Paxilline

Names

[ Name ]:
Paxilline

[Synonym ]:
2H-Pyrano(2'',3'':5',6')benz(1',2':6,7)indeno(1,2-b)indol-3(4bH)-one, 5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-, (2R,4bS,6aS,12bS,12cR,14aS)-
PAXILINE
2H-1-Benzopyrano[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one, 5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-, (2R,4bS,6aS,12bS,12cR,14aS)-
PAXILLINE,PENICILLIUM PAXILLI
DPNI-caged-GABA
(2R,4bS,6aS,12bS,12cR,14aS)-4b-Hydroxy-2-(2-hydroxy-2-propanyl)-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)-one
MFCD00083464
(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)-one
paxilline from penicillium paxilli
Paxilline 1
Paxilline

Biological Activity

[Description]:

Paxilline is an indole alkaloid mycotoxin from Penicillium paxilli, acts as a potent BK channels inhibitor by an almost exclusively closed-channel block mechanism. Paxilline also inhibits the sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) with IC50s between 5μM and 50μM for differing isoforms. Paxilline possesses significant anticonvulsant activity[1][2][3].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel

Research Areas >> Neurological Disease

[Target]

IC50: 5-50 μM (SERCA)[2], BK channel[1]

[References]

[1]. Zhou Y, et al. Paxilline inhibits BK channels by an almost exclusively closed-channel block mechanism. J Gen Physiol. 2014 Nov;144(5):415-40.

[2]. Bilmen JG, et al. The mechanism of inhibition of the sarco/endoplasmic reticulum Ca2+ ATPase by paxilline. Arch Biochem Biophys. 2002 Oct 1;406(1):55-64.

[3]. Sheehan JJ, et al. Anticonvulsant effects of the BK-channel antagonist paxilline. Epilepsia. 2009 Apr;50(4):711-20.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
648.8±55.0 °C at 760 mmHg

[ Melting Point ]:
252ºC

[ Molecular Formula ]:
C₂₇H₃₃NO₄

[ Molecular Weight ]:
435.555

[ Flash Point ]:
346.2±31.5 °C

[ Exact Mass ]:
435.240967

[ PSA ]:
82.55000

[ LogP ]:
3.77

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.661

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
Soluble in DMSO, acetone or chloroform.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ2830000

CAS REGISTRY NUMBER :: 57186-25-1

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C27-H33-N-O4

MOLECULAR WEIGHT :: 435.61

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >227 mg/kg

TOXIC EFFECTS :: Behavioral - tremor

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 41,1868,1988

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 150 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 41KEAL "Toxicology, Biochemistry and Pathology of Mycotoxins," Uraguchi, K. and M. Yamazaki, eds., New York, John Wiley & Sons, Inc., 1978 Volume(issue)/page/year: -,108,1978

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: >100 mg/kg

TOXIC EFFECTS :: Behavioral - tremor

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 41,1868,1988

Safety Information

[ Symbol ]:

GHS05, GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H311-H315-H318-H331-H335

[ Precautionary Statements ]:
P261-P280-P301 + P310-P305 + P351 + P338-P311

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R23/24/25

[ Safety Phrases ]:
26-36/37/39-45

[ RIDADR ]:
UN 2811 6

[ WGK Germany ]:
3

[ RTECS ]:
DJ2830000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
29419090

Precursor & DownStream

Precursor

DownStream

Articles

Large-conductance calcium-activated potassium current modulates excitability in isolated canine intracardiac neurons.

Am. J. Physiol. Cell Physiol. 304(3) , C280-6, (2013)

We studied principal neurons from canine intracardiac (IC) ganglia to determine whether large-conductance calcium-activated potassium (BK) channels play a role in their excitability. We performed whol...

Mitochondrial K+ channels are involved in ischemic postconditioning in rat hearts.

J. Physiol. Sci. 62(4) , 325-32, (2012)

The mitochondrial calcium-activated potassium channel (mitoK(Ca)) and the mitochondrial ATP-sensitive potassium channel (mitoK(ATP)) are both involved in cardiac preconditioning. Here, we examined whe...

Methamphetamine inhibits voltage-gated potassium currents in NG108-15 cells: possible contribution of large-conductance calcium-activated potassium channels.

Toxicol. Lett. 223(2) , 139-45, (2013)

Methamphetamine (MA), a highly abused amphetamine-like psychostimulant, has surged in popularity worldwide in the last decade. Repeated MA exposure has been shown to affect the alternative splice vari...

Related Compounds

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