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
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
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28878747 |
|||
4.0 null [pKi] | |||
6.2 null [pEC50] | |||
4.0 null [pEC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | KYBELLA Approved UseKYBELLA™ (deoxycholic acid) injection is indicated for improvement in the appearance of
moderate to severe convexity or fullness associated with submental fat in adults Launch Date1.43026566E12 |
|||
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
249 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25684122/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7241 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25684122/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25684122/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25684122/ |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=13 Page: 13.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=13 Page: 13.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=13 Page: 13.0 |
no | |||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0 |
unlikely | |||
unlikely | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0 |
unlikely | |||
unlikely | ||||
unlikely | ||||
unlikely | ||||
unlikely | ||||
unlikely | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0 |
unlikely | |||
unlikely | ||||
yes [Ki 21.7 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000PharmR.pdf#page=21 Page: 21.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Cholesterol 7alpha-hydroxylase. 2. Biochemical properties and participation of endogenous cholesterol in the assay in vitro. | 1975 Jun 16 |
|
Ursodeoxycholic acid prevents hepatic cytochrome P450 isozyme reduction in rats with deoxycholic acid-induced liver injury. | 1999 Aug |
|
Endogenous bile acids are ligands for the nuclear receptor FXR/BAR. | 1999 May |
|
Bile acids: natural ligands for an orphan nuclear receptor. | 1999 May 21 |
|
Identification of a nuclear receptor for bile acids. | 1999 May 21 |
|
The mechanism of bile salt-induced hemolysis. | 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 |
|
The inhibitory effects of camptothecin, a topoisomerase I inhibitor, on collagen synthesis in fibroblasts from patients with systemic sclerosis. | 2001 |
|
Osmotic stress-dependent serine phosphorylation of the histidine kinase homologue DokA. | 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 |
|
Role of humoral mediators in, and influence of a liposomal formulation on, acute amphotericin B nephrotoxicity. | 2001 Apr |
|
The effect of absorption enhancers on the initial degradation kinetics of insulin by alpha-chymotrypsin. | 2001 Apr 17 |
|
Successful treatment of invasive mould infection affecting lung and brain in an adult suffering from acute leukaemia. | 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 |
|
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 |
|
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 |
|
Effect of surfactants and natural detergents on phosphatidylcholine synthesis in photoreceptor membranes. | 2001 Jul |
|
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 |
|
Influence of butyric and lactic acids on the beta-glucuronidase activity of Clostridium perfringens. | 2001 Mar |
|
Bile-induced 'pili' in Campylobacter jejuni are bacteria-independent artifacts of the culture medium. | 2001 Mar |
|
Biliary lipid composition in cholesterol microlithiasis. | 2001 May |
|
Indirect evidence that intestinal bile salt absorption in rats and hamsters is under positive feedback control. | 2001 Nov |
|
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 |
|
Effect of environmental and chemotactic stimuli on the activity of the Campylobacter jejuni flaA sigma(28) promoter. | 2001 Nov 27 |
|
Butyrate suppression of colonocyte NF-kappa B activation and cellular proteasome activity. | 2001 Nov 30 |
|
Colonic transit influences deoxycholic acid kinetics. | 2001 Oct |
|
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 |
|
Solute-solvent interactions in micellar electrokinetic chromatography: IV. Characterization of electroosmotic flow and micellar markers. | 2002 Jan |
|
Solute-solvent interactions in micellar electrokinetic chromatography. III. Characterization of the selectivity of micellar electrokinetic chromatography systems. | 2002 Jan 4 |
|
Role of mitochondrial complexes I and II, reactive oxygen species and arachidonic acid metabolism in deoxycholate-induced apoptosis. | 2002 Mar 28 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28878747
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
Edited
Fri Jun 25 21:42:36 UTC 2021
by
admin
on
Fri Jun 25 21:42:36 UTC 2021
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Record UNII |
436LS6U35Y
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Record Status |
Validated (UNII)
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Record Version |
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-
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NCI_THESAURUS |
C843
Created by
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DB05780
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302-95-4
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302-95-4
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SUB15971MIG
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436LS6U35Y
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C80912
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Sodium deoxycholate
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206-132-7
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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
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |