Mirtazepine

Mirtazapine

Clinical data
Trade names	Remeron, others
Synonyms	Mepirzapine; 6-Azamianserin; ORG-3770
AHFS/Drugs.com	Monograph
MedlinePlus	a697009
License data	US FDA: Mirtazapine
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	Oral (tablets)
ATC code	N06AX11 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	50%
Protein binding	85%
Metabolism	Liver (CYP1A2, CYP2D6, CYP3A4)
Metabolites	Desmethylmirtazapine (contributes 3–10% of activity)
Biological half-life	20–40 hours
Excretion	Urine: 75% Feces: 15%
Identifiers
IUPAC name (±)-2-methyl-1,2,3,4,10,14b-hexahydropyrazino[2,1-a]pyrido[2,3-c][2]benzazepine
CAS Number	61337-67-5 Y
PubChem CID	4205
IUPHAR/BPS	7241
DrugBank	DB00370 Y
ChemSpider	4060 Y
UNII	A051Q2099Q
KEGG	D00563 Y
ChEBI	CHEBI:6950 N
ChEMBL	CHEMBL654 Y
ECHA InfoCard	100.169.128
Chemical and physical data
Formula	C17H19N3
Molar mass	265.35 g/mol
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
Density	1.22 g/cm3
Melting point	114 to 116 °C (237 to 241 °F)
Boiling point	432 °C (810 °F)
Solubility in water	Soluble in methanol and chloroform mg/mL (20 °C)
SMILES n1cccc3c1N4C(c2ccccc2C3)CN(C)CC4
InChI InChI=1S/C17H19N3/c1-19-9-10-20-16(12-19)15-7-3-2-5-13(15)11-14-6-4-8-18-17(14)20/h2-8,16H,9-12H2,1H3 Y Key:RONZAEMNMFQXRA-UHFFFAOYSA-N Y
NY (what is this?)

Mirtazapine, sold under the brand name Remeron among others, is an atypical antidepressant which is used primarily in the treatment of depression. In addition to its antidepressant properties, mirtazapine has anxiolytic, sedative, antiemetic, and appetite stimulant effects and is sometimes used in the treatment of anxiety disorders, insomnia, nausea and vomiting, and to produce weight gain when desirable. It is taken by mouth.

The drug acts as an antagonist of certain adrenergic and serotonin receptors, and is also a strong antihistamine. It is sometimes described as a noradrenergic and specific serotonergic antidepressant (NaSSA), although the actual evidence in support of this label has been regarded as poor. Chemically, mirtazapine is a tetracyclic antidepressant (TeCA), with four interconnected rings of atoms, and is a relative of the TeCA mianserin (Tolvon).

Mirtazapine was developed by Organon International in the Netherlands and was introduced in the United States in 1996. Its patent expired in 2004, so generic versions are available.