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Identification
Name Phenacemide
Accession Number DB01121 (APRD00089)
Type small molecule
Groups approved
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
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Display: 2D Structure | 3D Structure
Synonyms
Carbamide phenylacetate
Phenacetylcarbamide
Phenacetylurea
Phenylacetylurea
Phenylacetyluree
Salts Not Available
Brand names
Name Company
Acetylureum
Carbanmide
Cetylureum
Comitiadone
Eferon
Efron
Epheron
Epiclase
Felurea
Fenacemid
Fenacemide
Fenacetamide
Fenacetil-Karbamide
Fenilep
Fenised
Fenostenyl
Fenural
Fenurea
Fenurone
Fenylacetylmocovina
Fenytan
Neophedan
Neophenal
Phacetur
Phenacalum
Phenacereum
Phenacetur
Phenarone
Phenicarb
Phenuron
Phenurone
Phenutal
Phenyrit
Phetylureum
First Prev Next Last
Brand mixtures Not Available
Categories
  • Anticonvulsants
CAS number 63-98-9
Weight Average: 178.1879
Monoisotopic: 178.074227574
Chemical Formula C9H10N2O2
InChI Key InChIKey=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)
Plain Text
IUPAC Name
(2-phenylacetyl)urea
SMILES
NC(=O)NC(=O)CC1=CC=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
Substructures
  • Carboxylic Acids and Derivatives
  • Amino Ketones
  • Benzene and Derivatives
  • Ureas and Derivatives
  • Carbamates and Derivatives
  • Phenethylamines
  • Aromatic compounds
  • Carboxamides and Derivatives
Pharmacology
Indication Used to control certain seizures in the treatment of epilepsy.
Pharmacodynamics Phenacemide 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 action Phenacemide 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.
Absorption Almost completely absorbed.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Metabolized in the liver by hepatic microsomal enzymes, where it is inactivated by p-hydroxylation.
Route of elimination Not Available
Half life 22-25 hours.
Clearance Not Available
Toxicity Oral, mouse: LD50 = 987 mg/kg; Oral, rabbit: LD50 = 2500 mg/kg; Oral, rat: LD50 = 1600 mg/kg
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Abbott laboratories pharmaceutical products div
Packagers Not Available
Dosage forms
Form Route Strength
Tablet Oral
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 215 °C PhysProp
water solubility 10.2 g/L Not Available
logP 0.87 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 1.06e+00 g/l ALOGPS
logP 0.81 ALOGPS
logP 0.46 ChemAxon
logS -2.2 ALOGPS
pKa (strongest acidic) 11.75 ChemAxon
pKa (strongest basic) -7.8 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 72.19 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 47.43 ChemAxon
polarizability 17.49 ChemAxon
References
Synthesis Reference Not 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
Resource Link
KEGG Drug D00504 Link_out
KEGG Compound C07428 Link_out
PubChem Compound 4753 Link_out
PubChem Substance 46508400 Link_out
ChemSpider 4589 Link_out
Therapeutic Targets Database DAP000501 Link_out
PharmGKB PA164745309 Link_out
Wikipedia http://en.wikipedia.org/wiki/Phenacemide Link_out
ATC Codes
  • N03AX07
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (72.7 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • May be taken with food if stomach upset occurs.
Targets

1. Sodium channel protein type 1 subunit alpha

Pharmacological action: yes
Actions: inhibitor

Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient

Organism class: human
UniProt ID: P35498 Link_out
Gene: SCN1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 February 08, 2013 16:19