Bunamiodyl

Identification

Name
Bunamiodyl
Accession Number
DB04814
Type
Small Molecule
Groups
Withdrawn
Description

Withdrawn from the Canadian, US, and UK markets in 1963 due to nephropathy.

Structure
Thumb
Synonyms
  • 2-(3-Butyramido-3,4,6-triiodophenylmethylene)butyric acid
  • Bunamiodilo
  • Bunamiodylum
International/Other Brands
Bunamijodylum / Buniodyl
Categories
Not Available
UNII
IX9VVF69JR
CAS number
1233-53-0
Weight
Average: 639.0059
Monoisotopic: 638.826423643
Chemical Formula
C15H16I3NO3
InChI Key
CWRBDUIQDIHWJZ-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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
6436657
PubChem Substance
46504825
ChemSpider
4941281
ChEBI
135861
ChEMBL
CHEMBL2110636

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.0023 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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.6529
CYP450 2D6 inhibitorNon-inhibitor0.8545
CYP450 2C19 inhibitorNon-inhibitor0.6789
CYP450 3A4 inhibitorNon-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
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Cinnamic acids and derivatives
Sub Class
Cinnamic acids
Direct Parent
Cinnamic acids
Alternative Parents
Anilides / N-arylamides / Iodobenzenes / Fatty amides / Aryl iodides / Secondary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organoiodides
show 3 more
Substituents
Cinnamic acid / Anilide / N-arylamide / Halobenzene / Iodobenzene / Aryl halide / Aryl iodide / Monocyclic benzene moiety / Fatty acyl / Benzenoid
show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on September 11, 2007 14:05 / Updated on October 01, 2018 13:56