Phenacemide

Identification

Generic Name
Phenacemide
DrugBank Accession Number
DB01121
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 178.1879
Monoisotopic: 178.074227574
Chemical Formula
C9H10N2O2
Synonyms
  • Phenacemide

Pharmacology

Indication

Used to control certain seizures in the treatment of epilepsy.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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.

TargetActionsOrganism
ASodium channel protein type 1 subunit alpha
inhibitor
Humans
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

Adverse Effects
Adverseeffects
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Toxicity

Oral, mouse: LD50 = 987 mg/kg; Oral, rabbit: LD50 = 2500 mg/kg; Oral, rat: LD50 = 1600 mg/kg

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Phenacemide is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Phenacemide.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Phenacemide.
AclidiniumPhenacemide may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Phenacemide is combined with Agomelatine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Phenacemide.
AlimemazineThe risk or severity of adverse effects can be increased when Phenacemide is combined with Alimemazine.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Phenacemide.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Phenacemide.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Phenacemide.
Interactions
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Food Interactions
  • Take with or without food. Co-administration with food may reduce gastrointestinal upset.

Products

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International/Other Brands
Phenurone

Categories

ATC Codes
N03AX07 — Phenacemide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylacetamides
Direct Parent
Phenylacetamides
Alternative Parents
N-acyl ureas / Dicarboximides / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aromatic homomonocyclic compound / Carbonic acid derivative / Carbonyl group / Carboxylic acid derivative / Dicarboximide / Hydrocarbon derivative / N-acyl urea / Organic nitrogen compound / Organic oxide / Organic oxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
acetamides (CHEBI:8049)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
PAI7J52V09
CAS number
63-98-9
InChI Key
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

References

General References
  1. Coker SB: The use of phenacemide for intractable partial complex epilepsy in children. Pediatr Neurol. 1986 Jul-Aug;2(4):230-2. [Article]
  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. [Article]
Human Metabolome Database
HMDB0015253
KEGG Drug
D00504
KEGG Compound
C07428
PubChem Compound
4753
PubChem Substance
46508400
ChemSpider
4589
BindingDB
50240044
RxNav
33253
ChEBI
8049
ChEMBL
CHEMBL918
ZINC
ZINC000000001916
Therapeutic Targets Database
DAP000501
PharmGKB
PA164745309
Wikipedia
Phenacemide
MSDS
Download (72.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)215 °CPhysProp
water solubility10.2 g/LNot Available
logP0.87HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility1.06 mg/mLALOGPS
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 Area72.19 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.43 m3·mol-1ChemAxon
Polarizability17.49 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9401
Blood Brain Barrier+0.9935
Caco-2 permeable-0.6496
P-glycoprotein substrateNon-substrate0.7351
P-glycoprotein inhibitor INon-inhibitor0.9376
P-glycoprotein inhibitor IINon-inhibitor0.9913
Renal organic cation transporterNon-inhibitor0.8761
CYP450 2C9 substrateNon-substrate0.7678
CYP450 2D6 substrateNon-substrate0.7784
CYP450 3A4 substrateNon-substrate0.8055
CYP450 1A2 substrateNon-inhibitor0.7929
CYP450 2C9 inhibitorNon-inhibitor0.8962
CYP450 2D6 inhibitorNon-inhibitor0.942
CYP450 2C19 inhibitorNon-inhibitor0.9183
CYP450 3A4 inhibitorNon-inhibitor0.9088
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9183
Ames testNon AMES toxic0.8748
CarcinogenicityNon-carcinogens0.799
BiodegradationReady biodegradable0.8039
Rat acute toxicity2.0779 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9546
hERG inhibition (predictor II)Non-inhibitor0.9759
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
Mass Spectrum (Electron Ionization)MSsplash10-00kf-9200000000-38554ddfe2ad3808dc2a
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
1H NMR Spectrum1D NMRNot Applicable

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated sodium channel activity
Specific Function
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...
Gene Name
SCN1A
Uniprot ID
P35498
Uniprot Name
Sodium channel protein type 1 subunit alpha
Molecular Weight
228969.49 Da
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. [Article]
  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. [Article]
  3. Wong MG, Defina JA, Andrews PR: Conformational analysis of clinically active anticonvulsant drugs. J Med Chem. 1986 Apr;29(4):562-72. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created on June 13, 2005 13:24 / Updated on May 07, 2021 21:23