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Synopsis

Synopsis

Chemistry

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Also known as: 85650-52-8, Remeron, 61337-67-5, 6-azamianserin, Zispin, Mepirzepine
Molecular Formula
C17H19N3
Molecular Weight
265.35  g/mol
InChI Key
RONZAEMNMFQXRA-UHFFFAOYSA-N
FDA UNII
A051Q2099Q

Mirtazapine
A piperazinoazepine tetracyclic compound that enhances the release of NOREPINEPHRINE and SEROTONIN through blockage of presynaptic ALPHA-2 ADRENERGIC RECEPTORS. It also blocks both 5-HT2 and 5-HT3 serotonin receptors and is a potent HISTAMINE H1 RECEPTOR antagonist. It is used for the treatment of depression, and may also be useful for the treatment of anxiety disorders.
1 2D Structure

Mirtazapine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-methyl-2,5,19-triazatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),8,10,12,16,18-hexaene
2.1.2 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
2.1.3 InChI Key
RONZAEMNMFQXRA-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN1CCN2C(C1)C3=CC=CC=C3CC4=C2N=CC=C4
2.2 Other Identifiers
2.2.1 UNII
A051Q2099Q
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (n-methyl-11c)mirtazapine

2. (s)-mirtazapine

3. 6 Azamianserin

4. 6-azamianserin

5. Esmirtazapine

6. Norset

7. Org 3770

8. Org 50081

9. Org-3770

10. Org3770

11. Remergil

12. Remeron

13. Rexer

14. Zispin

2.3.2 Depositor-Supplied Synonyms

1. 85650-52-8

2. Remeron

3. 61337-67-5

4. 6-azamianserin

5. Zispin

6. Mepirzepine

7. Remergil

8. Rexer

9. Promyrtil

10. Remergon

11. Norset

12. Mirtazepine

13. Avanza

14. Remeron Soltab

15. Mepirzapin

16. Mirtazipine

17. Org 3770

18. Mirtazapina

19. Mirtazapinum

20. Mirtazapinum [inn-latin]

21. Mirtazapina [inn-spanish]

22. Mirtazapin

23. Org-3770

24. 2-methyl-1,2,3,4,10,14b-hexahydropyrazino[2,1-a]pyrido[2,3-c][2]benzazepine

25. Mirataz

26. 2-methyl-1,2,3,4,10,14b-hexahydrobenzo[c]pyrazino[1,2-a]pyrido[3,2-f]azepine

27. Org3770

28. Mirtazapine Anhydrous

29. 1,2,3,4,10,14b-hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c][2]benzazepine

30. 1,2,3,4,10,14b-hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)benzazepine

31. Chembl654

32. Mirtazapine (remeron, Avanza)

33. Chebi:6950

34. (r)-org3770;(r)-6-azamianserin

35. (s)-org3770;(s)-6-azamianserin

36. Pyrazino(2,1-a)pyrido(2,3-c)(2)benzazepine, 1,2,3,4,10,14b-hexahydro-2-methyl-

37. A051q2099q

38. Ncgc00025346-02

39. Pyrazino[2,1-a]pyrido[2,3-c][2]benzazepine, 1,2,3,4,10,14b-hexahydro-2-methyl-

40. Azamianserin

41. Mirtazapine [usan:ban:inn]

42. Smilon

43. 2-methyl-1,2,3,4,9,13b-hexahydro-2,4a,5-triaza-tribenzo[a,c,e]cycloheptene

44. 5-methyl-2,5,19-triazatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),8,10,12,16,18-hexaene

45. Smr000466347

46. Remeron (tn)

47. Sr-01000597530

48. Einecs 288-060-6

49. Mepirzapine

50. Unii-a051q2099q

51. 1,2,3,4,10,14b-hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c](2)benzazepine

52. Mirtazapine [usan:usp:inn:ban]

53. Mirtazapine Solution

54. Mirtazapine- Bio-x

55. Mfcd00865427

56. Reflex (tn)

57. (1)-1,2,3,4,10,14b-hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)(2)benzazepine

58. Mianserin, 6-aza-

59. 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

60. Me-2040

61. Mirtazapine [mi]

62. Mirtazapine [inn]

63. Mirtazapine [jan]

64. Dsstox_cid_3325

65. Mirtazapine [usan]

66. Mirtazapine [vandf]

67. Dsstox_rid_76979

68. Dsstox_gsid_23325

69. Schembl35408

70. Mirtazapine [usp-rs]

71. Mirtazapine [who-dd]

72. Mls000759460

73. Mls001076676

74. Mls001424294

75. Mls006011449

76. Mirtazapine (jan/usp/inn)

77. Gtpl7241

78. Dtxsid0023325

79. Mirtazapine [green Book]

80. Mirtazapine, (+/-)-

81. Mirtazapine, >=98% (hplc)

82. Mirtazapine [orange Book]

83. Hms2052h03

84. Hms2233k03

85. Hms3268f21

86. Hms3370b05

87. Hms3374j01

88. Hms3394h03

89. Hms3413c11

90. Hms3657m13

91. Hms3677c11

92. Hms3713p13

93. Hms3884o18

94. Mirtazapine [ep Monograph]

95. Mirtazapine [usp Monograph]

96. Bcp14560

97. Bcp22244

98. Hy-b0352

99. Mirtazapine 1.0 Mg/ml In Methanol

100. Tox21_110965

101. Bdbm50115644

102. Pdsp1_001529

103. Pdsp2_001513

104. S2016

105. Stk711107

106. Akos005530681

107. Bcp9000930

108. Ccg-101154

109. Ccg-220556

110. Db00370

111. Ks-1086

112. Nc00404

113. (14br)-2-methyl-1,2,3,4,10,14b-hexahydropyrazino[2,1-a]pyrido[2,3-c][2]benzazepine

114. Ncgc00025346-01

115. Ncgc00025346-08

116. 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

117. Ac-15480

118. Bm164672

119. Cas-61337-67-5

120. Ft-0601544

121. Ft-0628951

122. Ft-0672414

123. M-130

124. M2151

125. Sw197784-4

126. En300-49851

127. C07570

128. D00563

129. Ab00698265_08

130. 337m675

131. A914630

132. L001294

133. Q421930

134. Sr-01000597530-1

135. Sr-01000597530-4

136. Brd-a64977602-001-01-9

137. Brd-a64977602-001-04-3

138. Z2327131613

139. Mirtazapine, European Pharmacopoeia (ep) Reference Standard

140. Mirtazapine, United States Pharmacopeia (usp) Reference Standard

141. (+/-)-12-methyl-1,2,3,4,9,13b-hexahydro-2,4a,5-triaza-tribenzo[a,c,e]cycloheptene

142. 1,2,3,4,10,14b-hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c][2]benzazepine.

143. 2-methyl-1,2,3,4,10,14b-hexahydrobenzo-[c]pyrazino[1,2-a]pyrido[3,2-f]azepine

144. Mirtazapine For System Suitability, European Pharmacopoeia (ep) Reference Standard

145. Mirtazapine Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

146. 5-methyl-2,5,19-triazatetracyclo[13.4.0.0?,?.0?,??]nonadeca-1(15),8,10,12,16,18-hexaene

147. Pyrazino[2,1-a]pyrido[2,3-c][2]benzazepine, 1,2,3,4,10,14b-hexahydro-2-methyl-, (.+/-.)-

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 265.35 g/mol
Molecular Formula C17H19N3
XLogP33.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass265.157897619 g/mol
Monoisotopic Mass265.157897619 g/mol
Topological Polar Surface Area19.4 Ų
Heavy Atom Count20
Formal Charge0
Complexity345
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameMirtazapine
PubMed HealthMirtazapine (By mouth)
Drug ClassesAntidepressant
Drug LabelMirtazapine Tablets USP are an orally administered drug. Mirtazapine has a tetracyclic chemical structure and belongs to the piperazino-azepine group of compounds. It is designated 1,2,3,4,10,14b-Hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c]benzazep...
Active IngredientMirtazapine
Dosage FormTablet; Tablet, orally disintegrating
RouteOral
Strength7.5mg; 30mg; 15mg; 45mg
Market StatusPrescription
CompanyMylan Pharms; Actavis Labs Fl; Teva; Apotex; Aurobindo; Aurobindo Pharma; Sun Pharm Inds; Sandoz; Watson Labs; Mylan

2 of 6  
Drug NameRemeron
PubMed HealthMirtazapine (By mouth)
Drug ClassesAntidepressant
Drug LabelREMERON (mirtazapine) Tablets are an orally administered drug. Mirtazapine has a tetra-cyclic chemical structure and belongs to the piperazino-azepine group of compounds. It is designated 1,2,3,4,10,14b-hexahydro-2-methylpyrazino [2,1-a] pyrido [2,...
Active IngredientMirtazapine
Dosage FormTablet
RouteOral
Strength30mg; 15mg; 45mg
Market StatusPrescription
CompanyOrganon Usa

3 of 6  
Drug NameRemeron soltab
Active IngredientMirtazapine
Dosage FormTablet, orally disintegrating
RouteOral
Strength30mg; 15mg; 45mg
Market StatusPrescription
CompanyOrganon Usa

4 of 6  
Drug NameMirtazapine
PubMed HealthMirtazapine (By mouth)
Drug ClassesAntidepressant
Drug LabelMirtazapine Tablets USP are an orally administered drug. Mirtazapine has a tetracyclic chemical structure and belongs to the piperazino-azepine group of compounds. It is designated 1,2,3,4,10,14b-Hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c]benzazep...
Active IngredientMirtazapine
Dosage FormTablet; Tablet, orally disintegrating
RouteOral
Strength7.5mg; 30mg; 15mg; 45mg
Market StatusPrescription
CompanyMylan Pharms; Actavis Labs Fl; Teva; Apotex; Aurobindo; Aurobindo Pharma; Sun Pharm Inds; Sandoz; Watson Labs; Mylan

5 of 6  
Drug NameRemeron
PubMed HealthMirtazapine (By mouth)
Drug ClassesAntidepressant
Drug LabelREMERON (mirtazapine) Tablets are an orally administered drug. Mirtazapine has a tetra-cyclic chemical structure and belongs to the piperazino-azepine group of compounds. It is designated 1,2,3,4,10,14b-hexahydro-2-methylpyrazino [2,1-a] pyrido [2,...
Active IngredientMirtazapine
Dosage FormTablet
RouteOral
Strength30mg; 15mg; 45mg
Market StatusPrescription
CompanyOrganon Usa

6 of 6  
Drug NameRemeron soltab
Active IngredientMirtazapine
Dosage FormTablet, orally disintegrating
RouteOral
Strength30mg; 15mg; 45mg
Market StatusPrescription
CompanyOrganon Usa

4.2 Drug Indication

This drug is indicated for the treatment of major depressive disorder and its associated symptoms. Mirtazapine has been used off-label for a variety of conditions including panic disorder, generalized anxiety disorder, dysthymia, tension headaches, hot flushes, post-traumatic stress disorder (PTSD), sleep disorders, substance abuse disorders, and sexual disorders, among others.


FDA Label


For bodyweight gain in cats experiencing poor appetite and weight loss resulting from chronic medical conditions.


5 Pharmacology and Biochemistry
5.1 Pharmacology

**General effects and a note on suicidality** Mirtazapine is effective in treating moderate to severe depression and treats many symptoms normally associated with this condition. These symptoms may include disturbed sleep, lack of appetite, and anhedonia, in addition to anxiety.. It is important to note that suicidal ideation and behavior may emerge or increase during treatment with mirtazapine, as with any other antidepressant. This risk is especially pronounced in younger individuals. Patients, medical professionals, and families should monitor for suicidal thoughts, worsening depression, anxiety, agitation, sleep changes, irritable behavior, aggression, impulsivity, restlessness, and other unusual behavior when this drug is taken or the dose is adjusted. Do not administer mirtazapine to children. When deciding to prescribe this drug, carefully consider the increased risk of suicidal thoughts and behavior, especially in young adults. **Effects on appetite and weight gain** In addition to the above effects, mirtazapine exerts stimulating effects on appetite, and has been used for increasing appetite and decreasing nausea in cancer patients. Some studies and case reports have shown that this drug improves eating habits and weight gain in patients suffering from anorexia nervosa when administered in conjunction with psychotherapy and/or other psychotropic drugs. In a clinical trial, women with depression experienced a clinically significant mean increase in body weight, fat mass, and concentrations of leptin when treated with mirtazapine for a 6-week period, with a lack of effect on glucose homeostasis. **Effects on sleep** The use of mirtazapine to treat disordered sleep has been leveraged from its tendency to cause somnolence, which is a frequently experienced adverse effect by patients taking this drug. Mirtazapine has been shown to exert beneficial effects on sleep latency, duration, and quality due to its sedating properties. Insomnia is a common occurrence in patients with depression, and mirtazapine has been found to be efficacious in treating this condition.


5.2 MeSH Pharmacological Classification

Anti-Anxiety Agents

Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here. (See all compounds classified as Anti-Anxiety Agents.)


Serotonin 5-HT2 Receptor Antagonists

Drugs that bind to but do not activate SEROTONIN 5-HT2 RECEPTORS, thereby blocking the actions of SEROTONIN or SEROTONIN 5-HT2 RECEPTOR AGONISTS. Included under this heading are antagonists for one or more specific 5-HT2 receptor subtypes. (See all compounds classified as Serotonin 5-HT2 Receptor Antagonists.)


Adrenergic alpha-2 Receptor Antagonists

Drugs that bind to and block the activation of ADRENERGIC ALPHA-2 RECEPTORS. (See all compounds classified as Adrenergic alpha-2 Receptor Antagonists.)


Antidepressive Agents

Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)


Histamine H1 Antagonists

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. (See all compounds classified as Histamine H1 Antagonists.)


Serotonin 5-HT3 Receptor Antagonists

Drugs that bind to but do not activate SEROTONIN 5-HT3 RECEPTORS, thereby blocking the actions of SEROTONIN or SEROTONIN 5-HT3 RECEPTOR AGONISTS. (See all compounds classified as Serotonin 5-HT3 Receptor Antagonists.)


5.3 ATC Code

QN06AX11


N06AX11

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


N - Nervous system

N06 - Psychoanaleptics

N06A - Antidepressants

N06AX - Other antidepressants

N06AX11 - Mirtazapine


5.4 Absorption, Distribution and Excretion

Absorption

The absorption of this drug is rapid and complete. Due to first pass metabolism in the liver and metabolism in the gut wall, absolute bioavailability is about 50%. Peak blood concentrations are attained within about 2 hours after an oral dose. Food has little effect on the absorption of mirtazapine, and no dose adjustment is required if it is taken with food. Steady-state levels are achieved by about 5 days after the initial dose. Mirtazapine pharmacokinetics vary across gender and age range. Females and the elderly population have been shown to have higher blood concentrations in comparison to males and younger adults.


Route of Elimination

This drug is mainly excreted by the kidney. It is 75% eliminated in the urine and 15% eliminated in the feces.


Volume of Distribution

The volume of distribution after an oral steady-state dose was measured to be 107 42L in a pharmacokinetic study.


Clearance

Total body clearance in males was found to be 31 L/h in a clinical pharmacokinetics study after intravenous administration. **Clearance in elderly patients*

Mirtazapine clearance is slower in the elderly than in younger subjects. Exercise caution when this drug is given to elderly patients. In a clinical trial, elderly males showed a marked decrease in mirtazapine clearance when compared to young males taking the same dose. This difference was less significant when clearance was compared between elderly females and younger females taking mirtazapine. **Clearance in hepatic and renal impairment** Patients with hepatic and renal impairment have decreased rates of clearance and dosage adjustments may be necessary for these patients. Moderate renal impairment and hepatic impairment cause about a 30% decrease in mirtazapine clearance. Severe renal impairment leads to a 50% decrease in mirtazapine clearance.


5.5 Metabolism/Metabolites

Mirtazapine is heavily metabolized in humans. Demethylation and hydroxylation and subsequent glucuronide conjugation are the major pathways by which mirtazapine is metabolized. Data from in vitro studies on human liver microsomes show that cytochrome 2D6 and 1A2 lead to the formation of the _8-hydroxy metabolite_ of mirtazapine. The CYP3A enzyme metabolizes this drug into its _N-desmethyl and N-oxide_ metabolites. There are various other unconjugated metabolites of this drug that are pharmacologically active, but are measured in the blood at limited concentrations.


Mirtazapine has known human metabolites that include 8-hydroxy-mirtazapine, Mirtazapine N-oxide, and N-Desmethylmirtazapine.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.6 Biological Half-Life

20-40 hours


5.7 Mechanism of Action

**Summary** The mechanism of action of mirtazapine is not fully understood but may be explained by its effects on central adrenergic and serotonergic activity. This drug exhibits a fast onset of action, a high level of response, a manageable side-effect profile, and dual noradrenergic and serotonergic effects that are unique from the effects of other antidepressants. **Effects on various receptors** It has been shown that both noradrenergic and serotonergic activity increase following mirtazapine administration. The results of these studies demonstrate mirtazapine exerts antagonist activity at presynaptic 2-adrenergic inhibitory autoreceptors and heteroreceptors in the central nervous system. This is thought to lead to enhanced noradrenergic and serotonergic activity, which are known to improve the symptoms of depression and form the basis of antidepressant therapy. Mirtazapine is a strong antagonist of serotonin 5-HT2 and 5-HT3 receptors. It has not been found to bind significantly to the serotonin 5-HT1A and 5-HT1B receptors but indirectly increases 5-HT1A transmission. In addition to the above effects, mirtazapine is a peripheral 1-adrenergic antagonist. This action may explain episodes of orthostatic hypotension that have been reported after mirtazapine use. Mirtazapine is a potent histamine (H1) receptor antagonist, which may contribute to its powerful sedating effects. The pain-relieving effects of mirtazapine may be explained by its effects on opioid receptors.


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04-Jan-2021
31-Aug-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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DOSAGE - TABLET;ORAL - 15MG

USFDA APPLICATION NUMBER - 20415

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DOSAGE - TABLET;ORAL - 30MG

USFDA APPLICATION NUMBER - 20415

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DOSAGE - TABLET;ORAL - 45MG **Federal Registe...DOSAGE - TABLET;ORAL - 45MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20415

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DOSAGE - TABLET, ORALLY DISINTEGRATING;ORAL -...DOSAGE - TABLET, ORALLY DISINTEGRATING;ORAL - 15MG

USFDA APPLICATION NUMBER - 21208

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DOSAGE - TABLET, ORALLY DISINTEGRATING;ORAL -...DOSAGE - TABLET, ORALLY DISINTEGRATING;ORAL - 30MG

USFDA APPLICATION NUMBER - 21208

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DOSAGE - TABLET, ORALLY DISINTEGRATING;ORAL -...DOSAGE - TABLET, ORALLY DISINTEGRATING;ORAL - 45MG

USFDA APPLICATION NUMBER - 21208

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