:29 UTC 2023 , Edited by admin on Sat Dec 16 16:15:29 UTC 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> NON-INHIBITOR
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
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METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC