Dexamethasone

Title: Dexamethasone
CAS Registry Number: 50-02-2
CAS Name: (11b,16a)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
Additional Names: 9a-fluoro-16a-methylprednisolone; 16a-methyl-9a-fluoro-1,4-pregnadiene-11b,17a,21-triol-3,20-dione; 16a-methyl-9a-fluoroprednisolone; 1-dehydro-16a-methyl-9a-fluorohydrocortisone; 16a-methyl-9a-fluoro-D1-hydrocortisone; hexadecadrol
Trademarks: 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)
Molecular Formula: C22H29FO5
Molecular Weight: 392.46
Percent Composition: C 67.33%, H 7.45%, F 4.84%, O 20.38%
Literature References: Prepn: Arth et al., J. Am. Chem. Soc. 80, 3161 (1958); Oliveto et al., ibid. 4431; Muller et al., US 3007923 (1961 to Lab. Franc. Chimiothér.); Arth et al., DE 1113690 (1961 to Merck & Co.); GB 869511 (to Upjohn). Pharmacology in guinea pigs: L. Zicha et al., Arzneim.-Forsch. 10, 831 (1960). Clinical trial of anti-emetic efficacy in chemotherapy-induced nausea: M. Markman et al., N. Engl. J. Med. 311, 549 (1984); in combination with ondansetron, q.v.: 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); P. P. Hubain et al., Neuropsychobiology 16, 57 (1986); M. Ansseau et al., ibid. 68. Comprehensive description: E. M. Cohen, Anal. Profiles Drug Subs. 2, 163-197 (1973). Reviews of diagnostic use in Cushing's syndrome: L. Crapo, Metabolism 28, 955 (1979); in depression: L. Braddock, Br. J. Psychiatry 148, 363 (1986).
Properties: Crystals from ether, mp 262-264°; mp 268-271° (Arth, 1961). [a]D25 +77.5° (dioxane). Soly in water (25°): 10 mg/100 ml. Sol in acetone, ethanol, chloroform.
Melting point: mp 262-264°; mp 268-271° (Arth, 1961)
Optical Rotation: [a]D25 +77.5° (dioxane)
Derivative Type: 21-Acetate
CAS Registry Number: 1177-87-3
Trademarks: Decadronal (Merck & Co.); Decadron-LA (Merck & Co.); Dectancyl (Sanofi-Aventis)
Molecular Formula: C24H31FO6
Molecular Weight: 434.50
Percent Composition: 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). [a]D25 +73° (chloroform) (Arth, 1958); [a]D +77.6° (Oliveto). uv max: 239 nm (e 14900).
Melting point: mp 215-221° (Arth, 1958); mp 229-231° (Oliveto); mp 238-240° (Arth, 1961)
Optical Rotation: [a]D25 +73° (chloroform) (Arth, 1958); [a]D +77.6° (Oliveto)
Absorption maximum: uv max: 239 nm (e 14900)
Derivative Type: 21-Phosphate disodium salt
CAS Registry Number: 2392-39-4
Additional Names: Dexamethasone 21-(dihydrogen phosphate) disodium salt; dexamethasone sodium phosphate
Trademarks: 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)
Molecular Formula: C22H28FNa2O8P
Molecular Weight: 516.40
Percent Composition: C 51.17%, H 5.47%, F 3.68%, Na 8.90%, O 24.79%, P 6.00%
Literature 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: Crystals, mp 233-235°. [a]D +57° (water). Also reported as [a]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 (e 14000). Sol in water.
Melting point: mp 233-235°
Optical Rotation: [a]D +57° (water); [a]D25 +74 ±4° (calcd on water-free and alcohol-free basis, concn of 10 mg/ml): USP XIX, p 124
Absorption maximum: uv max (ethanol): 238-239 nm (e 14000)
Derivative Type: 21-Isonicotinate
Additional Names: Dexamethasone 21-(4-pyridinecarboxylate)
Trademarks: Auxisone (Boehringer, Ing.)
Molecular Formula: C28H32FNO6
Molecular Weight: 497.56
Percent Composition: C 67.59%, H 6.48%, F 3.82%, N 2.82%, O 19.29%
Properties: Crystals, mp 250-252°. [a]D27 +183.5° (dioxane).
Melting point: mp 250-252°
Optical Rotation: [a]D27 +183.5° (dioxane)
Derivative Type: 17,21-Dipropionate
Manufacturers' Codes: THS-101
Trademarks: Methaderm (Taiho)
Molecular Formula: C28H37FO7
Molecular Weight: 504.59
Percent Composition: C 66.65%, H 7.39%, F 3.77%, O 22.20%
Therap-Cat: Glucocorticoid; anti-inflammatory. Diagnostic aid (Cushing's syndrome, depression).
Therap-Cat-Vet: Glucocorticoid; anti-inflammatory.
Keywords: Antiallergic (Steroidal, Nasal); Antiasthmatic (Steroidal, Inhalant); Diagnostic Aid; Glucocorticoid.
Dexanabinol Dexetimide Dexmedetomidine Dextran Dextran Sulfate Sodium

Dexamethasone
Dexamethasone structure.svg
Dexamethasone3Dan.gif
Systematic (IUPAC) name
(8S,9R,10S,11S,13S,14S,16R,17R)-9- Fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17- dodecahydro-3H-cyclopenta[a]phenanthren-3-one
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a682792
Pregnancy cat. A (AU) C (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes Oral, IV, IM, SC and IO
Pharmacokinetic data
Bioavailability 80-90%
Protein binding 77%
Metabolism hepatic
Half-life 190 minutes
Excretion Urine (65%)
Identifiers
CAS number 50-02-2 YesY
ATC code A01AC02 C05AA09, D07AB19, D10AA03, H02AB02, R01AD03, S01BA01,S02BA06, S03BA01
PubChem CID 5743
DrugBank DB01234
ChemSpider 5541 YesY
UNII 7S5I7G3JQL YesY
KEGG D00292 YesY
ChEBI CHEBI:41879 YesY
ChEMBL CHEMBL384467 YesY
Chemical data
Formula C22H29FO5 
Mol. mass 392.461 g/mol
 N (what is this?)  (verify)

Dexamethasone is a potent synthetic member of the glucocorticoid class of steroid drugs that has anti-inflammatory and immunosuppressant effects. It is 25 times more potent than cortisol in its glucocorticoid effect, while having minimal mineralocorticoid effect.