ETIPREDNOL DICLOACETATE

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 Search

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
Sources: https://www.google.us/patents/US5981517
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
inflammatory response 47 Target ID: GO:0006954 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15212312	Inhibitor 8297
Glucocorticoid receptor 172 Target ID: CHEMBL3368 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12893841 \| https://www.google.us/patents/US5981517	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Crohn's disease 42 Sources: http://adisinsight.springer.com/drugs/800016206	Primary	Phase II 1132	Unknown Approved Use Unknown
Asthma 241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12893841 https://www.ncbi.nlm.nih.gov/pubmed/17020532	Primary	Phase II 1132	Unknown Approved Use Unknown
Allergic rhinitis 100 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17020532	Primary	Phase I 428	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
Compound Cloud	9935073

PubMed

Title	Date	PubMed
Potency and specificity of the pharmacological action of a new, antiasthmatic, topically administered soft steroid, etiprednol dicloacetate (BNP-166).	2003 Oct	12893841
Anti-inflammatory effect and soft properties of etiprednol dicloacetate (BNP-166), a new, anti-asthmatic steroid.	2004 May	15212312
Corticosteroid design for the treatment of asthma: structural insights and the therapeutic potential of soft corticosteroids.	2006	17020532

Patents

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

Name

Type

Language

ETIPREDNOL DICLOACETATE

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