Symbiotec Dexamethasone Symbiotec Dexamethasone

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Dexamethasone
Also known as: 50-02-2, Decadron, Maxidex, Dexamethazone, Hexadecadrol, Dexasone
Molecular Formula
C22H29FO5
Molecular Weight
392.5  g/mol
InChI Key
UREBDLICKHMUKA-CXSFZGCWSA-N
FDA UNII
7S5I7G3JQL

An anti-inflammatory 9-fluoro-glucocorticoid.
Dexamethasone is a Corticosteroid. The mechanism of action of dexamethasone is as a Corticosteroid Hormone Receptor Agonist.
1 2D Structure

Dexamethasone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
2.1.2 InChI
InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1
2.1.3 InChI Key
UREBDLICKHMUKA-CXSFZGCWSA-N
2.1.4 Canonical SMILES
CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)CO)O)C)O)F)C
2.1.5 Isomeric SMILES
C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)F)C
2.2 Other Identifiers
2.2.1 UNII
7S5I7G3JQL
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Decaject

2. Decaject L.a.

3. Decaject-l.a.

4. Decameth

5. Decaspray

6. Dexasone

7. Dexpak

8. Hexadecadrol

9. Hexadrol

10. Maxidex

11. Methylfluorprednisolone

12. Millicorten

13. Oradexon

2.3.2 Depositor-Supplied Synonyms

1. 50-02-2

2. Decadron

3. Maxidex

4. Dexamethazone

5. Hexadecadrol

6. Dexasone

7. Hexadrol

8. Decaspray

9. Millicorten

10. Oradexon

11. Prednisolone F

12. Fluormethylprednisolone

13. Aeroseb-dex

14. Cortisumman

15. Desametasone

16. Dexacortal

17. Dexacortin

18. Fortecortin

19. Gammacorten

20. Superprednol

21. Visumetazone

22. Auxiron

23. Calonat

24. Decaderm

25. Dexacort

26. Dexason

27. Azium

28. Dexone

29. Deltafluorene

30. Desamethasone

31. Mediamethasone

32. Aphtasolon

33. Decasone

34. Dectancyl

35. Dekacort

36. Dergramin

37. Desadrene

38. Desameton

39. Dexadeltone

40. Dexalona

41. Dexameth

42. Dexapolcort

43. Dextelan

44. Dinormon

45. Loverine

46. Luxazone

47. Mymethasone

48. Turbinaire

49. Corsone

50. Decalix

51. Mexidex

52. Dexa-cortidelt

53. Dexa-cortisyl

54. Dexa-scheroson

55. Prednisolon F

56. Dexa-sine

57. Isopto-dex

58. Aeroseb-d

59. Sk-dexamethasone

60. Anaflogistico

61. Decacortin

62. Deseronil

63. Dexafarma

64. Dexaprol

65. Dexinolon

66. Dexinoral

67. Policort

68. Spoloven

69. Decagel

70. Deronil

71. Dezone

72. Sunia Sol D

73. Bisu Ds

74. Dexa Mamallet

75. Hexadrol Elixir

76. Lokalison F

77. Ocu-trol

78. Dex-ide

79. Hl-dex

80. Dexamethasonum

81. Dexone 4

82. Fluorocort

83. Decaject

84. Decameth

85. Fluormone

86. Corson

87. Dexpak

88. Pet Derm Iii

89. Dxms

90. Dexamethasone Alcohol

91. Hexadrol Tablets

92. Dexamethasone Intensol

93. Methylfluorprednisolone

94. Desametasone [dcit]

95. Dexone 0.5

96. Dexone 1.5

97. Dexone 0.75

98. Dexametasona

99. Dexacidin

100. Maxitrol

101. Ozurdex

102. Dexametasona [inn-spanish]

103. Dexamethasonum [inn-latin]

104. Dexapos

105. Decadron Tablets, Elixir

106. 9alpha-fluoro-16alpha-methylprednisolone

107. Azium (veterinary)

108. Dexamethansone

109. Dextenza

110. Posurdex

111. Prodex

112. Oto-104

113. Mk 125

114. (3h)-dexamethasone

115. Azimycin (veterinary)

116. Nsc 34521

117. Dexametasone

118. Naquasone (veterinary)

119. Tresaderm (veterinary)

120. Dexycu

121. 16alpha-methyl-9alpha-fluoro-1-dehydrocortisol

122. Dexasite

123. 16alpha-methyl-9alpha-fluoroprednisolone

124. 16-alpha-methyl-9-alpha-fluoroprednisolone

125. 9-alpha-fluoro-16-alpha-methylprednisolone

126. 1-dehydro-16alpha-methyl-9alpha-fluorohydrocortisone

127. Delta1-9alpha-fluoro-16alpha-methylcortisol

128. Decacort

129. (11beta,16alpha)-9-fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione

130. 16-alpha-methyl-9-alpha-fluoro-1-dehydrocortisol

131. 16-alpha-methyl-9-alpha-fluoro-delta1-hydrocortisone

132. Delta(sup 1)-9-alpha-fluoro-16-alpha-methylcortisol

133. Isv-305

134. 9a-fluoro-16beta-methylprednisolone

135. 16alpha-methyl-9alpha-fluoro-delta(sup 1)-hydrocortisone

136. 16-alpha-methyl-9-alpha-fluoro-delta(sup 1)-hydrocortisone

137. Nsc-34521

138. Dexamethasone (dhap)

139. 7s5i7g3jql

140. 16.alpha.-methyl-9.alpha.-fluoroprednisolone

141. Chebi:41879

142. [3h]-dexamethasone

143. Decaject-l.a.

144. 23495-06-9

145. Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-16-methyl-, Labeled With Tritium, (11beta,16alpha)-

146. Aphthasolone

147. Dexamonozon

148. 9.alpha.-fluoro-16.alpha.-methylprednisolone

149. (1r,2s,10s,11s,13r,14r,15s,17s)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one

150. (8s,9r,10s,11s,13s,14s,16r,17r)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one

151. (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

152. C22h29fo5

153. 16.alpha.-methyl-9.alpha.-fluoro-1-dehydrocortisol

154. 1-dehydro-16.alpha.-methyl-9.alpha.-fluorohydrocortisone

155. Osurdex

156. Dexamethasone Base

157. Decadron (tn)

158. (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]ph

159. Smr000857119

160. Dxm [steroid]

161. Ccris 7067

162. Hsdb 3053

163. Dexamethasone (tetramethyl-rhodamine Conjugated )

164. Prednisolone, 9.alpha.-fluoro-16.alpha.-methyl-

165. Einecs 200-003-9

166. Mfcd00064136

167. Unii-7s5i7g3jql

168. Solurex

169. .delta.(sup 1)-9-.alpha.-fluoro-16-.alpha.-methylcortisol

170. 16.alpha.-methyl-9.alpha.-fluoro-.delta.(sup1)-hydrocortisone

171. Diodex

172. Nsc34521

173. Ai3-50934

174. .gamma.corten

175. 9-fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione

176. Apo-dexamethasone

177. Prednisolone, 9alpha-fluoro-16alpha-methyl-

178. Dexasone 4mg

179. Dtxsid3020384

180. Zema-pak

181. Phl-dexamethasone

182. Pms-dexamethasone

183. 9-fluoro-11.beta.,17,21-trihydroxy-16.alpha.-methylpregna-1,4-diene-3,20-dione

184. [3h]dexamethasone

185. Dexamethasone-omega

186. Ncgc00091019-08

187. Dexasone 0.5mg

188. Dexamethasone [usp:inn:ban:jan]

189. Dexasone 0.75mg

190. Sandoz Dexamethasone

191. Hemady

192. Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-16-methyl-, (11beta,16alpha)-

193. Dexamethasone, Topical

194. Maxidex Ont 0.1%

195. Maxidex Sus 0.1%

196. Dexamethasone-17-acetate

197. Dsstox_cid_384

198. Spectrum5_002019

199. Dexamethasone [mi]

200. Molmap_000018

201. 9-fluoro-11beta,17,21-trihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione

202. Dexamethasone [inn]

203. Dexamethasone [jan]

204. Schembl3774

205. 16-alpha-methyl-9-alpha-fluoro-1,4-pregnadiene-11-beta,17-alpha,21-triol-3,20-dione

206. 16-alpha-methyl-9-alpha-fluoro-11-beta,17-alpha,21-trihydroxypregna-1,4-diene-3,20-dione

207. 4-alpha-fluoro-16-alpha-methyl-11-beta,17,21-trihydroxypregna-1,4-diene-3,20-dione

208. 9-alpha-fluoro-16-alpha-methyl-1,4-pregnadiene-11-beta,17-alpha,21-triol-3,20-dione

209. Dexamethasone [hsdb]

210. Dsstox_rid_75557

211. Bidd:pxr0060

212. Dsstox_gsid_20384

213. Bspbio_000995

214. Dexamethasone [vandf]

215. Mls001055412

216. Mls001332507

217. Mls001332508

218. Bidd:er0494

219. Dexamethasone [mart.]

220. Sustained-release Dexamethasone

221. Dexamethasone [usp-rs]

222. Dexamethasone [who-dd]

223. Dexamethasone [who-ip]

224. Chembl384467

225. Gtpl2768

226. Gtpl3447

227. Sgcut00126

228. 9-fluoro-16-methylprednisolone

229. Ak Dex Oph Otic Soln 0.1%

230. Dexamethasone [ema Epar]

231. Bdbm18207

232. Dexamethasone (jp17/usp/inn)

233. 1p93

234. Dexamethasone [green Book]

235. Hms1792a17

236. Hms1990a17

237. Hms2089n13

238. Hms2235f08

239. Hms3039l11

240. Hms3259n11

241. Hms3403a17

242. Dexamethasone [orange Book]

243. Amy28815

244. To_000038

245. Zinc3875332

246. Dexamethasone [ep Monograph]

247. Tox21_200122

248. Dexamethasone [usp Monograph]

249. Dexamethasone, >=97.0% (hplc)

250. Ibi-10090

251. Mk-125

252. S1322

253. Dexamethasone 1.0 Mg/ml In Methanol

254. Dexamethasonum [who-ip Latin]

255. Pms Dexamethasone Elixir 0.5mg/5ml

256. Akos005259009

257. Akos015895509

258. Ciprodex Component Dexamethasone

259. Decadron Phosphate, Decdan, Dexacort,

260. Maxitrol Component Dexamethasone

261. Tobradex Component Dexamethasone

262. Ccg-264887

263. Cs-1505

264. Db01234

265. Ks-1451

266. Nc00645

267. Alpha -fluoro-16-alpha -methylcortisol

268. Cas-50-02-2

269. Dexacidin Component Dexamethasone

270. Pregna-1,4-diene-3,20-dione, 9-fluoro-11beta,17,21-trihydroxy-16alpha-methyl-

271. Smp1_000092

272. Dexamethasone 100 Microg/ml In Methanol

273. Dexamethasone, >=98% (hplc), Powder

274. Dexasporin Component Dexamethasone

275. Ncgc00091019-01

276. Ncgc00091019-02

277. Ncgc00091019-03

278. Ncgc00091019-04

279. Ncgc00091019-05

280. Ncgc00091019-06

281. Ncgc00091019-07

282. Ncgc00091019-23

283. Ncgc00257676-01

284. (11beta,16alpha)-9-fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione Labeled With Tritium

285. 9alpha-fluoro-16alpha-methyl-prednisolone

286. Ac-11056

287. Dexamethasone Component Of Ciprodex

288. Dexamethasone Component Of Maxitrol

289. Dexamethasone Component Of Tobradex

290. Hy-14648

291. Nci60_003067

292. Smr001227192

293. Tobradex St Component Dexamethasone

294. Dexamethasone 1000 Microg/ml In Methanol

295. Dexamethasone Component Of Dexacidin

296. 16alpha -methyl-9alpha -fluoroprednisolone

297. 9alpha -fluoro-16alpha -methylprednisolone

298. Dexamethasone Component Of Dexasporin

299. Dexamethasone, Tested According To Ph.eur.

300. Dexamethasone 100 Microg/ml In Acetonitrile

301. Dexamethasone Component Of Tobradex St

302. Betamethasone Impurity A [ep Impurity]

303. En300-52607

304. D00292

305. Dexamethasone, Meets Usp Testing Specifications

306. Prednisolone, 9alpha -fluoro-16alpha -methyl-

307. 9.alpha.-fluoro-16.alpha.-methyl-1,20-dione

308. Ab00918428-05

309. Ab00918428-08

310. Ab00918428-09

311. Ab00918428_10

312. 064d136

313. 16alpha -methyl-9alpha -fluoro-1-dehydrocortisol

314. Dexamethasone, Vetranal(tm), Analytical Standard

315. Q422252

316. Neomycin And Polymyxin B Sulphates And Dexamethasone

317. Q-200939

318. Brd-k38775274-001-02-3

319. Brd-k38775274-001-06-4

320. Dexamethasone Acetate Impurity A [ep Impurity]

321. 1-dehydro-16alpha -methyl-9alpha -fluorohydrocortisone

322. 9-fluoro-11alpha -methylpregna-1,4-diene-3,20-dione

323. Dexamethasone, British Pharmacopoeia (bp) Assay Standard

324. Z802671480

325. Pregna-1,4-diene-3,20-dione, 9-fluoro-11alpha -methyl-

326. Dexamethasone, European Pharmacopoeia (ep) Reference Standard

327. Wln: L E5 B666 Ov Ku Mutj A1 Bf Cq E1 Fv1q Fq G1

328. Dexamethasone, Powder, Bioreagent, Suitable For Cell Culture, >=97%

329. Dexamethasone, United States Pharmacopeia (usp) Reference Standard

330. 16-.alpha.-methyl-9-.alpha.-fluoro-1,17-.alpha.,21-triol-3,20-dione

331. 4.alpha.-fluoro-16.alpha.-methyl-11.beta.-17,4-diene-3,20-dione

332. Pregna-1,20-dione, 9-fluoro-11.beta.,17,21-trihydroxy-16.alpha.-methyl-

333. 16.alpha.-methyl-9.alpha.-fluoro-11.beta.-17.alpha.-21-trihydroxypregna-1,20-dione

334. 9-fluoro-11.beta.,21-trihydroxy-16.alpha.-methylpregna-1,4-diene-3,20-dione

335. 9-fluoro-16alpha-methyl-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione

336. 9.alpha.-fluoro-11.beta.-17.alpha.- 21-trihydroxy-16.alpha.-methylpregna-1,20-dione

337. Dexamethasone For Peak Identification, European Pharmacopoeia (ep) Reference Standard

338. Dexamethasone For System Suitability, European Pharmacopoeia (ep) Reference Standard

339. Dexamethasone Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

340. Dexamethasone, Pharmaceutical Secondary Standard; Certified Reference Material

341. Dexamethasone, Powder, Gamma-irradiated, Bioxtra, Suitable For Cell Culture, >=80% (hplc)

342. Pregna-1,20-dione, 9-fluoro-11,17,21-trihydroxy-16-methyl-, (11.beta.,16.alpha.)-

343. (11.beta.,16.alpha.)-9-fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione

344. (11alpha,14beta,16alpha,17alpha)-9-fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione

345. (1r,2s,10s,11s,13r,14r,15s,17s)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo-

346. (1r,2s,10s,11s,13r,14r,15s,17s)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadeca-3,6-dien-5-one

347. 1050677-47-8

348. 9.alpha.-fluoro-16.alpha.-methyl-11.beta.,21.beta.-trihydroxy-pregna-1,4-diene-3,20-dione

349. Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-16-methyl-,(11.beta.,16.alpha.)-9-fluoro-11.beta.,17,21-trihydroxy-16.alpha.-methylpregna-1,4-diene-3,20-dione

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 392.5 g/mol
Molecular Formula C22H29FO5
XLogP31.9
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass392.19990218 g/mol
Monoisotopic Mass392.19990218 g/mol
Topological Polar Surface Area94.8 Ų
Heavy Atom Count28
Formal Charge0
Complexity805
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 10  
Drug NameDexamethasone
PubMed HealthDexamethasone
Drug ClassesAntiemetic, Corticosteroid, Weak, Diagnostic Agent, Adrenocortical Function, Endocrine-Metabolic Agent, Immune Suppreant, Ophthalmologic Agent
Drug LabelEach 5 mL (teaspoonful) contains:Dexamethasone, USP . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 0.5 mgAlso contains:Benzoic Acid, USP . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 0.1% (as preservative)Alcohol (% v...
Active IngredientDexamethasone
Dosage FormElixir; Tablet; Solution
RouteOral
Strength0.5mg/5ml; 4mg; 1.5mg; 0.5mg; 6mg; 2mg; 1mg; 0.75mg
Market StatusPrescription
CompanyLyne; Vintage Pharms; Ecr; Sti Pharma; Wockhardt Eu Operatn; Par Pharm; Roxane

2 of 10  
Drug NameDexamethasone intensol
PubMed HealthDexamethasone
Drug ClassesAntiemetic, Corticosteroid, Weak, Diagnostic Agent, Adrenocortical Function, Endocrine-Metabolic Agent, Immune Suppreant, Ophthalmologic Agent
Drug LabelDexamethasone Tablets 0.5, 0.75, 1, 1.5, 2, 4 and 6 mg USP, Dexamethasone Oral Solution, 0.5 mg per 5 mL and Dexamethasone Intensol Oral Solution (Concentrate), 1 mg per mL are for oral administration.Each tablet contains:Dexamethasone 0.5, 0.75,...
Active IngredientDexamethasone
Dosage FormConcentrate
RouteOral
Strength1mg/ml
Market StatusPrescription
CompanyRoxane

3 of 10  
Drug NameMaxidex
PubMed HealthPolymyxin B/Neomycin/Dexamethasone (Into the eye)
Drug ClassesAminoglycoside/Corticosteroid Combination
Drug LabelMAXIDEX 0.1% (dexamethasone ophthalmic suspension) is an adrenocortical steroid prepared as a sterile topical ophthalmic suspension. The active ingredient is represented by the chemical structure:Chemical name: Pregna-1,4-diene-3,20-dione,9-fluoro-...
Active IngredientDexamethasone
Dosage FormSuspension/drops
RouteOphthalmic
Strength0.1%
Market StatusPrescription
CompanyAlcon

4 of 10  
Drug NameMaxitrol
PubMed HealthDexamethasone
Drug ClassesAntiemetic, Corticosteroid, Weak, Diagnostic Agent, Adrenocortical Function, Endocrine-Metabolic Agent, Immune Suppreant, Ophthalmologic Agent
Active IngredientDexamethasone; neomycin sulfate; polymyxin b sulfate
Dosage FormOintment; Suspension/drops
RouteOphthalmic
Strength10,000 units/ml; 0.1%; 10,000 units/gm; eq 3.5mg base/ml; eq 3.5mg base/gm
Market StatusPrescription
CompanyAlcon; Falcon Pharms

5 of 10  
Drug NameOzurdex
Drug LabelOZURDEX is an intravitreal implant containing 0.7 mg (700 mcg) dexamethasone in the NOVADUR solid polymer sustained-release drug delivery system. OZURDEX is preloaded into a single-use, DDS applicator to facilitate injection of the rod-shaped...
Active IngredientDexamethasone
Dosage FormImplant
RouteIntravitreal
Strength0.7mg
Market StatusPrescription
CompanyAllergan

6 of 10  
Drug NameDexamethasone
PubMed HealthDexamethasone
Drug ClassesAntiemetic, Corticosteroid, Weak, Diagnostic Agent, Adrenocortical Function, Endocrine-Metabolic Agent, Immune Suppreant, Ophthalmologic Agent
Drug LabelEach 5 mL (teaspoonful) contains:Dexamethasone, USP . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 0.5 mgAlso contains:Benzoic Acid, USP . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 0.1% (as preservative)Alcohol (% v...
Active IngredientDexamethasone
Dosage FormElixir; Tablet; Solution
RouteOral
Strength0.5mg/5ml; 4mg; 1.5mg; 0.5mg; 6mg; 2mg; 1mg; 0.75mg
Market StatusPrescription
CompanyLyne; Vintage Pharms; Ecr; Sti Pharma; Wockhardt Eu Operatn; Par Pharm; Roxane

7 of 10  
Drug NameDexamethasone intensol
PubMed HealthDexamethasone
Drug ClassesAntiemetic, Corticosteroid, Weak, Diagnostic Agent, Adrenocortical Function, Endocrine-Metabolic Agent, Immune Suppreant, Ophthalmologic Agent
Drug LabelDexamethasone Tablets 0.5, 0.75, 1, 1.5, 2, 4 and 6 mg USP, Dexamethasone Oral Solution, 0.5 mg per 5 mL and Dexamethasone Intensol Oral Solution (Concentrate), 1 mg per mL are for oral administration.Each tablet contains:Dexamethasone 0.5, 0.75,...
Active IngredientDexamethasone
Dosage FormConcentrate
RouteOral
Strength1mg/ml
Market StatusPrescription
CompanyRoxane

8 of 10  
Drug NameMaxidex
PubMed HealthPolymyxin B/Neomycin/Dexamethasone (Into the eye)
Drug ClassesAminoglycoside/Corticosteroid Combination
Drug LabelMAXIDEX 0.1% (dexamethasone ophthalmic suspension) is an adrenocortical steroid prepared as a sterile topical ophthalmic suspension. The active ingredient is represented by the chemical structure:Chemical name: Pregna-1,4-diene-3,20-dione,9-fluoro-...
Active IngredientDexamethasone
Dosage FormSuspension/drops
RouteOphthalmic
Strength0.1%
Market StatusPrescription
CompanyAlcon

9 of 10  
Drug NameMaxitrol
PubMed HealthDexamethasone
Drug ClassesAntiemetic, Corticosteroid, Weak, Diagnostic Agent, Adrenocortical Function, Endocrine-Metabolic Agent, Immune Suppreant, Ophthalmologic Agent
Active IngredientDexamethasone; neomycin sulfate; polymyxin b sulfate
Dosage FormOintment; Suspension/drops
RouteOphthalmic
Strength10,000 units/ml; 0.1%; 10,000 units/gm; eq 3.5mg base/ml; eq 3.5mg base/gm
Market StatusPrescription
CompanyAlcon; Falcon Pharms

10 of 10  
Drug NameOzurdex
Drug LabelOZURDEX is an intravitreal implant containing 0.7 mg (700 mcg) dexamethasone in the NOVADUR solid polymer sustained-release drug delivery system. OZURDEX is preloaded into a single-use, DDS applicator to facilitate injection of the rod-shaped...
Active IngredientDexamethasone
Dosage FormImplant
RouteIntravitreal
Strength0.7mg
Market StatusPrescription
CompanyAllergan

4.2 Therapeutic Uses

Anti-Inflammatory Agents, Steroidal; Antiemetics; Antineoplastic Agents, Hormonal; Glucocorticoids, Synthetic; Glucocorticoids, Topical

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Nasal corticosteroids are used in some patients for prophylaxis of seasonal rhinitis. This form of therapy is generally reserved for patients who have consistently demonstrated a need for nasal corticosteroids to control seasonal rhinitis syndromes. Antihistamines and decongestants are considered primary therapies for this disorder. Dexamethasone nasal aerosol is less frequently used because its use results in a significantly higher incidence of systemic adverse effects with no additional benefit over other nasal corticosteroids. /NOT included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 897


Ophthalmic corticosteroids are indicated in the treatment of corticosteroid-responsive allergic and inflammatory conditions of the palpebral and bulbar conjunctiva, cornea, and anterior segment of the globe. /Corticosteroids (Ophthalmic); Included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 906


Otic corticosteroids are indicated in the treatment of corticosteroid-responsive inflammatory disorders of the external auditory meatus such as: allergic otitis externa; infective otitis (treatment adjunct); (chronic eczematoid otitis externa or seborrheic otitis externa /NOT included in US product labeling/). Dexamethasone /is/ used in the treatment of these and other corticosteroid-responsive disorders of the external auditory meatus. /Included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 911


For more Therapeutic Uses (Complete) data for DEXAMETHASONE (42 total), please visit the HSDB record page.


4.3 Drug Warning

Dexamethasone improves the cure rate of childhood acute lymphoblastic leukemia (ALL) but causes physical and behavioral adverse events. The objective of the current study was to determine the effect of dexamethasone exposure on sleep and fatigue in pediatric patients with acute lymphoblastic leukemia. One hundred pediatric patients with low-risk or standard-risk acute lymphoblastic leukemia were enrolled on 1 of 3 protocols (St. Jude Total XV, Children's Oncology Group [COG] 9904, or COG 9905) at 3 institutions. The mean age of the cohort was 9.24 +/- 3.23 years (range, 5.03-18.14 years). The majority of patients were white (79%) males (62%) with standard-risk acute lymphoblastic leukemia (63%). The cohort was divided into 4 subgroups: St. Jude low-risk, St. Jude standard-risk, COG low-risk, and COG standard-risk. Patients wore a wrist actigraph to monitor sleep activity during 2 consecutive 5-day periods: During the first period, they did not receive dexamethasone; and, during the second period, they did. Patients and their parents completed fatigue instruments on Days 2 and 5 of each period, and parents completed sleep diaries. Actual sleep minutes, sleep duration, total daily nap minutes, and fatigue increased significantly during the dexamethasone treatment for 3 to 4 of the subgroups. Total daily nap minutes increased significantly for both standard-risk groups during the dexamethasone treatment. Parents reported significant increases in their child's nighttime awakenings, restless sleep, and nap time during dexamethasone treatment.Dexamethasone treatment during continuation therapy for childhood acute lymphoblastic leukemia significantly and adversely altered sleep and fatigue, confirming that sleep and fatigue are behavioral responses to dexamethasone.

PMID:17926333 Hinds PS et al; Cancer 110 (10): 2321-30 (2007)


Excreted in breast milk; nursing by mothers receiving pharmacologic doses not recommended.

US Pharmacopeial Convention; US Pharmacopeia Dispensing Information (USP DI); Drug Information for the Health Care Professional 12th ed, V.I p.59 (1992)


/Dexamethasone/ is distributed into breast milk. Nursing while receiving pharmacologic doses of dexamethasone is not recommended.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 899


Dexamethasone inhalation is not recommended for use in asthma because it has demonstrated a significantly higher incidence of systemic effects with no additional benefit over other inhaled corticosteroids. The high ratio of systemic glucocorticoid activity to local anti-inflammatory activity of inhaled dexamethasone may be due to its greater water solubility and longer metabolic hal life after absorption relative to the other inhaled corticosteroids.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 890


For more Drug Warnings (Complete) data for DEXAMETHASONE (42 total), please visit the HSDB record page.


4.4 Drug Indication

Dexamethasone and [ciprofloxacin] otic suspension is indicated for bacterial infections with inflammation in acute otitis media and acute otitis externa. Intramuscular and intravenous injections are indicated for a number of endocrine, rheumatic, collagen, dermatologic, allergic, ophthalmic, gastrointestinal, respiratory, hematologic, neoplastic, edematous, and other conditions. Oral tablets are indicated for the treatment of multiple myeloma. An intravitreal implant is indicated for some forms of macular edema and non-infectious posterior uveitis affecting the posterior of the eye. Various ophthalmic formulations are indicated for inflammatory conditions of the eye.


FDA Label


Treatment of multiple myeloma.


Ozurdex is indicated for the treatment of adult patients with macular oedema following either branch retinal-vein occlusion (BRVO) or central retinal-vein occlusion (CRVO).

Ozurdex is indicated for the treatment of adult patients with inflammation of the posterior segment of the eye presenting as noninfectious uveitis.

Ozurdex is indicated for the treatment of adult patients with visual impairment due to diabetic macular oedema (DME) who are pseudophakic or who are considered insufficiently responsive to, or unsuitable for non-corticosteroid therapy.


Treatment of postoperative pain and inflammation associated with ophthalmic surgery


Treatment of diabetic macular oedema


Chronic non-infectious intermediate or posterior uveitis


Other retinal vascular occlusion


5 Pharmacology and Biochemistry
5.1 Pharmacology

Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals. Dexamethasone's duration of action varies depending on the route. Corticosteroids have a wide therapeutic window as patients may require doses that are multiples of what the body naturally produces. Patients taking corticosteroids should be counselled regarding the risk of hypothalamic-pituitary-adrenal axis suppression and increased susceptibility to infections.


5.2 MeSH Pharmacological Classification

Anti-Inflammatory Agents

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)


Glucocorticoids

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system. (See all compounds classified as Glucocorticoids.)


Antineoplastic Agents, Hormonal

Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal.)


Antiemetics

Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
DEXAMETHASONE
5.3.2 FDA UNII
7S5I7G3JQL
5.3.3 Pharmacological Classes
Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
5.4 ATC Code

H02AB02


S01BA01


H02AB02

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


H02AB02

S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448


A - Alimentary tract and metabolism

A01 - Stomatological preparations

A01A - Stomatological preparations

A01AC - Corticosteroids for local oral treatment

A01AC02 - Dexamethasone


C - Cardiovascular system

C05 - Vasoprotectives

C05A - Agents for treatment of hemorrhoids and anal fissures for topical use

C05AA - Corticosteroids

C05AA09 - Dexamethasone


D - Dermatologicals

D07 - Corticosteroids, dermatological preparations

D07A - Corticosteroids, plain

D07AB - Corticosteroids, moderately potent (group ii)

D07AB19 - Dexamethasone


D - Dermatologicals

D07 - Corticosteroids, dermatological preparations

D07X - Corticosteroids, other combinations

D07XB - Corticosteroids, moderately potent, other combinations

D07XB05 - Dexamethasone


D - Dermatologicals

D10 - Anti-acne preparations

D10A - Anti-acne preparations for topical use

D10AA - Corticosteroids, combinations for treatment of acne

D10AA03 - Dexamethasone


H - Systemic hormonal preparations, excl. sex hormones and insulins

H02 - Corticosteroids for systemic use

H02A - Corticosteroids for systemic use, plain

H02AB - Glucocorticoids

H02AB02 - Dexamethasone


R - Respiratory system

R01 - Nasal preparations

R01A - Decongestants and other nasal preparations for topical use

R01AD - Corticosteroids

R01AD03 - Dexamethasone


S - Sensory organs

S01 - Ophthalmologicals

S01B - Antiinflammatory agents

S01BA - Corticosteroids, plain

S01BA01 - Dexamethasone


S - Sensory organs

S01 - Ophthalmologicals

S01C - Antiinflammatory agents and antiinfectives in combination

S01CB - Corticosteroids/antiinfectives/mydriatics in combination

S01CB01 - Dexamethasone


S - Sensory organs

S02 - Otologicals

S02B - Corticosteroids

S02BA - Corticosteroids

S02BA06 - Dexamethasone


S - Sensory organs

S03 - Ophthalmological and otological preparations

S03B - Corticosteroids

S03BA - Corticosteroids

S03BA01 - Dexamethasone


5.5 Absorption, Distribution and Excretion

Absorption

Absorption via the intramuscular route is slower than via the intravenous route. A 3mg intramuscular dose reaches a Cmax of 34.66.0ng/mL with a Tmax of 2.01.2h and an AUC of 11338ng\*h/mL. A 1.5mg oral dose reaches a Cmax of 13.96.8ng/mL with a Tmax of 2.00.5h and an AUC of 33150ng\*h/mL. Oral dexamethasone is approximately 70-78% bioavailable in healthy subjects.


Route of Elimination

Corticosteroids are generally eliminated predominantly in the urine. However, dexamethasone is <10% elminated in urine.


Volume of Distribution

A 1.5mg oral dose of dexamethasone has a volume of distribution of 51.0L, while a 3mg intramuscular dose has a volume of distribution of 96.0L.


Clearance

A 20mg oral tablet has a clearance of 15.7L/h. A 1.5mg oral dose of dexamethasone has a clearance of 15.64.9L/h while a 3.0mg intramuscular dose has a clearance of 9.91.4L/h.


Absorbed into aqueous humor, cornea, iris, choroid ciliary body, and retina. Systemic absorption occurs, but may be significant only at higher dosages or in extended pediatric therapy. /Corticosteroids (Ophthalmic)/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 906


Dogs (mixed-breed) were administered dexamethasone alcohol or dexamethasone 21-isonicotinate as a solution iv or im (1 mg/kg bw), or dexamethasone 21-isonicotinate as a suspension im (0.1 or 1 mg/kg bw). Plasma concentrations were determined with HPLC up to 120 hours after treatment. The elimination half-life after iv administration was 120-140 minutes for both formulations. Following im administration, absorption was rapid with peak plasma concentrations at 30-40 minutes for both solutions. Bioavailability after im administration was 100% for dexamethasone alcohol but 40% for dexamethasone 21-isonicotinate. After im administration of dexamethasone 21-isonicotinate as a suspension, dexamethasone was not detected in plasma, suggesting a long absorption phase

Joint FAO/WHO Expert Committee on Food Additives; WHO Food Additive Series 33: Toxicological Evaluation of Ceratain Veterinary Drug Residues in Food: Dexamethasone (1994). Available from, as of November 6, 2007: https://www.inchem.org/documents/jecfa/jecmono/v33je09.htm


Crl:SD(CD)BR rats were administered a single im dose of 9 ug, (1,2,4-3H)-dexamethasone/kg bw. Radioactivity was measured up to 96 hours after administration in plasma (pre- and post-freeze dried), urine, feces and expired air. Tritium exchange was measured in stored urine. Highest plasma levels were observed 6 hours after dosing (3.7 ug equivalents/g), declining rapidly thereafter to 0.15 ug equivalents/g. Within 24 hours 41% of the radioactivity was excreted in the urine. After 96 hours a mean of 44% of the radio-activity was excreted. Tritium exchange was observed both in plasma and urine. Following freeze-drying, the mean loss of radioactivity 96 hours after dosing was 87% and 37% in plasma and urine, respectively

Joint FAO/WHO Expert Committee on Food Additives; WHO Food Additive Series 33: Toxicological Evaluation of Ceratain Veterinary Drug Residues in Food: Dexamethasone (1994). Available from, as of November 6, 2007: https://www.inchem.org/documents/jecfa/jecmono/v33je09.htm


Male Wistar albino rats were administered 0.23 umol (1,2-3H) dexamethasone/kg bw, ip. Urine and feces were collected up to 4 days after treatment. Within 96 hours 74% of the dose was excreted, 30% in the urine and 44% in the feces

Joint FAO/WHO Expert Committee on Food Additives; WHO Food Additive Series 33: Toxicological Evaluation of Ceratain Veterinary Drug Residues in Food: Dexamethasone (1994). Available from, as of November 6, 2007: https://www.inchem.org/documents/jecfa/jecmono/v33je09.htm


For more Absorption, Distribution and Excretion (Complete) data for DEXAMETHASONE (11 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Dexamethasone is 6-hydroxylated by CYP3A4 to 6- and 6-hydroxydexamethasone. Dexamethasone is reversibly metabolized to 11-dehydrodexamethasone by corticosteroid 11-beta-dehydrogenase isozyme 2 and can also be converted back to dexamethasone by Corticosteroid 11-beta-dehydrogenase isozyme 1.


Male Wistar albino rats were administered (3)H-dexamethasone orally at a dose of 1.14 nmol/kg bw. Thirty-one percent of the administered radioactivity was excreted in the urine within 4 days (most of it within the first 24 hours) as unconjugated metabolites. Unchanged dexamethasone accounted for 14%, 6-hydroxydexamethasone for 7.4%, and 20-dihydrodexamethasone for 1.1% of the urine radioactivity.

Joint FAO/WHO Expert Committee on Food Additives; WHO Food Additive Series 33: Toxicological Evaluation of Ceratain Veterinary Drug Residues in Food: Dexamethasone (1994). Available from, as of November 6, 2007: https://www.inchem.org/documents/jecfa/jecmono/v33je09.htm


In the urine of rats administered 0.23 umol/kg bw (1,2-3H)- dexamethasone ip, 10% of the administered radioactivity was associated with one polar metabolite of dexamethasone, likely to be 6-hydroxy-dexamethasone

Joint FAO/WHO Expert Committee on Food Additives; WHO Food Additive Series 33: Toxicological Evaluation of Ceratain Veterinary Drug Residues in Food: Dexamethasone (1994). Available from, as of November 6, 2007: https://www.inchem.org/documents/jecfa/jecmono/v33je09.htm


No parent compound could be detected in urine of patients after oral administration of a small dose of dexamethasone (<4 mg/day) for a few weeks. However, 60% was recovered as 6-beta-hydroxy-dexamethasone and 5-10% as 6-beta-hydroxy-20-dihydrodexamethasone. After the administration of about 15 mg dexamethasone/day metabolism occurred by an additional route involving epoxidation and subsequent hydrolysis, resulting in glycol formation in ring A

Joint FAO/WHO Expert Committee on Food Additives; WHO Food Additive Series 33: Toxicological Evaluation of Ceratain Veterinary Drug Residues in Food: Dexamethasone (1994). Available from, as of November 6, 2007: https://www.inchem.org/documents/jecfa/jecmono/v33je09.htm


Dexamethasone has known human metabolites that include 6-alpha-OH DEXAMETHASONE and 6-beta-OH DEXAMETHASONE.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

The mean terminal half life of a 20mg oral tablet is 4 hours. A 1.5mg oral dose of dexamethasone has a half life of 6.64.3h, while a 3mg intramuscular dose has a half life of 4.21.2h.


190 minutes (plasma) /Dexamethasone sodium phosphate/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 898


Dogs (mixed-breed) were administered dexamethasone alcohol or dexamethasone 21-isonicotinate as a solution iv or im (1 mg/kg bw), or dexamethasone 21-isonicotinate as a suspension im (0.1 or 1 mg/kg bw). Plasma concentrations were determined with HPLC up to 120 hours after treatment. The elimination half-life after iv administration was 120-140 minutes for both formulations.

Joint FAO/WHO Expert Committee on Food Additives; WHO Food Additive Series 33: Toxicological Evaluation of Ceratain Veterinary Drug Residues in Food: Dexamethasone (1994). Available from, as of November 6, 2007: https://www.inchem.org/documents/jecfa/jecmono/v33je09.htm


5.8 Mechanism of Action

The short term effects of corticosteroids are decreased vasodilation and permeability of capillaries, as well as decreased leukocyte migration to sites of inflammation. Corticosteroids binding to the glucocorticoid receptor mediates changes in gene expression that lead to multiple downstream effects over hours to days. Glucocorticoids inhibit neutrophil apoptosis and demargination; they inhibit phospholipase A2, which decreases the formation of arachidonic acid derivatives; they inhibit NF-Kappa B and other inflammatory transcription factors; they promote anti-inflammatory genes like interleukin-10. Lower doses of corticosteroids provide an anti-inflammatory effect, while higher doses are immunosuppressive. High doses of glucocorticoids for an extended period bind to the mineralocorticoid receptor, raising sodium levels and decreasing potassium levels.


Corticosteroids diffuse across cell membranes and complex with specific cytoplasmic receptors. These complexes then enter the cell nucleus, bind to DNA, and stimulate transcription of mRNA and subsequent protein synthesis of enzymes ultimately responsible for anti-inflammatory effects of topical application of corticosteroids to the eye. In high concentrations which may be achieved after topical application, corticosteroids may exert direct membrane effects. Corticosteroids decrease cellular and fibrinous exudation and tissue infiltration, inhibit fibroblastic and collagen-forming activity, retard epithelial regeneration, diminish postinflammatory neovascularization and reduce toward normal levels the excessive permeability of inflamed capillaries. /Corticosteroids (Otic)/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 911


Glucocorticoids are capable of suppressing the inflammatory process through numerous pathways. They interact with specific intracellular receptor proteins in target tissues to alter the expression of corticosteroid-responsive genes. Glucocorticoid-specific receptors in the cell cytoplasm bind with steroid ligands to form hormone-receptor complexes that eventually translocate to the cell nucleus. There these complexes bind to specific DNA sequences and alter their expression. The complexes may induce the transcription of mRNA leading to synthesis of new proteins. Such proteins include lipocortin, a protein known to inhibit PLA2a and thereby block the synthesis of prostaglandins, leukotrienes, and PAF. Glucocorticoids also inhibit the production of other mediators including AA metabolites such as COX, cytokines, the interleukins, adhesion molecules, and enzymes such as collagenase. /Glucocorticoids/

Kahn, C.M. (Ed.); The Merck Veterinary Manual 9th ed. Merck & Co. Whitehouse Station, NJ. 2005, p. 2128


Corticosteroids diffuse across cell membranes and complex with specific cytoplasmic receptors. These complexes then enter the cell nucleus, bind to DNA (chromatin), and stimulate transcription of messenger RNA (mRNA) and subsequent protein synthesis of various inhibitory enzymes responsible for the anti-inflammatory effects of topical corticosteroids. These anti-inflammatory effects include inhibition of early processes such as edema, fibrin deposition, capillary dilatation, movement of phagocttes into the area, and phagocytic activities. Later processes, such as capillary production, collagen deposition, and keloid formation also are inhibited by corticosteroids. The overall actions of topical corticosteroids are catabolic. /Corticosteroids (topical)/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 919


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