Back اسید داوکسیکولیک AZB Дэзоксіхолевая кіслата Byelorussian Kyselina deoxycholová Czech Desoxycholsäure German Ácido desoxicólico Spanish اسید داوکسیکولیک Persian Acide désoxycholique French Aigéad dí-ocsacoileach Irish Ácido desoxicólico Galician Acido desossicolico Italian

Deoxycholic acid

Deoxycholic acid
Skeletal formula of deoxycholic acid
Ball-and-stick model of deoxycholic acid
White powder in a stoppered glass vial
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.344 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: KXGVEGMKQFWNSR-LLQZFEROSA-N checkY
  • 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
  • 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
C24H40O4
Molar mass 392.580 g·mol−1
Melting point 174–176 °C (345–349 °F; 447–449 K)
0.024%[1]
Acidity (pKa) 6.58[2]
-272.0·10−6 cm3/mol
Pharmacology
D11AX24 (WHO)
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Deoxycholic acid
Clinical data
Trade namesKybella, Belkyra
AHFS/Drugs.comMonograph
License data
Identifiers
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.001.344 Edit this at Wikidata

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]

  1. ^ "Deoxycholic acid" (PDF). Sigma Aldrich. Archived from the original (PDF) on 2020-06-06. Retrieved 2013-10-10.
  2. ^ Lide DR (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, FL: CRC Press. p. 1287. ISBN 978-0-8493-0594-8.
  3. ^ a b "Belkyra (deoxycholic acid solution for injection) Product Information" (PDF). TGA. Archived from the original on 25 June 2021. Retrieved 23 June 2021.
  4. ^ https://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.
  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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