Hydrocortisone acetate

Hydrocortisone acetate is a synthetic glucocorticoid corticosteroid and a corticosteroid ester.[1]

Hydrocortisone acetate
Clinical data
Other namesCortisol 21-acetate
Drug classCorticosteroid; Glucocorticoid
Identifiers
  • [2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-Dihydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.005 Edit this at Wikidata
Chemical and physical data
FormulaC23H32O6
Molar mass404.503 g·mol−1
3D model (JSmol)
  • CC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)O)C)O
  • InChI=1S/C23H32O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h10,16-18,20,26,28H,4-9,11-12H2,1-3H3/t16-,17-,18-,20+,21-,22-,23-/m0/s1
  • Key:ALEXXDVDDISNDU-JZYPGELDSA-N

The acetate group helps to protect the hydrocortisone molecule from being broken down by enzymes in the body (prolongs the duration of action of hydrocortisone) and allows it to be absorbed more easily.

Oral bioavailability

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Hydrocortisone has a lower bioavailability than hydrocortisone acetate when taken orally, because hydrocortisone is rapidly metabolized in the liver and excreted by the kidneys before reaching its target tissue. On the other hand, hydrocortisone acetate is more stable and less susceptible to metabolism, allowing a higher proportion of the drug to be absorbed and reach systemic circulation. Therefore, hydrocortisone acetate is often preferred for oral administration over hydrocortisone.[2]

References

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  1. ^ "Hydrocortisone Acetate". National Library of Medicine. Archived from the original on 4 April 2018. Retrieved 4 April 2018.
  2. ^ Leite FM, Longui CA, Kochi C, Faria CD, Borghi M, Calliari LE, et al. (February 2008). "[Comparative study of prednisolone versus hydrocortisone acetate for treatment of patients with the classic congenital adrenal hyperplasia due to 21-hydroxylase deficiency]". Arq Bras Endocrinol Metabol (in Portuguese). 52 (1): 101–8. doi:10.1590/s0004-27302008000100014. PMID 18345402.