CAS 61337-67-5|CAS 85650-52-8|CAS 61337-87-9|Avanza|5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(15),8(13),9,11,16,18-hexaene|Mirtazapine|5-methyl-2,5,19-triazatetracyclo[13.4...

General Information

Structure

Molecular Formula

C₁₇H₁₉N₃

Molecular Mass

265.35286

Exact Mass

265.15789762

Charge

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

InChIKey

RONZAEMNMFQXRA-UHFFFAOYSA-N

Canonic Smiles

CN1CCN2C(C1)c1ccccc1Cc1c2nccc1

Isomeric Smiles

N12C(CN(CC1)C)c1c(Cc3c2nccc3)cccc1

Calculated Properties

JChem

LogD (pH = 7.4)

3.13

LogD (pH = 5.5)

1.82

Log P

3.21

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

6.67

Polar Surface Area

19.37

Polarizability

30.34

Molar Refractivity

82.66

LOG S

-2.51

Data Source

Names and Identifiers

Synonyms

RemeronAvanzaMirtazapineOrg 3770Esmirtazapine6-AzamianserinMirtazapine1,2,3,4,10,14b-Hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c][2]benzazepineOrg-3770ZispinMepirzepineMirtazapinum [INN-Latin]mirtazapineMirtazapina [INN-Spanish]Mirtazapine [Usan:Ban:Inn]Mirtazepine5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(15),8(13),9,11,16,18-hexaene1,2,3,4,10,14b-Hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)benzazepinemirtazapineMirtazapine

IUPAC Traditional name

5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(15),8(13),9,11,16,18-hexaene mirtazapine 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 5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(19),8,10,12,15,17-hexaene

IUPAC name

5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(15),8(13),9,11,16,18-hexaene 5-methyl-2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(15),8,10,12,16,18-hexaene 5-methyl-2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(15),8(13),9,11,16,18-hexaene 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 5-methyl-2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(19),8,10,12,15,17-hexaene 5-methyl-2,5,19-triazatetracyclo[13.4.0.0²,⁷.0⁸,¹³]nonadeca-1(19),8(13),9,11,15,17-hexaene

Brand Name

Remeron, Avanza, ZispinNorsetMirtazonMirtabeneRemeron SoltabZispinPromyrtilRexerAvanzaAxitMirtazRemeronRemergonRemergil

API Name

Mirtazapine

International Nonproprietary Name (INN)

mirtazapinemirtazapinummirtazapina

Names and Identifiers

Registration numbers

Properties

Product Information

Safety Information

Storage Condition

-20°C

-20°C Freezer

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

MSDS Link

Download link

German water hazard class

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00370

Drug Groups

approved

Description

Mirtazapine is an antidepressant introduced by Organon International in 1996 used for the treatment of moderate to severe depression. Mirtazapine has a tetracyclic chemical structure and is classified as a noradrenergic and specific serotonergic antidepressant (NaSSA). It is the only tetracyclic antidepressant that has been approved by the Food and Drug Administration to treat depression. [Wikipedia]

Indication

For the treatment of major depressive disorder.

Pharmacology

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.

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]

Affected Organisms

Humans and other mammals

Biotransformation

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.

Absorption

Rapid and complete, but, due to first-pass metabolism, absolute bioavailability is 50%.

Half Life

20-40 hours

Protein Binding

85%

Elimination

This drug is known to be substantially excreted by the kidney (75%).

References

• 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]

• Burrows GD, Kremer CM: Mirtazapine: clinical advantages in the treatment of depression. J Clin Psychopharmacol. 1997 Apr;17 Suppl 1:34S-39S. [Pubmed]

• Velazquez C, Carlson A, Stokes KA, Leikin JB: Relative safety of mirtazapine overdose. Vet Hum Toxicol. 2001 Dec;43(6):342-4. [Pubmed]

• Gorman JM: Mirtazapine: clinical overview. J Clin Psychiatry. 1999;60 Suppl 17:9-13; discussion 46-8. [Pubmed]

• 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]

• [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S2016

Research Area: Neurological Disease
Biological Activity:
Mirtazapine (Remeron, Avanza) is a potent tetracyclic antidepressant. Mirtazapine (Remeron, Avanza) used primarily in the treatment of depression. It is also sometimes used as a hypnotic, antiemetic, and appetite stimulant, and for the treatment of anxiety, among other indications. In addition, along with its close analogues mianserin and setiptiline, mirtazapine (Remeron, Avanza) is one of the few noradrenergic and specific serotonergic antidepressants (NaSSAs). Additionally, the (S)-(+)-enantiomer of mirtazapine, which is also called esmirtazapine, is currently under development for the treatment of insomnia and menopausal symptoms. Mirtazapine’s primary use is the treatment of major depressive disorder. Mirtazapine (Remeron, Avanza) has been found to be useful in the treatment of many diseases, including generalized anxiety disorder, social anxiety disorder, obsessive-compulsive disorder, panic disorder, post-traumatic stress disorder, seasonal affective disorder, insomnia, nausea and vomiting, diminished appetite and associated weight loss, and itching as well. [1]References on Mirtazapine (Remeron, Avanza)[1] http://en.wikipedia.org/wiki/Mirtazapine, ,

M0443

Biochem/physiol Actions
Mirtazapine is a noradrenergic and specific serotonergic antidepressant (NaSSA). Mirtazapine agonizes selective adrenergic and serotonergic receptors so that both NE release and 5-HT1A mediated serotonergic signaling are increased.

TRC

M365000

An α2-Adrenergic blocker; analogue of Mianserin. Antidepressant.

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• Velazquez C, Carlson A, Stokes KA, Leikin JB: Relative safety of mirtazapine overdose. Vet Hum Toxicol. 2001 Dec;43(6):342-4. Pubmed

• Burrows GD, Kremer CM: Mirtazapine: clinical advantages in the treatment of depression. J Clin Psychopharmacol. 1997 Apr;17 Suppl 1:34S-39S. Pubmed

• Pubmed

• Gorman JM: Mirtazapine: clinical overview. J Clin Psychiatry. 1999;60 Suppl 17:9-13; discussion 46-8. Pubmed

• http://en.wikipedia.org/wiki/Mirtazapine

• De Boer, T., et al.: Neuropharmacology, 27, 399 (1988)

• Smith, W.T., et al.: Psychopharmacol. Bull., 26, 191 (1990)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

IUPAC name

Brand Name

Remeron, Avanza, ZispinNorsetMirtazonMirtabeneRemeron SoltabZispinPromyrtilRexerAvanzaAxitMirtazRemeronRemergonRemergil

API Name

Mirtazapine

International Nonproprietary Name (INN)

mirtazapinemirtazapinummirtazapina

Properties

Product Information

Safety Information

Storage Condition

-20°C

-20°C Freezer

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

MSDS Link

Download link

German water hazard class

Molecule Details

DrugBank

DB00370

Drug Groups

approved

Description

Indication

For the treatment of major depressive disorder.

Pharmacology

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]

Affected Organisms

Humans and other mammals

Biotransformation

Absorption

Rapid and complete, but, due to first-pass metabolism, absolute bioavailability is 50%.

Half Life

20-40 hours

Protein Binding

85%

Elimination

This drug is known to be substantially excreted by the kidney (75%).

References

• 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]

• Burrows GD, Kremer CM: Mirtazapine: clinical advantages in the treatment of depression. J Clin Psychopharmacol. 1997 Apr;17 Suppl 1:34S-39S. [Pubmed]

• Velazquez C, Carlson A, Stokes KA, Leikin JB: Relative safety of mirtazapine overdose. Vet Hum Toxicol. 2001 Dec;43(6):342-4. [Pubmed]

• Gorman JM: Mirtazapine: clinical overview. J Clin Psychiatry. 1999;60 Suppl 17:9-13; discussion 46-8. [Pubmed]

• [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

S2016

M0443

M365000

An α2-Adrenergic blocker; analogue of Mianserin. Antidepressant.

References

PubChem Literature

From Data Sources

• 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

• Velazquez C, Carlson A, Stokes KA, Leikin JB: Relative safety of mirtazapine overdose. Vet Hum Toxicol. 2001 Dec;43(6):342-4. Pubmed

• Burrows GD, Kremer CM: Mirtazapine: clinical advantages in the treatment of depression. J Clin Psychopharmacol. 1997 Apr;17 Suppl 1:34S-39S. Pubmed

• Pubmed

• Gorman JM: Mirtazapine: clinical overview. J Clin Psychiatry. 1999;60 Suppl 17:9-13; discussion 46-8. Pubmed

• http://en.wikipedia.org/wiki/Mirtazapine

• De Boer, T., et al.: Neuropharmacology, 27, 399 (1988)

• Smith, W.T., et al.: Psychopharmacol. Bull., 26, 191 (1990)

Bioactivity

PubChem BioAssay

Molecule

ID:254