BENCYCLANE FUMARATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H31NO.C4H4O4
Molecular Weight	405.5277
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.CN(C)CCCOC2(CC1=CC=CC=C1)CCCCCC2

InChI

InChIKey=LSTKNZAMFRGXCG-WLHGVMLRSA-N

InChI=1S/C19H31NO.C4H4O4/c1-20(2)15-10-16-21-19(13-8-3-4-9-14-19)17-18-11-6-5-7-12-18;5-3(6)1-2-4(7)8/h5-7,11-12H,3-4,8-10,13-17H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

HIDE SMILES / InChI

Molecular Formula	C19H31NO
Molecular Weight	289.4555
Charge	0
Count

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

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/?term=Bencyclane | http://www.egis.pl/43/dla-pacjenta/15/leki-chirurgii-naczyniowej/59/halidor-bencyclani-fumaras | https://www.drugs.com/international/halidor.html | https://www.ncbi.nlm.nih.gov/pubmed/6258679 | https://www.ncbi.nlm.nih.gov/pubmed/6276530 | https://www.ncbi.nlm.nih.gov/pubmed/2044395 | https://www.ncbi.nlm.nih.gov/pubmed/8602994 | https://www.ncbi.nlm.nih.gov/pubmed/19156122

Bencyclane, a cycloheptane, is a vasodilator, antiplasmodic and a platelet aggregation inhibitor found to be effective in a variety of peripheral circulation disorders. Bencyclane has various other potentially useful pharmacological effects such as smooth muscle relaxation. Under the trade name Halidor it is used in several European countries to treat the symptoms of atherosclerosis, occlusive arterial disease. Its mechanism may involve block of calcium channels. However as was shown in vitro it does not act by a direct influence on the Ca2+ pumps of vascular smooth muscle cells. In in vitro biochemical assays related to smooth muscle excitation-contraction coupling, binding to beta 1-, beta 2-, and alpha-adrenergic receptors, inhibition of phosphodiesterase activity, and antagonism of calcium accumulation bencyclane bound to alpha- and beta-receptors. Bencyclane appeared to be a promising anti-sickling agent that can be used orally in sickle cell anaemia (SCD).

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Sickle cell anemia 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8602994	Primary		Not Provided 504	Unknown Approved Use Unknown
Peripheral arterial disease 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19156122 https://www.ncbi.nlm.nih.gov/pubmed/2044395	Primary		Approved 8429	Halidor Approved Use Disorders of cerebral circulation. Diseases associated with peripheral vasospasm (spasm of the arteries after deep vein thrombosis, post-operative and post-traumatic circulatory disorders, pain in the extremities).

PubMed

Title	Date	PubMed
Effects of vasodilator drugs, alkaline phosphatase, and cyclic AMP-dependent protein kinase on the 45calcium uptake of sarcolemmal microsomes from human umbilical arteries.	1980 Dec	6258679
The long-term tolerability of bencyclane ('Fludilat') in patients with peripheral occlusive disease: a 48-week prospective double-blind controlled study versus placebo.	1991	2044395
Bencyclane as an anti-sickling agent.	1996 Feb	8602994
[An experience with the clinical use of halidor in the treatment of chronic lower limb ischemia].	2004	15627133
[Use of galidor in therapy of chronic brain ischemia].	2005	16447553
[Efficacy of halidor treatment for chronic ischemia of the lower extremities].	2006	16710244
[Severe bencyctane intoxication--a case report].	2007	17724891
[Halidor in the treatment of cerebral vascular diseases in emergency cases].	2008	19156122
[Patogenetic therapy of patients with diabetes mellitus type 2 and cerebral vascular insufficiency].	2008	18427536
Effect of bencyclane fumarate on intestinal ischaemia reperfusion injury.	2008 Jun	18522569
Treating frostbite.	2008 Mar	18337529
[Metabolic effects of mexidol in complex treatment of chronic brain ischemia].	2008 Nov-Dec	19140508

Patents

Sample Use Guides

In Vivo Use Guide

200 mg bencyclane twice daily

Route of Administration: Oral

In Vitro Use Guide

At 10(-5) molar concentration bencyclane inhibited platelet adhesiveness and ADP or collagen induced platelet aggregation. 10(-5) M of bencyclane induced a slight swelling of platelets. At 10(-4) M it inhibited the formation of tentacles completely and transformed the platelets into small spheres when investigated with interference-phase contrast microscopy. It is likely that the morphologic changes induced by bencyclane are responsible for the inhibitory effect on the different platelet function tests in vitro.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:03:07 GMT 2023` Edited by `admin` on `Fri Dec 15 16:03:07 GMT 2023`
Record UNII	OZN2MG334O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENCYCLANE FUMARATE

Common Name

English

Bencyclane fumarate [WHO-DD]

Common Name

English

EGYT-201

Code

English

BENCYCLANE FUMARATE [MART.]

Common Name

English

3-((1-BENZYLCYCLOHEPTYL)OXY)-N,N-DIMETHYLPROPYLAMINE FUMARATE

Systematic Name

English

BENCYCLANE FUMARATE [JAN]

Common Name

English

BENCYCLANE FUMARATE [MI]

Common Name

English

EGYT 201

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C333