SODIUM DESOXYCHOLATE

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

Structure Search

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

HIDE SMILES / InChI

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206333Orig1s000lbl.pdf | https://www.drugbank.ca/drugs/DB03619 | https://www.nature.com/articles/srep17528

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	Potency
Staphylococcus aureus 64 Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28878747	Inhibitor 7728
Formyl peptide receptor 1 3 Target ID: CHEMBL3359 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11853704 \| http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=biology&ligandId=610	Antagonist 2575	4.0 null [pKi]
G-protein coupled bile acid receptor 1 15 Target ID: CHEMBL5409 Sources: http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=biology&ligandId=610 \| https://www.ncbi.nlm.nih.gov/pubmed/12419312	Agonist 2470	6.2 null [pEC50]
Bile acid receptor FXR 29 Target ID: CHEMBL2047 Sources: http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=biology&ligandId=610 \| https://www.ncbi.nlm.nih.gov/pubmed/10334993 \| https://www.ncbi.nlm.nih.gov/pubmed/10360171	Agonist 2470	4.0 null [pEC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Subcutaneous fat disorders 2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206333Orig1s000lbl.pdf	Primary		Approved 8043	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
Lipoma 2 Sources: https://clinicaltrials.gov/ct2/show/NCT00608842	Primary		Phase II 1101	Unknown Approved Use Unknown

C_max

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

T_1/2

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

F_unbound

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
inhibitor 1467	inhibitor 1604	inhibitor 1702	inhibitor 1475

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1383 CYP2B6 717 CYP2C8 818 CYP2C19 1325 BSEP 376 P-gp 1330 OATP1B1 733 OATP1B3 657 OCT2 594 OAT1 554 OAT3 588 MRP2 346 MRP4 194 BCRP 643	BSEP 51	CYP1A 48 CYP2B6 501 CYP3A 118

Drug as perpetrator

Target	Modality	Activity
BCRP 713	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=13 Page: 13.0	no
MRP2 434	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=13 Page: 13.0	no
MRP4 226	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=13 Page: 13.0	no
OAT1 558	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
OAT3 590	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
OATP1B1 748	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
OATP1B3 666	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
OCT2 595	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
P-gp 1514	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
CYP1A 110	inducer 1440 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP1A2 1532	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2B6 884	inducer 1440 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2B6 884	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2C19 1392	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2C8 865	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2C9 1648	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2D6 1738	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP3A 271	inducer 1440 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP3A4 1772	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
BSEP 377	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	yes [Ki 21.7 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
BSEP 51	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1507	inhibitor 1489 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000PharmR.pdf#page=21 Page: 21.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:28834	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28834
ChemicalBook	CB8325514	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8325514
MolPort	MolPort-002-507-414	https://www.molport.com/shop/molecule-link/MolPort-002-507-414
ZINC	ZINC000003914810	http://zinc15.docking.org/substances/ZINC000003914810
eMolecules	29541141	https://www.emolecules.com/cgi-bin/more?vid=29541141
eMolecules	29549277	https://www.emolecules.com/cgi-bin/more?vid=29549277
eMolecules	496898	https://www.emolecules.com/cgi-bin/more?vid=496898

PubMed

Title	Date	PubMed
Bile acids: natural ligands for an orphan nuclear receptor.	1999 May 21	10334993
Identification of a nuclear receptor for bile acids.	1999 May 21	10334992
Ursodeoxycholic acid prevents cytochrome c release in apoptosis by inhibiting mitochondrial membrane depolarization and channel formation.	1999 Sep	10510466
In vitro anti-HIV-1 virucidal activity of tyrosine-conjugated tri- and dihydroxy bile salt derivatives.	2000 May	10797083
Frequency of tuberculous and non-tuberculous mycobacteria in HIV infected patients from Bogota, Colombia.	2001	11722797
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	11716783
Bone morphogenetic protein-5 (BMP-5) promotes dendritic growth in cultured sympathetic neurons.	2001	11580864
Role of humoral mediators in, and influence of a liposomal formulation on, acute amphotericin B nephrotoxicity.	2001 Apr	11322173
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	11479033
Establishment of an animal model of chronic atrophic gastritis and a study on the factors inducing atrophy.	2001 Dec	11793864
Selective involvement of calcium and calcium channels in stimulated mucin secretion from rat colon.	2001 Dec	11761027
Conjugation of low-molecular-weight heparin and deoxycholic acid for the development of a new oral anticoagulant agent.	2001 Dec 18	11748110
Colonic luminal contents induce cyclooxygenase 2 transcription in human colon carcinoma cells.	2001 Feb	11159881
Cholesterol solubilization in aqueous micellar solutions of quillaja saponin, bile salts, or nonionic surfactants.	2001 Jan	11170603
Empirical antifungal therapy for persistent fever in patients with neutropenia.	2001 Jan 15	11170928
[Perioperative nutritional management for patients with obstructive jaundice caused by biliary tract disease].	2001 May	11439612
Surface behaviour of bile salts and tetrahydrolipstatin at air/water and oil/water interfaces.	2001 May	11438285
Design and synthesis of novel chiral dendritic species derived from bile acids.	2001 May 4	11325268
Effect of environmental and chemotactic stimuli on the activity of the Campylobacter jejuni flaA sigma(28) promoter.	2001 Nov 27	11728714
Octreotide increases the proportions of arachidonic acid-rich phospholipids in gall-bladder bile.	2001 Sep	11552916
Nephrotoxicity of amphotericin B desoxycholate.	2001 Sep 15	11512101
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	11560454
The structure of truncated recombinant human bile salt-stimulated lipase reveals bile salt-independent conformational flexibility at the active-site loop and provides insights into heparin binding.	2001 Sep 21	11563913
7alpha-OH epimerisation of bile acids via oxido-reduction with Xanthomonas maltophilia.	2002 Jan	11728521
Solute-solvent interactions in micellar electrokinetic chromatography. III. Characterization of the selectivity of micellar electrokinetic chromatography systems.	2002 Jan 4	11822389

Patents

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.

Substance Class	Chemical Created by `admin` on `Fri Jun 25 21:42:36 UTC 2021` Edited by `admin` on `Fri Jun 25 21:42:36 UTC 2021`
Record UNII	436LS6U35Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SODIUM DESOXYCHOLATE

Common Name

English

ATX-101 (SODIUM DESOXYCHOLATE)

Code

English

SODIUM DEOXYCHOLIC ACID

Common Name

English

NSC-681065

Code

English

3-.ALPHA.,12-.ALPHA.-DIHYDROXY-5-.BETA.-CHOLAN-24-OIC ACID SODIUM SALT

Common Name

English

SODIUM DEOXYCHOLATE [INCI]

Common Name

English

DEOXYCHOLIC ACID, SODIUM SALT

Common Name

English

SODIUM DESOXYCHOLATE [II]

Common Name

English

SODIUM DEOXYCHOLATE

Official Name

English

KYBELLA

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C843