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Beclamide

Beclamide structure

CAS No:
501-68-8
Formula:
C10H12ClNO
Chemical Name:
Beclamide
Synonyms:
Propanamide,3-chloro-N-(phenylmethyl)-;Propionamide,N-benzyl-3-chloro-;3-Chloro-N-(phenylmethyl)propanamide;Beclamide;N-Benzyl-β-chloropropanamide;N-Benzyl-β-chloropropionamide;N-Benzyl-3-chloropropionamide;Chloracon;Chloroethylphenamide;Hibicon;Nydrane;Posedrine;N-(3-Chloropropionyl)benzylamine;Nidrane;Seclar;Chlorakon;Nydran;Beklamid;Beclamid;Neuracen;NSC 67062
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

Description

Beclamide is a drug that possesses anticonvulsant activity, has been used as a sedative and as an anticonvulsant.

Beclamide is a member of benzenes.|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.

Beclamide Basic Attributes

Molecular Weight：

197.664

Exact Mass：

197.66

EC Number：

207-927-1

UNII：

F5N0ALI65V

NSC Number：

759264|67062

DSSTox ID：

DTXSID5057755

ATC Code：

N - Nervous system

HScode：

2924299090

Characteristics

PSA：

29.1

XLogP3：

2.32260

Density：

1.145g/cm3

Melting Point：

94 °C

Boiling Point：

386.9ºC at 760mmHg

Flash Point：

187.8ºC

Refractive Index：

1.532

Water Solubility：

5.06e-04 M

Toxicity：

Oral-rat LD50: 3200 mg/kg; Oral-Mouse LD50: 1000 mg/kg

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxides and chloride fumes

Collision Cross Section：

142.3 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Storage features：

Ventilated, low temperature and dry

Precautionary statement(s)：

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P362, P403+P233, P405, P501

Hazard Statements：

H315

Toxicity

Toxicity class：

moderately toxic

Drug Information

Drug 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]

Absorption：

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.

Metabolism/Metabolites：

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).

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.

MeSH Entry Terms：

beclamide

Beclamide Use and Manufacturing

Uses

anticonvulsant, antiepileptic

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:197.66
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:197.0607417
Monoisotopic Mass:197.0607417
Topological Polar Surface Area:29.1
Heavy Atom Count:13
Complexity:155
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Beclamide

CAS No.: 501-68-8

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