ChemicalBook > CAS DataBase List > PAXILLINE

PAXILLINE

Product Name: PAXILLINE
CAS No.: 57186-25-1
Chemical Name: PAXILLINE
Synonyms: PAXILINE;mycillin;PAXILLINE;Paxicillin;Paxilline solution;Paxilline in Methanol;fromPenicilliumpaxilli;PAXILLINE, PENICILLIUM PAXILLI;paxilline from penicillium paxilli;Paxilline, Ca2+-activated K+channel blocker
CBNumber: CB2402640
Molecular Formula: C27H33NO4
Formula Weight: 435.56
MOL File: 57186-25-1.mol

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PAXILLINE Property

Flash point:: 2℃
storage temp.: 2-8°C
solubility: Soluble in DMSO, acetone or chloroform.
form: powder
color: faint yellow
InChIKey: ACNHBCIZLNNLRS-UBGQALKQSA-N
SMILES: N1C2=C(C=CC=C2)C2C[C@@]3([H])[C@](C)(C1=2)[C@@]1(C)CC[C@]2([H])O[C@H](C(O)(C)C)C(=O)C=C2[C@]1(O)CC3

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Safety

Hazard Codes: T,Xn,F
Risk Statements: 23/24/25-36/37/38-41-36-20/21/22-11
Safety Statements: 26-36/37/39-45-36/37-16
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: DJ2830000
HazardClass: 6.1(b)
PackingGroup: III
HS Code: 29419090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: P2928
Product name: Paxilline
Purity: powder, ≥98% (HPLC)
Packaging: 5mg
Price: $447
Updated: 2025/07/31

Cayman Chemical

Product number: 11345
Product name: Paxilline
Purity: ≥98%
Packaging: 1mg
Price: $45
Updated: 2024/03/01

Cayman Chemical

Product number: 11345
Product name: Paxilline
Purity: ≥98%
Packaging: 5mg
Price: $121
Updated: 2024/03/01

Sigma-Aldrich

Product number: P2928
Product name: Paxilline
Purity: powder, ≥98% (HPLC)
Packaging: 10mg
Price: $783
Updated: 2025/07/31

Cayman Chemical

Product number: 11345
Product name: Paxilline
Purity: ≥98%
Packaging: 10mg
Price: $220
Updated: 2024/03/01

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PAXILLINE Chemical Properties,Usage,Production

Description

A complex alkaloid, paxilline occurs in the mycelium of the mold Penicillium paxilli. The structure has been confirmed by X-ray crystallography. The crystals are orthorhombic with space group P2 12 121 and a = 31.009, b = 11.522 and c = 7.70 A.

Description

Paxilline is an indole diterpene from fungi which potently and reversibly inhibits large conductance Ca²⁺-activated K⁺ (BKCa) channels, as shown in patch clamp (K_i = 1.9 nM) and whole smooth muscle cell studies (K_i = 35.7 nM). It also enhances the binding of charybdotoxin , a peptidyl neurotoxin, to BKCa channels. Paxilline is currently used to evaluate the role of BKCa channels in various cell processes and responses.

Chemical Properties

Powder

Uses

Potent blocker of high-conductance calcium-activated potassium (BKCa) channels

Uses

Paxilline is a tremorgenic mycotoxin isolated from species of Penicillium, Acremonium and Emericella. Paxilline selectively blocks high-conductance Ca2+-activated potassium channels and inhibits binding to the cerebellar inositol 1,4,5-triphosphate (InsP(3)) receptor.

Definition

ChEBI: 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 mycotoxin, a Penicillium metabolite, an anticonvulsant, an Aspergillus metabolite, a potassium channel blocker, a genotoxin, a geroprotector and an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor. It is an organic heterohexacyclic compound, a tertiary alcohol, a terpenoid indole alkaloid, an enone and a diterpene alkaloid.

Biological Activity

Potent blocker of high-conductance Ca 2+ -activated K + (BK Ca ) channels. Binds to the α -subunit of BK Ca (K i = 1.9 nM for block of currents in α -subunit-expressing oocytes) and enhances binding of charybdotoxin to BK Ca channels in vascular smooth muscle. Also inhibits sarco/endoplasmic reticulum Ca 2+ -ATPase (IC 50 = 5-50 μ M).

Enzyme inhibitor

This BKCa/KCa1.1) channel blocker (FW = 435.56 g/mol; CAS 57186-25-1; Solubility: 100 mM in DMSO), also named (2R,4bS,6aS,12bS,12cR,14aS)- 5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1- methylethyl)-12b,12c-dimethyl-2H-pyrano[2'',3'': 5',6']benz[1',2':6,7]indeno [1,2-b]indol-3(4bH)-one, binds to the α-subunit of BKCa, exhibiting a Ki value of 1.9 nM in blocking currents in α-subunit-expressing oocytes and enhancing binding of to BKCa channels in vascular smooth muscle. (See Charybdotoxin) Paxilline also inhibits sarco/endoplasmic reticulum Ca2+-ATPase, IC50 = 5 - 50 μM.

storage

-20°C (desiccate)

References

Springer et ai., Tetrahedron Lett., 2531 (1975)

PAXILLINE Preparation Products And Raw materials

Raw materials

Preparation Products

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57186-25-1, PAXILLINERelated Search:

Ampicillin 4-tert-Butylcyclohexanol Diacetone Alcohol TRANS-4-TERT-BUTYLCYCLOHEXANOL 4-Methyl-3-decen-5-ol 2-TERT-BUTYL-1H-INDOLE 4-TERT-AMYLCYCLOHEXANOL TRANS-4-TERT-PENTYLCYCLOHEXANOL 1-VINYLCYCLOHEXANOL 97 4-METHYL-4-HEPTEN-3-OL 3,3-DIMETHYLCYCLOHEXYLIDENEACETALDEHYDE PAXILLINE 1 2 3 4-TETRAHYDROCYCLOPENT(B) INDOLE 5,6-dihydro-2H-pyran-3-methanol 3-N-OCTYLPYRROLE 2,7-dimethyloct-5-en-4-one 2-CYCLOHEXYL-1H-INDOLE 3-HEPTYLPYRROLE

(2R)-5,6,6aα,7,12,12b,12c,13,14,14aβ-Decahydro-4bβ-hydroxy-2-(1-hydroxy-1-methylethyl)-12bβ,12cα-dimethyl-2H-1-benzopyrano[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one

2h-1-benzopyrano(5’,6’:6,7)indeno(1,2-b)indol-3(4bh)-one,5,6,6a,7,12,12b,12c,1

4b-beta,6a-alpha,12b-beta,12c-alpha,14a-beta)-2-alph

paxilline from penicillium paxilli

PAXILINE

Paxicillin

(2R,4bS,6aS,12bS,12cR,14aS)-4b-Hydroxy-2-(1-hydroxy-1-methylethyl)-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 solution

Paxilline solution

PAXILLINE

PAXILLINE, PENICILLIUM PAXILLI

(2R,4BS,6AS,12BS,12CR,14AS)-5,6,6A,7,12,12B,12C,13,14,14A-DECAHYDRO-4B-HYDROXY-2-(1-HYDROXY-1-METHYLETHYL)-12B,12C-DIMETHYL-2H-PYRANO[2'',3'':5',6']BENZ[1',2':6,7]INDENO[1,2-B]INDOL-3(4BH)-ONE

14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-(

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,(2R,4bS,6aS,12bS,12cR,14aS)-5,6,6a,7,12,12b,12c,13,14,14a-Decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-2H-pyrano[2'',3'':5',6']benz[1',2':6,7]indeno[1,2-b]indol-3(4bH)-one

4b-Hydroxy-2-(1-hydroxy-1-methylethyl)-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

mycillin

Paxilline in Methanol

Paxilline, Ca2+-activated K+channel blocker

fromPenicilliumpaxilli

57186-25-1

C27H33NO4

BioChemical

Cell Biology

Cell Signaling and Neuroscience

Monovalent Ion Channels

Potassium Channel Modulators

Ion Channels

Voltage-gated Ion Channels

MoldVoltage-gated Ion Channels

Cell Signaling and Neuroscience

Monovalent Ion Channels

Potassium Channel Modulators

Toxins and Venoms

Potassium channel

antibiotic