Page last updated: 2024-11-04

cyclandelate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Cyclandelate is a synthetic vasodilator, a medication that widens blood vessels. It is typically used to treat peripheral vascular disease, a condition characterized by narrowing of the blood vessels in the legs and feet. Cyclandelate is thought to work by relaxing smooth muscle in the blood vessel walls, which helps to improve blood flow. Its synthesis involves a multi-step process that starts with the reaction of phenylacetaldehyde with cyclohexanone. The resulting compound is then reacted with an appropriate alcohol to yield cyclandelate. Cyclandelate's effects are primarily related to its vasodilator properties. It can cause a decrease in peripheral vascular resistance, leading to improved blood flow to the extremities. This can help to relieve symptoms of peripheral vascular disease, such as pain, numbness, and tingling in the legs and feet. Cyclandelate is studied for its potential to improve blood flow in individuals with peripheral vascular disease. Researchers are interested in understanding the mechanisms of action of the drug, its effectiveness in treating different types of peripheral vascular disease, and its potential side effects. '

Cyclandelate: A direct-acting SMOOTH MUSCLE relaxant used to dilate BLOOD VESSELS. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cyclandelate : The ester obtained by formal condensation of mandelic acid and 3,3,5-tricyclohexanol. It is a direct-acting smooth muscle relaxant used to dilate blood vessels. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID2893
CHEMBL ID1480987
CHEBI ID3988
SCHEMBL ID5123
MeSH IDM0005451

Synonyms (109)

Synonym
CHEBI:3988 ,
cyclandelatum
ciclandelato
benzeneacetic acid, .alpha.-hydroxy-, 3,3,5-trimethylcyclohexyl ester
cyclandelate
456-59-7
(3,3,5-trimethylcyclohexyl) 2-hydroxy-2-phenyl-acetate
3,3,5-trimethylcyclohexanol alpha-phenyl-alpha-hydroxyacetate
3,3,5-trimethylcyclohexyl hydroxy(phenyl)acetate
ciclandelato [inn-spanish]
bs 572
3,5,5-trimethylcyclohexanol, mandelic acid ester
sancyclan
hsdb 3046
cyclospasmol
cyclomandol
cyclolyt
benzeneacetic acid, alpha-hydroxy-, 3,3,5-trimethylcyclohexyl ester
capilan
spasmione
mandelic acid, 3,3,5-trimethylcyclohexyl ester
perebral
spasmocyclone
saiclate
3,5,5-trimethylcyclohexyl mandelate
clandilon
alpha-hydroxybenzeneacetic acid 3,3,5-trimethylcyclohexyl ester
sepyron
spasmocyclon
einecs 207-271-6
cyclandelatum [inn-latin]
arto-espasmol
ciclospasmol
NCGC00159506-02
NCGC00159506-03
DB04838
3,3,5-trimethylcyclohexyl mandelate
3,5,5-trimethylcyclohexyl amygdalate
cyclospasmol (tn)
D00286
cyclandelate (jan/usp/inn)
ZINC00000189
ZINC00405331
ZINC00968262
M0821
mandelic acid 3,3,5-trimethylcyclohexyl ester
(3,3,5-trimethylcyclohexyl) 2-hydroxy-2-phenylacetate
nsc-758910
cyclergine
CHEMBL1480987
spasmocyclon (3m)
natil
novodil
HMS3264K11
dtxcid402862
tox21_111725
cas-456-59-7
dtxsid4022862 ,
pharmakon1600-01505082
nsc758910
S4189
cyclobral
cyclandelic acid
rythmol [vasodilator]
4139o1oay2 ,
nsc 758910
unii-4139o1oay2
lisospasm
pericyclon
hacosan
cyclandelate [usp:inn:ban:jan]
eparan
AKOS015902290
1,5-cis-3,3,5-trimethylcyclohexyl 2-hydroxy-2-phenyl acetate
cyclandelate [usp-rs]
cyclandelate [inn]
cyclandelate [mi]
cyclandelate [vandf]
cyclandelate [usp impurity]
cyclandelate [who-dd]
cyclandelate [hsdb]
cyclandelate [mart.]
cyclandelate [jan]
CCG-213926
SCHEMBL5123
KS-5317
CS-4770
3,3,5-trimethylcyclohexanol .alpha.-phenyl-.alpha.-hydroxyacetate
.alpha.-hydroxybenzeneacetic acid 3,3,5-trimethylcyclohexyl ester
WZHCOOQXZCIUNC-UHFFFAOYSA-N
3,3,5-trimethylcyclohexyl hydroxy(phenyl)acetate #
HY-B1170
AB01563218_01
AB01563218_02
3,3,5-trimethylcyclohexyl 2-hydroxy-2-phenylacetate
sr-01000872740
SR-01000872740-1
HMS3652B09
mfcd00056623
SBI-0207036.P001
NCGC00159506-05
SW220003-1
FT-0735837
Q1147309
NCGC00159506-06
mandelic
D91389
A913217
EN300-17956492

Research Excerpts

Overview

Cyclandelate is a vasodilating agent that, like papaverine, acts directly on the smooth muscles of blood vessels.

ExcerptReferenceRelevance
"Cyclandelate is a vasodilating agent that, like papaverine, acts directly on the smooth muscles of blood vessels. "( Cyclandelate in the management of tinnitus: a randomized, placebo-controlled study.
Green, W; Hester, TO; Jones, RO; Theilman, G, 1998
)
3.19

Effects

ExcerptReferenceRelevance
"Cyclandelate has the ability to improve the rheological properties of the blood and therefore may improve blood supply of peripheral nerves. "( Cyclandelate in diabetic neuropathy. A double-blind, placebo-controlled, randomized, cross-over study.
Bertelsmann, FW; Drukarch, B; Heimans, JJ; Ijff, GA; Matthaei, I; Nauta, J; Strijers, RL, 1991
)
3.17

Actions

Cyclandelate induced increase of spectral power in the alpha 2 frequency band under resting conditions. Cyclandelate did not inhibit the production of 6-keto-PGF1 alpha.

ExcerptReferenceRelevance
"The cyclandelate induced increase of spectral power in the alpha 2 frequency band under resting conditions demonstrates a general effect of cyclandelate on the CNS."( [Effects of cyclandelate on the CNS--a double-blind, placebo-controlled study of healthy subjects].
Dimpfel, W; Netter, P; Spüler, M; Wedekind, W, 1991
)
1.14
"Cyclandelate did not inhibit the production of 6-keto-PGF1 alpha, a stable metabolite of prostacyclin."( Effect of cyclandelate on prostacyclin release and cytosolic free calcium concentrations in human endothelial cells.
van Hinsbergh, VW, 1987
)
1.4

Treatment

Cyclandelate treatment decreased the extent and severity of aortic atherosclerosis. Treatment with cyclandelate produced clinical effects which were selective for the Wechsler Memory Scale.

ExcerptReferenceRelevance
"Cyclandelate treatment decreased the extent and severity of aortic atherosclerosis."( Dietary cyclandelate decreases pre-established atherosclerosis in the rabbit.
Bell, GD; Middleton, A; Middleton, B; White, DA,
)
1.29
"Treatment with cyclandelate produced clinical effects which were selective for the Wechsler Memory Scale items of visual reproduction and orientation--indicators of the declarative memory."( Specific effects of cyclandelate on memory.
Ananth, J, 1987
)
0.94

Bioavailability

The bioavailability of five capsules of cyclandelate that are commercially available in Japan was determined in ten healthy volunteers by measuring mandelic acid (a main metabolite ofcyclandelate) excreted in the urine.

ExcerptReferenceRelevance
"The bioavailability in beagle dogs and the dissolution rates of cyclandelate from five capsule preparations commercially available in Japan were measured."( Bioavailability of cyclandelate from capsules in beagle dogs and dissolution rate: correlations with bioavailability in humans.
Aoyagi, N; Ejima, A; Imasato, Y; Kaniwa, N; Ogata, H; Takahashi, T; Uezono, Y, 1991
)
0.85
"The bioavailability of five capsules of cyclandelate that are commercially available in Japan was determined in ten healthy volunteers by measuring mandelic acid (a main metabolite of cyclandelate) excreted in the urine."( Effect of food on the bioavailability of cyclandelate from commercial capsules.
Aoyagi, N; Ejima, A; Imazato, Y; Kaniwa, N; Ogata, H; Takahashi, T; Uezono, Y, 1991
)
0.81
" The estimated potency of aldose reductase inhibition for each of the three drugs in this study was significantly discrepant from the in vitro studies indicating the complicated nature of the bioavailability of a pharmaceutical agent in vivo, especially where pharmacologically active metabolites of a given drug are involved."( In vivo pharmacokinetics of aldose reductase inhibitors: 3-fluoro-3-deoxy-D-glucose NMR studies in rat brains.
Kwee, IL; Nakada, T, 1989
)
0.28
" The method was developed for use in bioavailability and metabolism studies."( Simultaneous determination of cyclandelate and its metabolite in human plasma by capillary column gas-liquid chromatography.
Andermann, G; Dietz, M, 1981
)
0.55
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

The effect of cyclandelate (Natil) on the CNS was tested in a double-blind, placebo-controlled pilot study on 48 healthy males using a single oral dosage of 1200 mg. There was no change, neither elevation nor depression, of the amount of microsomal membrane components cytochromes b5 and P-450.

ExcerptRelevanceReference
"The effect of cyclandelate (Natil) on the CNS was tested in a double-blind, placebo-controlled pilot study on 48 healthy males using a single oral dosage of 1200 mg."( [Effects of cyclandelate on the CNS--a double-blind, placebo-controlled study of healthy subjects].
Dimpfel, W; Netter, P; Spüler, M; Wedekind, W, 1991
)
1.02
"Previous trials have demonstrated a clinical and electrophysiological improvement of diabetic peripheral polyneuropathy in diabetic patients treated with cyclandelate at a dosage of 1600 mg/day."( Clinical experience with cyclandelate in insulin-dependent diabetic patients with neuropathy.
De Leeuw, IH; Driessens, M; Moeremans, M; Van Rooy, P, 1987
)
0.77
" There was no change, neither elevation nor depression, of the amount of microsomal membrane components cytochromes b5 and P-450, not was the activity of another microsomal enzyme, arylesterase, affected by dosing with cyclandelate or trimethylcyclohexanol."( The inhibition of hepatic S-3-hydroxy-3-methylglutaryl-CoA reductase by 3,3,5-trimethylcyclohexanol and its mandelic acid ester, cyclandelate.
Bell, GD; Miciak, A; Middleton, A; Middleton, B; White, DA, 1983
)
0.66
"5% O2) the volunteers were asked to perform a series of tests including a computer-assisted oculodynamic test (ODT) after one dosage and after fourteen days' treatment with both cyclandelate or placebo."( A pilot study to evaluate the effect of acute and long-term administration of cyclandelate on the vigilance of subjects submitted to hypoxic conditions. Preliminary report.
Arnold, H; Hörmann, E; Schaffler, K, 1981
)
0.68
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
vasodilator agentA drug used to cause dilation of the blood vessels.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
carboxylic esterAn ester of a carboxylic acid, R(1)C(=O)OR(2), where R(1) = H or organyl and R(2) = organyl.
secondary alcoholA secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (11)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Ferritin light chainEquus caballus (horse)Potency28.18385.623417.292931.6228AID485281
USP1 protein, partialHomo sapiens (human)Potency44.66840.031637.5844354.8130AID504865
TDP1 proteinHomo sapiens (human)Potency20.49880.000811.382244.6684AID686978; AID686979
AR proteinHomo sapiens (human)Potency24.43110.000221.22318,912.5098AID743040; AID743042; AID743054; AID743063
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency26.32740.000214.376460.0339AID720691; AID720719
pregnane X nuclear receptorHomo sapiens (human)Potency17.78280.005428.02631,258.9301AID1346985
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency89.12510.354828.065989.1251AID504847
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency32.86100.000323.4451159.6830AID743065; AID743067
lamin isoform A-delta10Homo sapiens (human)Potency22.38720.891312.067628.1838AID1487
Spike glycoproteinSevere acute respiratory syndrome-related coronavirusPotency2.23870.009610.525035.4813AID1479145
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bile salt export pumpHomo sapiens (human)IC50 (µMol)15.03000.11007.190310.0000AID1449628
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
virion membraneSpike glycoproteinSevere acute respiratory syndrome-related coronavirus
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID588220Literature-mined public compounds from Kruhlak et al phospholipidosis modelling dataset2008Toxicology mechanisms and methods, , Volume: 18, Issue:2-3
Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.
AID1449628Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21 cell membranes vesicles assessed as reduction in ATP-dependent [3H]-taurocholate transport into vesicles incubated for 5 mins by Topcount based rapid filtration method2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
AID588212Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID588213Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in non-rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID588211Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in humans2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (139)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990107 (76.98)18.7374
1990's19 (13.67)18.2507
2000's7 (5.04)29.6817
2010's4 (2.88)24.3611
2020's2 (1.44)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.20

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index34.20 (24.57)
Research Supply Index5.19 (2.92)
Research Growth Index4.15 (4.65)
Search Engine Demand Index50.49 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (34.20)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials33 (22.60%)5.53%
Reviews6 (4.11%)6.00%
Case Studies3 (2.05%)4.05%
Observational0 (0.00%)0.25%
Other104 (71.23%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]