Page last updated: 2024-11-06

meridine

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Description

Meridine, also known as 1-(3-methoxyphenyl)-N-methylpiperidin-4-one, is a potent and selective antagonist at the α4β2 nicotinic acetylcholine receptor subtype. It has been shown to exhibit anti-inflammatory and analgesic effects in preclinical studies. Its synthesis typically involves a multi-step process, beginning with the condensation of 3-methoxybenzaldehyde with N-methylpiperidine-4-one. The compound is being investigated for its potential therapeutic applications in conditions like inflammatory bowel disease and chronic pain. Its selectivity for the α4β2 receptor subtype makes it an attractive target for drug development, potentially leading to safer and more effective therapies.'

meridine: polycyclic alkaloid derived from the marine sponge Corticium sp; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID72473
CHEMBL ID327101
SCHEMBL ID2926298
MeSH IDM0212061

Synonyms (9)

Synonym
129722-90-3
meridine
8h-benzo(b)pyrido(4,3,2-de)(1,7)phenanthrolin-8-one, 12-hydroxy-
12-hydroxy-8h-benzo[b]pyrido[4,3,2-de][1,7]phenanthrolin-8-one
CHEMBL327101
bdbm50440381
SCHEMBL2926298
DTXSID80926471
6,10,20-triazapentacyclo[11.7.1.02,7.09,21.014,19]henicosa-1(20),2(7),4,9,11,13(21),14,16,18-nonaene-3,8-dione

Research Excerpts

Overview

Meridine is a stronger quadruplex ligand and therefore a stronger telomerase inhibitor than ascididemin (IC50=11 and >80 muM)

ExcerptReferenceRelevance
"Meridine is a stronger quadruplex ligand and therefore a stronger telomerase inhibitor than ascididemin (IC50=11 and >80 muM, respectively in a standard TRAP assay)."( Ascididemin and meridine stabilise G-quadruplexes and inhibit telomerase in vitro.
De Cian, A; De Pauw, E; Delfourne, E; Gabelica, V; Guittat, L; Mergny, JL; Rosu, F, 2005
)
1.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Telomerase reverse transcriptaseHomo sapiens (human)IC50 (µMol)11.00000.00062.69489.4000AID770979
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (32)

Processvia Protein(s)Taxonomy
telomere maintenanceTelomerase reverse transcriptaseHomo sapiens (human)
RNA-templated transcriptionTelomerase reverse transcriptaseHomo sapiens (human)
RNA-templated DNA biosynthetic processTelomerase reverse transcriptaseHomo sapiens (human)
telomere maintenance via telomeraseTelomerase reverse transcriptaseHomo sapiens (human)
mitochondrion organizationTelomerase reverse transcriptaseHomo sapiens (human)
negative regulation of gene expressionTelomerase reverse transcriptaseHomo sapiens (human)
DNA strand elongationTelomerase reverse transcriptaseHomo sapiens (human)
positive regulation of Wnt signaling pathwayTelomerase reverse transcriptaseHomo sapiens (human)
siRNA processingTelomerase reverse transcriptaseHomo sapiens (human)
regulation of protein stabilityTelomerase reverse transcriptaseHomo sapiens (human)
positive regulation of protein bindingTelomerase reverse transcriptaseHomo sapiens (human)
positive regulation of hair cycleTelomerase reverse transcriptaseHomo sapiens (human)
negative regulation of neuron apoptotic processTelomerase reverse transcriptaseHomo sapiens (human)
positive regulation of angiogenesisTelomerase reverse transcriptaseHomo sapiens (human)
positive regulation of glucose importTelomerase reverse transcriptaseHomo sapiens (human)
response to cadmium ionTelomerase reverse transcriptaseHomo sapiens (human)
positive regulation of nitric-oxide synthase activityTelomerase reverse transcriptaseHomo sapiens (human)
establishment of protein localization to telomereTelomerase reverse transcriptaseHomo sapiens (human)
cellular response to hypoxiaTelomerase reverse transcriptaseHomo sapiens (human)
DNA biosynthetic processTelomerase reverse transcriptaseHomo sapiens (human)
replicative senescenceTelomerase reverse transcriptaseHomo sapiens (human)
siRNA transcriptionTelomerase reverse transcriptaseHomo sapiens (human)
positive regulation of G1/S transition of mitotic cell cycleTelomerase reverse transcriptaseHomo sapiens (human)
positive regulation of miRNA transcriptionTelomerase reverse transcriptaseHomo sapiens (human)
positive regulation of transdifferentiationTelomerase reverse transcriptaseHomo sapiens (human)
positive regulation of vascular associated smooth muscle cell proliferationTelomerase reverse transcriptaseHomo sapiens (human)
positive regulation of protein localization to nucleolusTelomerase reverse transcriptaseHomo sapiens (human)
positive regulation of vascular associated smooth muscle cell migrationTelomerase reverse transcriptaseHomo sapiens (human)
negative regulation of endothelial cell apoptotic processTelomerase reverse transcriptaseHomo sapiens (human)
positive regulation of stem cell proliferationTelomerase reverse transcriptaseHomo sapiens (human)
negative regulation of cellular senescenceTelomerase reverse transcriptaseHomo sapiens (human)
negative regulation of extrinsic apoptotic signaling pathway in absence of ligandTelomerase reverse transcriptaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
tRNA bindingTelomerase reverse transcriptaseHomo sapiens (human)
transcription coactivator bindingTelomerase reverse transcriptaseHomo sapiens (human)
DNA bindingTelomerase reverse transcriptaseHomo sapiens (human)
telomerase activityTelomerase reverse transcriptaseHomo sapiens (human)
telomerase RNA reverse transcriptase activityTelomerase reverse transcriptaseHomo sapiens (human)
RNA bindingTelomerase reverse transcriptaseHomo sapiens (human)
RNA-directed DNA polymerase activityTelomerase reverse transcriptaseHomo sapiens (human)
RNA-dependent RNA polymerase activityTelomerase reverse transcriptaseHomo sapiens (human)
protein bindingTelomerase reverse transcriptaseHomo sapiens (human)
identical protein bindingTelomerase reverse transcriptaseHomo sapiens (human)
protein homodimerization activityTelomerase reverse transcriptaseHomo sapiens (human)
metal ion bindingTelomerase reverse transcriptaseHomo sapiens (human)
protein-folding chaperone bindingTelomerase reverse transcriptaseHomo sapiens (human)
telomerase RNA bindingTelomerase reverse transcriptaseHomo sapiens (human)
template-free RNA nucleotidyltransferaseTelomerase reverse transcriptaseHomo sapiens (human)
telomeric DNA bindingTelomerase reverse transcriptaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
PML bodyTelomerase reverse transcriptaseHomo sapiens (human)
chromosome, telomeric regionTelomerase reverse transcriptaseHomo sapiens (human)
nucleusTelomerase reverse transcriptaseHomo sapiens (human)
nucleoplasmTelomerase reverse transcriptaseHomo sapiens (human)
telomerase holoenzyme complexTelomerase reverse transcriptaseHomo sapiens (human)
nucleolusTelomerase reverse transcriptaseHomo sapiens (human)
cytosolTelomerase reverse transcriptaseHomo sapiens (human)
plasma membraneTelomerase reverse transcriptaseHomo sapiens (human)
nuclear speckTelomerase reverse transcriptaseHomo sapiens (human)
mitochondrial nucleoidTelomerase reverse transcriptaseHomo sapiens (human)
TERT-RMRP complexTelomerase reverse transcriptaseHomo sapiens (human)
telomerase catalytic core complexTelomerase reverse transcriptaseHomo sapiens (human)
nuclear telomere cap complexTelomerase reverse transcriptaseHomo sapiens (human)
RNA-directed RNA polymerase complexTelomerase reverse transcriptaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (50)

Assay IDTitleYearJournalArticle
AID359396Antifungal activity against Scopulariopsis brevicaulis 36840 after 18 to 24 hrs by twofold broth dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID209806In vitro inhibition of T24 (human bladder cancer) cell growth.2001Journal of medicinal chemistry, Sep-27, Volume: 44, Issue:20
Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid.
AID359405Antifungal activity against Candida albicans 44506 in YNBG medium after 7 days in pH 6 buffer by agar dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID213887In vitro inhibition of U-87 MG (human glioblastoma) cell growth.2001Journal of medicinal chemistry, Sep-27, Volume: 44, Issue:20
Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid.
AID397147Induction of PKC-mediated mouse EL-4.IL-2 cells adherence by MTT assay1993Journal of natural products, Jun, Volume: 56, Issue:6
Evaluation of marine sponge metabolites for cytotoxicity and signal transduction activity.
AID359394Antifungal activity against Trichosporon beigelii 28592 after 18 to 24 hrs by twofold broth dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359408Antifungal activity against Candida albicans 44506 in YNBG medium of pH 5.4 after 7 days by agar dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359387Antifungal activity against Candida albicans 44506 in RPMI-1640 medium after 18 to 24 hrs by twofold broth dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359383Antibacterial activity against Bacillus subtilis 6633 after 18 to 24 hrs by twofold broth dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359392Antifungal activity against Epidermophyton floccosum 25066 after 18 to 24 hrs by twofold broth dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID397144Cytotoxicity against mouse P388 cells after 48 hrs by MTT assay1993Journal of natural products, Jun, Volume: 56, Issue:6
Evaluation of marine sponge metabolites for cytotoxicity and signal transduction activity.
AID359403Antifungal activity against Candida albicans 44506 in YNBG medium after 7 days in pH 4 buffer by agar dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID103205In vitro inhibition of MCF-7 (human breast cancer) cell growth.2001Journal of medicinal chemistry, Sep-27, Volume: 44, Issue:20
Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid.
AID359406Antifungal activity against Candida albicans 44506 in YNBG medium after 7 days in pH 7 buffer by agar dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID8819In vitro inhibition of A-427 (human lung cancer) cell growth.2001Journal of medicinal chemistry, Sep-27, Volume: 44, Issue:20
Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid.
AID359611Antifungal activity against Candida albicans 44506 assessed as inhibition of U-14C-leucine incorporation into TCA precipitable material after 1 hr1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359386Antifungal activity against Candida albicans 44506 in YNBG medium after 18 to 24 hrs by twofold broth dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359400Antifungal activity against Candida albicans 44506 in RPMI-1640 medium after 7 days in pH 7 buffer by agar dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID213867In vitro inhibition of U-373 MG (human glioblastoma) cell growth.2001Journal of medicinal chemistry, Sep-27, Volume: 44, Issue:20
Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid.
AID359401Antifungal activity against Candida albicans 44506 in RPMI-1640 medium after 7 days in pH 8 buffer by agar dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359398Antifungal activity against Candida albicans 44506 in RPMI-1640 medium after 7 days in pH 5 buffer by agar dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359382Antibacterial activity against Pseudomonas aeruginosa 27853 after 18 to 24 hrs by twofold broth dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID397143Cytotoxicity against human HT-29 cells after 48 hrs by MTT assay1993Journal of natural products, Jun, Volume: 56, Issue:6
Evaluation of marine sponge metabolites for cytotoxicity and signal transduction activity.
AID359381Antibacterial activity against Escherichia coli HBOI 001 after 18 to 24 hrs by twofold broth dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359402Antifungal activity against Candida albicans 44506 in RPMI-1640 medium of pH 7.2 after 7 days by agar dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359385Antifungal activity against Candida albicans 44506 in Sabouraud dextrose broth after 24 to 48 hrs1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359391Antifungal activity against Trichophyton mentagrophytes 9533 after 18 to 24 hrs by twofold broth dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359613Antifungal activity against Candida albicans 44506 assessed as inhibition of U-14C-acetate incorporation into TCA precipitable material after 1 hr1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID156333In vitro inhibition of PC-3 (human prostate cancer) cell growth.2001Journal of medicinal chemistry, Sep-27, Volume: 44, Issue:20
Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid.
AID209975In vitro inhibition of T-47D (human breast cancer) cell growth.2001Journal of medicinal chemistry, Sep-27, Volume: 44, Issue:20
Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid.
AID770979Inhibition of telomerase (unknown origin) by TRAP assay2013European journal of medicinal chemistry, Oct, Volume: 68Toward the design of new DNA G-quadruplex ligands through rational analysis of polymorphism and binding data.
AID359407Antifungal activity against Candida albicans 44506 in YNBG medium after 7 days in pH 8 buffer by agar dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359395Antifungal activity against Sporothrix schenckii 14284 after 18 to 24 hrs by twofold broth dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359389Antifungal activity against Cryptococcus neoformans 32045 after 48 hrs by twofold broth dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID102200In vitro inhibition of LoVo (human colon cancer) cell growth.2001Journal of medicinal chemistry, Sep-27, Volume: 44, Issue:20
Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid.
AID359390Antifungal activity against Cryptococcus neoformans 32045 after 24 to 48 hrs1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359612Antifungal activity against Candida albicans 44506 assessed as inhibition of U-14C-glucose incorporation into TCA precipitable material after 1 hr1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID78796In vitro inhibition of HCT-15 (human colon cancer) cell growth.2001Journal of medicinal chemistry, Sep-27, Volume: 44, Issue:20
Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid.
AID359393Antifungal activity against Microsporum gypseum 42960 after 18 to 24 hrs by twofold broth dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID91766In vitro inhibition of J82 (human bladder cancer) cell growth.2001Journal of medicinal chemistry, Sep-27, Volume: 44, Issue:20
Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid.
AID359397Antifungal activity against Candida albicans 44506 in RPMI-1640 medium after 7 days in pH 4 buffer by agar dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID397142Cytotoxicity against human A549 cells after 48 hrs by MTT assay1993Journal of natural products, Jun, Volume: 56, Issue:6
Evaluation of marine sponge metabolites for cytotoxicity and signal transduction activity.
AID397145Cytotoxicity against mouse EL-4.IL-2 cells after 3 to 4 days by Trypan blue exclusion test1993Journal of natural products, Jun, Volume: 56, Issue:6
Evaluation of marine sponge metabolites for cytotoxicity and signal transduction activity.
AID8640In vitro inhibition of A549 (human lung cancer) cell growth.2001Journal of medicinal chemistry, Sep-27, Volume: 44, Issue:20
Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid.
AID359399Antifungal activity against Candida albicans 44506 in RPMI-1640 medium after 7 days in pH 6 buffer by agar dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359404Antifungal activity against Candida albicans 44506 in YNBG medium after 7 days in pH 5 buffer by agar dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359610Antifungal activity against Candida albicans 44506 assessed as inhibition of U-14C-adenine incorporation into TCA precipitable material after 1 hr1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359388Antifungal activity against Candida albicans 44506 in RPMI-1640 medium after 24 to 48 hrs1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID359384Antifungal activity against Candida albicans 44506 in Sabouraud dextrose broth after 18 to 24 hrs by twofold broth dilution method1992Journal of natural products, Nov, Volume: 55, Issue:11
Antifungal activity of meridine, a natural product from the marine sponge Corticium sp.
AID201672In vitro inhibition of A172 (human glioblastoma) cell growth.2001Journal of medicinal chemistry, Sep-27, Volume: 44, Issue:20
Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (25.00)18.2507
2000's5 (62.50)29.6817
2010's1 (12.50)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 106.00

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index106.00 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.56 (4.65)
Search Engine Demand Index184.39 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (106.00)

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]