Losigamone
Skeletal formula of losigamone
Ball-and-stick model of the losigamone molecule
Clinical data
ATC code
  • none
Legal status
Legal status
  • Investigational
Identifiers
  • (2R)-2-[(S)-(2-chlorophenyl)-hydroxymethyl]-3-methoxy-2H-furan-5-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC12H11ClO4
Molar mass254.67 g·mol−1
3D model (JSmol)
  • Clc1ccccc1C(O)C2OC(=O)C=C2OC
  • 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-/m0/s1 ☒N
  • Key:ICDNYWJQGWNLFP-RYUDHWBXSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Losigamone (INN) is an investigational drug for the treatment of epilepsy. It has been studied as an add-on treatment for partial seizures.[1] Phase III clinical trials were conducted around the year 2000.[2]

Mechanism of action

The mechanism of action is not known. Data regarding the interaction of losigamone with GABA receptors are inconsistent: it increases GABA-induced chloride influx in spinal cord neuron cultures, but has no significant influence on GABAergic inhibitory postsynaptic potentials in hippocampal slices.[2] Interaction with potassium[2] and sodium channels[3] has been proposed. Results from both in vitro and in vivo experiments confirm that the pharmacological activity profiles of the two losigamone enantiomers are not identical and suggest further that excitatory amino acid-mediated processes are involved in the mode of action of (+)-losigamone (the compound shown in the image) whereas (–)-losigamone does not possess such properties.[4]

References

  1. ↑ Baulac M, Klement S (August 2003). "Efficacy and safety of Losigamone in partial seizures: a randomized double-blind study". Epilepsy Research. 55 (3): 177–89. doi:10.1016/S0920-1211(03)00108-6. PMID 12972172. S2CID 25270336.
  2. 1 2 3 Willmore LJ (December 2001). "Losigamone. Dr Willmar Schwabe". Current Opinion in Investigational Drugs. 2 (12): 1763–6. PMID 11892943.
  3. ↑ Draguhn A, Jungclaus M, Sokolowa S, Heinemann U (May 1997). "Losigamone decreases spontaneous synaptic activity in cultured hippocampal neurons". European Journal of Pharmacology. 325 (2–3): 245–51. doi:10.1016/S0014-2999(97)00121-0. PMID 9163572.
  4. ↑ Jones FA, Davies JA (November 1999). "The anticonvulsant effects of the enantiomers of losigamone". British Journal of Pharmacology. 128 (6): 1223–8. doi:10.1038/sj.bjp.0702919. PMC 1571758. PMID 10578135.
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