BECLAMIDE

First approved in 1952

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H12ClNO
Molecular Weight	197.661
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClCCC(=O)NCC1=CC=CC=C1

InChI

InChIKey=JPYQFYIEOUVJDU-UHFFFAOYSA-N

InChI=1S/C10H12ClNO/c11-7-6-10(13)12-8-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,13)

HIDE SMILES / InChI

Molecular Formula	C10H12ClNO
Molecular Weight	197.661
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugbank.ca/drugs/DB09011 | https://www.ncbi.nlm.nih.gov/pubmed/2183543 | https://books.google.ru/books?id=ppKbCgAAQBAJ&pg=PT174&lpg=PT174&dq=Benzchlorpropamide retrieved from The Treatment of Epilepsy edited by Simon Shorvon, Emilio Perucca, Jerome Engel, Jr. | http://onlinelibrary.wiley.com/doi/10.1111/j.1528-1167.2009.02041.x/pdf

Beclamide (N-benzyl-B-chloropropionamide) is a drug that possesses anticonvulsant activity. It is no longer used. It has been used as a sedative and as an anticonvulsant. Beclamide has been used in the management of both epilepsy and behavioral disorders associated with epilepsy. It was introduced into clinical practice in 1952 under the brand names Hibicon, Lederle and later it was withdrawn. This agent was shown to be effective in grand mal but not absence seizures. Early claims emphasized its safety, and it is not entirely clear why it was withdrawn from therapy for epilepsy. Interest in the drug was rekindled in the 1990s as an adjunct in the treatment of schizophrenia.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABAergic synapse 4 Target ID: map04727 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9890792 \| https://www.ncbi.nlm.nih.gov/pubmed/6139193	Modulator 817

Conditions

Condition	Modality	Targets	Highest Phase	Product
Epilepsy 122 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8583359 https://www.ncbi.nlm.nih.gov/pubmed/13651708	Primary		Approved 8307	Hibicon Approved Use Treatment of Epilepsy Launch Date -5.6808001E11
Schizophrenia 288 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2183543	Primary		Phase I 422	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
11 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1233999/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		BECLAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
59 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1233999/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		BECLAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1233999/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		BECLAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
50% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1233999/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		BECLAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY556978	https://www.001chemical.com/chem/501-68-8
AA Blocks	AA00DB5E	https://www.aablocks.com/goods/Goods/detail?id=AA00DB5E
AbMole Bioscience	M5445	http://www.abmole.com/products/beclamide.html
Achemo Scientific Limited	AC-83666	http://www.achemo.com/search/?Keyword= 501-68-8
Ambinter	Amb1931859	http://www.ambinter.com/reference/1931859
Angel Pharmatech	AG201281	http://www.angelpharmatech.com/501-68-8.html
AstaTech, Inc.	53642	http://www.astatechinc.com/CPSResult.php?CRNO=3909
Aurora Fine Chemicals LLC	A00.447.996	http://online.aurorafinechemicals.com/info?ID=A00.447.996
Aurora Fine Chemicals LLC	K02.068.350	http://online.aurorafinechemicals.com/info?ID=K02.068.350
Aurum Pharmatech LLC	X-1956	http://www.Aurumpharmatech.com/Product/ProductDetails/X_1956
BLD Pharm	BD115249	http://www.bldpharm.com/products/501-68-8.html
BioChemPartner	BCP29693	http://www.biochempartner.com/501-68-8-BCP29693
CSNpharm	CSN10386	https://www.csnpharm.com/products/beclamide.html
Chem Scene	CS-4794	http://www.chemscene.com/501-68-8.html
ChemMol	44016225	http://www.chemmol.com/chemmol/44016225.html
ChemMol	99115800	http://www.chemmol.com/chemmol/99115800.html
Chemspace	CSSB00011208716	https://chem-space.com/CSSB00011208716
Finetech	FT-0662480	http://www.finetechnology-ind.com/prod/detail/pub/501-68-8.html
LGC Standards	LGCAMP1825.00-11	https://www.lgcstandards.com/US/en/p/LGCAMP1825.00-11
LGC Standards	LGCFOR1825.00	https://www.lgcstandards.com/US/en/p/LGCFOR1825.00
LGC Standards	MM1825.00	https://www.lgcstandards.com/US/en/p/MM1825.00
Lab Network	LN00242544	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00242544
MedChem Express	HY-B1185	https://www.medchemexpress.com/Beclamide.html
Molcore	MC556978	https://www.molcore.com/product/501-68-8
MuseChem	I003764	https://www.musechem.com/product/I003764.html
Oakwood	26355	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=20233&ExtHyperLink=1
Selleck Chemicals	S5888	http://www.selleckchem.com/products/beclamide.html
Sigma-Aldrich	S358282_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/s358282
Sinfoo Biotech	S018672	http://www.sinfoobiotech.com/product/1022070
Smolecule	S577908	https://www.smolecule.com/products/s577908
THE BioTek	bt-315224	https://www.thebiotek.com/product/others/bt-315224
abcr GmbH	AB283503	http://www.abcr.com/shop/en/AB283503
eNovation Chemicals	D536190	https://www.enovationchem.com/ProductDetails.asp?ProductID=D536190
mcule	MCULE-2526925294	https://mcule.com/MCULE-2526925294/

PubMed

Title	Date	PubMed
Hibicon a new anticonvulsant.	1952 Mar	14906178
Effects of anticonvulsant drugs on the cerebral enzymes metabolizing GABA.	1975 Nov	9890792
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.	2010	22291486

Patents

Sample Use Guides

In Vivo Use Guide

Adult Dosage: 7.14 to 14.28 mg/kg, p.o, Frequency - 8 hourly

Route of Administration: Oral

In Vitro Use Guide

Succinic semialdehyde dehydrogenase activity was inhibited by 10 to 20% at low concentrations (0.01 to 0.1 mM) of diazepam, carbamazepine, beclamide, acetazolamide, and di-n-propylacetate, and by 40% or more at high concentrations (2.5 to 10.0 mM) of diazepam, phenobarbital, carbamazepine, Beclamide, and di-n-propylacetate in mouse brain homogenates. Beclamide at 100 umol/l significantly inhibited K+-evoked release of D-aspartate.

Substance Class	Chemical Created by `admin` on `Fri Dec 16 16:56:53 UTC 2022` Edited by `admin` on `Fri Dec 16 16:56:53 UTC 2022`
Record UNII	F5N0ALI65V
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BECLAMIDE

Official Name

English

Beclamide [WHO-DD]

Common Name

English

NSC-67062

Code

English

beclamide [INN]

Common Name

English

BECLAMIDE [MI]

Common Name

English

BECLAMIDE [MART.]

Common Name

English

N-BENZYL-3-CHLOROPROPIONAMIDE

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

N03AX30