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Deoxycholic acid information


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
CAS Number
  • 83-44-3 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B05128
ChEBI
  • CHEBI:28834 checkY
ChEMBL
  • ChEMBL406393 checkY
ChemSpider
  • 193196 checkY
DrugBank
  • DB07690 checkY
ECHA InfoCard 100.001.344 Edit this at Wikidata
IUPHAR/BPS
  • 610
KEGG
  • C04483 checkY
PubChem CID
  • 222528
UNII
  • 005990WHZZ checkY
CompTox Dashboard (EPA)
  • DTXSID0042662 Edit this at Wikidata
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 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
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%[1]
Acidity (pKa) 6.58[2]
Magnetic susceptibility (χ)
-272.0·10−6 cm3/mol
Pharmacology
ATC code
D11AX24 (WHO)
Pregnancy
category
  • AU: B1[3]
Legal status
  • AU: S4 (Prescription only)[3][4][5]
  • US: ℞-only[6]
  • EU: Rx-only[7]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references
Deoxycholic acid
Clinical data
Trade namesKybella, Belkyra
AHFS/Drugs.comMonograph
License data
  • US DailyMed: Deoxycholic_acid
Identifiers
PDB ligand
  • DXC (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID0042662 Edit this at Wikidata
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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