Identification
NameOxeladin
Accession NumberDB04822
TypeSmall Molecule
GroupsWithdrawn
Description

Withdrawn from the Canadian, US, and UK markets in 1976 due to carcinogenicity.

Structure
Thumb
Synonyms
2-(2-Diethylaminoethoxy)ethyl 2-ethyl-2-phenylbutyrate
Oxeladina
Oxeladine
Oxeladinum
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Oxeladin citrate5AEV5C340C 52432-72-1KVKJFNUGVOFNGU-UHFFFAOYSA-NDetails
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIISNC1080T5Y
CAS number468-61-1
WeightAverage: 335.4809
Monoisotopic: 335.246043927
Chemical FormulaC20H33NO3
InChI KeyIQADUMSPOQKAAO-UHFFFAOYSA-N
InChI
InChI=1S/C20H33NO3/c1-5-20(6-2,18-12-10-9-11-13-18)19(22)24-17-16-23-15-14-21(7-3)8-4/h9-13H,5-8,14-17H2,1-4H3
IUPAC Name
2-[2-(diethylamino)ethoxy]ethyl 2-ethyl-2-phenylbutanoate
SMILES
CCN(CC)CCOCCOC(=O)C(CC)(CC)C1=CC=CC=C1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesR05DB09 — Oxeladin
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)< 25 °CPhysProp
boiling point (°C)150 °C at 5.00E-01 mm HgPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0158 mg/mLALOGPS
logP4.62ALOGPS
logP4.43ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)9.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.77 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity98.97 m3·mol-1ChemAxon
Polarizability39.35 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9847
Blood Brain Barrier+0.9363
Caco-2 permeable+0.6538
P-glycoprotein substrateSubstrate0.6697
P-glycoprotein inhibitor INon-inhibitor0.6281
P-glycoprotein inhibitor IINon-inhibitor0.8685
Renal organic cation transporterNon-inhibitor0.6358
CYP450 2C9 substrateNon-substrate0.8558
CYP450 2D6 substrateNon-substrate0.889
CYP450 3A4 substrateNon-substrate0.5098
CYP450 1A2 substrateNon-inhibitor0.6155
CYP450 2C9 inhibitorNon-inhibitor0.9244
CYP450 2D6 inhibitorInhibitor0.9174
CYP450 2C19 inhibitorNon-inhibitor0.829
CYP450 3A4 inhibitorInhibitor0.677
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6412
Ames testNon AMES toxic0.8367
CarcinogenicityNon-carcinogens0.5665
BiodegradationNot ready biodegradable0.9781
Rat acute toxicity3.2320 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9043
hERG inhibition (predictor II)Inhibitor0.6033
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentPhenylpropanes
Alternative ParentsFatty acid esters / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Dialkyl ethers / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
SubstituentsPhenylpropane / Fatty acid ester / Fatty acyl / Amino acid or derivatives / Carboxylic acid ester / Tertiary amine / Tertiary aliphatic amine / Monocarboxylic acid or derivatives / Ether / Dialkyl ether
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Drug created on September 11, 2007 14:25 / Updated on June 11, 2017 20:59