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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 of BENCYCLANE FUMARATE

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
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).

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
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

PubMed

TitleDatePubMed
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
The long-term tolerability of bencyclane ('Fludilat') in patients with peripheral occlusive disease: a 48-week prospective double-blind controlled study versus placebo.
1991
[Halidor in the treatment of cerebral vascular diseases in emergency cases].
2008
Effect of bencyclane fumarate on intestinal ischaemia reperfusion injury.
2008 Jun
Treating frostbite.
2008 Mar
Patents

Patents

Sample Use Guides

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.
Name Type Language
BENCYCLANE FUMARATE
JAN   MART.   MI   WHO-DD  
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
Created by admin on Fri Dec 15 16:03:07 GMT 2023 , Edited by admin on Fri Dec 15 16:03:07 GMT 2023
Code System Code Type Description
CAS
14286-84-1
Created by admin on Fri Dec 15 16:03:07 GMT 2023 , Edited by admin on Fri Dec 15 16:03:07 GMT 2023
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FDA UNII
OZN2MG334O
Created by admin on Fri Dec 15 16:03:07 GMT 2023 , Edited by admin on Fri Dec 15 16:03:07 GMT 2023
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RXCUI
258328
Created by admin on Fri Dec 15 16:03:07 GMT 2023 , Edited by admin on Fri Dec 15 16:03:07 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m2305
Created by admin on Fri Dec 15 16:03:07 GMT 2023 , Edited by admin on Fri Dec 15 16:03:07 GMT 2023
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EVMPD
SUB00695MIG
Created by admin on Fri Dec 15 16:03:07 GMT 2023 , Edited by admin on Fri Dec 15 16:03:07 GMT 2023
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DRUG BANK
DBSALT002573
Created by admin on Fri Dec 15 16:03:07 GMT 2023 , Edited by admin on Fri Dec 15 16:03:07 GMT 2023
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NCI_THESAURUS
C73828
Created by admin on Fri Dec 15 16:03:07 GMT 2023 , Edited by admin on Fri Dec 15 16:03:07 GMT 2023
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SMS_ID
100000084994
Created by admin on Fri Dec 15 16:03:07 GMT 2023 , Edited by admin on Fri Dec 15 16:03:07 GMT 2023
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PUBCHEM
5282403
Created by admin on Fri Dec 15 16:03:07 GMT 2023 , Edited by admin on Fri Dec 15 16:03:07 GMT 2023
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ECHA (EC/EINECS)
238-204-9
Created by admin on Fri Dec 15 16:03:07 GMT 2023 , Edited by admin on Fri Dec 15 16:03:07 GMT 2023
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ChEMBL
CHEMBL2110767
Created by admin on Fri Dec 15 16:03:07 GMT 2023 , Edited by admin on Fri Dec 15 16:03:07 GMT 2023
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