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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19N3.C4H4O4
Molecular Weight 381.425
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ESMIRTAZAPINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.[H][C@]12CN(C)CCN1C3=C(CC4=C2C=CC=C4)C=CC=N3

InChI

InChIKey=RPUBHMMISKEXSR-MLCLTIQSSA-N
InChI=1S/C17H19N3.C4H4O4/c1-19-9-10-20-16(12-19)15-7-3-2-5-13(15)11-14-6-4-8-18-17(14)20;5-3(6)1-2-4(7)8/h2-8,16H,9-12H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t16-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C17H19N3
Molecular Weight 265.3529
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Esmirtazapine (S-(+)mirtazapine or ORG-50081) is an enantiomer of mirtazapine (REMERON®), a high-affinity antagonist at 5-HT2/5-HT3 and H1 receptors, used in the treatment of depression. Esmirtazapine has a shorter plasma half-life than the R(−) enantiomer. Esmirtazapine is preferentially metabolized into an 8-hydroxy glucuronide. Organon was developing esmirtazapine for the treatment of hot flushes (vasomotor symptoms) associated with the menopause and insomnia.

CNS Activity

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
Phase III trials: 0.5-18 mg once daily for 1-52 weeks
Route of Administration: Oral
Substance Class Chemical
Record UNII
I2U18E6JKA
Record Status Validated (UNII)
Record Version