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Details

Stereochemistry RACEMIC
Molecular Formula C12H11ClO4
Molecular Weight 254.6667
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOSIGAMONE

SMILES

COC1=CC(=O)O[C@@]1([H])[C@@]([H])(c2ccccc2Cl)O

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 254.6667
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Preclinical evaluation of newly approved and potential antiepileptic drugs against cocaine-induced seizures.
1999 Sep
Future prospects for the drug treatment of epilepsy.
2001
Losigamone add-on therapy in partial epilepsy: a placebo-controlled study.
2001 Apr
Losigamone. Dr Willmar Schwabe.
2001 Dec
The antiepileptic drug losigamone decreases the persistent Na+ current in rat hippocampal neurons.
2001 Nov 30
Therapeutic intensive seizure analysis (TISA) in presurgical evaluation of Losigamone.
2001 Oct
Novel anticonvulsant medications in development.
2002 Oct
Efficacy and safety of Losigamone in partial seizures: a randomized double-blind study.
2003 Aug
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.
2003 Jan 1
Perspectives of losigamone in epilepsy treatment.
2003 Sep-Oct
Influence of losigamone on the pharmacokinetics of a combined oral contraceptive in healthy female volunteers.
2004
Evidence for concurrent effects of exposure to environmental cadmium and lead on hepatic CYP2A6 phenotype and renal function biomarkers in nonsmokers.
2004 Nov
Voltage gated ion channels: targets for anticonvulsant drugs.
2005
Isobolographic analysis of interactions among losigamone analog AO-620 and two conventional antiepileptic drugs.
2005 Mar-Apr
Isobolographic analysis of interactions between losigamone and conventional antiepileptic drugs in the mouse maximal electroshock model.
2007 Jan 15
Interactions between two enantiomers of losigamone and conventional antiepileptic drugs in the mouse maximal electroshock model--an isobolographic analysis.
2007 Jul 12
Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions.
2009 Mar-Apr
Effects of XE991, retigabine, losigamone and ZD7288 on kainate-induced theta-like and gamma network oscillations in the rat hippocampus in vitro.
2009 Oct 27
Epilepsy (partial).
2010 Jun 28

Sample Use Guides

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 Sat Jun 26 11:21:11 UTC 2021
Edited
by admin
on Sat Jun 26 11:21:11 UTC 2021
Record UNII
84R8O3QM2G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOSIGAMONE
INN   MART.  
INN  
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
Created by admin on Sat Jun 26 11:21:11 UTC 2021 , Edited by admin on Sat Jun 26 11:21:11 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL2106442
Created by admin on Sat Jun 26 11:21:11 UTC 2021 , Edited by admin on Sat Jun 26 11:21:11 UTC 2021
PRIMARY
FDA UNII
84R8O3QM2G
Created by admin on Sat Jun 26 11:21:11 UTC 2021 , Edited by admin on Sat Jun 26 11:21:11 UTC 2021
PRIMARY
MESH
C065427
Created by admin on Sat Jun 26 11:21:11 UTC 2021 , Edited by admin on Sat Jun 26 11:21:11 UTC 2021
PRIMARY
INN
6423
Created by admin on Sat Jun 26 11:21:11 UTC 2021 , Edited by admin on Sat Jun 26 11:21:11 UTC 2021
PRIMARY
EVMPD
SUB08594MIG
Created by admin on Sat Jun 26 11:21:11 UTC 2021 , Edited by admin on Sat Jun 26 11:21:11 UTC 2021
PRIMARY
WIKIPEDIA
LOSIGAMONE
Created by admin on Sat Jun 26 11:21:11 UTC 2021 , Edited by admin on Sat Jun 26 11:21:11 UTC 2021
PRIMARY
PUBCHEM
10131269
Created by admin on Sat Jun 26 11:21:11 UTC 2021 , Edited by admin on Sat Jun 26 11:21:11 UTC 2021
PRIMARY
NCI_THESAURUS
C90707
Created by admin on Sat Jun 26 11:21:11 UTC 2021 , Edited by admin on Sat Jun 26 11:21:11 UTC 2021
PRIMARY
CAS
112856-44-7
Created by admin on Sat Jun 26 11:21:11 UTC 2021 , Edited by admin on Sat Jun 26 11:21:11 UTC 2021
PRIMARY
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