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

COC1=CC(=O)O[C@H]1[C@H](O)C2=CC=CC=C2Cl

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
Epilepsy (partial).	2010-06-28	21429248
Effects of XE991, retigabine, losigamone and ZD7288 on kainate-induced theta-like and gamma network oscillations in the rat hippocampus in vitro.	2009-10-27	19699191
Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions.	2008-03-02	19443931
Interactions between two enantiomers of losigamone and conventional antiepileptic drugs in the mouse maximal electroshock model--an isobolographic analysis.	2007-07-12	17482161
Isobolographic analysis of interactions between losigamone and conventional antiepileptic drugs in the mouse maximal electroshock model.	2007-01-15	16600575
Voltage gated ion channels: targets for anticonvulsant drugs.	2005	15638775
Evidence for concurrent effects of exposure to environmental cadmium and lead on hepatic CYP2A6 phenotype and renal function biomarkers in nonsmokers.	2004-11	15531436
Isobolographic analysis of interactions among losigamone analog AO-620 and two conventional antiepileptic drugs.	2004-07-08	15886423
Influence of losigamone on the pharmacokinetics of a combined oral contraceptive in healthy female volunteers.	2004	15112861
Efficacy and safety of Losigamone in partial seizures: a randomized double-blind study.	2003-08	12972172
Perspectives of losigamone in epilepsy treatment.	2003-06-12	14704462
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.	2003-01-01	12464242
Novel anticonvulsant medications in development.	2002-10	12387702
Losigamone. Dr Willmar Schwabe.	2001-12	11892943
The antiepileptic drug losigamone decreases the persistent Na+ current in rat hippocampal neurons.	2001-11-30	11716808
Therapeutic intensive seizure analysis (TISA) in presurgical evaluation of Losigamone.	2001-10	11589647
Losigamone add-on therapy in partial epilepsy: a placebo-controlled study.	2001-04	11328193
Future prospects for the drug treatment of epilepsy.	2001	11735615
Preclinical evaluation of newly approved and potential antiepileptic drugs against cocaine-induced seizures.	1999-09	10454489

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 `Mon Mar 31 18:13:49 GMT 2025` Edited by `admin` on `Mon Mar 31 18:13:49 GMT 2025`
Record UNII	84R8O3QM2G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

Preferred Name

English

LOSIGAMONE

Official Name

English

losigamone [INN]

Common Name

English

LOSIGAMONE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C264