NAV

Beclamide

Identification

Generic Name
Beclamide
DrugBank Accession Number
DB09011
Background

Beclamide (N-benzyl-B-chloropropionamide) is a no longer used drug that possesses anticonvulsant and sedative activity. It was studied in the 1950s for generalised tonic-clonic seizures but was not effective for absence seizures.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 197.661
Monoisotopic: 197.060741718
Chemical Formula
C10H12ClNO
Synonyms
  • Beclamida
  • Beclamide
  • Beclamidum
  • Benzchlorpropamide
  • Benzylamide
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Pharmacology

Indication

Has been used in the management of epilepsy and epilepsy related behavioural disorders. It was used for generalised tonic-clonic seizures, and was not effective for absence seizures.

More recently focus has shifted to the use of beclamide in behavioural disorders. In mentally handicapped epileptic patients it has been found to decrease anxiety, antisocial and demanding behaviours, and impulsivity. Mood stabilizing effects were also noted. [2]

Additionally, due to its effects on monoamines, beclamide may have a potential place in treating conditions such as tardive dyskinesia and hyperkinetic syndromes. [2]

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Beclamide has been used for over three decades with little knowledge of how it acts in the CNS. In one study using rats, beclamide was seen to reduce striatal dopamine and serotonin levels and increase the levels of dopamine's major metabolites (and thus dopamine turnover), while reducing the levels of serotonin's major metabolite below detectable levels. A similar effect on neurotransmitter levels was seen in the rat frontal cortices. It is theorized that animal aggression is linked to levels of biogenic monoamines such as dopamine and serotonin, however the exact role is unclear. 2

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Rapidly metabolized. Major pathway of metabolism is oxidation of the benzene ring to yield 3-hydroxyphenyl and 4-hydroxyphenyl metabolites, and oxidation of the benyl methylene to yield benzoic acid. 3 and 4 hydroxyphenyl metabolites are excreted extensively as gluconuride and sulphate conjugates, and benzoic acid is excreted as a glycine conjugate (hippuric acid).

Route of elimination

Metabolites appear in urine only. 4- hydroxybeclamide is present in the urine to a greater extent than 3 hydroxybeclamide. Approximately 20% of the radiolabel was excreted in urine.

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

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
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1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Beclamide is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Beclamide.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Beclamide.
AgomelatineThe risk or severity of CNS depression can be increased when Agomelatine is combined with Beclamide.
AlfentanilThe risk or severity of CNS depression can be increased when Alfentanil is combined with Beclamide.
Food Interactions
Not Available

Products

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International/Other Brands
Hibicon / Nydrane / Posedrine / Seclar

Categories

ATC Codes
N03AX30 — Beclamide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Not Available
Direct Parent
Benzene and substituted derivatives
Alternative Parents
Secondary carboxylic acid amides / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Alkyl chlorides
Substituents
Alkyl chloride / Alkyl halide / Aromatic homomonocyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxide
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
F5N0ALI65V
CAS number
501-68-8
InChI Key
JPYQFYIEOUVJDU-UHFFFAOYSA-N
InChI
InChI=1S/C10H12ClNO/c11-7-6-10(13)12-8-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,13)
IUPAC Name
N-benzyl-3-chloropropanamide
SMILES
ClCCC(=O)NCC1=CC=CC=C1

References

Synthesis Reference

Nicholls, P. J., & Luscombe, D. K. (1979). Facile synthesis of N‐(Methylene‐14C) benzyl‐3‐chloropropionamide (beclamide). Journal of Labelled Compounds and Radiopharmaceuticals, 16(2), 369-372.

General References
  1. Ahmadi M, Nicholls PJ, Smith HJ, Spencer PS, Preet-Ryatt MS, Spragg BP: Metabolism of beclamide after a single oral dose in man: quantitative studies. J Pharm Pharmacol. 1995 Oct;47(10):876-8. [Article]
  2. Darmani NA, Sewell RD, Nicholls PJ: Acute effects of beclamide on brain regional monoamine concentrations, their metabolites and radioligand binding studies. J Pharm Pharmacol. 1991 Jun;43(6):425-9. [Article]
  3. Raptis C, Garcia-Borreguero D, Weber MM, Dose M, Bremer D, Emrich HM: Anticonvulsants as adjuncts for the neuroleptic treatment of schizophrenic psychoses: a clinical study with beclamide. Acta Psychiatr Scand. 1990 Feb;81(2):162-7. [Article]
KEGG Drug
D07300
PubChem Compound
10391
PubChem Substance
347827817
ChemSpider
9962
RxNav
18846
ChEBI
134859
ChEMBL
CHEMBL64195
ZINC
ZINC000001694184
Wikipedia
Beclamide

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.436 mg/mLALOGPS
logP1.61ALOGPS
logP1.69Chemaxon
logS-2.7ALOGPS
pKa (Strongest Acidic)15.03Chemaxon
pKa (Strongest Basic)-2.2Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area29.1 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity53.43 m3·mol-1Chemaxon
Polarizability20.61 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01oy-9600000000-2779d01cd8983428dbbf
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9100000000-553816c6447c2883e025
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-2b2dbc8c95dfc6bb26df
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9100000000-f2eb28a83e527497babc
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-a5f9358d8ac9bf1f8921
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9100000000-29149e4439d0e3f99931
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-137.22466
predicted
DeepCCS 1.0 (2019)
[M+H]+141.052
predicted
DeepCCS 1.0 (2019)
[M+Na]+150.05864
predicted
DeepCCS 1.0 (2019)

Drug created at June 20, 2014 19:28 / Updated at February 21, 2021 18:52