Compounds > cymserine
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cymserine

Description

cymserine: butyrylcholinesterase inhibitor; structure in first source [MeSH]

Cross-References

ID SourceID
PubMed CID9907847
CHEMBL ID129837
MeSH IDM0497364

Synonyms (15)

Synonym
4-isopropylphenserine
cymserine
cymserine.tartaric acid
(3as,8ar)-1,3a,8-trimethyl-1h,2h,3h,3ah,8h,8ah-pyrrolo[2,3-b]indol-5-yl n-[4-(propan-2-yl)phenyl]carbamate
bdbm10960
CHEMBL129837
(-)-cymserine
145209-39-8
DTXSID10432696
EOI96371PZ ,
carbamic acid, n-(4-(1-methylethyl)phenyl)-, (3as,8ar)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-yl ester
[(3ar,8bs)-3,4,8b-trimethyl-2,3a-dihydro-1h-pyrrolo[2,3-b]indol-7-yl] n-(4-propan-2-ylphenyl)carbamate
unii-eoi96371pz
carbamic acid, n-[4-(1-methylethyl)phenyl]-, (3as,8ar)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-yl ester
PD182241

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
CholinesteraseHomo sapiens (human)IC500.2529AID1164690; AID1796572; AID1796574; AID1820979; AID1916836
AcetylcholinesteraseMus musculus (house mouse)IC508.4000AID464986
AcetylcholinesteraseHomo sapiens (human)IC500.4808AID1164699; AID1796572; AID1796574; AID1820943; AID1916835; AID262754; AID31501; AID511766
CholinesteraseMus musculus (house mouse)IC500.2400AID464987

Bioassays (18)

Assay IDTitleYearJournalArticle
AID464987Inhibition of mouse serum BChE after 1 hr by modified Ellman's colorimetric method2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
ISSN: 1464-3405		Design, synthesis, evaluation and QSAR analysis of N(1)-substituted norcymserine derivatives as selective butyrylcholinesterase inhibitors.
AID1916835Inhibition of AChE (unknown origin)2022European journal of medicinal chemistry, Oct-05, Volume: 240ISSN: 1768-3254Recent advance on carbamate-based cholinesterase inhibitors as potential multifunctional agents against Alzheimer's disease.
AID1916836Inhibition of BChE (unknown origin)2022European journal of medicinal chemistry, Oct-05, Volume: 240ISSN: 1768-3254Recent advance on carbamate-based cholinesterase inhibitors as potential multifunctional agents against Alzheimer's disease.
AID464988Selectivity ratio of IC50 for mouse serum BChE over IC50 for mouse brain AChE2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
ISSN: 1464-3405		Design, synthesis, evaluation and QSAR analysis of N(1)-substituted norcymserine derivatives as selective butyrylcholinesterase inhibitors.
AID1164690Inhibition of recombinant human BChE by Ellman method2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
ISSN: 1520-4804		Discovery, biological evaluation, and crystal structure of a novel nanomolar selective butyrylcholinesterase inhibitor.
AID511766Inhibition of human AChE by Ellmans test2010Journal of medicinal chemistry, Sep-09, Volume: 53, Issue:17
ISSN: 1520-4804		Novel carbamates as orally active acetylcholinesterase inhibitors found to improve scopolamine-induced cognition impairment: pharmacophore-based virtual screening, synthesis, and pharmacology.
AID262755Anticholinesterase activity against human plasma BChE2006Journal of medicinal chemistry, Apr-06, Volume: 49, Issue:7
ISSN: 0022-2623		Inhibition of human acetyl- and butyrylcholinesterase by novel carbamates of (-)- and (+)-tetrahydrofurobenzofuran and methanobenzodioxepine.
AID1820943Inhibition of AChE (unknown origin)2022European journal of medicinal chemistry, Feb-05, Volume: 229ISSN: 1768-3254Design, synthesis, and biological evaluation of carbamate derivatives of N-salicyloyl tryptamine as multifunctional agents for the treatment of Alzheimer's disease.
AID1820979Inhibition of BuChE (unknown origin)2022European journal of medicinal chemistry, Feb-05, Volume: 229ISSN: 1768-3254Design, synthesis, and biological evaluation of carbamate derivatives of N-salicyloyl tryptamine as multifunctional agents for the treatment of Alzheimer's disease.
AID464986Inhibition of mouse brain AChE after 1 hr by modified Ellman's colorimetric method2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
ISSN: 1464-3405		Design, synthesis, evaluation and QSAR analysis of N(1)-substituted norcymserine derivatives as selective butyrylcholinesterase inhibitors.
AID1164699Inhibition of AChE (unknown origin)2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
ISSN: 1520-4804		Discovery, biological evaluation, and crystal structure of a novel nanomolar selective butyrylcholinesterase inhibitor.
AID1916838Selectivity index, ratio of IC50 for AChE (unknown origin) to BChE (unknown origin)2022European journal of medicinal chemistry, Oct-05, Volume: 240ISSN: 1768-3254Recent advance on carbamate-based cholinesterase inhibitors as potential multifunctional agents against Alzheimer's disease.
AID31501In vitro inhibition of human erythrocyte acetylcholinesterase.2001Journal of medicinal chemistry, Nov-22, Volume: 44, Issue:24
ISSN: 0022-2623		Methyl analogues of the experimental Alzheimer drug phenserine: synthesis and structure/activity relationships for acetyl- and butyrylcholinesterase inhibitory action.
AID262757Selectivity for BChE over AChE2006Journal of medicinal chemistry, Apr-06, Volume: 49, Issue:7
ISSN: 0022-2623		Inhibition of human acetyl- and butyrylcholinesterase by novel carbamates of (-)- and (+)-tetrahydrofurobenzofuran and methanobenzodioxepine.
AID262754Anticholinesterase activity against human erythrocyte AChE2006Journal of medicinal chemistry, Apr-06, Volume: 49, Issue:7
ISSN: 0022-2623		Inhibition of human acetyl- and butyrylcholinesterase by novel carbamates of (-)- and (+)-tetrahydrofurobenzofuran and methanobenzodioxepine.
AID44293In vitro inhibition of human plasma butyrylcholinesterase.2001Journal of medicinal chemistry, Nov-22, Volume: 44, Issue:24
ISSN: 0022-2623		Methyl analogues of the experimental Alzheimer drug phenserine: synthesis and structure/activity relationships for acetyl- and butyrylcholinesterase inhibitory action.
AID1796574Cholinesterase Inhibition Assay from Article 10.1021/jm010080x: \\Methyl analogues of the experimental Alzheimer drug phenserine: synthesis and structure/activity relationships for acetyl- and butyrylcholinesterase inhibitory action.\\2001Journal of medicinal chemistry, Nov-22, Volume: 44, Issue:24
ISSN: 0022-2623		Methyl analogues of the experimental Alzheimer drug phenserine: synthesis and structure/activity relationships for acetyl- and butyrylcholinesterase inhibitory action.
AID1796572Cholinesterase Inhibition Assay from Article 10.1021/jm010491d: \\Anticholinesterase activity of compounds related to geneserine tautomers. N-Oxides and 1,2-oxazines.\\2002Journal of medicinal chemistry, Aug-15, Volume: 45, Issue:17
ISSN: 0022-2623		Anticholinesterase activity of compounds related to geneserine tautomers. N-Oxides and 1,2-oxazines.

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's6 (50.00)29.6817
2010's4 (33.33)24.3611
2020's2 (16.67)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (8.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (91.67%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
huperzine a
2
quinolone2002200620.0low000200
bw 284 c 51
1
2006200618.0high000100
tacrine
4
acridines;
aromatic amine		EC 3.1.1.7 (acetylcholinesterase) inhibitor2002201416.0low000310
donepezil
4
aromatic ether;
indanones;
piperidines;
racemate		EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
nootropic agent		2002202214.0low000301
profenamine
1
phenothiazines;
tertiary amino compound		adrenergic antagonist;
antidyskinesia agent;
antiparkinson drug;
histamine antagonist;
muscarinic antagonist		2014201410.0low000010
phenolsulfonphthalein
1
2,1-benzoxathiole;
arenesulfonate ester;
phenols;
sultone		acid-base indicator;
diagnostic agent;
two-colour indicator		202220222.0low000001
1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate
1
pyrroloindole2001200123.0medium000100
tetraisopropylpyrophosphamide
1
phosphoramide2006200618.0low000100
physostigmine
7
carbamate ester;
indole alkaloid		antidote to curare poisoning;
EC 3.1.1.8 (cholinesterase) inhibitor;
miotic		2001202213.6medium000502
galantamine
2
benzazepine alkaloid fundamental parent;
benzazepine alkaloid;
organic heterotetracyclic compound;
tertiary amino compound		antidote to curare poisoning;
cholinergic drug;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
plant metabolite		2002200620.0low000200
benzenaminium, 4,4'-(3-oxo-1,5-pentanediyl)bis(n,n-dimethyl-n-2-propenyl-), dibromide
1
2006200618.0low000100
bambuterol
1
carbamate ester;
phenylethanolamines		anti-asthmatic drug;
beta-adrenergic agonist;
bronchodilator agent;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
prodrug;
sympathomimetic agent;
tocolytic agent		202220222.0low000001
geneserine
1
indoles2002200222.0high000100
physostigmine heptyl
4
2002202214.0medium000301
rivastigmine
4
carbamate ester;
tertiary amino compound		cholinergic drug;
EC 3.1.1.8 (cholinesterase) inhibitor;
neuroprotective agent		2002201416.0low000310
quilostigmine
1
pyrroloindole2010201014.0medium000100
phenserine
5
2001202212.6medium000302
physovenine
3
indoles2006202211.3high000201
physostigmine salicylate
1
azaheterocycle salicylate salt;
salicylates		2002200222.0low000100
curcumin
1
aromatic ether;
beta-diketone;
diarylheptanoid;
enone;
polyphenol		anti-inflammatory agent;
antifungal agent;
antineoplastic agent;
biological pigment;
contraceptive drug;
dye;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor;
EC 1.8.1.9 (thioredoxin reductase) inhibitor;
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor;
EC 3.5.1.98 (histone deacetylase) inhibitor;
flavouring agent;
food colouring;
geroprotector;
hepatoprotective agent;
immunomodulator;
iron chelator;
ligand;
lipoxygenase inhibitor;
metabolite;
neuroprotective agent;
nutraceutical;
radical scavenger		202220222.0low000001
phenethylcymserine
2
201020228.0high000101
ganstigmine
1
2002200222.0low000100
tolserine
5
2001202215.8high000401
n-salicyloyltryptamine
1
202220222.0medium000001
xanthostigmine
1
202220222.0medium000001
scopolamine hydrobromide
1
2010201014.0low000100
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
physostigmine
4
carbamate ester;
indole alkaloid		antidote to curare poisoning;
EC 3.1.1.8 (cholinesterase) inhibitor;
miotic		2006201714.0low000310
pyridostigmine bromide
1
pyridinium salt2009200915.0low000100
rivastigmine
1
carbamate ester;
tertiary amino compound		cholinergic drug;
EC 3.1.1.8 (cholinesterase) inhibitor;
neuroprotective agent		2009200915.0low000100
phenserine
1
2009200915.0low000100
physovenine
1
indoles2009200915.0low000100
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Acute Confusional Senile Dementia0
5
200620229.0high000212
Alzheimer Disease0
5
200620229.0high000212