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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H32FO9S.Na
Molecular Weight 598.612
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXAMETHASONE SODIUM METASULFOBENZOATE

SMILES

[Na+].[H][C@@]12C[C@@H](C)[C@](O)(C(=O)COC(=O)C3=CC(=CC=C3)S([O-])(=O)=O)[C@@]1(C)C[C@H](O)[C@@]4(F)[C@@]2([H])CCC5=CC(=O)C=C[C@]45C

InChI

InChIKey=RPBJOYICBFNIMN-RDWMNNCQSA-M
InChI=1S/C29H33FO9S.Na/c1-16-11-22-21-8-7-18-13-19(31)9-10-26(18,2)28(21,30)23(32)14-27(22,3)29(16,35)24(33)15-39-25(34)17-5-4-6-20(12-17)40(36,37)38;/h4-6,9-10,12-13,16,21-23,32,35H,7-8,11,14-15H2,1-3H3,(H,36,37,38);/q;+1/p-1/t16-,21+,22+,23+,26+,27+,28+,29+;/m1./s1

HIDE SMILES / InChI

Molecular Formula C29H32FO9S
Molecular Weight 575.622
Charge -1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Dexamethasone acetate (NEOFORDEX®) is the acetate salt form of dexamethasone, which is a synthetic glucocorticoid; it combines high anti-inflammatory effects with low mineralocorticoid activity. At high doses (e.g. 40 mg), it reduces the immune response. Dexamethasone acetate (NEOFORDEX®) is indicated in adults for the treatment of symptomatic multiple myeloma in combination with other medicinal products. Dexamethasone has been shown to induce multiple myeloma cell death (apoptosis) via a down-regulation of nuclear factor-κB activity and an activation of caspase-9 through second mitochondria-derived activator of caspase (Smac; an apoptosis promoting factor) release. Prolonged exposure was required to achieve maximum levels of apoptotic markers along with increased caspase-3 activation and DNA fragmentation. Dexamethasone also down-regulated anti apoptotic genes and increased IκB-alpha protein levels. Dexamethasone apoptotic activity is enhanced by the combination with thalidomide or its analogues and with proteasome inhibitor (e.g. bortezomib).

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
4.6 nM [Kd]
3.7 nM [Kd]
0.73 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MAXIDEX
Primary
MAXIDEX
Primary
MAXIDEX
Primary
MAXIDEX
Primary
MAXIDEX
Primary
MAXIDEX
Primary
MAXIDEX
Primary
MAXIDEX
Primary
Neofordex

Cmax

ValueDoseCo-administeredAnalytePopulation
9.87 ng/mL
2 mg single, oral
DEXAMETHASONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
51.2 ng × h/mL
2 mg single, oral
DEXAMETHASONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.93 h
2 mg single, oral
DEXAMETHASONE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
30%
DEXAMETHASONE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
One or two drops topically in the conjunctival sac(s). In severe disease, drops may be used hourly. In mild disease, drops may be used up to four to six times daily.
Route of Administration: Other
In Vitro Use Guide
Caco-2 cells were treated with 1 μM dexamethasone and SGK1 mRNA levels were determined by Northern blot analysis. Figure 1A shows that dexamethasone rapidly induced SGK1 mRNA expression as early as 30 min and maintained the elevated expression for at least 24 h.
Substance Class Chemical
Record UNII
4T1RAI19H8
Record Status Validated (UNII)
Record Version