DEOXYCHOLIC ACID

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 Search

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

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 67 Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28878747	Inhibitor 8297
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 2778	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 2678	6.2 null [pEC50]
Bile acid receptor FXR 31 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 2678	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 8429	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 2015
Lipoma 2 Sources: https://clinicaltrials.gov/ct2/show/NCT00608842	Primary		Phase II 1132	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 1587	inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2B6 810 CYP2C8 911 CYP2C19 1478 BSEP 402 P-gp 1461 OATP1B1 788 OATP1B3 706 OCT2 647 OAT1 599 OAT3 642 MRP2 383 MRP4 204 BCRP 699	BSEP 52	CYP1A 56 CYP2B6 547 CYP3A 129

Drug as perpetrator

Target	Modality	Activity
BCRP 773	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=13 Page: 13.0	no
MRP2 475	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=13 Page: 13.0	no
MRP4 238	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=13 Page: 13.0	no
OAT1 603	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
OAT3 644	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
OATP1B1 803	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
OATP1B3 715	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
OCT2 648	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
P-gp 1650	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	no
CYP1A 121	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2B6 1001	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP3A 298	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/206333Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	unlikely
BSEP 403	inhibitor 3277 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 52	substrate 3367 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 1647	inhibitor 1626 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
Cholesterol 7alpha-hydroxylase. 2. Biochemical properties and participation of endogenous cholesterol in the assay in vitro.	1975 Jun 16	1175606
The mechanism of bile salt-induced hemolysis.	2001	11753435
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
Differential modulation of cellular death and survival pathways by conjugated bile acids.	2001	11707155
Upregulation of nitric oxide synthase in mice with severe hypoxia-induced pulmonary hypertension.	2001	11686901
Bone morphogenetic protein-5 (BMP-5) promotes dendritic growth in cultured sympathetic neurons.	2001	11580864
The inhibitory effects of camptothecin, a topoisomerase I inhibitor, on collagen synthesis in fibroblasts from patients with systemic sclerosis.	2001	11549373
Successful treatment of invasive mould infection affecting lung and brain in an adult suffering from acute leukaemia.	2001 Aug	11722602
Deoxycholic acid stimulates migration in colon cancer cells.	2001 Aug	11507360
Hyodeoxycholic acid efficiently suppresses atherosclerosis formation and plasma cholesterol levels in mice.	2001 Aug	11483626
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
Combined use of Lactobacillus reuteri and soygerm powder as food supplement.	2001 Dec	11737624
Bile acid metabolism by fresh human colonic contents: a comparison of caecal versus faecal samples.	2001 Dec	11709519
Effects of cisapride on gall bladder emptying, intestinal transit, and serum deoxycholate: a prospective, randomised, double blind, placebo controlled trial.	2001 Dec	11709518
Triphasic vascular responses to bradykinin in the mesenteric resistance artery of the rat.	2001 Dec 14	11755140
Conjugation of low-molecular-weight heparin and deoxycholic acid for the development of a new oral anticoagulant agent.	2001 Dec 18	11748110
Biosynthetic requirements for the repair of membrane damage in pressure-treated Escherichia coli.	2001 Dec 4	11764887
Effect of surfactants and natural detergents on phosphatidylcholine synthesis in photoreceptor membranes.	2001 Jul	11699863
Fetal bile acid metabolism: analysis of urinary 3beta-monohydroxy-delta(5) bile acid in preterm infants.	2001 Jul	11474144
Quantitative determination of amygdalin epimers by cyclodextrin-modified micellar electrokinetic chromatography.	2001 Jul 20	11510547
Enhancement of endothelial nitric oxide production by chenodeoxycholic acids in patients with hepatobiliary diseases.	2001 May	11605772
Indirect evidence that intestinal bile salt absorption in rats and hamsters is under positive feedback control.	2001 Nov	11778152
Nasal absorption enhancement of insulin by sodium deoxycholate in combination with cyclodextrins.	2001 Nov	11749800
Lowering of sodium deoxycholate-induced nasal ciliotoxicity with cyclodextrins.	2001 Nov	11749799
Effect of environmental and chemotactic stimuli on the activity of the Campylobacter jejuni flaA sigma(28) promoter.	2001 Nov 27	11728714
Butyrate suppression of colonocyte NF-kappa B activation and cellular proteasome activity.	2001 Nov 30	11572859
Role of calcium homeostasis in gastric mucosal injury and protection.	2001 Nov 9	11758834
Structural characteristics of size-controlled self-aggregates of deoxycholic acid-modified chitosan and their application as a DNA delivery carrier.	2001 Nov-Dec	11716684
A nifedipine coground mixture with sodium deoxycholate. II. Dissolution characteristics and stability.	2001 Oct	11763473
A nifedipine coground mixture with sodium deoxycholate. I. Colloidal particle formation and solid-state analysis.	2001 Oct	11763472
The effect of a functional group in penicillin derivatives on the interaction with bile salt micelles studied by micellar electrokinetic chromatography.	2001 Oct	11669544
Colonic transit influences deoxycholic acid kinetics.	2001 Oct	11606495
Effect of different bile salts on the relative hypoglycemia of witepsol W35 suppositories containing insulin in diabetic Beagle dogs.	2001 Sep	11699836
Ursodeoxycholic acid and in vitro vasoactivity of hydrophobic bile acids.	2001 Sep	11575458
External biliary drainage plus bile acid feeding is not equal to internal drainage in preserving the cellular immunity following prolonged obstructive jaundice.	2001 Sep	11575437
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
Summaries for patients. Itraconazole and amphotericin B to treat fungal infections in patients with cancer who are receiving chemotherapy.	2001 Sep 18	11575279
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
Functional alterations of splenocytes in severe acute pancreatitis.	2002 Feb	11796014
Solute-solvent interactions in micellar electrokinetic chromatography: IV. Characterization of electroosmotic flow and micellar markers.	2002 Jan	11824622
7alpha-OH epimerisation of bile acids via oxido-reduction with Xanthomonas maltophilia.	2002 Jan	11728521
Intestinal absorption and biodistribution of cosalane and its amino acid conjugates: novel anti-HIV agents.	2002 Jan 14	11755272
Increased corneal hydration induced by potential ocular penetration enhancers: assessment by differential scanning calorimetry (DSC) and by desiccation.	2002 Jan 31	11790497
Solute-solvent interactions in micellar electrokinetic chromatography. III. Characterization of the selectivity of micellar electrokinetic chromatography systems.	2002 Jan 4	11822389
Role of mitochondrial complexes I and II, reactive oxygen species and arachidonic acid metabolism in deoxycholate-induced apoptosis.	2002 Mar 28	11825660

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 `Sat Dec 16 16:15:28 GMT 2023` Edited by `admin` on `Sat Dec 16 16:15:28 GMT 2023`
Record UNII	005990WHZZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEOXYCHOLIC ACID

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

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