BEPHENIUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H22NO
Molecular Weight	256.3627
Optical Activity	NONE
Defined Stereocenters	0 / 0
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

Molecular Formula	C17H22NO
Molecular Weight	256.3627
Charge	1
Count

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

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 2678		7.7 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Helminthiasis 39 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13762408	Curative		Approved 8429	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 n = 51 Health Status: unhealthy Condition: hookworm infested Age Group: 8 - 79 years Sex: M+F Population Size: 51 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 n = 51 Health Status: unhealthy Condition: hookworm infested Age Group: 8 - 79 years Sex: M+F Population Size: 51 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 n = 51 Health Status: unhealthy Condition: hookworm infested Age Group: 8 - 79 years Sex: M+F Population Size: 51 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 n = 51 Health Status: unhealthy Condition: hookworm infested Age Group: 8 - 79 years Sex: M+F Population Size: 51 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 n = 51 Health Status: unhealthy Condition: hookworm infested Age Group: 8 - 79 years Sex: M+F Population Size: 51 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 n = 51 Health Status: unhealthy Condition: hookworm infested Age Group: 8 - 79 years Sex: M+F Population Size: 51 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 n = 51 Health Status: unhealthy Condition: hookworm infested Age Group: 8 - 79 years Sex: M+F Population Size: 51 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 n = 51 Health Status: unhealthy Condition: hookworm infested Age Group: 8 - 79 years Sex: M+F Population Size: 51 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 n = 51 Health Status: unhealthy Condition: hookworm infested Age Group: 8 - 79 years Sex: M+F Population Size: 51 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 n = 51 Health Status: unhealthy Condition: hookworm infested Age Group: 8 - 79 years Sex: M+F Population Size: 51 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
AK Scientific, Inc. (AKSCI)	2263AH	http://www.aksci.com/item_detail.php?cat=2263AH
AbMole Bioscience	M5452	http://www.abmole.com/products/bephenium-hydroxynaphthoate.html
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
BOC Sciences	3818-50-6	https://www.bocsci.com/bephenium-hydroxynaphthoate-cas-3818-50-6-item-84-114460.html
BioCrick	BCC3735	http://www.biocrick.com/Bephenium-Hydroxynaphthoate-BCC3735.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
Finetech	FT-0712569	http://www.finetechnology-ind.com/prod/detail/pub/3818-50-6.html
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
Lab Network	LN01275304	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01275304
MedChem Express	HY-12639A	https://www.medchemexpress.com/Bephenium-hydroxynaphthoate.html
MolPort	MolPort-006-115-725	https://www.molport.com/shop/molecule-link/MolPort-006-115-725
Molcore	MC552246	https://www.molcore.com/product/3818-50-6
MuseChem	I003402	https://www.musechem.com/product/I003402.html
Sigma-Aldrich	B5650_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/b5650?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1065006_USP	https://www.sigmaaldrich.com/catalog/product/usp/1065006?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Yuhao Chemical	RT3475	http://www.chemyuhao.com/3818-50-6.html
eNovation Chemicals	D130132	https://www.enovationchem.com/ProductDetails.asp?ProductID=D130132
eNovation Chemicals	D679865	https://www.enovationchem.com/ProductDetails.asp?ProductID=D679865

PubMed

Title	Date	PubMed
Paraherquamide and 2-deoxy-paraherquamide distinguish cholinergic receptor subtypes in Ascaris muscle.	2002 Sep	12183640
Methyridine (2-[2-methoxyethyl]-pyridine]) and levamisole activate different ACh receptor subtypes in nematode parasites: a new lead for levamisole-resistance.	2003 Nov	14581174
Oxantel is an N-type (methyridine and nicotine) agonist not an L-type (levamisole and pyrantel) agonist: classification of cholinergic anthelmintics in Ascaris.	2004 Aug	15313135
Brief application of AF2 produces long lasting potentiation of nAChR responses in Ascaris suum.	2005 Jan	15610819
Contractile activity and motility responses of the dog heartworm Dirofilaria immitis to classical anthelmintics and other compounds.	2005 Nov 25	16076531
Pharmacology of N-, L-, and B-subtypes of nematode nAChR resolved at the single-channel level in Ascaris suum.	2006 Dec	17056760
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 Jul	19609360

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:35:17 GMT 2023` Edited by `admin` on `Fri Dec 15 18:35:17 GMT 2023`
Record UNII	PXO9B4983I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BEPHENIUM

Common Name

English

BEPHENIUM [HSDB]

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