Etiprednol dicloacetate

Identification

Name
Etiprednol dicloacetate
Accession Number
DB05442
Description

Etiprednol dicloacetate (BNP-166) is a soft corticosteroid with anti-inflammatory properties that has been indicated in the treatment of asthma and Chron's disease. Anti-asthmatic effects were associated with decreased cytokine production in lipopolysaccharide-stimulated lymphocytes and attenuated lectin-induced proliferation of blood mononuclear cells in tissue culture.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 485.4
Monoisotopic: 484.1419441
Chemical Formula
C24H30Cl2O6
Synonyms
Not Available
External IDs
  • BNP-166

Pharmacology

Indication

Investigated for use/treatment in asthma and crohn's disease.

Contraindications & Blackbox Warnings
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Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UInterleukin-1 betaNot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half-life
Not Available
Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid esters
Direct Parent
Steroid esters
Alternative Parents
Androgens and derivatives / 3-oxo delta-1,4-steroids / 11-beta-hydroxysteroids / Delta-1,4-steroids / Dicarboxylic acids and derivatives / Alpha-halocarboxylic acid derivatives / Secondary alcohols / Cyclic ketones / Cyclic alcohols and derivatives / Carboxylic acid esters
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Substituents
11-beta-hydroxysteroid / 11-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Alkyl chloride / Alkyl halide / Alpha-halocarboxylic acid derivative / Alpha-halocarboxylic acid or derivatives
show 20 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
332VLD554F
CAS number
199331-40-3
InChI Key
QAIOVDNCIZSSSF-RFAJLIJZSA-N
InChI
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
IUPAC Name
ethyl (1S,2R,10S,11S,14R,15S,17S)-14-[(2,2-dichloroacetyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-14-carboxylate
SMILES
[H][[email protected]@]12CC[[email protected]](OC(=O)C(Cl)Cl)(C(=O)OCC)[[email protected]@]1(C)C[[email protected]](O)[[email protected]@]1([H])[[email protected]@]2([H])CCC2=CC(=O)C=C[[email protected]]12C

References

General References
  1. Kurucz I, Nemeth K, Meszaros S, Torok K, Nagy Z, Zubovics Z, Horvath K, Bodor N: Anti-inflammatory effect and soft properties of etiprednol dicloacetate (BNP-166), a new, anti-asthmatic steroid. Pharmazie. 2004 May;59(5):412-6. [PubMed:15212312]
  2. Patthy M, Seres G, Csanadi A, Szekeres T, Zubovics Z, Bodor N: HPLC separation of related impurities in etiprednol dicloacetate, a novel soft corticosteroid. Pharmazie. 2004 May;59(5):382-6. [PubMed:15212306]
  3. Csanadi A, Horvath G, Szekeres T, Hasko T, Ila L, Ivanics J, Patthy M, Salat J, Seres G, Pallagi I, Toth G, Szederkenyi F, Konya A, Tegdes A, Bodor N, Zubovics Z: Etiprednol dicloacetate, a new soft glucocorticoid drug candidate. Development of chemistry. Pharmazie. 2004 May;59(5):349-59. [PubMed:15212300]
  4. Kurucz I, Toth S, Nemeth K, Torok K, Csillik-Perczel V, Pataki A, Salamon C, Nagy Z, Szekely JI, Horvath K, Bodor N: Potency and specificity of the pharmacological action of a new, antiasthmatic, topically administered soft steroid, etiprednol dicloacetate (BNP-166). J Pharmacol Exp Ther. 2003 Oct;307(1):83-92. Epub 2003 Jul 31. [PubMed:12893841]
  5. Miklos A, Magyar Z, Kiss E, Novak I, Grosz M, Nyitray M, Dereszlay I, Czegeni E, Druga A, Howes J, Bodor N: 28-day oral toxicity study with soft corticosteroid BNP-166 in rats and dogs, followed by a 14-day recovery period. Pharmazie. 2002 Feb;57(2):142-6. [PubMed:11878192]
PubChem Compound
9935073
PubChem Substance
175427004
ChemSpider
8110701
ChEBI
135783
ChEMBL
CHEMBL2107614
ZINC
ZINC000003979944

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentCrohn's Disease (CD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00235 mg/mLALOGPS
logP3.49ALOGPS
logP3.99ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)14.88ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area89.9 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity121.88 m3·mol-1ChemAxon
Polarizability49.4 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9951
Blood Brain Barrier+0.978
Caco-2 permeable+0.5984
P-glycoprotein substrateSubstrate0.7263
P-glycoprotein inhibitor IInhibitor0.6481
P-glycoprotein inhibitor IINon-inhibitor0.5444
Renal organic cation transporterNon-inhibitor0.7913
CYP450 2C9 substrateNon-substrate0.8263
CYP450 2D6 substrateNon-substrate0.919
CYP450 3A4 substrateSubstrate0.8081
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.8686
CYP450 2D6 inhibitorNon-inhibitor0.6692
CYP450 2C19 inhibitorNon-inhibitor0.9045
CYP450 3A4 inhibitorNon-inhibitor0.6965
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8271
Ames testNon AMES toxic0.9405
CarcinogenicityNon-carcinogens0.9161
BiodegradationNot ready biodegradable0.9892
Rat acute toxicity1.9813 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9712
hERG inhibition (predictor II)Non-inhibitor0.5293
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein domain specific binding
Specific Function
Potent proinflammatory cytokine. Initially discovered as the major endogenous pyrogen, induces prostaglandin synthesis, neutrophil influx and activation, T-cell activation and cytokine production, ...
Gene Name
IL1B
Uniprot ID
P01584
Uniprot Name
Interleukin-1 beta
Molecular Weight
30747.7 Da

Drug created on November 18, 2007 11:25 / Updated on June 12, 2020 10:52

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