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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Withdrawn from the Canadian, US, and UK markets in 1963 due to nephropathy.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
SaltsNot Available
Brand names
NameCompany
BunamijodylumNot Available
BuniodylNot Available
Brand mixturesNot 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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassPhenylpropanoids and Polyketides
ClassCinnamic Acids and Derivatives
SubclassCinnamic Acids
Direct parentCinnamic Acids
Alternative parentsAnilides; Phenylpropenes; Iodobenzenes; Aryl Iodides; Enones; Secondary Carboxylic Acid Amides; Enolates; Carboxylic Acids; Polyamines; Organoiodides
Substituentsacetanilide; phenylpropene; iodobenzene; benzene; aryl halide; aryl iodide; enone; secondary carboxylic acid amide; carboxamide group; polyamine; carboxylic acid derivative; enolate; carboxylic acid; organoiodide; organohalogen; amine; organonitrogen compound
Classification descriptionThis compound belongs to the cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
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
Property Value Probability
Human Intestinal Absorption + 0.9091
Blood Brain Barrier + 0.853
Caco-2 permeable + 0.5295
P-glycoprotein substrate Non-substrate 0.5625
P-glycoprotein inhibitor I Non-inhibitor 0.798
P-glycoprotein inhibitor II Non-inhibitor 0.978
Renal organic cation transporter Non-inhibitor 0.9513
CYP450 2C9 substrate Non-substrate 0.8522
CYP450 2D6 substrate Non-substrate 0.8424
CYP450 3A4 substrate Substrate 0.5205
CYP450 1A2 substrate Non-inhibitor 0.6493
CYP450 2C9 substrate Non-inhibitor 0.6529
CYP450 2D6 substrate Non-inhibitor 0.8545
CYP450 2C19 substrate Non-inhibitor 0.6789
CYP450 3A4 substrate Non-inhibitor 0.8903
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7281
Ames test Non AMES toxic 0.7757
Carcinogenicity Non-carcinogens 0.8419
Biodegradation Not ready biodegradable 0.9034
Rat acute toxicity 2.2704 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9691
hERG inhibition (predictor II) Non-inhibitor 0.8973
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility2.30e-03 g/lALOGPS
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 area66.4ChemAxon
rotatable bond count6ChemAxon
refractivity116.2ChemAxon
polarizability43.5ChemAxon
number of rings1ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound6436657
PubChem Substance46504825
ChemSpider4941281
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