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

[H][C@@]12OC(=O)[C@@]34O[C@@H]3C[C@@](O)([C@@H]5[C@@H]([C@H]1OC5=O)C(C)=C)[C@@]24C

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

Molecular Formula	C15H16O6
Molecular Weight	292.2839
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27423910	Blocker 537
Glycine receptor subunit alpha-2 8 Target ID: CHEMBL2328 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17405877	Blocker 537		2.4 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
The atypical M2 segment of the beta subunit confers picrotoxinin resistance to inhibitory glycine receptor channels.	1992 Dec	1385113
A single amino acid in gamma-aminobutyric acid rho 1 receptors affects competitive and noncompetitive components of picrotoxin inhibition.	1995 Dec 5	8524842
Mutations affecting the glycine receptor agonist transduction mechanism convert the competitive antagonist, picrotoxin, into an allosteric potentiator.	1995 Jun 9	7775436
Mechanisms for picrotoxinin and picrotin blocks of alpha2 homomeric glycine receptors.	2007 Jun 1	17405877
A proposed structural basis for picrotoxinin and picrotin binding in the glycine receptor pore.	2007 Oct	17714449
Ginkgolide B and bilobalide block the pore of the 5-HT₃receptor at a location that overlaps the picrotoxin binding site.	2011 Feb-Mar	21059362
Binding sites for bilobalide, diltiazem, ginkgolide, and picrotoxinin at the 5-HT3 receptor.	2011 Jul	21505038
The binding mode of picrotoxinin in GABA(A-ρ) receptors: Insight into the subunit's selectivity in the transmembrane domain.	2016 Oct	27423910

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:39:22 GMT 2023` Edited by `admin` on `Fri Dec 15 15:39:22 GMT 2023`
Record UNII	9K011NUF0R
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PICROTOXININ

Common Name

English

PICROTOXININ [MI]

Common Name

English

NSC-129537

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C688