U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of BENCYCLANE

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
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
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
INN   MI   WHO-DD  
INN  
Official Name English
BENCYCLANE [MI]
Common 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
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
NCI_THESAURUS C333
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
WHO-VATC QC04AX11
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
Code System Code Type Description
DRUG BANK
DB13488
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY
CAS
2179-37-5
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY
PUBCHEM
2312
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY
NCI_THESAURUS
C74226
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY
RXCUI
1367
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY RxNorm
EVMPD
SUB05705MIG
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY
INN
2111
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY
DRUG CENTRAL
301
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY
MERCK INDEX
m2305
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY Merck Index
MESH
D001537
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY
SMS_ID
100000086613
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY
FDA UNII
6I97Z6S135
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY
ChEMBL
CHEMBL2110767
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY
WIKIPEDIA
BENCYCLANE
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY
ECHA (EC/EINECS)
218-547-0
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY
EPA CompTox
DTXSID0022646
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY