Hydrocortisone acetate

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

Hydrocortisone acetate

Clinical data
Other names	Cortisol 21-acetate
Drug class	Corticosteroid; Glucocorticoid
Identifiers
IUPAC name [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	50-03-3 Y
PubChem CID	5744
DrugBank	DB14539
ChemSpider	5542
UNII	3X7931PO74
KEGG	D00165
ChEBI	CHEBI:17609
ChEMBL	ChEMBL1091
CompTox Dashboard (EPA)	DTXSID20962156 DTXSID0048686, DTXSID20962156
ECHA InfoCard	100.000.005
Chemical and physical data
Formula	C23H32O6
Molar mass	404.503 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 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

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

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.