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Identification
Name2-CHLORO-4-[(7R,7AS)-7-HYDROXY-1,3-DIOXOTETRAHYDRO-1H-PYRROLO[1,2-C]IMIDAZOL-2(3H)-YL]-3-METHYLBENZONITRILE
Accession NumberDB07286
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS numberNot Available
WeightAverage: 305.716
Monoisotopic: 305.056718972
Chemical FormulaC14H12ClN3O3
InChI KeyKEJORAMIZFOODM-PWSUYJOCSA-N
InChI
InChI=1S/C14H12ClN3O3/c1-7-9(3-2-8(6-16)11(7)15)18-13(20)12-10(19)4-5-17(12)14(18)21/h2-3,10,12,19H,4-5H2,1H3/t10-,12+/m1/s1
IUPAC Name
4-[(7R,7aS)-7-hydroxy-1,3-dioxo-hexahydro-1H-pyrrolo[1,2-c]imidazolidin-2-yl]-2-chloro-3-methylbenzonitrile
SMILES
[H][C@@]1(O)CCN2C(=O)N(C(=O)[C@]12[H])C1=C(C)C(Cl)=C(C=C1)C#N
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentPhenylhydantoins
Alternative Parents
Substituents
  • 3-phenylhydantoin
  • Phenylimidazolidine
  • Aminotoluene
  • Benzonitrile
  • Ureide
  • Toluene
  • Halobenzene
  • Chlorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Pyrrolidine
  • Urea
  • Tertiary amine
  • Secondary alcohol
  • Carboxamide group
  • Azacycle
  • Nitrile
  • Carbonitrile
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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+1.0
Blood Brain Barrier+0.8633
Caco-2 permeable-0.5166
P-glycoprotein substrateNon-substrate0.5065
P-glycoprotein inhibitor INon-inhibitor0.754
P-glycoprotein inhibitor IINon-inhibitor0.779
Renal organic cation transporterNon-inhibitor0.8427
CYP450 2C9 substrateNon-substrate0.6876
CYP450 2D6 substrateNon-substrate0.8372
CYP450 3A4 substrateSubstrate0.5854
CYP450 1A2 substrateNon-inhibitor0.5391
CYP450 2C9 substrateNon-inhibitor0.7438
CYP450 2D6 substrateNon-inhibitor0.8775
CYP450 2C19 substrateNon-inhibitor0.6014
CYP450 3A4 substrateNon-inhibitor0.9159
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8492
Ames testNon AMES toxic0.6911
CarcinogenicityNon-carcinogens0.8544
BiodegradationNot ready biodegradable0.9747
Rat acute toxicity2.3568 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8174
hERG inhibition (predictor II)Non-inhibitor0.7634
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.09 mg/mLALOGPS
logP1ALOGPS
logP1.1ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)12.27ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area84.64 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.79 m3·mol-1ChemAxon
Polarizability29.36 Å3ChemAxon
Number of Rings3ChemAxon
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

Targets

1. Androgen receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Androgen receptor P10275 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

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Drug created on September 15, 2010 15:20 / Updated on September 16, 2013 18:06