BENCYCLANE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H31NO
Molecular Weight	289.4555
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CCCOC2(CC1=CC=CC=C1)CCCCCC2

InChI

InChIKey=FYJJXENSONZJRG-UHFFFAOYSA-N

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

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

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 511	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 8583	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).

C_max

Value	Dose	Analyte	Population
2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/965131/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	BENCYCLANE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/965131/	200 mg single, intravenous dose: 200 mg route of administration: Intravenous experiment type: SINGLE co-administered:	BENCYCLANE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
41 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4009414/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	BENCYCLANE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
480 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/965131/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		BENCYCLANE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
20% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/965131/			BENCYCLANE unknown	Homo sapiens

Doses

Dose	Population	Adverse events
200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2044395/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2044395/	Sources: https://pubmed.ncbi.nlm.nih.gov/2044395/

PubMed

Title	Date	PubMed
[Metabolic effects of mexidol in complex treatment of chronic brain ischemia].	2009-01-15	19140508
Effect of bencyclane fumarate on intestinal ischaemia reperfusion injury.	2008-06	18522569
Treating frostbite.	2008-03	18337529
[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
[Severe bencyctane intoxication--a case report].	2007	17724891
[Efficacy of halidor treatment for chronic ischemia of the lower extremities].	2006	16710244
[Use of galidor in therapy of chronic brain ischemia].	2005	16447553
[An experience with the clinical use of halidor in the treatment of chronic lower limb ischemia].	2004	15627133
Bencyclane as an anti-sickling agent.	1996-02	8602994
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
Effects of vasodilator drugs, alkaline phosphatase, and cyclic AMP-dependent protein kinase on the 45calcium uptake of sarcolemmal microsomes from human umbilical arteries.	1980-12	6258679

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 `Wed Apr 02 06:52:07 GMT 2025` Edited by `admin` on `Wed Apr 02 06:52:07 GMT 2025`
Record UNII	6I97Z6S135
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENCYCLANE [MI]

Preferred Name

English

BENCYCLANE

Official Name

English

bencyclane [INN]

Common Name

English

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

Systematic Name

English

Bencyclane [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C04AX11