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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H30Cl2O6
Molecular Weight 485.397
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETIPREDNOL DICLOACETATE

SMILES

CCOC(=O)[C@]1(CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@]12C)OC(=O)C(Cl)Cl

InChI

InChIKey=QAIOVDNCIZSSSF-RFAJLIJZSA-N
InChI=1S/C24H30Cl2O6/c1-4-31-21(30)24(32-20(29)19(25)26)10-8-16-15-6-5-13-11-14(27)7-9-22(13,2)18(15)17(28)12-23(16,24)3/h7,9,11,15-19,28H,4-6,8,10,12H2,1-3H3/t15-,16-,17-,18+,22-,23-,24-/m0/s1

HIDE SMILES / InChI

Description

Etiprednol dicloacetate (BNP-166; ethyl-17alpha-dichloroacetoxy-11beta-hydroxyandrosta-1,4-diene-3-one-17beta-carboxylate) is a new soft steroid. The compound proved to be a dissociated glucocorticoid, showing a reduction in transactivating activity while preserving transrepressive abilities. The compound effectively decreased cytokine production in lipopolysaccharide-stimulated lymphocytes and attenuated lectin-induced proliferation of blood mononuclear cells in tissue culture. The significant local effect of the compound will very likely be accompanied by a drastically reduced systemic activity indicating an encouraging selectivity of the pharmacological action of etiprednol dicloacetate. Etiprednol dicloacetate had been in a clinical trial for the treatment of allergic rhinitis, asthma and Crohn's disease. However, development has been discontinued.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
Sensitized rats were treated intratracheally with different doses (0.1, 1, 10, and 100 g/kg) of etiprednol dicloacetate and 2 h later were challenged with ovalbumin aerosol.
Route of Administration: Intratracheal
In Vitro Use Guide
Unknown