Structure via PubChem · Public domain (PubChem)
maprotiline
Sign in to saveAlso known as LUD276
Maprotiline, sold under the brand name Ludiomil among others, is a tetracyclic antidepressant (TeCA) that is used in the treatment of depression. It may alternatively be classified as a tricyclic antidepressant (TCA), specifically a secondary amine. 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, albeit with more distinct anxiolytic effects. Additionally, whereas protriptyline tends to be somewhat more stimulating and in any case is distinctly more-or-less non-sedat
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 477169275
- Drug.IUPAC_name
- N-Methyl-9,10-ethanoanthracene-9(10H)-propanamine
- Drug.image
- Maprotiline structure.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200px
- Drug.image2
- Maprotiline ball-and-stick model.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 200px
- Drug.tradename
- Ludiomil, others
- Drug.MedlinePlus
- a682158
- Drug.pregnancy_US_comment
- B3[in US?]
- Drug.legal_AU
- S4
- Drug.legal_BR
- C1
- Drug.legal_US
- Rx-only
- Drug.routes_of_administration
- Oral, intramuscular, intravenous
- Drug.bioavailability
- 66–70%
via Wikipedia infobox
Chemical data
- Formula
- C20H23N
- Molecular weight
- 277.4 g/mol
- IUPAC name
- N-methyl-3-(1-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl)propan-1-amine
- SMILES
- CNCCCC12CCC(C3=CC=CC=C31)C4=CC=CC=C24
- InChIKey
- QSLMDECMDJKHMQ-UHFFFAOYSA-N
- XLogP
- 4.6
- Polar surface area
- 12 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
1,332 papers- Maprotiline.Modern problems of pharmacopsychiatry · 1982
- Maprotiline-induced ataxia.Journal of clinical psychopharmacology · 1986
- Maprotiline Ameliorates High Glucose-Induced Dysfunction in Renal Glomerular Endothelial Cells.Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association · 2022
- Maprotiline: a review of its pharmacological properties and therapeutic efficacy in mental depressive states.Drugs · 1977
- Maprotiline-induced myoclonus.Journal of clinical psychopharmacology · 1983
via PubMed
Wikidata facts
- Mass
- 277.18305
Show 4 more facts
- chemical formula
- C₂₀H₂₃N
- World Health Organisation international non-proprietary name
- maprotiline
- Commons category
- Maprotiline
- canonical SMILES
- CNCCCC12CCC(C3=CC=CC=C31)C4=CC=CC=C24
Sources (6)
via Wikidata · CC0
~21 min read
Article
19 sectionsContents
- Medical uses
- Available forms
- Contraindications
- Absolute
- Special caution needed
- Suicidal patients
- Pregnancy and lactation
- Side effects
- Withdrawal
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Generic names
- Brand names
- References
Maprotiline, sold under the brand name Ludiomil among others, is a tetracyclic antidepressant (TeCA) that is used in the treatment of depression. It may alternatively be classified as a tricyclic antidepressant (TCA), specifically a secondary amine. 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, albeit with more distinct anxiolytic effects. Additionally, whereas protriptyline tends to be somewhat more stimulating and in any case is distinctly more-or-less non-sedating, mild degrees of sedation may be experienced with maprotiline.
==Medical uses== Maprotiline is used in the treatment of depression, such as depression associated with agitation or anxiety and has similar efficacy to the antidepressant drug moclobemide. This finding has also been validated by a group of general practitioners who compared the respective efficacy and tolerability of maprotiline and moclobemide. Treatment of depression of all forms and severities (endogenous, psychotic, involutional, and neurotic), especially depression associated with agitation or anxiety Panic disorder Neuropathic pain, including painful polyneuropathy in diabetics and non-diabetics alike. Treatment of the depressive phase of bipolar affective disorder For the symptomatic relief of anxiety, tension or insomnia