4787. Hydrocortisone

Nomenclature

CAS number: 50-23-7
(11β)-11,17,21-Trihydroxypregn-4-ene-3,20-dione; cortisol; 4-pregnene-11β,17α,21-triol-3,20-dione; 17-hydroxycorticosterone; anti-inflammatory hormone; Kendall's compound F; Reichstein's substance M; Ala-Cort (Del-Ray); Cetacort (Coria); Cort-Dome (Bayer); Cortef (Pharmacia & Upjohn); Cortenema (Solvay); Cortril (Pfizer); Dermacort (Melaleuca); Dioderm (Dermal); Efcortelan (GSK); Ficortril (Pfizer); Hydracort (Galderma); Hydrocort (Meda); Hydrocortisyl (Sanofi-Aventis); Hydrocortone (Merck & Co.); Hytone (Dermik); Mildison (Astellas); Nutracort (Galderma); Proctocort (Salix).
C21H30O5; mol wt 362.46.
C 69.59%, H 8.34%, O 22.07%.

Description and references

Principal glucocorticoid hormone produced by the adrenal cortex. Biosynthesis stimulated by ACTH, q.v. Circulates in plasma primarily bound to corticosteroid-binding globulin, also known as transcortin, and to albumin. Isoln from adrenal glands: Reichstein, Helv. Chim. Acta 20, 953 (1937); Mason et al., J. Biol. Chem. 124, 459 (1938); from urine: Mason, Sprague, ibid. 175, 451 (1948); from blood: Reich et al., ibid. 187, 411 (1950). Configuration: von Euw, Reichstein, Helv. Chim. Acta 25, 988 (1942); 30, 205 (1947). Synthesis: N. L. Wendler et al., J. Am. Chem. Soc. 72, 5793 (1950). Biosynthesis by isolated adrenal glands: O. Hechter et al., Arch. Biochem. Biophys. 25, 457 (1950); A. Zaffaroni et al., J. Am. Chem. Soc. 73, 1390 (1951). Prepn by microbial transformation: H. C. Murray, D. H. Peterson, US 2602769 (1952 to Upjohn); D. R. Colingsworth et al., J. Biol. Chem. 203, 807 (1953). Total biosynthesis in yeast: F. M. Szczebara et al., Nat. Biotechnol. 21, 143 (2003). Comprehensive description: K. Florey, Anal. Profiles Drug Subs. 12, 277-324 (1983). Review of clinical use in dermatoses: A. M. Kligman, K. H. Kaidbey, Cutis 22, 232-244 (1978). Review of clinical assays in serum and urine: A. Moore et al., Ann. Clin. Biochem. 22, 435-454 (1985). Physiological role in immunity: W. M. Jefferies, Med. Hypotheses 34, 198-208 (1991); in fetal maturation: G. C. Liggins, Reprod. Fertil. Dev. 6, 141-150 (1994).

Chemical structure

Properties

Bitter-tasting crystalline, striated blocks from abs ethanol or isopropanol, mp 217-220° with some decompn. [α]D22 +167° (abs ethanol). uv max: 242 nm (E1%1cm 445). Soly (mg/ml) at 25°: water 0.28; ethanol 15.0; methanol 6.2; acetone 9.3; chloroform 1.6; propylene glycol 12.7; ether about 0.35. Sol in concd sulfuric acid with intense green fluorescence.

Derivative

21-Acetate.

Nomenclature

CAS number: 50-03-3
Colifoam (Meda); Colofoam (Meda); Cortaid (J & J); Cortifoam (Schwarz); Lanacort (Combe); Lenirit (Bonomelli); Sigmacort (Sigma); Sintotrat (Bracco).
C23H32O6; mol wt 404.50.
C 68.29%, H 7.97%, O 23.73%.

Properties

Monoclinic, sphenoidal, tabular crystals from dil acetone. Tasteless. d420 1.289; dec 223°. [α]D25 +166° (c = 0.4 in dioxane); [α]D25 +150.7° (c = 0.5 in acetone). uv max (methanol): 242 nm (E1%1cm 390). Somewhat hygroscopic. Soly in water: 1 mg/100 ml; in ethanol: 0.45 g/100 ml; in methanol: 3.9 mg/ml; in acetone: 1.1 mg/g; in ether: 0.15 mg/ml. One gram dissolves in about 200 ml chloroform. Very sol in DMF; sol in dioxane.

Derivative

17-Butyrate.

Nomenclature

CAS number: 13609-67-1
Alfason (Astellas); Locoid (Yamanouchi); Plancol (Chugai).
C25H36O6; mol wt 432.55.
C 69.42%, H 8.39%, O 22.19%.

Derivative

21-Phosphate disodium salt.

Nomenclature

CAS number: 6000-74-4
Hydrocortisone sodium phosphate; Cleiton (Sankyo); Efcortesol (GSK).
C21H29Na2O8P; mol wt 486.40.
C 51.86%, H 6.01%, Na 9.45%, O 26.31%, P 6.37%.

Properties

White powder. uv max (methanol): 242 nm (A1%1cm 298-341). [α]D25 +120° (H2O). Soly in water (25°): >500 mg/ml. pH of a 1% aq soln: 7.5-8.5.

Derivative

21-Sodium succinate.

Nomenclature

CAS number: 125-04-2
Hydrocortisone hemisuccinate sodium salt; Corlan (UCB); Efcortelan (GSK); Saxizon (Nikken); Solu-Cortef (Pharmacia & Upjohn).
C25H33NaO8; mol wt 484.51.
C 61.97%, H 6.87%, Na 4.74%, O 26.42%.

Properties

Amorphous, hygroscopic, white powder, mp 169.0-171.2°. Soly in water: ≈500 mg/ml. Similarly sol in methanol, ethanol; sparingly sol in chloroform.

Derivative

17-Valerate.

Nomenclature

CAS number: 57524-89-7
Hydrocortisone valerate; Westcort (Westwood).
C26H38O6; mol wt 446.58.
C 69.93%, H 8.58%, O 21.50%.

Therapeutic Category

Glucocorticoid.

Therapeutic Category (Veterinary)

Glucocorticoid.

Keywords

Glucocorticoid