Chemical Properties
white powder
Definition
ChEBI: Cortisol 21-acetate is a tertiary alpha-hydroxy ketone and a cortisol ester.
Brand name
Cortef
Acetate (Pharmacia & Upjohn); Cortifoam (Schwarz
Pharma); Cortril (Pfizer); Dricort (Ingram); Hydrocortone
(Merck).
Clinical Use
Corticosteroid:
Local inflammation of joints and soft tissue
Drug interactions
Potentially hazardous interactions with other drugs
Aldesleukin: avoid concomitant use.
Antibacterials: metabolism accelerated by rifampicin;
metabolism possibly inhibited by erythromycin;
concentration of isoniazid possibly reduced.
Anticoagulants: efficacy of coumarins and
phenindione may be altered.
Antiepileptics: metabolism accelerated by
carbamazepine, phenobarbital, fosphenytoin,
phenytoin and primidone.
Antifungals: increased risk of hypokalaemia with
amphotericin - avoid; metabolism possibly inhibited
by itraconazole and ketoconazole.
Antivirals: concentration possibly increased by
ritonavir.
Ciclosporin: rare reports of convulsions in patients
on ciclosporin and high-dose corticosteroids
.
Cobicistat: concentration of hydrocortisone possibly
increased - increased risk of adrenal suppression.
Diuretics: enhanced hypokalaemic effects of
acetazolamide, loop diuretics and thiazide diuretics.
Vaccines: high dose corticosteroids can impair
immune response to vaccines - avoid concomitant
use with live vaccines.
Metabolism
Hydrocortisone is metabolised in the liver and most
body tissues to hydrogenated and degraded forms such as
tetrahydrocortisone and tetrahydrocortisol.
These are excreted in the urine, mainly conjugated as
glucuronides, with a very small proportion of unchanged
hydrocortisone.
Purification Methods
The acetate recrystallises from Me2CO/Et2O or aqueous Me2CO as hygroscopic monoclinic crystals. UV has max at 242 nm (A1cm 1% 390) in MeOH. Its solubility at 25o is: H2O (0.001%), EtOH (0.45%), MeOH (0.04%), Me2CO (1.1%), CHCl3 (0.5%), Et2O (0.15%), and it is very soluble in Me2NCHO. [Wendler et al. J Am Chem Soc 74 3630 1952; Antonucci et al. J Org Chem 18 7081 1953, Beilstein 8 IV 3424.]
