Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H33NO4 |
| Molecular Weight | 435.5552 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(O)[C@H]1O[C@H]2CC[C@]3(C)[C@]4(C)[C@H](CC5=C4NC6=C5C=CC=C6)CC[C@@]3(O)C2=CC1=O
InChI
InChIKey=ACNHBCIZLNNLRS-UBGQALKQSA-N
InChI=1S/C27H33NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,14-15,21,23,28,30-31H,9-13H2,1-4H3/t15-,21-,23-,25+,26+,27+/m0/s1
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24836752 |
https://www.ncbi.nlm.nih.gov/pubmed/24836752
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24836752 |
https://www.ncbi.nlm.nih.gov/pubmed/24836752
Paxilline is a toxic, tremorgenic indole alkaloid produced by Penicillium paxilli. Paxilline is inhibitor of BK channels, and is widely used as a tool compound to test role of BK channels in various conditions. Paxilline demonstrated therapeutic benefit in preclinical model of acute pancreatitis, and was able to induce apoptosis of glioma cell lines in vitro.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL4304 |
50.0 nM [IC50] | ||
Target ID: CHEMBL2111451 |
6.7 µM [Ki] | ||
Target ID: CHEMBL3136 |
5.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| ROS-independent preconditioning in neurons via activation of mitoK(ATP) channels by BMS-191095. | 2008-06 |
|
| Astrocyte-derived CO is a diffusible messenger that mediates glutamate-induced cerebral arteriolar dilation by activating smooth muscle Cell KCa channels. | 2008-02-01 |
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| Sub-plasmalemmal [Ca2+]i upstroke in myocytes of the guinea-pig small intestine evoked by muscarinic stimulation: IP3R-mediated Ca2+ release induced by voltage-gated Ca2+ entry. | 2008-02 |
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| Infarct size limitation by adrenomedullin: protein kinase A but not PI3-kinase is linked to mitochondrial KCa channels. | 2008-01-15 |
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| The regulation of mitochondrial respiration by opening of mKCa channels is age-dependent. | 2008-01-14 |
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| Riluzole-induced block of voltage-gated Na+ current and activation of BKCa channels in cultured differentiated human skeletal muscle cells. | 2008-01-02 |
|
| Essential role of mitochondrial Ca2+-activated and ATP-sensitive K+ channels in sildenafil-induced late cardioprotection. | 2008-01 |
|
| 20-HETE inhibits the proliferation of vascular smooth muscle cells via transforming growth factor-beta. | 2008-01 |
|
| The function of the NADPH oxidase of phagocytes and its relationship to other NOXs in plants, invertebrates, and mammals. | 2008 |
|
| Opening the calcium-activated potassium channel participates in the cardioprotective effect of puerarin. | 2007-11-28 |
|
| Mitochondrial big conductance KCa channel and cardioprotection in infant rabbit heart. | 2007-11 |
|
| Carbon monoxide and Ca2+-activated K+ channels in cerebral arteriolar responses to glutamate and hypoxia in newborn pigs. | 2007-11 |
|
| Potential biochemical therapy of glioma cancer. | 2007-10-19 |
|
| Expression of human BK ion channels in Sf9 cells, their purification using metal affinity chromatography, and functional reconstitution into planar lipid bilayers. | 2007-10-01 |
|
| A new pyrone derivative from the endophytic fungus Penicillium paxilli PSU-A71. | 2007-09 |
|
| Reverse electron flow-induced ROS production is attenuated by activation of mitochondrial Ca2+-sensitive K+ channels. | 2007-09 |
|
| The role of mitochondria in protection of the heart by preconditioning. | 2007-08 |
|
| delta-, but not mu-, opioid receptor stabilizes K(+) homeostasis by reducing Ca(2+) influx in the cortex during acute hypoxia. | 2007-07 |
|
| Mitochondrial Ca2+-activated K+ channels more efficiently reduce mitochondrial Ca2+ overload in rat ventricular myocytes. | 2007-07 |
|
| Defining paxilline biosynthesis in Penicillium paxilli: functional characterization of two cytochrome P450 monooxygenases. | 2007-06-08 |
|
| Inhibition of intermediate-conductance Ca2+-activated K+ channel and cytoprotective properties of 4-piperidinomethyl-2-isopropyl-5-methylphenol. | 2007-05 |
|
| Activation by zonisamide, a newer antiepileptic drug, of large-conductance calcium-activated potassium channel in differentiated hippocampal neuron-derived H19-7 cells. | 2007-04 |
|
| Ionizing non-fatal whole-body irradiation inhibits Ca2+-dependent K+ channels in endothelial cells of rat coronary artery: possible contribution to depression of endothelium-dependent vascular relaxation. | 2007-03 |
|
| Verruculogen associated with Aspergillus fumigatus hyphae and conidia modifies the electrophysiological properties of human nasal epithelial cells. | 2007-01-23 |
|
| Characterisation of large-conductance calcium-activated potassium channels (BK(Ca)) in human NT2-N cells. | 2007-01-19 |
|
| [Cardioprotective effect of ischemic postconditioning and preconditioning against prolonged ischemia and reperfusion induced injury in isolated rat heart]. | 2007-01 |
|
| [Involvement of potassium channel in hemin-induced cardioprotection in rat hearts]. | 2007-01 |
|
| Mitochondrial Ca2+-induced K+ influx increases respiration and enhances ROS production while maintaining membrane potential. | 2007-01 |
|
| [Effect of paxilline on Ca(2+)-dependent K+ current in smooth muscle cells isolated from rat vas deferens]. | 2007 |
|
| [Mushroom poisonings: syndromic diagnosis and treatment]. | 2007 |
|
| Role of ATP in trauma-associated cytokine release and apoptosis by P2X7 ion channel stimulation. | 2006-12 |
|
| Contribution of epoxyeicosatrienoic acids to the hypoxia-induced activation of Ca2+ -activated K+ channel current in cultured rat hippocampal astrocytes. | 2006-12 |
|
| A complex gene cluster for indole-diterpene biosynthesis in the grass endophyte Neotyphodium lolii. | 2006-10 |
|
| MaxiK blockade selectively inhibits the lipopolysaccharide-induced I kappa B-alpha /NF-kappa B signaling pathway in macrophages. | 2006-09-15 |
|
| Properties of ion channels in rabbit mesenchymal stem cells from bone marrow. | 2006-09-15 |
|
| TRPV4-mediated regulation of epithelial permeability. | 2006-09 |
|
| Expression and function of calcium-activated potassium channels in human glioma cells. | 2006-08-15 |
|
| The antibacterial activity of human neutrophils and eosinophils requires proton channels but not BK channels. | 2006-06 |
|
| Genetic ablation of caveolin-1 modifies Ca2+ spark coupling in murine arterial smooth muscle cells. | 2006-06 |
|
| [Inhibitory effect of blocking MaxiK channel on human monocyte-derived macrophages differentiation into foam cells]. | 2006-05 |
|
| Bidirectional modulation of GABAergic transmission by cholecystokinin in hippocampal dentate gyrus granule cells of juvenile rats. | 2006-04-15 |
|
| Diosgenin, a plant-derived sapogenin, stimulates Ca2+-activated K+ current in human cortical HCN-1A neuronal cells. | 2006-04 |
|
| A role for voltage-gated, but not Ca2+-activated, K+ channels in regulating spontaneous contractile activity in myometrium from virgin and pregnant rats. | 2006-04 |
|
| Four gene products are required for the fungal synthesis of the indole-diterpene, paspaline. | 2006-03-06 |
|
| Changes in membrane cholesterol of pituitary tumor (GH3) cells regulate the activity of large-conductance Ca2+-activated K+ channels. | 2006-02-28 |
|
| Early pharmacological preconditioning by erythropoietin mediated by inducible NOS and mitochondrial ATP-dependent potassium channels in the rat heart. | 2006-02 |
|
| Glucocorticoids stimulate the activity of large-conductance Ca2+ -activated K+ channels in pituitary GH3 and AtT-20 cells via a non-genomic mechanism. | 2006-02 |
|
| Contribution of BK(Ca)-channel activity in human cardiac fibroblasts to electrical coupling of cardiomyocytes-fibroblasts. | 2006 |
|
| Cocaine elicits action potential bursts in a central snail neuron: the role of delayed rectifying K+ current. | 2006 |
|
| BKCa channels activating at resting potential without calcium in LNCaP prostate cancer cells. | 2005-12 |
Patents
Sample Use Guides
In the model of acute pancreatitis, under pentobarbital anesthesia (50 mg/kg body weight), a laparotomy was performed and 5% sodium taurocholate (1 ml/kg body weight) was injected into the biliopancreatic duct of the rat in one minute. Then the rat recovered from the anesthesia and was allowed access to water. Paxilline (2.2 μg/kg) was intravenously injected to rats 1 h before or after the injection of sodium taurocholate, respectively. Treatment with paxilline inhibited lockade inhibited the release of inflammatory mediators in rats during acute pancreatitis.
Route of Administration:
Intravenous
To study inhibition of BK channels, HEK293 cells were transfected with human BK channel alpha-subunit. Whole-cell patch clamp technique was used to study effect of paxilline. The initial membrane potential was 23 mV and characterized by brief hyperpolarizing fluctuations caused by spontaneous channel openings. Application of 1uM paxilline depoarized the cell to -5mV and completely blocked the BK current. The effect of th~ BK-channel blocker paxilline on activation curves was studied in the presence of 0.5 and 30 uM Ca2+. At 30 uM internal Ca2+the maximal current amplitudes in the presence of 30 and 100 nM mixilline were decreased relative to the control experiment. The IC50 value of paxilline was estimated at 50 nM.
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105008
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DTXSID10972643
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PAXILLINE
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3T9U9Z96L7
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658707
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C048220
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57186-25-1
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SUBSTANCE RECORD
