Maprotiline

Maprotiline
Clinical data
Trade names	Ludiomil, others
Other names	Maprotiline hydrochloride; Maprotiline methanesulfonate; Ba 34276
AHFS/Drugs.com	Monograph
MedlinePlus	a682158
Routes of; administration	Oral, intramuscular, intravenous
ATC code	N06AA21 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); US: ℞-only;
Pharmacokinetic data
Bioavailability	66–70%
Protein binding	88%
Metabolism	hepatic
Onset of action	6 hours
Elimination half-life	27–58 hours
Excretion	Urine (57%) and bile (30%) as glucuronides, 3–4% as unchanged drug
Identifiers
	IUPAC name N-Methyl-9,10-ethanoanthracene-9(10H)-propanamine;
CAS Number	10262-69-8 ; 10347-81-6 (hydrochloride); 58902-67-3 (mesylate);
PubChem CID	4011;
IUPHAR/BPS	2402;
DrugBank	DB00934 ;
ChemSpider	23719117 ;
UNII	2U1W68TROF;
KEGG	D02566 ;
ChEMBL	ChEMBL21731 ;
CompTox Dashboard (EPA)	DTXSID7045029 ;
ECHA InfoCard	100.030.532
Chemical and physical data
Formula	C20H23N
Molar mass	277.411 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CNCCC[C@]12CC[C@H](c3ccccc31)c1ccccc12;
	InChI InChI=1S/C20H23N/c1-21-14-6-12-20-13-11-15(16-7-2-4-9-18(16)20)17-8-3-5-10-19(17)20/h2-5,7-10,15,21H,6,11-14H2,1H3/t15-,20+ ; Key:QSLMDECMDJKHMQ-GSXCWMCISA-N ;
	(what is this?) (verify)

Maprotiline, sold under the brand name Ludiomil among others, is a tetracyclic antidepressant (TeCA) that is used in the treatment of depression.^[5] It may alternatively be classified as a tricyclic antidepressant (TCA), specifically a secondary amine.^[5] In terms of its chemistry and pharmacology, maprotiline is closely related to such-other secondary-amine TCAs as nortriptyline and protriptyline and has similar effects to them,^[6]^[5] albeit with more distinct anxiolytic effects.^[7]^[8]^[9] Additionally, whereas protriptyline tends to be somewhat more stimulating and in any case is distinctly more-or-less non-sedating,^[10] mild degrees of sedation may be experienced with maprotiline.^[11]

^ Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ ^a ^b ^c Cite error: The named reference LemkeWilliams2012 was invoked but never defined (see the help page).
^ Cite error: The named reference Zhou2013 was invoked but never defined (see the help page).
^ Guimarães FS, Zuardi AW, Graeff FG (January 1987). "Effect of chlorimipramine and maprotiline on experimental anxiety in humans". Journal of Psychopharmacology. 1 (3): 184–192. doi:10.1177/026988118700100305. PMID 22158980. S2CID 8444656.
^ Vinader-Caerols C, Martos AJ, Monleón S, Arenas MC, Parra A (2006). "Acute effects of maprotiline on learning, anxiety, activity and analgesia in male and female mice". Acta Neurobiologiae Experimentalis. 66 (1): 23–31. doi:10.55782/ane-2006-1584. PMID 16617674.
^ Pecknold JC, Familamiri P, McClure DJ, Elie R, Chang H (May 1985). "Trimipramine and maprotiline: antidepressant, anxiolytic, and cardiotoxic comparison". The Journal of Clinical Psychiatry. 46 (5): 166–171. PMID 2859273.
^ Brownell LG, Perez-Padilla R, West P, Kryger MH (1983). "The role of protriptyline in obstructive sleep apnea". Bulletin Européen de Physiopathologie Respiratoire. 19 (6): 621–4. PMID 6360257.
^ Holmberg G (May 1988). "Sedative effects of maprotiline and amitriptyline". Acta Psychiatrica Scandinavica. 77 (5): 584–6. doi:10.1111/j.1600-0447.1988.tb05171.x. PMID 3044007. S2CID 41977086.

[Elks2014-1] Cite error: The named reference Elks2014 was invoked but never defined (see the help page).

[IndexNominum2000-2] Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).

[Drugs.com-3] Cite error: The named reference Drugs.com was invoked but never defined (see the help page).

[4] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[LemkeWilliams2012-5] Cite error: The named reference LemkeWilliams2012 was invoked but never defined (see the help page).

[Zhou2013-6] Cite error: The named reference Zhou2013 was invoked but never defined (see the help page).

[7] Guimarães FS, Zuardi AW, Graeff FG (January 1987). "Effect of chlorimipramine and maprotiline on experimental anxiety in humans". Journal of Psychopharmacology. 1 (3): 184–192. doi:10.1177/026988118700100305. PMID 22158980. S2CID 8444656.

[8] Vinader-Caerols C, Martos AJ, Monleón S, Arenas MC, Parra A (2006). "Acute effects of maprotiline on learning, anxiety, activity and analgesia in male and female mice". Acta Neurobiologiae Experimentalis. 66 (1): 23–31. doi:10.55782/ane-2006-1584. PMID 16617674.

[9] Pecknold JC, Familamiri P, McClure DJ, Elie R, Chang H (May 1985). "Trimipramine and maprotiline: antidepressant, anxiolytic, and cardiotoxic comparison". The Journal of Clinical Psychiatry. 46 (5): 166–171. PMID 2859273.

[pmid6360257-10] Brownell LG, Perez-Padilla R, West P, Kryger MH (1983). "The role of protriptyline in obstructive sleep apnea". Bulletin Européen de Physiopathologie Respiratoire. 19 (6): 621–4. PMID 6360257.

[pmid3044007-11] Holmberg G (May 1988). "Sedative effects of maprotiline and amitriptyline". Acta Psychiatrica Scandinavica. 77 (5): 584–6. doi:10.1111/j.1600-0447.1988.tb05171.x. PMID 3044007. S2CID 41977086.

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