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

Details

Stereochemistry MIXED
Molecular Formula C17H24O3
Molecular Weight 276.3707
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLANDELATE

SMILES

CC1CC(CC(C)(C)C1)OC(=O)C(O)C2=CC=CC=C2

InChI

InChIKey=WZHCOOQXZCIUNC-UHFFFAOYSA-N
InChI=1S/C17H24O3/c1-12-9-14(11-17(2,3)10-12)20-16(19)15(18)13-7-5-4-6-8-13/h4-8,12,14-15,18H,9-11H2,1-3H3

HIDE SMILES / InChI
Cyclandelate is a vasodilator developed for the treatment of cardiovascular diseases. The drug was used in many countries for such diseases as intermittent claudication, arteriosclerosis obliterans, thrombophlebitis, nocturnal leg cramps, local frostbite, Raynaud's phenomenon. In the USA it was also approved for intermittent claudication and cognitive dysfunction in Alzheimer's disease under the name Cyclospasmol. Cyclandelate exerts its effect by blocking calcium channels and inhibiting smooth muscles contration. Cyclandelate was withdrawn from the market in the USA for lack of effectiveness.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CYCLOSPASMOL

Approved Use

A treatment for intermittent claudication and a treatment for cognitive dysfunction in Alzheimer's disease.
Palliative
CYCLOSPASMOL

Approved Use

A treatment for intermittent claudication and a treatment for cognitive dysfunction in Alzheimer's disease.
Doses

Doses

DosePopulationAdverse events​
1600 mg 2 times / day multiple, oral
Highest studied dose
Dose: 1600 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 2 times / day
Co-administed with::
Cholestyramine, p.o(16g, b.i.d)
Sources: Page: p.132
unhealthy, 36 - 60
n = 10
Health Status: unhealthy
Condition: Familial hypercholesterolaemia
Age Group: 36 - 60
Sex: M+F
Population Size: 10
Sources: Page: p.132
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
Vasospastic amaurosis fugax.
2003 Feb
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.
2010
Patents

Sample Use Guides

The usual dose of cyclandelaye is between 400 - 800 mg per day, given in two or four divided doses. If indicated, higher doses of 1200 mg to 1600 mg per day may be given in four divided doses before meals and at bedtime, for two to four weeks, and then reduced by 200 mg decrements to the usual dose.
Route of Administration: Oral
In Vitro Use Guide
Cyclandelate in concentrations between 10 and 50 uM induced a dose-dependent increase in the basal level of cytosolic Ca++ of unstimulated platelets. In platelets stimulated with thrombin (5 U/ml) or platelet activating factor (1 uM), cyclandelate strongly inhibited the increase of cystolic Ca++ in the presence of extracellular Ca++, but in the absence of extracellular Ca++ only a weak inhibition was observed. This inhibition was dose dependent and optimal at about 50 uM, the concentration at which Ca++ mobilisation was suppressed to about 10% of control values, and at which cyclandelate inhibits platelet aggregation.
Name Type Language
CYCLANDELATE
HSDB   INN   JAN   MART.   MI   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
NOVODIL
Brand Name English
CYCLANDELATE [VANDF]
Common Name English
PEREBRAL
Brand Name English
CYCLANDELATE [MART.]
Common Name English
Cyclandelate [WHO-DD]
Common Name English
CYCLOBRAL
Brand Name English
CYCLANDELATE [JAN]
Common Name English
NATIL
Brand Name English
1,5-cis-3,3,5-Trimethylcyclohexyl 2-hydroxy-2-phenyl acetate
Systematic Name English
CYCLOMANDOL
Brand Name English
SPASMOCYCLON (3M)
Brand Name English
CYCLANDELATE [USP IMPURITY]
Common Name English
NSC-758910
Code English
CYCLOLYT
Brand Name English
CYCLANDELATE [USP-RS]
Common Name English
CYCLERGINE
Brand Name English
CYCLANDELATE [MI]
Common Name English
CYCLANDELATE [HSDB]
Common Name English
cyclandelate [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29707
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
LIVERTOX 245
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
WHO-VATC QC04AX01
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
WHO-ATC C04AX01
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
Code System Code Type Description
CAS
456-59-7
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY
FDA UNII
4139O1OAY2
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY
WIKIPEDIA
CYCLANDELATE
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY
RS_ITEM_NUM
1152701
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY
SMS_ID
100000092568
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PRIMARY
EVMPD
SUB06841MIG
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PRIMARY
PUBCHEM
2893
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY
CHEBI
3988
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY
EPA CompTox
DTXSID4022862
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PRIMARY
MESH
D003495
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY
RXCUI
2970
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB04838
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY
DRUG CENTRAL
747
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY
HSDB
3046
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-271-6
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY
ChEMBL
CHEMBL1480987
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY
NSC
758910
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY
INN
821
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY
NCI_THESAURUS
C77072
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY
MERCK INDEX
m3967
Created by admin on Sat Dec 16 10:47:29 UTC 2023 , Edited by admin on Sat Dec 16 10:47:29 UTC 2023
PRIMARY Merck Index