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1. Ba-34,276
2. Ba34,276
3. Deprilept
4. Dibencycladine
5. Hydrochloride, Maprotiline
6. Ludiomil
7. Maprolu
8. Maprotilin
9. Maprotilin Holsten
10. Maprotilin Neuraxpharm
11. Maprotilin Ratiopharm
12. Maprotilin Teva
13. Maprotilin Von Ct
14. Maprotilin-neuraxpharm
15. Maprotilin-ratiopharm
16. Maprotilin-teva
17. Maprotiline Hydrochloride
18. Maprotiline Mesylate
19. Mesylate, Maprotiline
20. Mirpan
21. N-methyl-9,10-ethanoanthracene-9(10h)-propylamine
22. Novo Maprotiline
23. Novo-maprotiline
24. Psymion
1. 10262-69-8
2. Maprotylina [polish]
3. Maprotylina
4. Maprotilinum [inn-latin]
5. Maprotilina [inn-spanish]
6. N-methyl-9,10-ethanoanthracene-9(10h)-propylamine
7. 9,10-ethanoanthracene-9(10h)-propanamine, N-methyl-
8. 276-ba
9. Chebi:6690
10. Maprotiline (usan)
11. 3-(9,10-dihydro-9,10-ethanoanthracen-9-yl)-n-methylpropan-1-amine
12. 3-(9,10-dihydro-9,10-ethanoanthracen-9-yl)propylmethylamine
13. 2u1w68trof
14. 9,10-ethanoanthracene-9(10h)-propylamine, N-methyl-
15. Ba-34276 Free Base
16. Ba-34,276 Free Base
17. Ba-34276
18. N-methyl-3-(1-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl)propan-1-amine
19. Ncgc00015708-04
20. Maprotilina
21. Maprotilinum
22. Ba-34,276 [as Hydrochloride]
23. 3-(9,10-ethanoanthracen-9(10h)-yl)-n-methylpropan-1-amine
24. Maprotiline [usan]
25. Dsstox_cid_25029
26. Dsstox_rid_80649
27. Dsstox_gsid_45029
28. N-methyl-9,10-ethanoanthracene-9(10h)-propanamine;n-methyl-9,10-ethanoanthracene-9(10h)-propanamine
29. Cas-10262-69-8
30. Einecs 233-599-4
31. Cas-10347-81-6
32. Unii-2u1w68trof
33. Brn 2385493
34. Maprotiline [usan:inn:ban]
35. N-methyl-9,10-ethanoanthracene-9(10h)-propanamine
36. Spectrum_000887
37. Tocris-0935
38. Maprotiline [mi]
39. Prestwick0_000346
40. Prestwick1_000346
41. Prestwick2_000346
42. Prestwick3_000346
43. Spectrum2_000139
44. Spectrum3_000483
45. Spectrum4_000035
46. Spectrum5_000918
47. Lopac-m-9651
48. Maprotiline [inn]
49. C07107
50. Maprotiline [vandf]
51. Maprotiline [mart.]
52. Lopac0_000812
53. Schembl33993
54. Bspbio_000411
55. Bspbio_001945
56. Kbiogr_000469
57. Kbioss_001367
58. Maprotiline [who-dd]
59. Mls001201766
60. Chembl21731
61. Divk1c_000891
62. Schembl121015
63. Spbio_000218
64. Spbio_002332
65. 2,6-dimethoxbenzoylacetonitrile
66. Bpbio1_000453
67. Gtpl2402
68. Chembl1201257
69. Dtxsid7045029
70. Schembl21994200
71. Hy-b0444a
72. Kbio1_000891
73. Kbio2_001367
74. Kbio2_003935
75. Kbio2_006503
76. Kbio3_001445
77. Ba-34276 [as Hydrochloride]
78. Ninds_000891
79. Hms2089k11
80. Hms2962e12
81. Dibencycladine, Deprilept, Ludiomil
82. Zinc1530688
83. Tox21_110200
84. Ar-111
85. Bbl010079
86. Bdbm50101973
87. Bdbm50378025
88. Stk711156
89. Akos005530670
90. Tox21_110200_1
91. Ccg-204896
92. Db00934
93. Sdccgsbi-0050789.p005
94. Idi1_000891
95. Smp1_000169
96. Ncgc00015708-01
97. Ncgc00015708-02
98. Ncgc00015708-03
99. Ncgc00015708-05
100. Ncgc00015708-06
101. Ncgc00015708-07
102. Ncgc00015708-08
103. Ncgc00015708-09
104. Ncgc00015708-10
105. Ncgc00015708-11
106. Ncgc00015708-12
107. Ncgc00015708-13
108. Ncgc00015708-15
109. Ncgc00015708-17
110. Ncgc00015708-19
111. Ncgc00015708-25
112. Ncgc00016691-01
113. Ncgc00018217-01
114. Ncgc00024886-01
115. Ncgc00024886-02
116. Ncgc00024886-03
117. Ac-12507
118. Smr000641863
119. Sbi-0050789.p003
120. Ab00514665
121. Cs-0013653
122. D02566
123. Ab00053679-33
124. Ab00053679_34
125. Ab00053679_35
126. Ab01275432-01
127. 262m698
128. L001173
129. Q418361
130. J-000745
131. Brd-k03319035-001-01-3
132. Brd-k03319035-003-02-7
133. Brd-k25433859-003-11-4
134. Brd-k25433859-003-14-8
135. Methyl(3-{tetracyclo[6.6.2.0^{2,7}.0^{9,14}]hexadeca-2(7),3,5,9(14),10,12-hexaen-1-yl}propyl)amine
| Molecular Weight | 277.4 g/mol |
|---|---|
| Molecular Formula | C20H23N |
| XLogP3 | 4.6 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 4 |
| Exact Mass | 277.183049738 g/mol |
| Monoisotopic Mass | 277.183049738 g/mol |
| Topological Polar Surface Area | 12 Ų |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Complexity | 339 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
For treatment of depression, including the depressed phase of bipolar depression, psychotic depression, and involutional melancholia, and may also be helpful in treating certain patients suffering severe depressive neurosis.
Maprotiline is a tetracyclic antidepressant. Although its main therapeutic use is in the treatment of depression, it has also been shown to exert a sedative effect on the anxiety component that often accompanies depression. In one sleep study, it was shown that maprotiline increases the duration of the REM sleep phase in depressed patients, compared to imipramine which reduced the REM sleep phase. Maprotiline is a strong inhibitor of noradrenaline reuptake in the brain and peripheral tissues, however it is worthy to note that it is a weak inhibitor of serotonergic uptake. In addition, it displays strong antihistaminic action (which may explain its sedative effects) as well as weak anticholinergic action. Maprotiline also has lower alpha adrenergic blocking activity than amitriptyline.
Adrenergic Uptake Inhibitors
Drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants (ANTIDEPRESSIVE AGENTS, TRICYCLIC) and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin. (See all compounds classified as Adrenergic Uptake Inhibitors.)
Antidepressive Agents, Second-Generation
A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake. (See all compounds classified as Antidepressive Agents, Second-Generation.)
N - Nervous system
N06 - Psychoanaleptics
N06A - Antidepressants
N06AA - Non-selective monoamine reuptake inhibitors
N06AA21 - Maprotiline
Absorption
Slowly, but completely absorbed from the GI tract following oral administration.
Route of Elimination
Approximately 60% of a single orally administered dose is excreted in urine as conjugated metabolites within 21 days; 30% is eliminated in feces.
Volume of Distribution
Maprotiline and its metabolites may be detected in the lungs, liver, brain, and kidneys; lower concentrations may be found in the adrenal glands, heart and muscle. Maprotiline is readily distributed into breast milk to similar concentrations as those in maternal blood.
Hepatic. Maprotiline is metabolized by N-demethylation, deamination, aliphatic and aromatic hydroxylations and by formation of aromatic methoxy derivatives. It is slowly metabolized primarily to desmethylmaprotiline, a pharmacologically active metabolite. Desmethylmaprotiline may undergo further metabolism to maprotiline-N-oxide.
Maprotiline has known human metabolites that include 2-hydroxy-maprotiline, 3-hydroxy-maprotiline, and desmethylmaprotiline.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560
Average ~ 51 hours (range: 27-58 hours)
Maprotiline exerts its antidepressant action by inhibition of presynaptic uptake of catecholamines, thereby increasing their concentration at the synaptic clefts of the brain. In single doses, the effect of maprotiline on the EEG revealed a rise in the alpha-wave density, a reduction of the alpha-wave frequency and an increase in the alpha-wave amplitude. However, as with other tricyclic antidepressants, maprotiline lowers the convulsive threshold. Maprotiline acts as an antagonist at central presynaptic α2-adrenergic inhibitory autoreceptors and hetero-receptors, an action that is postulated to result in an increase in central noradrenergic and serotonergic activity. Maprotiline is also a moderate peripheral α1 adrenergic antagonist, which may explain the occasional orthostatic hypotension reported in association with its use. Maprotiline also inhibits the amine transporter, delaying the reuptake of noradrenaline and norepinephrine. Lastly, maprotiline is a strong inhibitor of the histamine H1 receptor, which explains its sedative actions.
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