Product Name

Mirtazapine

CAS Number

61337-67-5

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Product Name:
Mirtazapine
CAS Number:
61337-67-5
Indication:
For the treatment of major depressive disorder.
Mode of Action:

Mirtazapine acts as an antagonist at central pre-synaptic alpha(_)-receptors, inhibiting negative feedback to the presynaptic nerve and causing an increase in NE release. Blockade of heteroreceptors, alpha(_)-receptors contained in serotenergic neurons, enhances the release of 5-HT, increasing the interactions between 5-HT and 5-HT_ receptors and contributing to the anxiolytic effects of mirtazapine. Mirtazapine also acts as a weak antagonist at 5-HT_ receptors and as a potent antagonist at 5-HT_ (particularly subtypes _A and _C) and 5-HT_ receptors. Blockade of these receptors may explain the lower incidence of adverse effects such as anxiety, insomnia, and nausea. Mirtazapine also exhibits significant antagonism at H_-receptors, resulting in sedation. Mirtazapine has no effects on the reuptake of either NE or 5-HT and has only minimal activity at dopaminergic and muscarinic receptors.

Pharmacodynamics:

Mirtazapine, an antidepressant of the piperazinoazepine class, is a tetracyclic compound with an anxiolytic effect. Mirtazapine has fewer ADRs than tricyclic antidepressants and is better tolerated. Selective blockade of specific serotonin receptors by mirtazapine likey minimizes side effects typical of other antidepressants.

Metabolism:

Mirtazapine is extensively metabolized by demethylation and hydroxylation followed by glucuronide conjugation. Cytochrome P450 2D6 and cytochrome P450 1A2 are involved in formation of the 8-hydroxy metabolite of mirtazapine, and cytochrome P450 3A4 is responsible for the formation of the N-desmethyl and N-oxide metabolites. Several metabolites possess pharmacological activity, but plasma levels are very low.

Toxicity:

Symptoms of overdose include disorientation, drowsiness, impaired memory, and tachycardia. LD50 is 600-720mg/kg (oral, mice) and 320-490mg/kg (oral, rat) [PMID: 10333982]

IUPAC:
5-methyl-2, 5, 19-triazatetracyclo[13.4.0.0, {2, 7}.0, {8, 13}]nonadeca-1(19), 8(13), 9, 11, 15, 17-hexaene
ATC:
N06AX11
PubChem:
4205
DrugBank:
DB00370 (APRD00685)
Formula:
C13H17ClN2O2
Molecular Mass:
265.3529
Synonyms:
Mepirzepine Mirtazapina [INN-Spanish] Mirtazapine [Usan:Ban:Inn] Mirtazapinum [INN-Latin] Mirtazepine
SMILES:
CN1CCN2C(C1)C1=CC=CC=C1CC1=C2N=CC=C1
AHFS Code:
28:16.04.92
InChi:
RONZAEMNMFQXRA-UHFFFAOYSA-N
General Reference:
General Reference:

  1. Gillman PK: A systematic review of the serotonergic effects of mirtazapine in humans: implications for its dual action status. Hum Psychopharmacol. 2006 Mar;21(2):117-25. Pubmed
  2. Burrows GD, Kremer CM: Mirtazapine: clinical advantages in the treatment of depression. J Clin Psychopharmacol. 1997 Apr;17 Suppl 1:34S-39S. Pubmed
  3. Velazquez C, Carlson A, Stokes KA, Leikin JB: Relative safety of mirtazapine overdose. Vet Hum Toxicol. 2001 Dec;43(6):342-4. Pubmed
  4. Gorman JM: Mirtazapine: clinical overview. J Clin Psychiatry. 1999;60 Suppl 17:9-13; discussion 46-8. Pubmed
  5. Baldwin DS, Anderson IM, Nutt DJ, Bandelow B, Bond A, Davidson JR, den Boer JA, Fineberg NA, Knapp M, Scott J, Wittchen HU: Evidence-based guidelines for the pharmacological treatment of anxiety disorders: recommendations from the British Association for Psychopharmacology. J Psychopharmacol. 2005 Nov;19(6):567-96. Pubmed
  6. Pubmed

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