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Merck
CN

P2928

Paxilline

≥98% (HPLC), Maxi-K potassium channel blocker, powder

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About This Item

Empirical Formula (Hill Notation):
C27H33NO4
CAS Number:
57186-25-1
Molecular Weight:
435.56
UNSPSC Code:
12352200
PubChem Substance ID:
24898374
NACRES:
NA.77
MDL number:
MFCD00083464

Key Documents

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Product Name

Paxilline, powder, ≥98% (HPLC)

SMILES string

CC(C)(O)C1OC2CCC3(C)C(O)(CCC4Cc5c([nH]c6ccccc56)C34C)C2=CC1=O

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

InChI key

ACNHBCIZLNNLRS-UBGQALKQSA-N

assay

≥98% (HPLC)

form

powder

color

faintly yellow

storage temp.

2-8°C

Quality Level

200

Related Categories

Other Notes

Major toxin in Penicillium paxilli

Application

Paxilline has been used to block large conductance calcium activated potassium channels (BKCa) in murine smooth muscle cells and in myometrial cells of uterine samples. Paxilline acts as an agonist and activates liver X receptor in atlantic salmon.

Biochem/physiol Actions

Paxilline is a selective blocker of high-conductance Ca2+-activated (Maxi-K) potassium channels. It also blocks big potassium (BK) channels.

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

General description

Paxilline is an indole diterpene metabolite produced by fungi. It has a functionalized pentacyclic core and is a template for the synthesis of a wide variety of derivatives.

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
0000476092
0000308068
0000308068
0000243763
0000217766

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Sonal Shruti et al.
Neurobiology of disease, 30(3), 323-330 (2008-04-05)
A heritable gain-of-function in BK channel activity has been associated with spontaneous seizures in both rodents and humans. We find that chemoconvulsant-induced seizures induce a gain-of-function in BK channel current that is associated with abnormal, elevated network excitability. Action potential
Membrane-delimited inhibition of maxi-K channel activity by the intermediate conductance Ca2+-activated K channel
Thompson J and Begenisich T
The Journal of General Physiology, 127(2), 159-169 (2006)
Electrophysiological and functional effects of the KCNQ channel blocker XE991 on murine portal vein smooth muscle cells
Yeung SYM and Greenwood IA
British Journal of Pharmacology, 146(4), 585-595 (2005)
Contribution of the functional coupling between the human myometrial beta2-adrenoreceptor and the BKCa channel to uterine quiescence
Chanrachakul B, et al.
American Journal of Physiology. Cell Physiology, 287(C1747?C1752), 585-595 (2004)
Conservation of lipid metabolic gene transcriptional regulatory networks in fish and mammals
Carmona-Antonanzas, Greta and Tocher, Douglas R and Martinez-Rubio, Laura and Leaver, Michael J
Gene, 534(1), 1-9 (2014)
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