Compounds > cycleanine
Page last updated: 2024-11-07

cycleanine

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

Description

Cycleanine is an alkaloid isolated from the plant *Zygophyllum fabago*. It has shown promising biological activity, particularly as an anti-inflammatory and analgesic agent. Researchers are interested in its potential therapeutic applications due to its unique chemical structure and pharmacological properties. Studies have investigated its mechanism of action, which involves inhibition of the enzyme cyclooxygenase (COX), a key player in the inflammatory cascade. Cycleanine's synthesis remains an area of ongoing research, with various approaches being explored to achieve efficient and sustainable production.'

cycleanine: a bisbenzyl-bisisoquinoline alkaloid isolated from Chinese herb Stephania epigeae Lu; used for controlling blood pressure during anesthesia; RN refers to the R,R-isomer (cycleanine); isocycleanine is the R,S-isomer; [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
StephaniagenusA plant genus of the family MENISPERMACEAE. Members contain cycleanine.[MeSH]AsteraceaeA large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH]
StephaniagenusA plant genus of the family MENISPERMACEAE. Members contain cycleanine.[MeSH]MenispermaceaeA plant family of the order Ranunculales, subclass Magnoliidae, class Magnoliopsida. Members are mostly vines and shrubs and they contain isoquinoline alkaloids, some of which have been used as arrow poisons.[MeSH]

Cross-References

ID SourceID
PubMed CID121313
CHEMBL ID443389
CHEBI ID81051
SCHEMBL ID21974
MeSH IDM0112485

Synonyms (30)

Synonym
isocycleanine
cycleanine + other alkaloids
518-94-5
cycleanine
o,o-dimethylisochondrodendrine
8,11:20,23-dietheno-1h,12h-(1,10)dioxacyclooctadecino(2,3,4-ij:11,12,13-i'j')diisoquinoline, 2,3,12a,13,14,15,24,24a-octahydro-1,13-dimethyl-5,6,17,18-tetramethoxy-, (12ar-(12ar*,24ar*))-
(-)-cycleanine
dimethylisochondodendrine
o,o-dimethylisochondodendrin
o-methylnorcycleanine
CHEMBL443389
chebi:81051 ,
C17387
bn8r5t4kq9 ,
unii-bn8r5t4kq9
bdbm85446
cycleanine (r,r)
SCHEMBL21974
Q-100582
DTXSID40199740
(11r,26r)-4,5,19,20-tetramethoxy-10,25-dimethyl-2,17-dioxa-10,25-diazaheptacyclo[26.2.2.213,16.13,7.118,22.011,36.026,33]hexatriaconta-1(31),3(36),4,6,13,15,18(33),19,21,28(32),29,34-dodecaene
cycleanin
AKOS037514606
Q15410908
HY-N2005
8,11:20,23-dietheno-1h,12h-(1,10)dioxacyclooctadecino(2,3,4-ij:11,12,13-i'j')diisoquinoline, 2,3,12a,13,14,15,24,24a-octahydro-5,6,17,18-tetramethoxy-1,13-dimethyl-, (12ar,24ar)-
(12ar,24ar)-2,3,12a,13,14,15,24,24a-octahydro-5,6,17,18-tetramethoxy-1,13-dimethyl-8,11:20,23-dietheno-1h,12h-(1,10)dioxacyclooctadecino(2,3,4-ij:11,12,13-i'j')diisoquinoline
cycleanine [who-dd]
CS-0018325
MS-30801
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
isoquinolinesA class of organic heteropolycyclic compound consisting of isoquinoline and its substitution derivatives.
bisbenzylisoquinoline alkaloidA type of benzylisoquinoline alkaloid whose structures are built up of two benzylisoquinoline units linked by ether bridges. Various structural patterns resulting from additional bridging between the two units by direct carbon-carbon bridging or by methylenedioxy groups are common.
[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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID1391326Antiproliferative activity against human A2780 cells after 72 hrs by SRB assay2018Bioorganic & medicinal chemistry letters, 05-15, Volume: 28, Issue:9
Synthesis of (aminoalkyl)cycleanine analogues: cytotoxicity, cellular uptake, and apoptosis induction in ovarian cancer cells.
AID1391344Selectivity index, ratio of IC50 for human ovarian epithelial cells to IC50 for human IGROV1 cells2018Bioorganic & medicinal chemistry letters, 05-15, Volume: 28, Issue:9
Synthesis of (aminoalkyl)cycleanine analogues: cytotoxicity, cellular uptake, and apoptosis induction in ovarian cancer cells.
AID1391328Cytotoxicity against human ovarian epithelial cells assessed as reduction in cell viability after 72 hrs by SRB assay2018Bioorganic & medicinal chemistry letters, 05-15, Volume: 28, Issue:9
Synthesis of (aminoalkyl)cycleanine analogues: cytotoxicity, cellular uptake, and apoptosis induction in ovarian cancer cells.
AID1391342Selectivity index, ratio of IC50 for human ovarian epithelial cells to IC50 for human OVCAR8 cells2018Bioorganic & medicinal chemistry letters, 05-15, Volume: 28, Issue:9
Synthesis of (aminoalkyl)cycleanine analogues: cytotoxicity, cellular uptake, and apoptosis induction in ovarian cancer cells.
AID1391325Antiproliferative activity against human OVCAR8 cells after 72 hrs by SRB assay2018Bioorganic & medicinal chemistry letters, 05-15, Volume: 28, Issue:9
Synthesis of (aminoalkyl)cycleanine analogues: cytotoxicity, cellular uptake, and apoptosis induction in ovarian cancer cells.
AID1391341Drug uptake in human OVCAR8 cells at 20 uM after 48 hrs by Alexa 488 azide dye-based confocal fluorescence microscopy2018Bioorganic & medicinal chemistry letters, 05-15, Volume: 28, Issue:9
Synthesis of (aminoalkyl)cycleanine analogues: cytotoxicity, cellular uptake, and apoptosis induction in ovarian cancer cells.
AID1391327Antiproliferative activity against human IGROV1 cells after 72 hrs by SRB assay2018Bioorganic & medicinal chemistry letters, 05-15, Volume: 28, Issue:9
Synthesis of (aminoalkyl)cycleanine analogues: cytotoxicity, cellular uptake, and apoptosis induction in ovarian cancer cells.
AID1391343Selectivity index, ratio of IC50 for human ovarian epithelial cells to IC50 for human A2780 cells2018Bioorganic & medicinal chemistry letters, 05-15, Volume: 28, Issue:9
Synthesis of (aminoalkyl)cycleanine analogues: cytotoxicity, cellular uptake, and apoptosis induction in ovarian cancer cells.
AID1799661Inhibition Assay from Article 10.3109/14756369809035823: \\Trypanocidal bisbenzylisoquinoline alkaloids are inhibitors of trypanothione reductase.\\1998Journal of enzyme inhibition, Feb, Volume: 13, Issue:1
Trypanocidal bisbenzylisoquinoline alkaloids are inhibitors of trypanothione reductase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (14.29)18.7374
1990's7 (50.00)18.2507
2000's1 (7.14)29.6817
2010's3 (21.43)24.3611
2020's1 (7.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.07

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 Index20.07 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index5.15 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.07)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
verapamil
Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.		1.9910aromatic ether;
nitrile;
polyether;
tertiary amino compound
nifedipine
Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.		1.9910C-nitro compound;
dihydropyridine;
methyl ester		calcium channel blocker;
human metabolite;
tocolytic agent;
vasodilator agent
oxidopamine
Oxidopamine: A neurotransmitter analogue that depletes noradrenergic stores in nerve endings and induces a reduction of dopamine levels in the brain. Its mechanism of action is related to the production of cytolytic free-radicals.. oxidopamine : A benzenetriol that is phenethylamine in which the hydrogens at positions 2, 4, and 5 on the phenyl ring are replaced by hydroxy groups. It occurs naturally in human urine, but is also produced as a metabolite of the drug DOPA (used for the treatment of Parkinson's disease).		1.9610benzenetriol;
catecholamine;
primary amino compound		drug metabolite;
human metabolite;
neurotoxin
spiperone
Spiperone: A spiro butyrophenone analog similar to HALOPERIDOL and other related compounds. It has been recommended in the treatment of SCHIZOPHRENIA.. spiperone : An azaspiro compound that is 1,3,8-triazaspiro[4.5]decane which is substituted at positions 1, 4, and 8 by phenyl, oxo, and 4-(p-fluorophenyl)-4-oxobutyl groups, respectively.		1.9610aromatic ketone;
azaspiro compound;
organofluorine compound;
piperidines;
tertiary amino compound		alpha-adrenergic antagonist;
antipsychotic agent;
dopaminergic antagonist;
psychotropic drug;
serotonergic antagonist
apomorphine
Apomorphine: A derivative of morphine that is a dopamine D2 agonist. It is a powerful emetic and has been used for that effect in acute poisoning. It has also been used in the diagnosis and treatment of parkinsonism, but its adverse effects limit its use.		1.9610aporphine alkaloidalpha-adrenergic drug;
antidyskinesia agent;
antiparkinson drug;
dopamine agonist;
emetic;
serotonergic drug
adenosine diphosphate
Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.		2.4110adenosine 5'-phosphate;
purine ribonucleoside 5'-diphosphate		fundamental metabolite;
human metabolite
isoquinoline
[no description available]		2.2110azaarene;
isoquinolines;
mancude organic heterobicyclic parent;
ortho-fused heteroarene
berbamine
[no description available]		2.6930phenylpropanoid
cepharanthine
cepharanthine: isoquinoline alkaloid from tubers of STEPHANIA; stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation. cepharanthine : A bisbenzylisoquinoline alkaloid from tubers of Stephania; stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation.		2.9140bisbenzylisoquinoline alkaloid;
isoquinolines
chondocurine
chondocurine: inhibits quick death of mice treated with bacillus Calmetta Guerin & elicited with lipopolysaccharide; structure given in first source		2.6730
magnocurarine
magnocurarine: RN given refers to (R)-isomer		2.2110isoquinolines
tetrandrine
tetrandrine: a bisbenzylisoquinoline that exhibits antifibrogenic activity		2.4220bisbenzylisoquinoline alkaloid;
isoquinolines
magnoflorine
magnoflorine: opium alkaloid having the aporphine configuration; RN given refers to parent cpd(S)-isomer; structure. (S)-magnoflorine : An aporphine alkaloid that is (S)-corytuberine in which the nitrogen has been quaternised by an additional methyl group.		2.2110aporphine alkaloid;
quaternary ammonium ion		plant metabolite
dauricine
dauricine: RN given refers to parent cpd. dauricine : A bisbenzylisoquinoline alkaloid resulting from the formal oxidative dimerisation of 4-{[(1R)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}phenol by attachment of the phenolic oxygen of one molecule to the benzene ring of the second (ortho to the phenolic hydroxy group of the latter).		1.9610aromatic ether;
bisbenzylisoquinoline alkaloid;
isoquinolines;
phenols;
tertiary amino compound		plant metabolite
fangchinoline
fangchinoline: RN given refers to parent cpd; limacine is the (1'beta)-isomer; 7-O-demethyltetrandrine is the (1S,1'S)-isomer. fangchinoline : A bisbenzylisoquinoline alkaloid that is (1beta)- berbaman which has been substituted by methyl groups at the 2 and 2' positions, by methoxy groups at the 6, 6', and 12 positions, and by a hydroxy group at position 7. Isolated from Stephania tetrandra, it has been found to possess neuroprotective and anti-tumour activity.		1.9910
chondocurine (1beta)-(+-)-isomer
curine: structure in first source		2.4520aromatic ether
isotetrandrine
[no description available]		1.9910
ribose
ribopyranose : The pyranose form of ribose.		2.4110D-ribose;
ribopyranose
ConditionIndicatedRelationship StrengthStudiesTrials
Benign Neoplasms
[description not available]		02.4110
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.4110
Acute Liver Injury, Drug-Induced
[description not available]		02.3820
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		02.3820
Muscle Contraction
A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.		01.9910
Breast Cancer
[description not available]		01.9910
Breast Neoplasms
Tumors or cancer of the human BREAST.		01.9910
Anochlesia
[description not available]		01.9610