DEX

DEXAMETHASONE

Created:2002-07-19
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count57
Chiral Atom Count8
Bond Count60
Aromatic Bond Count0
2D diagram of DEX
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Chemical Component Summary

NameDEXAMETHASONE
Synonyms9A-FLUORO-16BETA-METHYLPREDNISOLONE
Systematic Name (OpenEye OEToolkits)(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyethanoyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
FormulaC22 H29 F O5
Molecular Weight392.461
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs10.04O=C(CO)C3(O)C2(CC(O)C4(F)C1(C(=CC(=O)C=C1)CCC4C2CC3C)C)C
SMILESCACTVS3.341C[CH]1C[CH]2[CH]3CCC4=CC(=O)C=C[C]4(C)[C]3(F)[CH](O)C[C]2(C)[C]1(O)C(=O)CO
SMILESOpenEye OEToolkits1.5.0CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)CO)O)C)O)F)C
Canonical SMILESCACTVS3.341 C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO
Canonical SMILESOpenEye OEToolkits1.5.0 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
InChIInChI1.03 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
InChIKeyInChI1.03 UREBDLICKHMUKA-CXSFZGCWSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank IDDB01234 
NameDexamethasone
Groups
  • investigational
  • vet_approved
  • approved
DescriptionDexamethasone, or MK-125, is a corticosteroid fluorinated at position 9 used to treat endocrine, rheumatic, collagen, dermatologic, allergic, ophthalmic, gastrointestinal, respiratory, hematologic, neoplastic, edematous, and other conditions.[L10701] Developed in 1957, it is structurally similar to other corticosteroids like [hydrocortisone] and [prednisolone].[A188724] Dexamethasone was granted FDA approval on 30 October 1958.[L10695] In a press release for the Randomized Evaluation of COVID-19 Therapy (RECOVERY) trial on 16 June 2020, dexamethasone was recommended for use in COVID-19 patients with severe respiratory symptoms. Dexamethasone reduced deaths by approximately one third in patients requiring ventilation and by one fifth in those requiring oxygen.[L14318]
Synonyms
  • 1-Dehydro-16α-methyl-9α-fluorohydrocortisone
  • 16α-Methyl-9α-fluoro-1-dehydrocortisol
  • Dexaméthasone
  • Dexamethasone phosphate
  • Dexametasona
Brand Names
  • Dexamethasone Sod Phosph Inj 10mg/ml USP
  • Dexamethasone Sod Phos Inj 4mg/ml
  • Maxidex
  • PMS-dexamethasone Sod Phosphate Dps 1mg/ml
  • Neomycin Sulfate, Polymyxin B Sulfate and Dexamethasone
IndicationDexamethasone and [ciprofloxacin] otic suspension is indicated for bacterial infections with inflammation in acute otitis media and acute otitis externa.[L10698] Intramuscular and intravenous injections are indicated for a number of endocrine, rheumatic, collagen, dermatologic, allergic, ophthalmic, gastrointestinal, respiratory, hematologic, neoplastic, edematous, and other conditions.[L10701] Oral tablets are indicated for the treatment of multiple myeloma.[L10710] An intravitreal implant is indicated for some forms of macular edema and non-infectious posterior uveitis affecting the posterior of the eye.[L10719] Various ophthalmic formulations are indicated for inflammatory conditions of the eye.[L10704,L10707,L10713,L10716,L10722,L10725]
Categories
  • Adrenal Cortex Hormones
  • Adrenals
  • Agents Causing Muscle Toxicity
  • Agents for Treatment of Hemorrhoids and Anal Fissures for Topical Use
  • Alimentary Tract and Metabolism
ATC-Code
  • R01AD53
  • D07XB05
  • R01AD03
  • D10AA03
  • S01CB01
CAS number50-02-2

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
NameTarget SequencePharmacological ActionActions
Glucocorticoid receptorMDSKESLTPGREENPSSVLAQERGDVMDFYKTLRGGATVKVSASSPSLAV...unknownagonist
Nuclear receptor subfamily 0 group B member 1MAGENHQWQGSILYNMLMSAKQTRAAPEAPETRLVDQCWGCSCGDEPGVG...unknownstimulator
Annexin A1MAMVSEFLKQAWFIENEEQEYVQTVKSSKGGPGSAVSPYPTFNPSSDVAA...unknownagonist
Nitric oxide synthase, inducibleMACPWKFLFKTKFHQYAMNGEKDINNNVEKAPCATSSPVTQDDLQYHNLS...unknownnegative modulator
Nuclear receptor subfamily 1 group I member 2MEVRPKESWNHADFVHCEDTESVPGKPSVNADEEVGGPQICRVCGDKATG...unknownagonist
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL384467
PubChem 5743
ChEMBL CHEMBL384467
ChEBI CHEBI:41879
CCDC/CSD DEXMET11, DEXMET10, BEGKUX01, HAYBAO, HAYBAO01, BEGKUX, DEXMET12
COD 2213772, 7245187, 7245188