U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

[H][C@@]12CC[C@](OC(=O)C(Cl)Cl)(C(=O)OCC)[C@@]1(C)C[C@H](O)[C@@]3([H])[C@@]2([H])CCC4=CC(=O)C=C[C@]34C

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
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12893841 | https://www.ncbi.nlm.nih.gov/pubmed/15212312 | http://adisinsight.springer.com/drugs/800016206

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

Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/12893841

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Potency and specificity of the pharmacological action of a new, antiasthmatic, topically administered soft steroid, etiprednol dicloacetate (BNP-166).
2003 Oct
Anti-inflammatory effect and soft properties of etiprednol dicloacetate (BNP-166), a new, anti-asthmatic steroid.
2004 May
Corticosteroid design for the treatment of asthma: structural insights and the therapeutic potential of soft corticosteroids.
2006
Patents

Sample Use Guides

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
Curator's Comment: Etiprednol dicloacetate effectively decreased cytokine production in lipopolysaccharide stimulated lymphocytes and attenuated lectin-induced proliferation of blood mononuclear cells in tissue culture.
Unknown
Name Type Language
ETIPREDNOL DICLOACETATE
INN   MI   USAN  
INN   USAN  
Official Name English
Etiprednol dicloacetate [WHO-DD]
Common Name English
Ethyl 17-[(dichloroacetyl)oxy]-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylate
Common Name English
ETIPREDNOL DICLOACETATE [MI]
Common Name English
etiprednol dicloacetate [INN]
Common Name English
ETIPREDNOL DICLOACETATE [USAN]
Common Name English
ANDROSTA-1,4-DIENE-17-CARBOXYLIC ACID, 17-((DICHLOROACETYL)OXY)-11-HYDROXY-3-OXO-, ETHYL ESTER, (11.BETA.,17.ALPHA.)-
Common Name English
BNP-166
Code English
Classification Tree Code System Code
NCI_THESAURUS C521
Created by admin on Fri Dec 15 15:28:45 GMT 2023 , Edited by admin on Fri Dec 15 15:28:45 GMT 2023
Code System Code Type Description
USAN
OO-37
Created by admin on Fri Dec 15 15:28:45 GMT 2023 , Edited by admin on Fri Dec 15 15:28:45 GMT 2023
PRIMARY
CAS
199331-40-3
Created by admin on Fri Dec 15 15:28:45 GMT 2023 , Edited by admin on Fri Dec 15 15:28:45 GMT 2023
PRIMARY
NCI_THESAURUS
C80816
Created by admin on Fri Dec 15 15:28:45 GMT 2023 , Edited by admin on Fri Dec 15 15:28:45 GMT 2023
PRIMARY
FDA UNII
332VLD554F
Created by admin on Fri Dec 15 15:28:45 GMT 2023 , Edited by admin on Fri Dec 15 15:28:45 GMT 2023
PRIMARY
MERCK INDEX
m1141
Created by admin on Fri Dec 15 15:28:45 GMT 2023 , Edited by admin on Fri Dec 15 15:28:45 GMT 2023
PRIMARY Merck Index
INN
8329
Created by admin on Fri Dec 15 15:28:45 GMT 2023 , Edited by admin on Fri Dec 15 15:28:45 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107614
Created by admin on Fri Dec 15 15:28:45 GMT 2023 , Edited by admin on Fri Dec 15 15:28:45 GMT 2023
PRIMARY
SMS_ID
300000034134
Created by admin on Fri Dec 15 15:28:45 GMT 2023 , Edited by admin on Fri Dec 15 15:28:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID401313806
Created by admin on Fri Dec 15 15:28:45 GMT 2023 , Edited by admin on Fri Dec 15 15:28:45 GMT 2023
PRIMARY
PUBCHEM
9935073
Created by admin on Fri Dec 15 15:28:45 GMT 2023 , Edited by admin on Fri Dec 15 15:28:45 GMT 2023
PRIMARY
DRUG CENTRAL
3209
Created by admin on Fri Dec 15 15:28:45 GMT 2023 , Edited by admin on Fri Dec 15 15:28:45 GMT 2023
PRIMARY
DRUG BANK
DB05442
Created by admin on Fri Dec 15 15:28:45 GMT 2023 , Edited by admin on Fri Dec 15 15:28:45 GMT 2023
PRIMARY