Paxilline
Grundinformationen
- CAS
1233509-81-3- Standard-SMILES
CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4Cc5c([nH]c6ccccc56)[C@@]43C)C2=CC1=O- InChIKey
ACNHBCIZLNNLRS-UBGQALKQSA-N- Summenformel
- C27H33NO4
- Durchschnittliche Molmasse
- 435,6 g/mol
- Monoisotopische Masse
- 435,24095853
Überblick
Paxilline is an indole diterpene alkaloid with formula C27H33NO4 isolated from Penicillium paxilli. It is a potent inhibitor of large conductance Ca2+- and voltage-activated K+ (BK)-type channels. It has a role as a geroprotector, a mycotoxin, an anticonvulsant, a potassium channel blocker, a genotoxin, an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor, an Aspergillus metabolite and a Penicillium metabolite. It is a diterpene alkaloid, a tertiary alcohol, an enone, an organic heterohexacyclic compound and a terpenoid indole alkaloid.
Namen und Bezeichner
- Bevorzugter Name
- Paxilline
- IUPAC
- (1S,2R,5S,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-9,16(24),17,19,21-pentaen-8-one
Namen und Synonyme
paxilline57186-25-1DTXSID109726433T9U9Z96L7(1s,2r,5s,7r,11s,14s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-9,16(24),17,19,21-pentaen-8-oneNSC-658707(1S,2R,5S,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo(12.10.0.02,11.05,10.016,24.017,22)tetracosa-9,16(24),17,19,21-pentaen-8-oneRefChem:858745DTXCID80153012311-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo(12.10.0.0^(2,11).0^(5,10).0^(16,24).0^(17,22))tetracosa-9,16(24),17,19,21-pentaen-8-one637-206-011-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo(12.10.0.02,11.05,10.016,24.017,22)tetracosa-9,16(24),17,19,21-pentaen-8-one
Weitere Namen anzeigen
NSC 658707BRN 5317894MLS000028812(2R,4bS,6aS,12bS,12cR,14aS)-4b-hydroxy-2-(2-hydroxypropan-2-yl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-chromeno[5',6':6,7]indeno[1,2-b]indol-3(4bH)-oneSMR000058863A1C9G(2R,4bS,6aS,12bS,12cR,14aS)-4b-hydroxy-2-(2-hydroxypropan-2-yl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-[1]benzopyrano[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one(2R,4bS,6aS,12bS,12cR,14aS)-5,6,6a, 7,12,12b,12c,13,14,14a-Decahydro-4b-hydroxy-2-(1-h ydroxy-1-methylethyl)-12b,12c-dimethyl-2H-pyrano[2 '',3'':5',6']benz[1',2':6,7]indeno[1,2-b]indol-3(4bH)-one
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,5
- Polarare Oberfläche (TPSA)
- 82,6 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 32
- Formalladung
- 0
- Komplexität
- 868
Experimentelle und physikochemische Eigenschaften
Melting Point252 °C
Physical DescriptionSolid
Collision Cross Section201 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H301+H311+H331 (42.6%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 68 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Toxikologische Informationen
Treatment
To control severe tremors caused by tremorgenic mycotoxins, methocarbamol should be administered. Generalized seizures may be treated with diazepam followed by methocarbamol or a barbiturate such as pentobarbital sodium. Gastric lavage should be performed and activated charcoal administered to limit further absorption of toxins. (A744)
Health EffectsTremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of cattle known as "staggers syndrome". (A2976)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary
Tremorgenic mycotoxins exert their toxic effects by interfering with neurotransmitter release, possibly by causing degeneration of nerve terminals. They are thought to inhibit gamma-aminobutyric acid (GABA) receptors, both pre- and postsynaptic, as well as inhibit transmitter breakdown at the GABA-T receptors. This would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, then lead to decreased levels of neurotransmitter in the synapse. In addition, paxilline inhibits presynaptic high-conductance Ca+2 activated maxi-K+ channels in the smooth muscle. Paxilline is also genotoxic and causes DNA damage. (A2976, A2993, A3026)
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological ClassificationA class of drugs that act by inhibition of potassium efflux through cell membranes. Blockade of potassium channels prolongs the duration of ACTION POTENTIALS. They are used as ANTI-ARRHYTHMIA AGENTS and VASODILATOR AGENTS.
Cellular LocationsExtracellular
Verwendung und Herstellung
UsesPaxilline is a tremorgenic mycotoxin that has been found in fungus Penicillium paxilli. It may be found in contaminated cereal crops such as oats, barley, millet, corn and rice. (A2976, A3082)
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