Page last updated: 2024-12-07

metaphit

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

Description

metaphit: site-directed acylating agent of phencyclidine receptors in rat brain; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID114745
CHEMBL ID41541
SCHEMBL ID8867543
MeSH IDM0130401

Synonyms (31)

Synonym
metaphit
1-(1-(3-isothiocyanatophenyl)cyclohexyl)piperidine
1-[1-(3-isothiocyanato-phenyl)-cyclohexyl]-piperidine
bdbm50044426
HMS3266M08
LOPAC0_000843
1-[1-(3-isothiocyanato)phenyl]cyclohexylpiperidine methanesulfonate salt
NCGC00024655-01
tocris-0568
CHEMBL41541 ,
methaphit
96316-00-6
1-[1-(3-isothiocyanatophenyl)cyclohexyl]piperidine
CCG-204926
nfs3hjc8wd ,
piperidine, 1-(1-(3-isothiocyanatophenyl)cyclohexyl)-
unii-nfs3hjc8wd
SCHEMBL8867543
metaphit|1-(1-(3-isothiocyanato)phenyl)cyclohexylpiperidine
AKOS024458565
SR-01000076019-3
sr-01000076019
1-[1-(3-isothiocyanatophenyl)cyclohexyl]pi-peridine
DTXSID00914572
FGSGBQAQSPSRJK-UHFFFAOYSA-N
HMS3675E20
HMS3411E20
Q6553528
piperidine, 1-[1-(3-isothiocyanatophenyl)cyclohexyl]-
HY-100998
CS-0020680

Research Excerpts

Effects

ExcerptReferenceRelevance
"Metaphit has been shown to induce audiogenic seizures after systemic and intracerebroventricular administration and to be truly epileptic in small rodents, although about 8 h after metaphit administration, the power spectra increased and was more intense in the period of sound onset and seizure events. "( [Behavioral and electroencephalographic effects of delta sleep inducing peptide and its analogue on metaphit-induced audiogenic seizures in rats].
Mirković, S; Stanojlović, O; Vucević, D; Zivanović, D,
)
1.79

Treatment

In metaphit-pretreated animals a significant reduction of glutamate BBB uptake was found. EEGs appeared as polyspikes and spike-wave complexes while the power spectra were increasing for 30-h period. Metaphit treatment followed 24 h later by NMDA dose of 50 mg/kg provoked no spontaneous convulsions.

ExcerptReferenceRelevance
"In metaphit-pretreated animals a significant reduction of glutamate BBB uptake was found, in comparison with that of controls."( The possible role of glutamate uptake in metaphit-induced seizures.
Holland, T; Killian, C; Lajtha, A; Lipovac, MN; Poleksic, A, 2003
)
1.1
"In metaphit-treated animals, EEGs appeared as polyspikes and spike-wave complexes while the power spectra were increasing for 30-h period."( Delta sleep-inducing peptide and its tetrapeptide analogue alleviate severity of metaphit seizures.
Mikhaleva, I; Mirković, S; Stanojlović, O; Zivanović, D, 2004
)
1.06
"Metaphit-treated animals displaying seizure in eight previous tests received DSIP or DSIP-12 and afterwards audiogenic stimuli were applied at hourly intervals for the next 30 h."( Antiepileptic activity of delta sleep-inducing peptide and its analogue in metaphit-provoked seizures in rats.
Mikhaleva, II; Mirković, SD; Stanojlović, OP; Zivanović, DP, 2005
)
1.28
"Metaphit-treated rats displaying seizures in 8 previous tests were i.p."( Delta-sleep-inducing peptide potentiates anticonvulsive activity of valproate against metaphit-provoked audiogenic seizure in rats.
Hrncić, D; Stanojlović, O; Susić, V; Zivanović, D, 2006
)
1.28
"In metaphit-treated animals, the EEG appeared as polyspikes, spike-wave complexes and sleep-like patterns, whereas the power spectra were increased compared with the corresponding controls."( Anticonvulsant, but not antiepileptic, action of valproate on audiogenic seizures in metaphit-treated rats.
Hrncić, DR; Stanojlović, OP; Susić, VT; Zivanović, DP, 2007
)
1.08
"In metaphit-treated animals EEGs appeared as polyspikes and spike-wave complexes, while power spectra were increasing. "( [Delta sleep-inducing peptide and its analogues alleviate the severity of metaphit-induced audiogenic seizures in rats].
Hrncić, D; Stanojlović, O; Susić, V; Turjacanin, D; Zivanović, D,
)
0.98
"Metaphit treatment (10 mg/kg) followed 24 h later by NMDA dose of 50 mg/kg provoked no spontaneous convulsions, while metaphit in combination with a higher NMDA dose of 70 mg/kg resulted in spontaneous and AGS-induced seizures only in one time point [25]."( [Potentiation of metaphit-induced audiogenic epilepsy with N-methyl-D-aspartate in rats].
Stanojlović, O; Susić, V; Zivanović, D,
)
1.19
"Metaphit pretreatment increased the cataleptic effects induced by cumulative doses of PCP-type drugs (i.e., PCP, ketamine and m-amino PCP) and of drugs that have PCP-like actions (i.e., dexoxadrol, LY 154716 and cyclazocine)."( Effects of metaphit, a proposed phencyclidine receptor acylator, on catalepsy in pigeons.
Domino, EF; Head, R; Holsztynska, EJ; Jacobson, AE; Koek, W; Lessor, RA; Rafferty, MF; Rice, KC; Woods, JH, 1985
)
1.38
"Pretreatment with metaphit (1-[1-(3-isothiocyanotophenyl)cyclohexyl]piperidine), a putative irreversible antagonist of phencyclidine (PCP) receptors, did not antagonize PCP-induced passive avoidance deficit in rats, and did not decrease [3H]MK-801 (5-methyl-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine maleate) binding to PCP recognition sites coupled to NMDA receptors. "( Metaphit fails to antagonize PCP-induced passive avoidance deficit.
Danysz, W, 1991
)
2.06
"Pretreatment with metaphit blocked PCP-induced hypothermia; however, pretreatment with PCP did not affect the subsequent hypothermic response to PCP."( Metaphit antagonizes phencyclidine-induced hypothermia in the rat.
Chun, BM; George, R; Jacobson, AE; Pechnick, RN; Rice, KC; Thurkauf, A; Wu, AA, 1989
)
2.04
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (31)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency1.00000.004023.8416100.0000AID485290
USP1 protein, partialHomo sapiens (human)Potency39.81070.031637.5844354.8130AID504865
TDP1 proteinHomo sapiens (human)Potency25.16180.000811.382244.6684AID686978; AID686979
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency10.00000.00207.533739.8107AID891
cellular tumor antigen p53 isoform aHomo sapiens (human)Potency31.62280.316212.443531.6228AID902
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency15.84890.031610.279239.8107AID884; AID885
lethal factor (plasmid)Bacillus anthracis str. A2012Potency25.11890.020010.786931.6228AID912
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency15.84891.000012.224831.6228AID885
[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)
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)Ki0.53500.00030.86666.6900AID145239
Lysosomal Pro-X carboxypeptidaseHomo sapiens (human)Ki0.01600.01600.01600.0160AID156837
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)Ki0.53500.00030.68056.6900AID145239
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)Ki0.53500.00030.70716.6900AID145239
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)Ki0.53500.00030.81966.6900AID145239
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)Ki0.53500.00030.70726.6900AID145239
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)Ki0.53500.00030.70726.6900AID145239
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)Ki0.53500.00030.70726.6900AID145239
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
regulation of thyroid hormone mediated signaling pathwayLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
plasma kallikrein-kinin cascadeLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
proteolysisLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
glucose homeostasisLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
energy homeostasisLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
regulation of reactive oxygen species metabolic processLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
angiogenesis involved in wound healingLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
negative regulation of systemic arterial blood pressureLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
regulation of blood vessel endothelial cell migrationLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
serine-type carboxypeptidase activityLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
protein bindingLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
dipeptidyl-peptidase activityLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
plasma membraneLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
azurophil granule membraneLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
intracellular membrane-bounded organelleLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
basal part of cellLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
extracellular exosomeLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
ficolin-1-rich granule membraneLysosomal Pro-X carboxypeptidaseHomo sapiens (human)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID144821Tested for the % inactivation of [3H]dizocilpine binding to NMDA receptor at 10 uM1993Journal of medicinal chemistry, Aug-20, Volume: 36, Issue:17
Synthesis and binding properties of MK-801 isothiocyanates; (+)-3-isothiocyanato-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten- 5,10-imine hydrochloride: a new, potent and selective electrophilic affinity ligand for the NMDA receptor-coupled phencycli
AID145239Tested for the inhibition of [3H]dizocilpine binding to N-methyl-D-aspartate (NMDA) receptor-coupled phencyclidine binding site1993Journal of medicinal chemistry, Aug-20, Volume: 36, Issue:17
Synthesis and binding properties of MK-801 isothiocyanates; (+)-3-isothiocyanato-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten- 5,10-imine hydrochloride: a new, potent and selective electrophilic affinity ligand for the NMDA receptor-coupled phencycli
AID156837Compound was tested for its binding affinity towards PCP receptor using [3H](+)-NANM in the presence of 5 uM haloperidol from rat brain1998Journal of medicinal chemistry, May-07, Volume: 41, Issue:10
1'-Benzyl-3,4-dihydrospiro[2H-1- benzothiopyran-2,4'-piperidine] (spipethiane), a potent and highly selective sigma1 ligand.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347154Primary screen GU AMC 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.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (59)

TimeframeStudies, This Drug (%)All Drugs %
pre-199028 (47.46)18.7374
1990's13 (22.03)18.2507
2000's14 (23.73)29.6817
2010's2 (3.39)24.3611
2020's2 (3.39)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.66

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 Index20.66 (24.57)
Research Supply Index4.23 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.66)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.47%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other67 (98.53%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]