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
1. 85650-52-8
2. 61337-67-5
3. Zispin
4. 6-azamianserin
5. Mepirzepine
6. Remergil
7. Promyrtil
8. Remergon
9. Norset
10. Avanza
11. Remeron Soltab
12. Mepirzapin
13. Mirtazapina
14. Mirtazipine
15. Mirtazapinum
16. Mirtazapinum [inn-latin]
17. 2-methyl-1,2,3,4,10,14b-hexahydropyrazino[2,1-a]pyrido[2,3-c][2]benzazepine
18. Mirtazapina [inn-spanish]
19. Mirataz
20. Mirtazapin
21. Smilon
22. Mirtazapine Anhydrous
23. Mepirzapine
24. Einecs 288-060-6
25. Chebi:6950
26. Dtxsid0023325
27. Unii-a051q2099q
28. 1,2,3,4,10,14b-hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)benzazepine
29. A051q2099q
30. (1)-1,2,3,4,10,14b-hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)(2)benzazepine
31. Pyrazino(2,1-a)pyrido(2,3-c)(2)benzazepine, 1,2,3,4,10,14b-hexahydro-2-methyl-
32. Dtxcid503325
33. Mirtazapine [usan:usp:inn:ban]
34. Mirtazapinum (inn-latin)
35. Mirtazapina (inn-spanish)
36. Pyrazino[2,1-a]pyrido[2,3-c][2]benzazepine, 1,2,3,4,10,14b-hexahydro-2-methyl-
37. Mirtazapine (usp-rs)
38. Mirtazapine [usp-rs]
39. Mirtazapine (ep Monograph)
40. Mirtazapine [ep Monograph]
41. Mirtazapine (usp Monograph)
42. Mirtazapine [usp Monograph]
43. Mirtazapine (usan:usp:inn:ban)
44. 6 Azamianserin
45. Remeronsoltab
46. 1,2,3,4,10,14b-hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c]benzazepine
47. 2-methyl-1,2,3,4,10,14b-hexahydropyrazino(2,1-a)pyrido(2,3-c)(2)benzazepine
48. Mirtazapine, (+-)-
49. N06ax11
50. (14brs)-1,2,3,4,10,14b-hexahydro-2-methylpyrazino(2,1-a)pyrido(2,3-c)(2)benzazepine
51. 288-060-6
52. Remeron
53. Rexer
54. Mirtazepine
55. Org 3770
56. Org-3770
57. 2-methyl-1,2,3,4,10,14b-hexahydrobenzo[c]pyrazino[1,2-a]pyrido[3,2-f]azepine
58. Mfcd00865427
59. Chembl654
60. 1,2,3,4,10,14b-hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c][2]benzazepine
61. Mirtazapine (remeron, Avanza)
62. Reflex (tn)
63. (s)-org3770;(s)-6-azamianserin
64. Ncgc00025346-02
65. 5-methyl-2,5,19-triazatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),8,10,12,16,18-hexaene
66. Azamianserin
67. Mirtazapine [usan:ban:inn]
68. 2-methyl-1,2,3,4,9,13b-hexahydro-2,4a,5-triaza-tribenzo[a,c,e]cycloheptene
69. Smr000466347
70. Remeron (tn)
71. Sr-01000597530
72. Org3770
73. (r)-org3770;(r)-6-azamianserin
74. 1,2,3,4,10,14b-hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c](2)benzazepine
75. 1,2,3,4,10,14b-hexahydro-2-methylpyrazino[2,1-a]pyrido[2,3-c][2]benzazepine;mepirzepine;org-3770
76. Mianserin, 6-aza-
77. Me-2040
78. Mirtazapine (standard)
79. Mirtazapine [mi]
80. Mirtazapine [inn]
81. Mirtazapine [jan]
82. Mirtazapine [usan]
83. Mirtazapine [vandf]
84. Schembl35408
85. Mirtazapine [who-dd]
86. Mls000759460
87. Mls001076676
88. Mls001424294
89. Mls006011449
90. Mirtazapine (jan/usp/inn)
91. Gtpl7241
92. Mirtazapine - Bio-x Trade Mark
93. Mirtazapine [green Book]
94. Hy-b0352r
95. Mirtazapine, (+/-)-
96. Mirtazapine, >=98% (hplc)
97. Mirtazapine, 1mg/ml In Methanol
98. Mirtazapine [orange Book]
99. Hms2052h03
100. Hms2233k03
101. Hms3268f21
102. Hms3370b05
103. Hms3374j01
104. Hms3394h03
105. Hms3413c11
106. Hms3657m13
107. Hms3677c11
108. Hms3713p13
109. Hms3884o18
110. Ps11 - Mirtazapine/normirtazapine
111. Bcp14560
112. Bcp22244
113. Hy-b0352
114. Mirtazapine 1.0 Mg/ml In Methanol
115. Tox21_110965
116. Bdbm50115644
117. Pdsp1_001529
118. Pdsp2_001513
119. S2016
120. Stk711107
121. Akos005530681
122. Bcp9000930
123. Ccg-101154
124. Ccg-220556
125. Db00370
126. Fm26014
127. Ks-1086
128. Nc00404
129. (14br)-2-methyl-1,2,3,4,10,14b-hexahydropyrazino[2,1-a]pyrido[2,3-c][2]benzazepine
130. Ncgc00025346-01
131. Ncgc00025346-08
132. 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
133. Ac-15480
134. Bm164672
135. Cas-61337-67-5
136. M2151
137. Ns00009441
138. Sw197784-4
139. En300-49851
140. C07570
141. D00563
142. Ab00698265_08
143. L001294
144. Q421930
145. Sr-01000597530-1
146. Sr-01000597530-4
147. Brd-a64977602-001-01-9
148. Brd-a64977602-001-04-3
149. Brd-a64977602-001-13-4
150. Brd-a64977602-001-14-2
151. Brd-a64977602-001-15-9
152. Z905065772
153. Mirtazapine, European Pharmacopoeia (ep) Reference Standard
154. Mirtazapine, United States Pharmacopeia (usp) Reference Standard
155. (+/-)-12-methyl-1,2,3,4,9,13b-hexahydro-2,4a,5-triaza-tribenzo[a,c,e]cycloheptene
156. 2-methyl-1,2,3,4,10,14b-hexahydrobenzo-[c]pyrazino[1,2-a]pyrido[3,2-f]azepine
157. Mirtazapine For System Suitability, European Pharmacopoeia (ep) Reference Standard
158. 5-methyl-2,5,19-triazatetracyclo[13.4.0.0?,?.0?,??]nonadeca-1(15),8,10,12,16,18-hexaene
159. 5-methyl-2,5,19-triazatetracyclo[13.4.0.0^{2,7}.0^{8,13}]nonadeca-1(19),8,10,12,15,17-hexaene
160. Pyrazino[2,1-a]pyrido[2,3-c][2]benzazepine, 1,2,3,4,10,14b-hexahydro-2-methyl-, (.+/-.)-
| Molecular Weight | 265.35 g/mol |
|---|---|
| Molecular Formula | C17H19N3 |
| XLogP3 | 3.3 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 0 |
| Exact Mass | Da |
| Monoisotopic Mass | Da |
| Topological Polar Surface Area | 19.4 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Complexity | 345 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
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.
Mirtazapine is an atypical antidepressant primarily prescribed to treat major depressive disorder. This drug was first synthesized in 1989 and received approval for treating major depressive disorder in the Netherlands in 1994. Mirtazapine was FDA-approved in 1996 as a treatment for moderate and severe depression. Mirtazapine is not FDA-approved for pediatric patients.
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.)
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.)
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.)
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
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.
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 Mirtazapine N-oxide, 8-hydroxy-mirtazapine, and N-Desmethylmirtazapine.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560
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. Route of Elimination: This drug is known to be substantially excreted by the kidney (75%). Half Life: 20-40 hours
20-40 hours
**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.
