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
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+
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 |
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Primary | Unknown Approved UseUnknown |
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Primary | Halidor Approved UseDisorders 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 |
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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 |
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The long-term tolerability of bencyclane ('Fludilat') in patients with peripheral occlusive disease: a 48-week prospective double-blind controlled study versus placebo. | 1991 |
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Bencyclane as an anti-sickling agent. | 1996 Feb |
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[An experience with the clinical use of halidor in the treatment of chronic lower limb ischemia]. | 2004 |
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[Use of galidor in therapy of chronic brain ischemia]. | 2005 |
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[Efficacy of halidor treatment for chronic ischemia of the lower extremities]. | 2006 |
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[Severe bencyctane intoxication--a case report]. | 2007 |
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[Halidor in the treatment of cerebral vascular diseases in emergency cases]. | 2008 |
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[Patogenetic therapy of patients with diabetes mellitus type 2 and cerebral vascular insufficiency]. | 2008 |
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Effect of bencyclane fumarate on intestinal ischaemia reperfusion injury. | 2008 Jun |
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Treating frostbite. | 2008 Mar |
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[Metabolic effects of mexidol in complex treatment of chronic brain ischemia]. | 2008 Nov-Dec |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1243666
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.
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C333
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14286-84-1
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OZN2MG334O
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258328
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m2305
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SUB00695MIG
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DBSALT002573
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CHEMBL2110767
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
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