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

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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 proposed structural basis for picrotoxinin and picrotin binding in the glycine receptor pore.	2007 Oct	17714449
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

Name

Type

Language

PICROTOXININ

Common Name

English

PICROTOXININ [MI]

Common Name

English

NSC-129537

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C688