Panamesine

Clinical data
Other names	EMD-57455
Pharmacokinetic data
Metabolites	EMD-59983
Identifiers
IUPAC name (5S)-5-[[4-(1,3-Benzodioxol-5-yl)-4-hydroxypiperidin-1-yl]methyl]-3-(4-methoxyphenyl)-1,3-oxazolidin-2-one
CAS Number	139225-22-2
PubChem CID	3047810
UNII	023D9E916L
ChEMBL	ChEMBL45686
CompTox Dashboard (EPA)	DTXSID00160971
Chemical and physical data
Formula	C23H26N2O6
Molar mass	426.469 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC=C(C=C1)N2C[C@@H](OC2=O)CN3CCC(CC3)(C4=CC5=C(C=C4)OCO5)O
InChI InChI=1S/C23H26N2O6/c1-28-18-5-3-17(4-6-18)25-14-19(31-22(25)26)13-24-10-8-23(27,9-11-24)16-2-7-20-21(12-16)30-15-29-20/h2-7,12,19,27H,8-11,13-15H2,1H3/t19-/m0/s1 Key:NINYZUDVKTUKIA-IBGZPJMESA-N

Panamesine (INNTooltip International Nonproprietary Name; developmental code name EMD-57455) is a sigma receptor antagonist that was under development by Merck as a potential antipsychotic for the treatment of schizophrenia in the 1990s but was never marketed.^[1] It is a selective antagonist of both sigma receptor subtypes, the σ₁ and σ₂ receptors (IC₅₀ = 6 nM).^{[2][additional citation(s) needed]} In addition, the major metabolite of the drug, EMD-59983, has high affinity for the sigma receptors (IC₅₀ = 24 nM) and the dopamine D₂ (IC₅₀ = 23 nM) and D₃ receptors, with potent antidopaminergic activity.^[3][4][5] Panamesine reached phase II clinical trials for schizophrenia prior to the discontinuation of its development.^[1]

CNS review:^[6]

See also

• BMY-14802
• Eliprodil
• Rimcazole

References

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