Title: Hydrocortisone
CAS Registry Number: 50-23-7
CAS Name: (11b)-11,17,21-Trihydroxypregn-4-ene-3,20-dione
Additional Names: cortisol; 4-pregnene-11b,17a,21-triol-3,20-dione; 17-hydroxycorticosterone; anti-inflammatory hormone; Kendall's compound F; Reichstein's substance M
Trademarks: Aeroseb-HC (Allergan); Ala-Cort (Del-Ray); Anflam (Cox); Cetacort (Galderma); Cort-Dome (Miles); Cortef (Pfizer); Cortenema (Solvay); Cortril (Pfizer); Dermacort (Solvay); Dermocortal (Pfizer); Dermolate (Schering-Plough); Dioderm (Dermal); Efcortelan (GSK); Evacort (Evans); Ficortril (Pfizer); Hydracort (Galderma); Hydro-Adreson (Organon); Hydrocort (Pharmagalen); Hydrocortisyl (Aventis); Hydrocortone (Merck & Co.); Hytone (Dermik); Lacticare-HC (Stiefel); Medicort (Care); Mildison (Yamanouchi); Nutracort (Galderma); Penecort (Allergan); Proctocort (Solvay); Scheroson F (Schering AG); Synacort (Syntex); Texacort (Genderm); Timocort (Reckitt & Colman); Zenoxone (Biorex)
Molecular Formula: C21H30O5
Molecular Weight: 362.46
Percent Composition: C 69.59%, H 8.34%, O 22.07%
Literature 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).
Properties: Bitter-tasting crystalline, striated blocks from abs ethanol or isopropanol, mp 217-220° with some decompn. [a]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.
Melting point: mp 217-220° with some decompn
Optical Rotation: [a]D22 +167° (abs ethanol)
Absorption maximum: uv max: 242 nm (E1%1cm 445)
Derivative Type: 21-Acetate
CAS Registry Number: 50-03-3
Trademarks: Colifoam (Stafford-Miller); Colofoam (Stafford-Miller); Cortaid (Pfizer); Cordes (Ichthyol); Cortifoam (Schwarz); Hc45 (Crookes); Hydrocal (Bioglan); Hydrocortistab (Boots); Lanacort (Combe); Lenirit (Bonomelli); Sigmacort (Sigma); Sintotrat (Edmond); Velopural (Optimed)
Molecular Formula: C23H32O6
Molecular Weight: 404.50
Percent Composition: C 68.29%, H 7.97%, O 23.73%
Properties: Monoclinic, sphenoidal, tabular crystals from dil acetone. Tasteless. d420 1.289; dec 223°. [a]D25 +166° (c = 0.4 in dioxane); [a]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.
Optical Rotation: [a]D25 +166° (c = 0.4 in dioxane); [a]D25 +150.7° (c = 0.5 in acetone)
Absorption maximum: uv max (methanol): 242 nm (E1%1cm 390)
Density: d420 1.289
Derivative Type: 17-Butyrate
CAS Registry Number: 13609-67-1
Trademarks: Alfason (Yamanouchi); Laticort (Medphano); Locoid (Yamanouchi); Plancol (Chugai)
Molecular Formula: C25H36O6
Molecular Weight: 432.55
Percent Composition: C 69.42%, H 8.39%, O 22.19%
Derivative Type: 21-Phosphate disodium salt
CAS Registry Number: 6000-74-4
Additional Names: Hydrocortisone sodium phosphate
Trademarks: Cleiton (Sankyo Zoki); Efcortesol (GSK)
Molecular Formula: C21H29Na2O8P
Molecular Weight: 486.40
Percent Composition: 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). [a]D25 +120° (H2O). Soly in water (25°): >500 mg/ml. pH of a 1% aq soln: 7.5-8.5.
Optical Rotation: [a]D25 +120° (H2O)
Absorption maximum: uv max (methanol): 242 nm (A1%1cm 298-341)
Derivative Type: 21-Sodium succinate
CAS Registry Number: 125-04-2
Additional Names: Hydrocortisone hemisuccinate sodium salt
Trademarks: A-hydroCort (Abbott); Buccalsone (Will-Pharma); Corlan (Evans); Efcortelan Soluble (GSK); Saxizon (Nikken); Solu-Cortef (Pfizer); Solu-Glyc (Erco)
Molecular Formula: C25H33NaO8
Molecular Weight: 484.51
Percent Composition: 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.
Melting point: mp 169.0-171.2°
Derivative Type: 17-Valerate
CAS Registry Number: 57524-89-7
Additional Names: Hydrocortisone valerate
Trademarks: Westcort (Westwood)
Molecular Formula: C26H38O6
Molecular Weight: 446.58
Percent Composition: C 69.93%, H 8.58%, O 21.50%
Therap-Cat: Glucocorticoid.
Therap-Cat-Vet: Glucocorticoid.
Keywords: Glucocorticoid. |