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Identification
NameOxeladin
Accession NumberDB04822
TypeSmall Molecule
GroupsWithdrawn
Description

Withdrawn from the Canadian, US, and UK markets in 1976 due to carcinogenicity.

Structure
Thumb
Synonyms
SynonymLanguageCode
2-(2-Diethylaminoethoxy)ethyl 2-ethyl-2-phenylbutyrateNot AvailableNot Available
OxeladinaSpanishINN
OxeladineFrenchINN
OxeladinumLatinINN
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Phenylpropane
  • Fatty acid ester
  • Fatty acyl
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
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
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.9244
CYP450 2D6 substrateInhibitor0.9174
CYP450 2C19 substrateNon-inhibitor0.829
CYP450 3A4 substrateInhibitor0.677
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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point< 25 °CPhysProp
boiling point150 °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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on September 11, 2007 14:25 / Updated on September 16, 2013 17:25