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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

[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
Molecular Formula C24H30Cl2O6
Molecular Weight 485.397
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Soft Drugs
1
Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/12893841

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
Compound Cloud
9935073
PubMed

PubMed

TitleDatePubMed
Anti-inflammatory effect and soft properties of etiprednol dicloacetate (BNP-166), a new, anti-asthmatic steroid.
2004 May
Patents

Patents

US5981517
1
US9345664
1
US9616024
1

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
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:28:45 GMT 2023
Edited
by admin
on Fri Dec 15 15:28:45 GMT 2023
Record UNII
332VLD554F
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
INTERLEUKIN-1 .BETA. HUMAN
TARGET->INHIBITOR OF RELEASE
Related Record Type Details
Structure of 17-((DICHLOROACETYL)OXY)-11-HYDROXY-3-OXO-ANDROSTA-1,4-DIENE-17-CARBOXYLIC ACID, (11.BETA.,17.ALPHA.)-
METABOLITE INACTIVE -> PARENT
MAJOR
PLASMA
Structure of ETIPREDNOL
METABOLITE INACTIVE -> PARENT
ETIPREDNOL DICLOACETATE is a soft steroid hydrolysis occurs by an esterase.
MAJOR
PLASMA
Related Record Type Details
Structure of ETIPREDNOL DICLOACETATE
ACTIVE MOIETY
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