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
Structure for Beclamide (DB09011)
- Weight
- Average: 197.661
Monoisotopic: 197.060741718 - Chemical Formula
- C10H12ClNO
- Synonyms
- Beclamida
- Beclamide
- Beclamidum
- Benzchlorpropamide
- Benzylamide
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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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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Beclamide is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Beclamide. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Beclamide. Aclidinium Beclamide may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Agomelatine The risk or severity of adverse effects can be increased when Agomelatine is combined with Beclamide. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Beclamide. Alimemazine The risk or severity of adverse effects can be increased when Alimemazine is combined with Beclamide. Almotriptan The risk or severity of adverse effects can be increased when Almotriptan is combined with Beclamide. Alosetron The risk or severity of adverse effects can be increased when Alosetron is combined with Beclamide. Alprazolam The risk or severity of adverse effects can be increased when Alprazolam is combined with Beclamide. 
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- Not Available
Products
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- 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
- 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]
- 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]
- 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]
- External Links
- KEGG Drug
- D07300
- PubChem Compound
- 10391
- PubChem Substance
- 347827817
- ChemSpider
- 9962
- 18846
- ChEBI
- 134859
- ChEMBL
- CHEMBL64195
- ZINC
- ZINC000001694184
- Wikipedia
- Beclamide
Clinical Trials
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
Property Value Source Water Solubility 0.436 mg/mL ALOGPS logP 1.61 ALOGPS logP 1.69 Chemaxon logS -2.7 ALOGPS pKa (Strongest Acidic) 15.03 Chemaxon pKa (Strongest Basic) -2.2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 29.1 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 53.43 m3·mol-1 Chemaxon Polarizability 20.61 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created at June 20, 2014 19:28 / Updated at February 21, 2021 18:52