PICROTOXININ

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H16O6
Molecular Weight	292.2839
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=C)[C@@H]1[C@H]2OC(=O)[C@@H]1[C@]3(O)C[C@H]4O[C@]45C(=O)O[C@H]2[C@]35C

InChI

InChIKey=PIMZUZSSNYHVCU-YKWPQBAZSA-N

InChI=1S/C15H16O6/c1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h6-10,18H,1,4H2,2-3H3/t6-,7+,8-,9-,10-,13-,14-,15+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17405877
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27423910

Pircotoxinin is a component of pircotoxin, a poisonous compound from Anamirta cocculus. It exerts its action by blockade of anion channels, such as GABA-A or GlyR.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27423910	Blocker 555
Glycine receptor subunit alpha-2 8 Target ID: CHEMBL2328 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17405877	Blocker 555		2.4 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
The binding mode of picrotoxinin in GABAA-ρ receptors: Insight into the subunit's selectivity in the transmembrane domain.	2016-10	27423910
Binding sites for bilobalide, diltiazem, ginkgolide, and picrotoxinin at the 5-HT3 receptor.	2011-07	21505038
Ginkgolide B and bilobalide block the pore of the 5-HT₃receptor at a location that overlaps the picrotoxin binding site.	2010-08-12	21059362
A proposed structural basis for picrotoxinin and picrotin binding in the glycine receptor pore.	2007-10	17714449
Mechanisms for picrotoxinin and picrotin blocks of alpha2 homomeric glycine receptors.	2007-06-01	17405877
A single amino acid in gamma-aminobutyric acid rho 1 receptors affects competitive and noncompetitive components of picrotoxin inhibition.	1995-12-05	8524842
Mutations affecting the glycine receptor agonist transduction mechanism convert the competitive antagonist, picrotoxin, into an allosteric potentiator.	1995-06-09	7775436
The atypical M2 segment of the beta subunit confers picrotoxinin resistance to inhibitory glycine receptor channels.	1992-12	1385113

Patents

Sample Use Guides

In Vivo Use Guide

Picrotoxinin is used as a tool compound to study effect of GABAA blockade. It was administered to SD rats intravenously in dose 2 mg/kg.

Route of Administration: Intravenous

In Vitro Use Guide

Outside-out patch clamp recordings of responses of GlyR-transfected CHO1 cells on glycine co-administred with picrotoxinin show that picrotoxinin dose-dependendly blocks GlyR channels with IC50 of 2.4 uM

Name

Type

Language

PICROTOXININ

Common Name

English

NSC-129537

Preferred Name

English

PICROTOXININ [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C688