Losigamone

Losigamone

Clinical data
ATC code	none
Legal status
Legal status	Investigational
Identifiers
IUPAC name (2R)-2-[(S)-(2-chlorophenyl)-hydroxymethyl]-3-methoxy-2H-furan-5-one
CAS Number	112856-44-7
PubChem (CID)	6918049
ChemSpider	5293266
UNII	84R8O3QM2G
Chemical and physical data
Formula	C12H11ClO4
Molar mass	254.666 g/mol
3D model (Jmol)	Interactive image
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 (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; 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.