LOSIGAMONE

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H11ClO4
Molecular Weight	254.666
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]1(OC(=O)C=C1OC)[C@H](O)C2=C(Cl)C=CC=C2

InChI

InChIKey=ICDNYWJQGWNLFP-VXGBXAGGSA-N

InChI=1S/C12H11ClO4/c1-16-9-6-10(14)17-12(9)11(15)7-4-2-3-5-8(7)13/h2-6,11-12,15H,1H3/t11-,12-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C12H11ClO4
Molecular Weight	254.666
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800003609 | Eadie, M.J., Vajda, F. (2012) Antiepileptic Drugs: Pharmacology and Therapeutics, page 520, retrieved from: https://books.google.ru/books?id=8iv6CAAAQBAJ | https://www.ncbi.nlm.nih.gov/pubmed/10578135

Losigamone possesses an unique anticonvulsant activity profile and has an excellent tolerability. Losigamone causes dose-dependent inhibition of the tonic hind leg extension produced by electric shock, pentylenetetrazole, bicuculline, nicotine and 4-aminopyridine. Losigamone also inhibits clonic seizures induced by pentylenetetrazole, bicuculline and picrotoxin, whereas it has no effect on the hind leg extension caused by strychnine and picrotoxin or the clonic seizures induced by NMDA. Losigamone had been in phase III clinical trial for the treatment of partial epilepsies. However, this development was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Future prospects for the drug treatment of epilepsy.	2001	11735615
Losigamone add-on therapy in partial epilepsy: a placebo-controlled study.	2001 Apr	11328193
The antiepileptic drug losigamone decreases the persistent Na+ current in rat hippocampal neurons.	2001 Nov 30	11716808
Perspectives of losigamone in epilepsy treatment.	2003 Sep-Oct	14704462
Voltage gated ion channels: targets for anticonvulsant drugs.	2005	15638775
Isobolographic analysis of interactions among losigamone analog AO-620 and two conventional antiepileptic drugs.	2005 Mar-Apr	15886423
Interactions between two enantiomers of losigamone and conventional antiepileptic drugs in the mouse maximal electroshock model--an isobolographic analysis.	2007 Jul 12	17482161
Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions.	2009 Mar-Apr	19443931
Epilepsy (partial).	2010 Jun 28	21429248

Sample Use Guides

In Vivo Use Guide

750 mg/day in the first two days after randomization and then maintained at 1500 mg/day from the third day for the eight weeks.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:56:16 UTC 2023` Edited by `admin` on `Fri Dec 15 15:56:16 UTC 2023`
Record UNII	84R8O3QM2G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LOSIGAMONE

Official Name

English

losigamone [INN]

Common Name

English

LOSIGAMONE [MART.]

Common Name

English

(5R*)-5-((.ALPHA.S*)-O-CHLORO-.ALPHA.-HYDROXYBENZYL)-4-METHOXY-2(5H)-FURANONE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C264