BEPHENIUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H22NO
Molecular Weight	256.3627
Optical Activity	NONE
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

C[N+](C)(CCOC1=CC=CC=C1)CC2=CC=CC=C2

InChI

InChIKey=AVWWVJUMXRXPNF-UHFFFAOYSA-N

InChI=1S/C17H22NO/c1-18(2,15-16-9-5-3-6-10-16)13-14-19-17-11-7-4-8-12-17/h3-12H,13-15H2,1-2H3/q+1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1814038/pdf/brmedj02622-0054.pdf | https://www.ncbi.nlm.nih.gov/pubmed/22526556

Bephenium is an anthelmintic agent formerly used in the treatment of hookworm infections and ascariasis (as a hydroxynaphthoate salt). Bephenium exerts its anti-helminthic action by inducing muscle contraction in parasites. The contraction is suggested to be mediated by B-type AChR receptors, which are activated upon administration of bephenium.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
B-type AChR 1 Target ID: B-type AChR Sources: https://www.ncbi.nlm.nih.gov/pubmed/22526556	Agonist 2752		7.7 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Helminthiasis 39 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13762408	Curative		Approved 8583	ALCOPAR Approved Use Helminthiasis

C_max

Value	Dose	Co-administered	Analyte	Population
17 μg/g EXPERIMENT https://www.cabdirect.org/cabdirect/abstract/19902222270	0.24 g/kg single, oral dose: 0.24 g/kg route of administration: Oral experiment type: SINGLE co-administered:		BEPHENIUM blood	Ovis aries population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
5 g single, oral Recommended Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/	unhealthy, 8 - 79 years Health Status: unhealthy Age Group: 8 - 79 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/	Other AEs: Nausea, Abdominal pain... Other AEs: Nausea (24 patients) Abdominal pain (21 patient) Diarrhea (21 patient) Headache (11 patient) Vomiting (5 patients) Vertigo (5 patients) Anorexia (1 patient) Weakness (1 patient) Chest pain (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/

AEs

AE	Significance	Dose	Population
Anorexia	1 patient	5 g single, oral Recommended Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/	unhealthy, 8 - 79 years Health Status: unhealthy Age Group: 8 - 79 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/
Chest pain	1 patient	5 g single, oral Recommended Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/	unhealthy, 8 - 79 years Health Status: unhealthy Age Group: 8 - 79 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/
Weakness	1 patient	5 g single, oral Recommended Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/	unhealthy, 8 - 79 years Health Status: unhealthy Age Group: 8 - 79 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/
Headache	11 patient	5 g single, oral Recommended Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/	unhealthy, 8 - 79 years Health Status: unhealthy Age Group: 8 - 79 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/
Abdominal pain	21 patient	5 g single, oral Recommended Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/	unhealthy, 8 - 79 years Health Status: unhealthy Age Group: 8 - 79 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/
Diarrhea	21 patient	5 g single, oral Recommended Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/	unhealthy, 8 - 79 years Health Status: unhealthy Age Group: 8 - 79 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/
Nausea	24 patients	5 g single, oral Recommended Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/	unhealthy, 8 - 79 years Health Status: unhealthy Age Group: 8 - 79 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/
Vertigo	5 patients	5 g single, oral Recommended Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/	unhealthy, 8 - 79 years Health Status: unhealthy Age Group: 8 - 79 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/
Vomiting	5 patients	5 g single, oral Recommended Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/	unhealthy, 8 - 79 years Health Status: unhealthy Age Group: 8 - 79 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12913463/

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-056463	http://www.3bsc.com/index/pro_info.php?id=94973
AA Blocks	AA00BY6Z	https://www.aablocks.com/goods/Goods/detail?id=AA00BY6Z
AbMole Bioscience	M5452	http://www.abmole.com/products/bephenium-hydroxynaphthoate.html
AK Scientific, Inc. (AKSCI)	2263AH	http://www.aksci.com/item_detail.php?cat=2263AH
Alfa Chemistry	AP3818506	https://reagents.alfa-chemistry.com/product/bephenium-hydroxynaphthoate-cas-3818-50-6-10883.html
Ambinter	Amb10843833	http://www.ambinter.com/reference/10843833
Angel Pharmatech	AG224002	http://www.angelpharmatech.com/3818-50-6.html
ApexBio Technology	A8376	http://www.apexbt.com/bephenium-hydroxynaphthoate.html
Aurora Fine Chemicals LLC	A17.877.539	http://online.aurorafinechemicals.com/info?ID=A17.877.539
BioCrick	BCC3735	http://www.biocrick.com/Bephenium-Hydroxynaphthoate-BCC3735.html
BOC Sciences	3818-50-6	https://www.bocsci.com/bephenium-hydroxynaphthoate-cas-3818-50-6-item-84-114460.html
Chem Scene	CS-3886	http://www.chemscene.com/3818-50-6.html
ChemMol	99085599	http://www.chemmol.com/chemmol/99085599.html
Chemspace	CSSB00009827777	https://chem-space.com/CSSB00009827777
DC Chemicals	DC22482	http://www.dcchemicals.com/product_show-DC22482.html
eNovation Chemicals	D130132	https://www.enovationchem.com/ProductDetails.asp?ProductID=D130132
eNovation Chemicals	D679865	https://www.enovationchem.com/ProductDetails.asp?ProductID=D679865
Finetech	FT-0712569	http://www.finetechnology-ind.com/prod/detail/pub/3818-50-6.html
Lab Network	LN01275304	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01275304
LGC Standards	LGCFOR1832.00	https://www.lgcstandards.com/US/en/p/LGCFOR1832.00
LGC Standards	MM1832.00	https://www.lgcstandards.com/US/en/p/MM1832.00
MedChem Express	HY-12639A	https://www.medchemexpress.com/Bephenium-hydroxynaphthoate.html
Molcore	MC552246	https://www.molcore.com/product/3818-50-6
MolPort	MolPort-006-115-725	https://www.molport.com/shop/molecule-link/MolPort-006-115-725
MuseChem	I003402	https://www.musechem.com/product/I003402.html
Sigma-Aldrich	1065006_USP	https://www.sigmaaldrich.com/catalog/product/usp/1065006?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	B5650_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/b5650?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Yuhao Chemical	RT3475	http://www.chemyuhao.com/3818-50-6.html

PubMed

Title	Date	PubMed
The nicotinic acetylcholine receptors of the parasitic nematode Ascaris suum: formation of two distinct drug targets by varying the relative expression levels of two subunits.	2009-07	19609360
Pharmacology of N-, L-, and B-subtypes of nematode nAChR resolved at the single-channel level in Ascaris suum.	2006-12	17056760
Contractile activity and motility responses of the dog heartworm Dirofilaria immitis to classical anthelmintics and other compounds.	2005-11-25	16076531
Brief application of AF2 produces long lasting potentiation of nAChR responses in Ascaris suum.	2005-01	15610819
Oxantel is an N-type (methyridine and nicotine) agonist not an L-type (levamisole and pyrantel) agonist: classification of cholinergic anthelmintics in Ascaris.	2004-08	15313135
Methyridine (2-[2-methoxyethyl]-pyridine]) and levamisole activate different ACh receptor subtypes in nematode parasites: a new lead for levamisole-resistance.	2003-11	14581174
Paraherquamide and 2-deoxy-paraherquamide distinguish cholinergic receptor subtypes in Ascaris muscle.	2002-09	12183640

Patents

Sample Use Guides

In Vivo Use Guide

5 g is taken as a single dose. The granules may be suspended in water.

Route of Administration: Oral

In Vitro Use Guide

Nippostrongylus brasiliensis was incubated with bephenium (hydroxynaphthoate salt) and the minimum inhibitory concentration was found to be 225.7 uM.

Name

Type

Language

BEPHENIUM [HSDB]

Preferred Name

English

BEPHENIUM

Common Name

English

AMMONIUM, BENZYLDIMETHYL(2-PHENOXYETHYL)-

Systematic Name

English

BENZENEMETHANAMINIUM, N,N-DIMETHYL-N-(2-PHENOXYETHYL)-

Systematic Name

English

BENZYLDIMETHYL(2-PHENOXYETHYL)AMMONIUM

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

P02CX02