Deoxycholic acid

Deoxycholic acid
Clinical data
Trade names	Kybella, Belkyra
AHFS/Drugs.com	Monograph
License data	US DailyMed: Deoxycholic_acid;
Identifiers
PDB ligand	DXC (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID0042662 ;
ECHA InfoCard	100.001.344

Deoxycholic acid
Names
	IUPAC name 3α,12α-Dihydroxy-5β-cholan-24-oic acid
	Systematic IUPAC name (4R)-4-[(1R,3aS,3bR,5aR,7R,9aS,9bS,11S,11aR)-7,11-Dihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid
	Other names Deoxycholate
Identifiers
CAS Number	83-44-3 ;
3D model (JSmol)	Interactive image;
3DMet	B05128;
ChEBI	CHEBI:28834 ;
ChEMBL	ChEMBL406393 ;
ChemSpider	193196 ;
DrugBank	DB07690 ;
ECHA InfoCard	100.001.344
IUPHAR/BPS	610;
KEGG	C04483 ;
PubChem CID	222528;
UNII	005990WHZZ ;
CompTox Dashboard (EPA)	DTXSID0042662 ;
	InChI 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 Key: KXGVEGMKQFWNSR-LLQZFEROSA-N ; InChI=1/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 Key: KXGVEGMKQFWNSR-LLQZFEROBK;
	SMILES C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C;
Properties
Chemical formula	C24H40O4
Molar mass	392.580 g·mol−1
Melting point	174–176 °C (345–349 °F; 447–449 K)
Solubility in water	0.024%
Acidity (pKa)	6.58
Magnetic susceptibility (χ)	-272.0·10−6 cm3/mol
Pharmacology
ATC code	D11AX24 (WHO)
Pregnancy; category	AU: B1; ;
Legal status	AU: S4 (Prescription only); US: ℞-only; EU: Rx-only;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Deoxycholic acid is a bile acid. Deoxycholic acid is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. The two primary bile acids secreted by the liver are cholic acid and chenodeoxycholic acid. Bacteria metabolize chenodeoxycholic acid into the secondary bile acid lithocholic acid, and they metabolize cholic acid into deoxycholic acid. There are additional secondary bile acids, such as ursodeoxycholic acid. Deoxycholic acid is soluble in alcohol and acetic acid. When pure, it exists in a white to off-white crystalline powder form.

Deoxycholic acid is available as a generic medication in the United States as of April 2021, sold under the brand name Kybella among others.^[8]

^ "Deoxycholic acid" (PDF). Sigma Aldrich. Archived from the original (PDF) on 2020-06-06. Retrieved 2013-10-10.
^ Lide DR (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, FL: CRC Press. p. 1287. ISBN 978-0-8493-0594-8.
^ ^a ^b "Belkyra (deoxycholic acid solution for injection) Product Information" (PDF). TGA. Archived from the original on 25 June 2021. Retrieved 23 June 2021.
^ https://www.ebs.tga.gov.au/servlet/xmlmillr6?dbid=ebs/PublicHTML/pdfStore.nsf&docid=6CC2E7A2D27AA7C5CA2585D80042A1CC&agid=(PrintDetailsPublic)&actionid=1^{[permanent dead link]}
^ "Prescription medicines: registration of new chemical entities in Australia, 2016". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 10 April 2023. Retrieved 10 April 2023.
^ "Kybella- deoxycholic acid injection, solution". DailyMed. Archived from the original on 24 June 2021. Retrieved 20 June 2021.
^ "Active substance: deoxycholic acid" (PDF). European Medicines Agency (EMA). 10 December 2020. Archived (PDF) from the original on 28 August 2021. Retrieved 23 January 2021.
^ "Deoxycholic acid: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 24 June 2021. Retrieved 19 June 2021.

[1] "Deoxycholic acid" (PDF). Sigma Aldrich. Archived from the original (PDF) on 2020-06-06. Retrieved 2013-10-10.

[hand-2] Lide DR (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, FL: CRC Press. p. 1287. ISBN 978-0-8493-0594-8.

[Belkyra_AU_label-3] "Belkyra (deoxycholic acid solution for injection) Product Information" (PDF). TGA. Archived from the original on 25 June 2021. Retrieved 23 June 2021.

[4] ttps://www.ebs.tga.gov.au/servlet/xmlmillr6?dbid=ebs/PublicHTML/pdfStore.nsf&docid=6CC2E7A2D27AA7C5CA2585D80042A1CC&agid=(PrintDetailsPublic)&actionid=1^{[permanent dead link]}

[5] "Prescription medicines: registration of new chemical entities in Australia, 2016". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 10 April 2023. Retrieved 10 April 2023.

[Kybella_FDA_label-6] "Kybella- deoxycholic acid injection, solution". DailyMed. Archived from the original on 24 June 2021. Retrieved 20 June 2021.

[7] "Active substance: deoxycholic acid" (PDF). European Medicines Agency (EMA). 10 December 2020. Archived (PDF) from the original on 28 August 2021. Retrieved 23 January 2021.

[8] "Deoxycholic acid: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 24 June 2021. Retrieved 19 June 2021.

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