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Identification
NamePhenacemide
Accession NumberDB01121  (APRD00089)
Typesmall molecule
Groupsapproved
Description

Phenacemide is used to control certain seizures in the treatment of epilepsy. This medicine acts on the central nervous system (CNS) to reduce the number and severity of seizures.

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand names
NameCompany
PhenuroneNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number63-98-9
WeightAverage: 178.1879
Monoisotopic: 178.074227574
Chemical FormulaC9H10N2O2
InChI KeyInChIKey=XPFRXWCVYUEORT-UHFFFAOYSA-N
InChI
InChI=1S/C9H10N2O2/c10-9(13)11-8(12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H3,10,11,12,13)
IUPAC Name
(2-phenylacetyl)urea
SMILES
NC(=O)NC(=O)CC1=CC=CC=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassOrganic Carbonic Acids and Derivatives
SubclassUreas
Direct parentN-Acyl Ureas
Alternative parentsBenzene and Substituted Derivatives; N-unsubstituted Carboxylic Acid Imides; Secondary Carboxylic Acid Amides; Enolates; Carboxylic Acids; Polyamines
Substituentsbenzene; carboxylic acid imide, n-unsubstituted; secondary carboxylic acid amide; carboxamide group; carboxylic acid derivative; enolate; polyamine; carboxylic acid; amine; organonitrogen compound
Classification descriptionThis compound belongs to the n-acyl ureas. These are compounds containing an urea bearing a N-acyl group.
Pharmacology
IndicationUsed to control certain seizures in the treatment of epilepsy.
PharmacodynamicsPhenacemide is a ureal anticonvulsant indicated for control of severe epilepsy, particularly mixed forms of complex partial (psychomotor or temporal lobe) seizures, refractory to other anticonvulsants. Phenacemide elevates the threshold for minimal electroshock convulsions and abolishes the tonic phase of maximal electroshock seizures. It also prevents or modifies seizures induced by pentylenetetrazol or other convulsants.
Mechanism of actionPhenacemide binds to and blocks neuronal sodium channels or voltage sensitive calcium channels. This blocks or suppresses neuronal depolarization and hypersynchronization. Hypersynchronization is what often causes seizures.
AbsorptionAlmost completely absorbed.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Metabolized in the liver by hepatic microsomal enzymes, where it is inactivated by p-hydroxylation.

Route of eliminationNot Available
Half life22-25 hours.
ClearanceNot Available
ToxicityOral, mouse: LD50 = 987 mg/kg; Oral, rabbit: LD50 = 2500 mg/kg; Oral, rat: LD50 = 1600 mg/kg
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9401
Blood Brain Barrier + 0.9935
Caco-2 permeable - 0.6496
P-glycoprotein substrate Non-substrate 0.7351
P-glycoprotein inhibitor I Non-inhibitor 0.9376
P-glycoprotein inhibitor II Non-inhibitor 0.9913
Renal organic cation transporter Non-inhibitor 0.8761
CYP450 2C9 substrate Non-substrate 0.7678
CYP450 2D6 substrate Non-substrate 0.7784
CYP450 3A4 substrate Non-substrate 0.8055
CYP450 1A2 substrate Non-inhibitor 0.7929
CYP450 2C9 substrate Non-inhibitor 0.8962
CYP450 2D6 substrate Non-inhibitor 0.942
CYP450 2C19 substrate Non-inhibitor 0.9183
CYP450 3A4 substrate Non-inhibitor 0.9088
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9183
Ames test Non AMES toxic 0.8748
Carcinogenicity Non-carcinogens 0.799
Biodegradation Ready biodegradable 0.8039
Rat acute toxicity 2.0779 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9546
hERG inhibition (predictor II) Non-inhibitor 0.9759
Pharmacoeconomics
Manufacturers
  • Abbott laboratories pharmaceutical products div
PackagersNot Available
Dosage forms
FormRouteStrength
TabletOral
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point215 °CPhysProp
water solubility10.2 g/LNot Available
logP0.87HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility1.06e+00 g/lALOGPS
logP0.81ALOGPS
logP0.46ChemAxon
logS-2.2ALOGPS
pKa (strongest acidic)11.75ChemAxon
pKa (strongest basic)-7.8ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count2ChemAxon
polar surface area72.19ChemAxon
rotatable bond count2ChemAxon
refractivity47.43ChemAxon
polarizability17.49ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Coker SB: The use of phenacemide for intractable partial complex epilepsy in children. Pediatr Neurol. 1986 Jul-Aug;2(4):230-2. Pubmed
  2. Coker SB, Holmes EW, Egel RT: Phenacemide therapy of complex partial epilepsy in children: determination of plasma drug concentrations. Neurology. 1987 Dec;37(12):1861-6. Pubmed
External Links
ResourceLink
KEGG DrugD00504
KEGG CompoundC07428
PubChem Compound4753
PubChem Substance46508400
ChemSpider4589
Therapeutic Targets DatabaseDAP000501
PharmGKBPA164745309
WikipediaPhenacemide
ATC CodesN03AX07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(72.7 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Sodium channel protein type 1 subunit alpha

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium channel protein type 1 subunit alpha P35498 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Wong MG, Defina JA, Andrews PR: Conformational analysis of clinically active anticonvulsant drugs. J Med Chem. 1986 Apr;29(4):562-72. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on January 10, 2014 11:44