PANAMESINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H26N2O6
Molecular Weight	426.4623
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1)N2C[C@H](CN3CCC(O)(CC3)C4=CC=C5OCOC5=C4)OC2=O

InChI

InChIKey=NINYZUDVKTUKIA-IBGZPJMESA-N

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

HIDE SMILES / InChI

Molecular Formula	C23H26N2O6
Molecular Weight	426.4623
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10333165 | https://adisinsight.springer.com/drugs/800001428

Panamesine (also known as EMD 57445) was studied as a sigma receptor ligand alleged to have antipsychotic effects. Panamesine reached phase II clinical trials for schizophrenia before the discontinuation of its development.

Originator

Approval Year

PubMed

Title	Date	PubMed
Induction of c-fos gene expression by the selective sigma receptor ligand EMD 57445 in rat brain.	1996 Aug	8880084
Neuropharmacological profile of EMD 57445, a sigma receptor ligand with potential antipsychotic activity.	1996 Nov 21	8982660
Effect of sigma ligands on the cocaine-induced convulsions in mice.	1999 Nov-Dec	10817525

Sample Use Guides

In Vivo Use Guide

In a treatment period of 4 weeks, 12 patients received EMD 57445 up to 60 mg/day for 4 weeks.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:09:23 UTC 2023` Edited by `admin` on `Fri Dec 15 16:09:23 UTC 2023`
Record UNII	023D9E916L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PANAMESINE

Official Name

English

(5S)-5-((4-HYDROXY-4-(3,4-(METHYLENEDIOXY)PHENYL)PIPERIDINO)METHYL)-3-(P-METHOXYPHENYL)-2-OXAZOLIDINONE

Common Name

English

panamesine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29710