Losigamone

Losigamone

Systematic (IUPAC) name
(2R)-2-[(S)-(2-chlorophenyl)-hydroxymethyl]-3-methoxy-2H-furan-5-one
Clinical data
Legal status	Investigational
Identifiers
CAS Number	112856-44-7
ATC code	none
PubChem	CID 6918049
ChemSpider	5293266
UNII	84R8O3QM2G
Chemical data
Formula	C12H11ClO4
Molar mass	254.666 g/mol
SMILES Clc1ccccc1C(O)C2OC(=O)C=C2OC
InChI 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 Key:ICDNYWJQGWNLFP-RYUDHWBXSA-N
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Losigamone 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; Losigamone Study, Group (2003). "Efficacy and Safety of Losigamone in Partial Seizures: A Randomized Double-Blind Study". Epilepsy Res 55 (3): 177–189. doi:10.1016/S0920-1211(03)00108-6. PMID 12972172.
2. Willmore, LJ (December 2001). "Losigamone. Dr Willmar Schwabe". Curr Opin Investig 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): 245–251. doi:10.1016/S0014-2999(97)00121-0. PMID 9163572.
4. Jones, F; Davies, J (Nov 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.