Compounds > a 85380
Page last updated: 2024-08-01 14:24:20

a 85380

Description

A 85380: structure given in first source; A-85380 is the S-enantiomer; A-159470 is the R-enantiomer [MeSH]

Cross-References

ID SourceID
PubMed CID5310969
CHEMBL ID59986
SCHEMBL ID676026
MeSH IDM0272455

Synonyms (17)

Synonym
(s)-3-(azetidin-2-ylmethoxy)pyridine
bdbm50049750
3-((s)-1-azetidin-2-ylmethoxy)-pyridine
a-85380
a 85380
CHEMBL59986 ,
a-159470
3-[[(2s)-azetidin-2-yl]methoxy]pyridine
gtpl5460
a85380
3-[(2s)-azetidin-2-ylmethoxy]pyridine
SCHEMBL676026
161416-98-4
3-(2(s)-azetidinylmethoxy)pyridine
NCGC00387223-01
Q27074089
pyridine, 3-(2-azetidinylmethoxy)-, (s)-

Protein Targets (22)

Potency Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
cytochrome P450 2D6Homo sapiens (human)Potency26.8370AID1645840

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Acetylcholine receptor subunit alphaHomo sapiens (human)Ki0.3140AID1179333
Acetylcholine receptor subunit alphaTetronarce californica (Pacific electric ray)Ki0.3140AID219643
Neuronal acetylcholine receptor subunit alpha-3Rattus norvegicus (Norway rat)Ki0.0145AID145682; AID145685; AID146006; AID146162
Acetylcholine receptor subunit gammaHomo sapiens (human)Ki0.3140AID1179333
Neuronal acetylcholine receptor subunit alpha-4Rattus norvegicus (Norway rat)IC500.0015AID146322
Neuronal acetylcholine receptor subunit alpha-4Rattus norvegicus (Norway rat)Ki0.0013AID145682; AID145685; AID146486; AID146772; AID700118
Acetylcholine receptor subunit betaHomo sapiens (human)Ki0.3140AID1179333
Neuronal acetylcholine receptor subunit alpha-2Rattus norvegicus (Norway rat)Ki0.0001AID145682; AID145685; AID145983
Neuronal acetylcholine receptor subunit beta-2Rattus norvegicus (Norway rat)IC500.0015AID146322
Neuronal acetylcholine receptor subunit beta-2Rattus norvegicus (Norway rat)Ki0.0001AID145682; AID145685; AID145983; AID146006; AID146486; AID700118
Neuronal acetylcholine receptor subunit beta-3Rattus norvegicus (Norway rat)Ki0.0002AID145682; AID145685
Neuronal acetylcholine receptor subunit beta-4Rattus norvegicus (Norway rat)Ki0.0159AID145682; AID145685; AID146162; AID146772
Neuronal acetylcholine receptor subunit beta-2Homo sapiens (human)IC500.0015AID414713
Neuronal acetylcholine receptor subunit beta-2Homo sapiens (human)Ki0.0000AID1143254; AID146300; AID146301
Neuronal acetylcholine receptor subunit alpha-5Rattus norvegicus (Norway rat)Ki0.0002AID145682; AID145685
Neuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)Ki0.1480AID1143255; AID146786; AID146788
Neuronal acetylcholine receptor subunit alpha-6Rattus norvegicus (Norway rat)Ki0.0002AID145682; AID145685
Neuronal acetylcholine receptor subunit alpha-9Rattus norvegicus (Norway rat)Ki0.0002AID145682; AID145685
Neuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)IC500.0015AID414713
Neuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)Ki0.0000AID1143254; AID146300; AID146301
Neuronal acetylcholine receptor subunit alpha-7Rattus norvegicus (Norway rat)Ki0.0002AID145682; AID145685
Acetylcholine receptor subunit deltaHomo sapiens (human)Ki0.3140AID1179333
Neuronal acetylcholine receptor subunit alpha-10Rattus norvegicus (Norway rat)Ki0.0002AID145682; AID145685

Activation Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Neuronal acetylcholine receptor subunit alpha-4Rattus norvegicus (Norway rat)EC500.7000AID1179366; AID146297
Neuronal acetylcholine receptor subunit beta-2Rattus norvegicus (Norway rat)EC500.7000AID1179366; AID146297
Neuronal acetylcholine receptor subunit beta-2Homo sapiens (human)EC500.7016AID1179366; AID146297; AID414714; AID710187
Neuronal acetylcholine receptor subunit beta-4Homo sapiens (human)EC500.7000AID145356
Neuronal acetylcholine receptor subunit alpha-3Homo sapiens (human)EC500.7000AID145356; AID225721
Neuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)EC508.9000AID146778; AID146779; AID710185
Neuronal acetylcholine receptor subunit alpha-4Homo sapiens (human)EC500.7016AID1179366; AID146297; AID414714; AID710187

Bioassays (66)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
ISSN: 2472-5560		Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
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
ISSN: 1091-6490		Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
ISSN: 1521-0111		A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
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
ISSN: 1091-6490		Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
ISSN: 1521-0111		A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID414715Intrinsic activity at human alpha4beta2 nAChR expressed in HEK293 cells assessed as intracellular calcium level by FLIPR assay relative to (-)nicotine2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
ISSN: 1520-4804		Complementary three-dimensional quantitative structure-activity relationship modeling of binding affinity and functional potency: a study on alpha4beta2 nicotinic ligands.
AID146786Binding affinity against human Nicotinic acetylcholine receptor alpha-7 was determined1999Journal of medicinal chemistry, Jun-17, Volume: 42, Issue:12
ISSN: 0022-2623		Synthesis and nicotinic acetylcholine receptor in vivo binding properties of 2-fluoro-3-[2(S)-2-azetidinylmethoxy]pyridine: a new positron emission tomography ligand for nicotinic receptors.
AID146611Binding affinity towards Nicotinic acetylcholine receptor alpha4-beta2 in rat brain using [3H]-cytisine as radioligand1998Bioorganic & medicinal chemistry letters, Oct-06, Volume: 8, Issue:19
ISSN: 0960-894X		Structure-activity studies related to ABT-594, a potent nonopioid analgesic agent: effect of pyridine and azetidine ring substitutions on nicotinic acetylcholine receptor binding affinity and analgesic activity in mice.
AID146788Compound was evaluated for its ability to displace [125I]alpha-bungarotoxin (alpha-BgT) from K28 cells expressing human Nicotinic acetylcholine receptor alpha71998Journal of medicinal chemistry, Feb-12, Volume: 41, Issue:4
ISSN: 0022-2623		Identification and initial structure-activity relationships of (R)-5-(2-azetidinylmethoxy)-2-chloropyridine (ABT-594), a potent, orally active, non-opiate analgesic agent acting via neuronal nicotinic acetylcholine receptors.
AID146322In vitro binding affinity for Nicotinic acetylcholine receptor alpha4-beta2 in rat cerebral cortical membrane using [3H]cytisine as radioligand2000Journal of medicinal chemistry, Jun-01, Volume: 43, Issue:11
ISSN: 0022-2623		Novel potent ligands for the central nicotinic acetylcholine receptor: synthesis, receptor binding, and 3D-QSAR analysis.
AID710185Agonist activity at human alpha7 nAChR2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
ISSN: 1520-4804		Discovery of highly potent and selective α4β2-nicotinic acetylcholine receptor (nAChR) partial agonists containing an isoxazolylpyridine ether scaffold that demonstrate antidepressant-like activity. Part II.
AID414714Agonist activity at human alpha4beta2 nAChR expressed in HEK293 cells assessed as intracellular calcium level by FLIPR assay2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
ISSN: 1520-4804		Complementary three-dimensional quantitative structure-activity relationship modeling of binding affinity and functional potency: a study on alpha4beta2 nicotinic ligands.
AID1143254Agonist activity at alpha4beta2 nAChR (unknown origin)2014Journal of medicinal chemistry, May-22, Volume: 57, Issue:10
ISSN: 1520-4804		Discovery of novel 2-((pyridin-3-yloxy)methyl)piperazines as α7 nicotinic acetylcholine receptor modulators for the treatment of inflammatory disorders.
AID91540Maximal response of compound was determined in an in vitro [86Rb+] release assay using IMR-32 cells1998Bioorganic & medicinal chemistry letters, Oct-06, Volume: 8, Issue:19
ISSN: 0960-894X		Structure-activity studies related to ABT-594, a potent nonopioid analgesic agent: effect of pyridine and azetidine ring substitutions on nicotinic acetylcholine receptor binding affinity and analgesic activity in mice.
AID231913Ratio between the binding affinities towards rat alpha3-beta4 and forebrain nACh Receptor using [3H]EB2004Bioorganic & medicinal chemistry letters, Apr-19, Volume: 14, Issue:8
ISSN: 0960-894X		Pharmacology of the agonist binding sites of rat neuronal nicotinic receptor subtypes expressed in HEK 293 cells.
AID710188Binding affinity to human alpha7 nAChR in human brain2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
ISSN: 1520-4804		Discovery of highly potent and selective α4β2-nicotinic acetylcholine receptor (nAChR) partial agonists containing an isoxazolylpyridine ether scaffold that demonstrate antidepressant-like activity. Part II.
AID710186Agonist activity at ganglionic nAChR2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
ISSN: 1520-4804		Discovery of highly potent and selective α4β2-nicotinic acetylcholine receptor (nAChR) partial agonists containing an isoxazolylpyridine ether scaffold that demonstrate antidepressant-like activity. Part II.
AID94464Compound was evaluated for functional activation to [86Rb+] efflux from human K177 cells expressing recombinant alpha4-beta2 receptors.1998Journal of medicinal chemistry, Feb-12, Volume: 41, Issue:4
ISSN: 0022-2623		Identification and initial structure-activity relationships of (R)-5-(2-azetidinylmethoxy)-2-chloropyridine (ABT-594), a potent, orally active, non-opiate analgesic agent acting via neuronal nicotinic acetylcholine receptors.
AID146779Compound was evaluated for functional potencies and efficacies at human Nicotinic acetylcholine receptor alpha71997Journal of medicinal chemistry, Dec-19, Volume: 40, Issue:26
ISSN: 0022-2623		Neuronal nicotinic acetylcholine receptors as targets for drug discovery.
AID145983Binding affinity towards rat nicotinic acetylcholine receptor alpha2-beta2 expressed in HEK293 cells using [3H]EB as radioligand2004Bioorganic & medicinal chemistry letters, Apr-19, Volume: 14, Issue:8
ISSN: 0960-894X		Pharmacology of the agonist binding sites of rat neuronal nicotinic receptor subtypes expressed in HEK 293 cells.
AID242876Maximal response against Nicotinic acetylcholine receptor alpha3-beta42005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
ISSN: 0022-2623		Neuronal nicotinic acetylcholine receptors: structural revelations, target identifications, and therapeutic inspirations.
AID132950Analgesic activity in a mouse hot plate assay1998Bioorganic & medicinal chemistry letters, Oct-06, Volume: 8, Issue:19
ISSN: 0960-894X		Structure-activity studies related to ABT-594, a potent nonopioid analgesic agent: effect of pyridine and azetidine ring substitutions on nicotinic acetylcholine receptor binding affinity and analgesic activity in mice.
AID91525Ability to stimulate Rb+ efflux from human IMR-32 cell preparations containing human alpha3-betaX receptors1996Journal of medicinal chemistry, Feb-16, Volume: 39, Issue:4
ISSN: 0022-2623		Novel 3-Pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors.
AID710189Binding affinity to muscle type alpha1beta1gammadelta-nAChR2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
ISSN: 1520-4804		Discovery of highly potent and selective α4β2-nicotinic acetylcholine receptor (nAChR) partial agonists containing an isoxazolylpyridine ether scaffold that demonstrate antidepressant-like activity. Part II.
AID1179362Binding affinity to human brain alpha4beta2* nAChR2014Journal of medicinal chemistry, Oct-23, Volume: 57, Issue:20
ISSN: 1520-4804		Recent developments in novel antidepressants targeting α4β2-nicotinic acetylcholine receptors.
AID700124Agonist activity at human alpha4beta2 nACHR expressed in SH-EP1 cells at 10 uM by 86Rb+ efflux assay2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
ISSN: 1520-4804		Identification of novel α4β2-nicotinic acetylcholine receptor (nAChR) agonists based on an isoxazole ether scaffold that demonstrate antidepressant-like activity.
AID1179363Binding affinity to human brain alpha3beta4* nAChR2014Journal of medicinal chemistry, Oct-23, Volume: 57, Issue:20
ISSN: 1520-4804		Recent developments in novel antidepressants targeting α4β2-nicotinic acetylcholine receptors.
AID220120Binding affinity for alpha4 beta-2 nAChR using [3H]epibatidine in rat brain1998Journal of medicinal chemistry, Sep-10, Volume: 41, Issue:19
ISSN: 0022-2623		2-, 5-, and 6-Halo-3-(2(S)-azetidinylmethoxy)pyridines: synthesis, affinity for nicotinic acetylcholine receptors, and molecular modeling.
AID176047compound was evaluated for functional potencies and efficacies at rat nAChR subtype DA release1997Journal of medicinal chemistry, Dec-19, Volume: 40, Issue:26
ISSN: 0022-2623		Neuronal nicotinic acetylcholine receptors as targets for drug discovery.
AID225720Binding affinity towards rat alpha2-beta4 nACh receptor expressed in HEK293 cells using [3H]EB as radioligand2004Bioorganic & medicinal chemistry letters, Apr-19, Volume: 14, Issue:8
ISSN: 0960-894X		Pharmacology of the agonist binding sites of rat neuronal nicotinic receptor subtypes expressed in HEK 293 cells.
AID145685Binding affinity towards rat forebrain nicotinic acetylcholine receptor using [3H]EB as radioligand2004Bioorganic & medicinal chemistry letters, Apr-19, Volume: 14, Issue:8
ISSN: 0960-894X		Pharmacology of the agonist binding sites of rat neuronal nicotinic receptor subtypes expressed in HEK 293 cells.
AID242877Maximal response against Nicotinic acetylcholine receptor alpha4-beta22005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
ISSN: 0022-2623		Neuronal nicotinic acetylcholine receptors: structural revelations, target identifications, and therapeutic inspirations.
AID146301Compound was evaluated for its ability to displace [3H]cytisine from K177 cells expressing human Nicotinic acetylcholine receptor alpha4-beta21998Journal of medicinal chemistry, Feb-12, Volume: 41, Issue:4
ISSN: 0022-2623		Identification and initial structure-activity relationships of (R)-5-(2-azetidinylmethoxy)-2-chloropyridine (ABT-594), a potent, orally active, non-opiate analgesic agent acting via neuronal nicotinic acetylcholine receptors.
AID132955Compound was evaluated for the analgesic activity by mouse hotplate assay at the doses of 0.62 and 6.2; No significant effect observed at the doses tested1998Journal of medicinal chemistry, Feb-12, Volume: 41, Issue:4
ISSN: 0022-2623		Identification and initial structure-activity relationships of (R)-5-(2-azetidinylmethoxy)-2-chloropyridine (ABT-594), a potent, orally active, non-opiate analgesic agent acting via neuronal nicotinic acetylcholine receptors.
AID146772Binding affinity towards rat Nicotinic acetylcholine receptor alpha4-beta4 expressed in HEK293 cells using [3H]EB as radioligand2004Bioorganic & medicinal chemistry letters, Apr-19, Volume: 14, Issue:8
ISSN: 0960-894X		Pharmacology of the agonist binding sites of rat neuronal nicotinic receptor subtypes expressed in HEK 293 cells.
AID146300Binding affinity against human Nicotinic acetylcholine receptor alpha4-beta21999Journal of medicinal chemistry, Jun-17, Volume: 42, Issue:12
ISSN: 0022-2623		Synthesis and nicotinic acetylcholine receptor in vivo binding properties of 2-fluoro-3-[2(S)-2-azetidinylmethoxy]pyridine: a new positron emission tomography ligand for nicotinic receptors.
AID146486Binding affinity towards rat Nicotinic acetylcholine receptor alpha4-beta2 expressed in HEK293 cells using [3H]EB as radioligand2004Bioorganic & medicinal chemistry letters, Apr-19, Volume: 14, Issue:8
ISSN: 0960-894X		Pharmacology of the agonist binding sites of rat neuronal nicotinic receptor subtypes expressed in HEK 293 cells.
AID1179366Agonist activity at human alpha4beta2 nAChR2014Journal of medicinal chemistry, Oct-23, Volume: 57, Issue:20
ISSN: 1520-4804		Recent developments in novel antidepressants targeting α4β2-nicotinic acetylcholine receptors.
AID145682Binding affinity against Nicotinic Acetylcholine Receptor was determined by measuring the displacement of [3H]cytisine from a preparation of whole rat brain.1996Journal of medicinal chemistry, Feb-16, Volume: 39, Issue:4
ISSN: 0022-2623		Novel 3-Pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors.
AID242872Maximal response against Nicotinic acetylcholine receptor alpha 72005Journal of medicinal chemistry, Jul-28, Volume: 48, Issue:15
ISSN: 0022-2623		Neuronal nicotinic acetylcholine receptors: structural revelations, target identifications, and therapeutic inspirations.
AID225721Functional activation of human sympathetic ganglionic type nAChRs in IMR-32 cells containing alpha-3 subtype1998Journal of medicinal chemistry, Feb-12, Volume: 41, Issue:4
ISSN: 0022-2623		Identification and initial structure-activity relationships of (R)-5-(2-azetidinylmethoxy)-2-chloropyridine (ABT-594), a potent, orally active, non-opiate analgesic agent acting via neuronal nicotinic acetylcholine receptors.
AID91534Maximum efficacy relative to 100(uM) (S)-nicotine for cell preparations containing alpha3-betaX IMR32 cells1996Journal of medicinal chemistry, Feb-16, Volume: 39, Issue:4
ISSN: 0022-2623		Novel 3-Pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors.
AID1179365Binding affinity to rat brain alpha4beta2* nAChR2014Journal of medicinal chemistry, Oct-23, Volume: 57, Issue:20
ISSN: 1520-4804		Recent developments in novel antidepressants targeting α4β2-nicotinic acetylcholine receptors.
AID145688Binding affinity towards nicotinic acetylcholine receptor using [3H]nicotine as radioligand in rat brain homogenates2002Bioorganic & medicinal chemistry letters, Aug-05, Volume: 12, Issue:15
ISSN: 0960-894X		A comparison of the binding of three series of nicotinic ligands.
AID146006Binding affinity towards rat Nicotinic acetylcholine receptor alpha3-beta2 expressed in HEK293 cells using [3H]EB as radioligand2004Bioorganic & medicinal chemistry letters, Apr-19, Volume: 14, Issue:8
ISSN: 0960-894X		Pharmacology of the agonist binding sites of rat neuronal nicotinic receptor subtypes expressed in HEK 293 cells.
AID94463Maximum efficacy relative to 100(uM) (S)-nicotine for cell preparations containing alpha4-beta2 K177 cells1996Journal of medicinal chemistry, Feb-16, Volume: 39, Issue:4
ISSN: 0022-2623		Novel 3-Pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors.
AID1179364Binding affinity to human brain alpha7* nAChR2014Journal of medicinal chemistry, Oct-23, Volume: 57, Issue:20
ISSN: 1520-4804		Recent developments in novel antidepressants targeting α4β2-nicotinic acetylcholine receptors.
AID700118Displacement of [3H]epibatidine from rat alpha4beta2 nACHR2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
ISSN: 1520-4804		Identification of novel α4β2-nicotinic acetylcholine receptor (nAChR) agonists based on an isoxazole ether scaffold that demonstrate antidepressant-like activity.
AID231915Ratio between the binding affinities towards rat alpha4-beta4 and alpha4-beta2 nACh receptor using [3H]EB as radioligand2004Bioorganic & medicinal chemistry letters, Apr-19, Volume: 14, Issue:8
ISSN: 0960-894X		Pharmacology of the agonist binding sites of rat neuronal nicotinic receptor subtypes expressed in HEK 293 cells.
AID414713Displacement of [3H]cytisine from human alpha4beta2 nAChR expressed in HEK293 cells2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
ISSN: 1520-4804		Complementary three-dimensional quantitative structure-activity relationship modeling of binding affinity and functional potency: a study on alpha4beta2 nicotinic ligands.
AID1179333Antagonist activity at human alpha1beta1gammadelta nAChR2014Journal of medicinal chemistry, Oct-23, Volume: 57, Issue:20
ISSN: 1520-4804		Recent developments in novel antidepressants targeting α4β2-nicotinic acetylcholine receptors.
AID146162Binding affinity towards rat Nicotinic acetylcholine receptor alpha3-beta4 expressed in HEK293 cells using [3H]EB as radioligand2004Bioorganic & medicinal chemistry letters, Apr-19, Volume: 14, Issue:8
ISSN: 0960-894X		Pharmacology of the agonist binding sites of rat neuronal nicotinic receptor subtypes expressed in HEK 293 cells.
AID146778Compound was evaluated for functional activation from channel currents at human Nicotinic acetylcholine receptor alpha-7 expressed in oocytes.1998Journal of medicinal chemistry, Feb-12, Volume: 41, Issue:4
ISSN: 0022-2623		Identification and initial structure-activity relationships of (R)-5-(2-azetidinylmethoxy)-2-chloropyridine (ABT-594), a potent, orally active, non-opiate analgesic agent acting via neuronal nicotinic acetylcholine receptors.
AID1143255Agonist activity at alpha7 nAChR (unknown origin)2014Journal of medicinal chemistry, May-22, Volume: 57, Issue:10
ISSN: 1520-4804		Discovery of novel 2-((pyridin-3-yloxy)methyl)piperazines as α7 nicotinic acetylcholine receptor modulators for the treatment of inflammatory disorders.
AID231912Ratio between the binding affinities towards rat alpha3-beta4 and alpha3-beta2 nACh receptor using [3H]EB as radioligand2004Bioorganic & medicinal chemistry letters, Apr-19, Volume: 14, Issue:8
ISSN: 0960-894X		Pharmacology of the agonist binding sites of rat neuronal nicotinic receptor subtypes expressed in HEK 293 cells.
AID1179367Agonist activity at human alpha3beta4* nAChR2014Journal of medicinal chemistry, Oct-23, Volume: 57, Issue:20
ISSN: 1520-4804		Recent developments in novel antidepressants targeting α4β2-nicotinic acetylcholine receptors.
AID145686Compound was evaluated for its ability to displace [3H]-cytisine binding from high-affinity Nicotinic acetylcholine receptor in rat brain (principally the alpha4-beta2 nAChR subtype)1998Journal of medicinal chemistry, Feb-12, Volume: 41, Issue:4
ISSN: 0022-2623		Identification and initial structure-activity relationships of (R)-5-(2-azetidinylmethoxy)-2-chloropyridine (ABT-594), a potent, orally active, non-opiate analgesic agent acting via neuronal nicotinic acetylcholine receptors.
AID231911Ratio between the binding affinities towards rat alpha2-beta4 and alpha2-beta2 nACh receptor using [3H]-EB as radioligand2004Bioorganic & medicinal chemistry letters, Apr-19, Volume: 14, Issue:8
ISSN: 0960-894X		Pharmacology of the agonist binding sites of rat neuronal nicotinic receptor subtypes expressed in HEK 293 cells.
AID219643Compound was evaluated for its ability to displace [125 I]alpha-bungarotoxin (alpha-BgT) from torpedo alpha1-beta1-gamma1 electroplax1998Journal of medicinal chemistry, Feb-12, Volume: 41, Issue:4
ISSN: 0022-2623		Identification and initial structure-activity relationships of (R)-5-(2-azetidinylmethoxy)-2-chloropyridine (ABT-594), a potent, orally active, non-opiate analgesic agent acting via neuronal nicotinic acetylcholine receptors.
AID146297Compound was evaluated for functional potencies and efficacies at human Nicotinic acetylcholine receptor alpha4-beta21997Journal of medicinal chemistry, Dec-19, Volume: 40, Issue:26
ISSN: 0022-2623		Neuronal nicotinic acetylcholine receptors as targets for drug discovery.
AID710187Agonist activity at human alpha4beta2 nAChR2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
ISSN: 1520-4804		Discovery of highly potent and selective α4β2-nicotinic acetylcholine receptor (nAChR) partial agonists containing an isoxazolylpyridine ether scaffold that demonstrate antidepressant-like activity. Part II.
AID710191Binding affinity to alpha4beta2 nAChR in rat brain2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
ISSN: 1520-4804		Discovery of highly potent and selective α4β2-nicotinic acetylcholine receptor (nAChR) partial agonists containing an isoxazolylpyridine ether scaffold that demonstrate antidepressant-like activity. Part II.
AID710190Binding affinity to alpha4beta2 nAChR in human brain2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
ISSN: 1520-4804		Discovery of highly potent and selective α4β2-nicotinic acetylcholine receptor (nAChR) partial agonists containing an isoxazolylpyridine ether scaffold that demonstrate antidepressant-like activity. Part II.
AID94460Ability to stimulate Rb+ efflux from human K177 cell preparations containing human alpha4-beta2 receptors1996Journal of medicinal chemistry, Feb-16, Volume: 39, Issue:4
ISSN: 0022-2623		Novel 3-Pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors.
AID225722Intrinsic activity against human sympathetic ganglionic type nAChRs in IMR-32 cells containing alpha-3 subtype1998Journal of medicinal chemistry, Feb-12, Volume: 41, Issue:4
ISSN: 0022-2623		Identification and initial structure-activity relationships of (R)-5-(2-azetidinylmethoxy)-2-chloropyridine (ABT-594), a potent, orally active, non-opiate analgesic agent acting via neuronal nicotinic acetylcholine receptors.
AID145356Compound was evaluated for functional potencies and efficacies at human Nicotinic acetylcholine receptor subtype IMR-32 (ganglionic)1997Journal of medicinal chemistry, Dec-19, Volume: 40, Issue:26
ISSN: 0022-2623		Neuronal nicotinic acetylcholine receptors as targets for drug discovery.

Research

Studies (101)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's16 (15.84)18.2507
2000's63 (62.38)29.6817
2010's19 (18.81)24.3611
2020's3 (2.97)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.99%)5.53%
Reviews6 (5.94%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other94 (93.07%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
choline
2
cholinesallergen;
Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
neurotransmitter;
nutrient;
plant metabolite;
Saccharomyces cerevisiae metabolite		2004200519.5low000200
bupropion
2
aromatic ketone;
monochlorobenzenes;
secondary amino compound		antidepressant;
environmental contaminant;
xenobiotic		2005201414.5low000110
epibatidine
6
alkaloid1996200524.2medium004200
dimethylphenylpiperazinium iodide
2
piperazines1997200523.0medium001100
granisetron
1
aromatic amide;
indazoles		1999199925.0low001000
mecamylamine
2
primary aliphatic amine1997200523.0low001100
succinylcholine
1
quaternary ammonium ion;
succinate ester		drug allergen;
muscle relaxant;
neuromuscular agent		1997199727.0low001000
carbachol
1
ammonium salt;
carbamate ester		cardiotonic drug;
miotic;
muscarinic agonist;
nicotinic acetylcholine receptor agonist;
non-narcotic analgesic		2004200420.0low000100
dimethylphenylpiperazinium iodide
1
N-arylpiperazine;
organic iodide salt;
piperazinium salt;
quaternary ammonium salt		nicotinic acetylcholine receptor agonist2004200420.0low000100
physostigmine
1
carbamate ester;
indole alkaloid		antidote to curare poisoning;
EC 3.1.1.8 (cholinesterase) inhibitor;
miotic		1999199925.0low001000
cytisine
5
alkaloid;
bridged compound;
lactam;
organic heterotricyclic compound;
secondary amino compound		nicotinic acetylcholine receptor agonist;
phytotoxin;
plant metabolite		1997201420.2low002210
dihydro-beta-erythroidine
1
delta-lactone;
organic heterotetracyclic compound;
tertiary amino compound		nicotinic antagonist2014201410.0low000010
sertraline
2
dichlorobenzene;
secondary amino compound;
tetralins		antidepressant;
serotonin uptake inhibitor		2012201212.0low000020
nicotine
8
3-(1-methylpyrrolidin-2-yl)pyridineanxiolytic drug;
biomarker;
immunomodulator;
mitogen;
neurotoxin;
nicotinic acetylcholine receptor agonist;
peripheral nervous system drug;
phytogenic insecticide;
plant metabolite;
psychotropic drug;
teratogenic agent;
xenobiotic		1996201220.6low003320
3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole
2
1997201219.5low001010
isoarecolone methiodide
1
1997199727.0high001000
varenicline
3
2012201411.3low000030
pozanicline
1
1997199727.0low001000
anatoxin a
1
tropane alkaloid1997199727.0low001000
abt 594
3
1998200523.7high002100
trans-metanicotine
1
1997199727.0low001000
3-(2,4-dimethoxybenzylidene)anabaseine
2
dimethoxybenzene1997200523.0low001100
5-ia-85380
2
aromatic ether1998201418.0high001010
a 84543
2
1996199727.5high002000
pnu-282987
1
carbonyl compound;
organohalogen compound		2014201410.0low000010
ispronicline
2
2005201414.5medium000110
deschloroepibatidine
1
2005200519.0low000100
dianicline
1
2005200519.0medium000100
f-a 85380
3
1998199925.7high003000
sazetidine-a
1
2014201410.0low000010
3-bromocytisine
1
2005200519.0medium000100
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
gamma-aminobutyric acid
1
amino acid zwitterion;
gamma-amino acid;
monocarboxylic acid		human metabolite;
neurotransmitter;
Saccharomyces cerevisiae metabolite;
signalling molecule		2011201113.0low000010
choline
1
cholinesallergen;
Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
neurotransmitter;
nutrient;
plant metabolite;
Saccharomyces cerevisiae metabolite		2008200816.0low000100
menthol
1
p-menthane monoterpenoid;
secondary alcohol		volatile oil component2013201311.0low000010
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
3
methylpyridines;
phenylpyridine;
tetrahydropyridine		neurotoxin2002200819.3low000300
amitriptyline
1
carbotricyclic compound;
tertiary amine		adrenergic uptake inhibitor;
antidepressant;
environmental contaminant;
tropomyosin-related kinase B receptor agonist;
xenobiotic		2004200420.0low000100
clonidine
1
clonidine;
imidazoline		2000200024.0low001000
fentanyl
1
anilide;
monocarboxylic acid amide;
piperidines		adjuvant;
anaesthesia adjuvant;
anaesthetic;
intravenous anaesthetic;
mu-opioid receptor agonist;
opioid analgesic		201920195.0low000010
lidocaine
1
benzenes;
monocarboxylic acid amide;
tertiary amino compound		anti-arrhythmia drug;
drug allergen;
environmental contaminant;
local anaesthetic;
xenobiotic		1998199826.0low001000
isoflurane
1
organofluorine compoundinhalation anaesthetic2013201311.0low000010
ketamine
1
cyclohexanones;
monochlorobenzenes;
secondary amino compound		analgesic;
environmental contaminant;
intravenous anaesthetic;
neurotoxin;
NMDA receptor antagonist;
xenobiotic		2002200222.0low000100
mecamylamine
8
primary aliphatic amine1998201619.0low004130
methiothepin
1
aryl sulfide;
dibenzothiepine;
N-alkylpiperazine;
tertiary amino compound		antipsychotic agent;
dopaminergic antagonist;
geroprotector;
serotonergic antagonist		2004200420.0low000100
oxidopamine
1
benzenetriol;
catecholamine;
primary amino compound		drug metabolite;
human metabolite;
neurotoxin		2011201113.0low000010
pirenzepine
1
pyridobenzodiazepineanti-ulcer drug;
antispasmodic drug;
muscarinic antagonist		2007200717.0low000100
xylazine
1
1,3-thiazine;
methylbenzene;
secondary amino compound		alpha-adrenergic agonist;
analgesic;
emetic;
muscle relaxant;
sedative		2002200222.0low000100
phentolamine
1
imidazoles;
phenols;
substituted aniline;
tertiary amino compound		alpha-adrenergic antagonist;
vasodilator agent		2001200123.0low000100
dimethylphenylpiperazinium iodide
1
N-arylpiperazine;
organic iodide salt;
piperazinium salt;
quaternary ammonium salt		nicotinic acetylcholine receptor agonist2006200618.0low000100
physostigmine
2
carbamate ester;
indole alkaloid		antidote to curare poisoning;
EC 3.1.1.8 (cholinesterase) inhibitor;
miotic		2003200520.0low000200
levodopa
1
amino acid zwitterion;
dopa;
L-tyrosine derivative;
non-proteinogenic L-alpha-amino acid		allelochemical;
antidyskinesia agent;
antiparkinson drug;
dopaminergic agent;
hapten;
human metabolite;
mouse metabolite;
neurotoxin;
plant growth retardant;
plant metabolite;
prodrug		2011201113.0low000010
chlorisondamine
2
isoindoles1998200423.0low001100
phencyclidine
1
benzenes;
piperidines		anaesthetic;
neurotoxin;
NMDA receptor antagonist;
psychotropic drug		201620168.0low000010
quinoxalines
4
mancude organic heterobicyclic parent;
naphthyridine;
ortho-fused heteroarene		2006201115.2low000220
isoxazoles
1
isoxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene		2005200519.0low000100
galantamine
1
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		2005200519.0low000100
cytisine
8
alkaloid;
bridged compound;
lactam;
organic heterotricyclic compound;
secondary amino compound		nicotinic acetylcholine receptor agonist;
phytotoxin;
plant metabolite		1998201421.0low004310
dihydro-beta-erythroidine
2
delta-lactone;
organic heterotetracyclic compound;
tertiary amino compound		nicotinic antagonist2004201315.5low000110
fluorodeoxyglucose f18
2
2-deoxy-2-((18)F)fluoro-D-glucose;
2-deoxy-2-fluoro-aldehydo-D-glucose		2012201212.0low000020
nicotine
18
3-(1-methylpyrrolidin-2-yl)pyridineanxiolytic drug;
biomarker;
immunomodulator;
mitogen;
neurotoxin;
nicotinic acetylcholine receptor agonist;
peripheral nervous system drug;
phytogenic insecticide;
plant metabolite;
psychotropic drug;
teratogenic agent;
xenobiotic		1996201618.2medium0041130
epibatidine
22
1998201319.9medium0061420
methyllycaconitine
1
2011201113.0low000010
3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole
1
2005200519.0low000100
rti 121
2
2002200819.0low000200
5-iodobenzovesamicol
1
2007200717.0low000100
varenicline
3
2007201114.3low000120
arachidonic acid
1
icosa-5,8,11,14-tetraenoic acid;
long-chain fatty acid;
omega-6 fatty acid		Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
human metabolite;
mouse metabolite		2002200222.0low000100
cocaine
2
benzoate ester;
methyl ester;
tertiary amino compound;
tropane alkaloid		adrenergic uptake inhibitor;
central nervous system stimulant;
dopamine uptake inhibitor;
environmental contaminant;
local anaesthetic;
mouse metabolite;
plant metabolite;
serotonin uptake inhibitor;
sodium channel blocker;
sympathomimetic agent;
vasoconstrictor agent;
xenobiotic		2002200819.0low000200
cotinine
1
N-alkylpyrrolidine;
pyridines;
pyrrolidin-2-ones;
pyrrolidine alkaloid		antidepressant;
biomarker;
human xenobiotic metabolite;
plant metabolite		2008200816.0low000100
cystine
1
2007200717.0low000100
fg 9041
1
quinoxaline derivative2006200618.0low000100
rubidium
1
alkali metal atom2002200222.0low000100
cysteine
1
cysteiniumfundamental metabolite2005200519.0low000100
exametazime
1
ketoxime2011201113.0low000010
piperacillin
3
2000200819.0low001200
lurasidone hydrochloride
1
hydrochlorideadrenergic antagonist;
dopaminergic antagonist;
second generation antipsychotic;
serotonergic antagonist		201620168.0low000010
pnu-282987
1
201620168.0low000010
scopolamine hydrobromide
1
1998199826.0low001000
picrotoxin
1
2006200618.0low000100
piperidines
1
2007200717.0low000100
aconitine
1
2011201113.0low000010
tc 2559
1
2007200717.0low000100
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Absence Seizure0
1
1998199826.0low001000
Ache0
5
1998200622.2low003200
Acute Confusional Senile Dementia0
3
2000200421.3low001200
Acute Hypercapnic Respiratory Failure0
1
201920195.0low000010
Acute Onset Vascular Dementia0
2
2004201116.5low000110
ADDH0
1
2011201113.0low000010
Adenoma, beta-Cell0
1
2006200618.0low000100
Adipocere0
2
2005200718.0low000200
Age-Related Memory Disorders0
1
2009200915.0low000100
Aging0
1
2009200915.0low000100
Altered Level of Consciousness0
1
2006200618.0low000100
Alzheimer Disease0
3
2000200421.3low001200
Anasarca0
1
2000200024.0low001000
Atherosclerotic Parkinsonism0
1
2002200222.0low000100
Attention Deficit Disorder with Hyperactivity0
1
2011201113.0low000010
Autosomal Dominant Juvenile Parkinson Disease0
2
2004200718.5low000200
Behavior Disorders0
1
2006200618.0low000100
Brain Diseases0
1
2004200420.0low000100
Brain Disorders0
1
2004200420.0low000100
Cognition Disorders0
3
2009201611.0low000120
Congenital Zika Syndrome0
1
202020204.0low000010
Cortical Lewy Body Disease0
2
2004200619.0low000200
Dementia, Vascular0
2
2004201116.5low000110
Depression0
1
2014201410.0low000010
Depression, Endogenous0
1
2004200420.0low000100
Depressive Disorder0
1
2004200420.0low000100
Disease Models, Animal0
5
2004202012.8low000230
Drug Withdrawal Symptoms0
2
2006200916.5low000200
Dyskinesia, Drug-Induced0
1
2011201113.0low000010
Dyskinesia, Medication-Induced0
1
2011201113.0low000010
Edema0
1
2000200024.0low001000
Idiopathic Parkinson Disease0
9
2004201415.3low000540
Injuries, Spinal Cord0
1
2005200519.0low000100
Insulinoma0
1
2006200618.0low000100
Lewy Body Disease0
2
2004200619.0low000200
Memory Disorders0
1
2009200915.0low000100
Mental Disorders0
1
2006200618.0low000100
MPTP Neurotoxicity Syndrome0
1
2006200618.0low000100
Multiple System Atrophy0
2
2012201212.0low000020
Multiple System Atrophy Syndrome0
2
2012201212.0low000020
Muscle Contraction0
1
1998199826.0low001000
Neuroblastoma0
2
1998201219.0low001010
Nicotine Addiction0
2
2007200916.0low000200
Ophthalmoplegia, Progressive Supranuclear0
1
2007200717.0low000100
Pain0
5
1998200622.2low003200
Parkinson Disease0
9
2004201415.3low000540
Parkinson Disease, Secondary0
1
2002200222.0low000100
Parkinsonian Disorders0
2
2004200718.5low000200
Pregnancy0
1
201920195.0low000010
Respiratory Insufficiency0
1
201920195.0low000010
Seizures0
1
1998199826.0low001000
Smoking Cessation0
2
2007200916.0low000200
Spinal Cord Injuries0
1
2005200519.0low000100
Substance Withdrawal Syndrome0
2
2006200916.5low000200
Supranuclear Palsy, Progressive0
1
2007200717.0low000100
Tobacco Use Disorder0
2
2007200916.0low000200
Zika Virus Infection0
1
202020204.0low000010

Bioavailability (2)

ArticleYear
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology, , Volume: 96, Issue:5		2019
Discovery of novel 2-((pyridin-3-yloxy)methyl)piperazines as α7 nicotinic acetylcholine receptor modulators for the treatment of inflammatory disorders.
Journal of medicinal chemistry, , May-22, Volume: 57, Issue:10		2014

Dosage (1)

ArticleYear
Acute effects of physostigmine and galantamine on the binding of [18F]fluoro-A-85380: a PET study in monkeys.
Synapse (New York, N.Y.), , Jun-15, Volume: 56, Issue:4		2005