2943. Dexamethasone

Nomenclature

CAS number: 50-02-2
(11β,16α)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione; 9α-fluoro-16α-methylprednisolone; 16α-methyl-9α-fluoro-1,4-pregnadiene-11β,17α,21-triol-3,20-dione; 16α-methyl-9α-fluoroprednisolone; 1-dehydro-16α-methyl-9α-fluorohydrocortisone; 16α-methyl-9α-fluoro-Δ1-hydrocortisone; hexadecadrol; Aeroseb-Dex (Allergan); Decadron (Merck & Co.); Dexacortal (Organon); Dexacortin (Streuli); Dexamonozon (Medice); Dexapos (Ursapharm); Dexa-sine (Alcon); Dexasone (Valeant); Fortecortin (Merck KGaA); Isopto-Dex (Alcon); Loverine (Isei); Luxazone (Allergan); Maxidex (Alcon).
C22H29FO5; mol wt 392.46.
C 67.33%, H 7.45%, F 4.84%, O 20.38%.

Description and references

Synthetic adrenocortical steroid. Prepn and anti-inflammatory activity: G. E. Arth et al., J. Am. Chem. Soc. 80, 3161 (1958); E. P. Oliveto et al., ibid. 4431; G. E. Arth et al., DE 1113690 (1961 to Merck & Co.); GB 869511 (1961 to Upjohn). Comprehensive description: E. M. Cohen, Anal. Profiles Drug Subs. 2, 163-197 (1973). Review of analytical methods: S. Saeed-Ul-Hassan et al., Acta Pharm. Turc. 43, 33-42 (2001). HPLC determn in plasma: Y.-K. Song et al., J. Liq. Chromatogr. Relat. Technol. 27, 2293 (2004). Clinical trial as anti-emetic in chemotherapy-induced nausea: M. Markman et al., N. Engl. J. Med. 311, 549 (1984); F. Roila et al., ibid. 342, 1554 (2000). Use as diagnostic aid in depression: B. J. Carroll et al., Arch. Gen. Psychiatry 38, 15 (1981); and suicide prediction: W. Coryell, M. Schlesser, Am. J. Psychiatry 158, 748 (2001). Diagnostic use in Cushing's syndrome: L. Crapo, Metabolism 28, 955 (1979); A. M. Isidori et al., J. Clin. Endocrinol. Metab. 88, 5299 (2003).

Chemical structure

Properties

White to practically white, odorless crystals from ether, mp 262-264°; mp 268-271° (Arth, 1961). [α]D25 +77.5° (dioxane). Soly in water (25°): 10 mg/100 ml. Sol in acetone, ethanol, chloroform.

Derivative

21-Acetate.

Nomenclature

CAS number: 1177-87-3
Decadronal (Merck & Co.); Decadron-LA (Merck & Co.); Dectancyl (Sanofi-Aventis).
C24H31FO6; mol wt 434.50.
C 66.34%, H 7.19%, F 4.37%, O 22.09%.

Properties

Crystals, mp 215-221° (Arth, 1958); mp 229-231° (Oliveto); mp 238-240° (Arth, 1961). [α]D25 +73° (chloroform) (Arth, 1958); [α]D +77.6° (Oliveto). uv max: 239 nm (ε 14900).

Derivative

21-Phosphate disodium salt.

Nomenclature

CAS number: 2392-39-4
Dexamethasone 21-(dihydrogen phosphate) disodium salt; dexamethasone sodium phosphate; Ak-Dex (Akorn); Dalalone (Forest); Desocort (Bausch & Lomb); Dexabene (Merckle); Hexadrol (Organon); Oradexon (Organon); Orgadrone (Han Wha); SoluDecadron (Merck & Co.); Soldesam (Farmacologico); Solupen N (Winzer); Totocortin (Winzer).
C22H28FNa2O8P; mol wt 516.40.
C 51.17%, H 5.47%, F 3.68%, Na 8.90%, O 24.79%, P 6.00%.

Description and references

Used as an injectable form of dexamethasone. Prepn: Chemerda et al., US 2939873 (1960 to Merck & Co.); Irmscher, Chem. Ind. (London) 1961, 1035.

Properties

White or slightly yellow crystalline powder, mp 233-235°. Exceedingly hygroscopic. [α]D +57° (water). Also reported as [α]D25 +74 ±4° (calcd on water-free and alcohol-free basis, concn of 10 mg/ml): USP XIX, p 124. uv max (ethanol): 238-239 nm (ε 14000). Sol in water.

Derivative

21-Isonicotinate.

Nomenclature

Dexamethasone 21-(4-pyridinecarboxylate); Auxisone (Boehringer, Ing.).
C28H32FNO6; mol wt 497.56.
C 67.59%, H 6.48%, F 3.82%, N 2.82%, O 19.29%.

Properties

Crystals, mp 250-252°. [α]D27 +183.5° (dioxane).

Derivative

17,21-Dipropionate.

Nomenclature

THS-101; Methaderm (Taiho).
C28H37FO7; mol wt 504.59.
C 66.65%, H 7.39%, F 3.77%, O 22.20%.

Therapeutic Category

Glucocorticoid.; antiemetic; diagnostic aid (Cushing's syndrome, depression).

Therapeutic Category (Veterinary)

Glucocorticoid.

Keywords

Antiallergic (Steroidal, Nasal); Antiasthmatic (Steroidal, Inhalant); Diagnostic Aid; Glucocorticoid; Antiemetic