Panamesine

Last updated

Panamesine
Panamesine.svg
Clinical data
Other namesEMD-57455
Pharmacokinetic data
Metabolites EMD-59983
Identifiers
  • (5S)-5-[[4-(1,3-Benzodioxol-5-yl)-4-hydroxypiperidin-1-yl]methyl]-3-(4-methoxyphenyl)-1,3-oxazolidin-2-one
CAS Number
PubChem CID
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C23H26N2O6
Molar mass 426.469 g·mol−1
3D model (JSmol)
  • COC1=CC=C(C=C1)N2C[C@@H](OC2=O)CN3CCC(CC3)(C4=CC5=C(C=C4)OCO5)O
  • 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 (INN Tooltip 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

References

  1. 1 2 "Panamesine". AdisInsight.
  2. ↑ Guitart X, Codony X, Monroy X (2004). "Sigma receptors: biology and therapeutic potential". Psychopharmacology. 174 (3): 301–19. doi:10.1007/s00213-004-1920-9. PMID   15197533. S2CID   23606712.
  3. ↑ Frieboes RM, Murck H, Wiedemann K, Holsboer F, Steiger A (1997). "Open clinical trial on the sigma ligand panamesine in patients with schizophrenia". Psychopharmacology. 132 (1): 82–8. doi:10.1007/s002130050323. PMID   9272763. S2CID   20525608.
  4. ↑ Huber MT, Gotthardt U, Schreiber W, Krieg JC (1999). "Efficacy and safety of the sigma receptor ligand EMD 57445 (panamesine) in patients with schizophrenia: an open clinical trial". Pharmacopsychiatry. 32 (2): 68–72. doi:10.1055/s-2007-979194. PMID   10333165. S2CID   12424244.
  5. ↑ Gründer G, Müller MJ, Andreas J, Heydari N, Wetzel H, Schlösser R, Schlegel S, Nickel O, Eissner D, Benkert O (1999). "Occupancy of striatal D(2)-like dopamine receptors after treatment with the sigma ligand EMD 57445, a putative atypical antipsychotic". Psychopharmacology. 146 (1): 81–6. doi:10.1007/s002130051091. PMID   10485968. S2CID   7039752.
  6. ↑ Bartoszyk, G. D., Bender, H. M., Hellmann, J., Schnorr, C., Seyfried, C. A. (June 1996). "EMD 57445: A Selective Sigma Receptor Ligand with the Profile of an Atypical Neuroleptic". CNS Drug Reviews. 2 (2): 175–194. doi:10.1111/j.1527-3458.1996.tb00296.x.


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