Mirtazapine

Mirtazapine

Clinical data
Trade names	Originally branded Remeron, many generics
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 and CYP3A4)
Biological half-life	20–40 hours
Excretion	Urine (75%) Faeces (15%)
Identifiers
IUPAC name (±)-2-methyl-1,2,3,4,10,14b-hexahydropyrazino[2,1-a]pyrido[2,3-c][2]benzazepine
Synonyms	6-Azamianserin, Org 3770
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 (Jmol)	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 (originally branded Remeron, many generics) is an atypical antidepressant with noradrenergic and specific serotonergic activity. It blocks the α₂ adrenergic auto- and heteroreceptors (enhancing norepinephrine release), and selectively antagonizes the 5-HT₂ serotonin receptors in the central and peripheral nervous system. It also enhances serotonin neurotransmission at the 5-HT₁ receptor and blocks the histaminergic (H₁) and muscarinic receptors. Mirtazapine is not a serotonin or norepinephrine reuptake inhibitor but may increase serotonin and norepinephrine by other mechanisms of action.

Mirtazapine is a noradrenergic and specific serotonergic antidepressant (NaSSA) introduced by Organon International in the United States in 1996, and is used primarily in the treatment of depression. It is also commonly used as an anxiolytic, hypnotic, antiemetic and appetite stimulant. In structure, mirtazapine can also be classified as a tetracyclic antidepressant (TeCA) and is the 6-aza analogue of mianserin. It is also racemic – occurs as a combination of both (R)-(−)- and (S)-(+)-stereoisomers, both of which are active.