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Identification
NameBunamiodyl
Accession NumberDB04814
TypeSmall Molecule
GroupsWithdrawn
Description

Withdrawn from the Canadian, US, and UK markets in 1963 due to nephropathy.

Structure
Thumb
Synonyms
SynonymLanguageCode
2-(3-Butyramido-3,4,6-triiodophenylmethylene)butyric acidNot AvailableNot Available
3-(3-Butylamido-2,4,6-triiodphenyl)-2-ethylacrylsaeureNot AvailableNot Available
BunamiodiloSpanishINN
BunamiodylumLatinINN
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
BunamijodylumNot Available
BuniodylNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number1233-53-0
WeightAverage: 639.0059
Monoisotopic: 638.826423643
Chemical FormulaC15H16I3NO3
InChI KeyCWRBDUIQDIHWJZ-SOFGYWHQSA-N
InChI
InChI=1S/C15H16I3NO3/c1-3-5-12(20)19-14-11(17)7-10(16)9(13(14)18)6-8(4-2)15(21)22/h6-7H,3-5H2,1-2H3,(H,19,20)(H,21,22)/b8-6+
IUPAC Name
(2E)-2-[(3-butanamido-2,4,6-triiodophenyl)methylidene]butanoic acid
SMILES
CCCC(=O)NC1=C(I)C=C(I)C(\C=C(/CC)C(O)=O)=C1I
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acids
Direct ParentCinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • N-arylamide
  • Phenylpropene
  • Iodobenzene
  • Halobenzene
  • Fatty acyl
  • Benzenoid
  • Fatty amide
  • Monocyclic benzene moiety
  • Aryl iodide
  • Aryl halide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organoiodide
  • Organohalogen compound
  • Carbonyl group
  • 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
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9091
Blood Brain Barrier+0.853
Caco-2 permeable+0.5295
P-glycoprotein substrateNon-substrate0.5625
P-glycoprotein inhibitor INon-inhibitor0.798
P-glycoprotein inhibitor IINon-inhibitor0.978
Renal organic cation transporterNon-inhibitor0.9513
CYP450 2C9 substrateNon-substrate0.8522
CYP450 2D6 substrateNon-substrate0.8424
CYP450 3A4 substrateSubstrate0.5205
CYP450 1A2 substrateNon-inhibitor0.6493
CYP450 2C9 substrateNon-inhibitor0.6529
CYP450 2D6 substrateNon-inhibitor0.8545
CYP450 2C19 substrateNon-inhibitor0.6789
CYP450 3A4 substrateNon-inhibitor0.8903
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7281
Ames testNon AMES toxic0.7757
CarcinogenicityNon-carcinogens0.8419
BiodegradationNot ready biodegradable0.9034
Rat acute toxicity2.2704 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9691
hERG inhibition (predictor II)Non-inhibitor0.8973
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0023 mg/mLALOGPS
logP4.1ALOGPS
logP6.15ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)2.37ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity116.2 m3·mol-1ChemAxon
Polarizability43.5 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
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 14:05 / Updated on September 16, 2013 17:25