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Details

Stereochemistry ACHIRAL
Molecular Formula C20H23N
Molecular Weight 277.4033
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MAPROTILINE

SMILES

CNCCCC12CCC(C3=CC=CC=C13)C4=CC=CC=C24

InChI

InChIKey=QSLMDECMDJKHMQ-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Maprotiline is a tetracyclic antidepressant with similar pharmacological properties to tricyclic antidepressants (TCAs). Similar to TCAs, maprotiline inhibits neuronal norepinephrine reuptake, possesses some anticholinergic activity, and does not affect monoamine oxidase activity. It differs from TCAs in that it does not appear to block serotonin reuptake. Maprotiline may be used to treat depressive affective disorders, including dysthymic disorder (depressive neurosis) and major depressive disorder. Maprotiline is effective at reducing symptoms of anxiety associated with depression. The mechanism of action of maprotiline is not precisely known. It does not act primarily by stimulation of the central nervous system and is not a monoamine oxidase inhibitor. The postulated mechanism of maprotiline is that it acts primarily by potentiation of central adrenergic synapses by blocking reuptake of norepinephrine at nerve endings. This pharmacologic action is thought to be responsible for the drug’s antidepressant and anxiolytic effects. The mean time to peak is 12 hours. The half-life of elimination averages 51 hours.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MAPROTILINE HYDROCHLORIDE
Primary
MAPROTILINE HYDROCHLORIDE
PubMed

PubMed

TitleDatePubMed
Severe mania after maprotiline-induced coma.
1992 Jul
The serotonin syndrome.
1992 Oct
Differential effects of antidepressants on glucocorticoid receptors in human primary blood cells and human monocytic U-937 cells.
2003 Apr
Optimised procedures for the reversed-phase liquid chromatographic analysis of formulations containing tricyclic antidepressants.
2003 Apr 24
Analysis of eighteen antidepressants, four atypical antipsychotics and active metabolites in serum by liquid chromatography: a simple tool for therapeutic drug monitoring.
2003 Aug 25
Differential effects of K(ATP) channel blockers on [(3)H]-noradrenaline overflow after short- and long-term exposure to (+)-oxaprotiline or desipramine.
2003 Feb
Chronic treatment with antidepressants decreases intraoperative core hypothermia.
2003 Jul
Bi-phasic change in BDNF gene expression following antidepressant drug treatment.
2003 Jun
Current perception thresholds of patients with long-term administration of maprotiline.
2003 Mar-Apr
Olanzapine in the treatment-resistant, combat-related PTSD--a series of case reports.
2003 May
Tricyclic antidepressants as long-acting local anesthetics.
2003 May
In vivo measurement of the serotonin transporter with (S)-([18F]fluoromethyl)-(+)-McN5652.
2003 Nov
Effects of some antidepressant drugs on tryptaminergic responses of the rat jejunum.
2003 Oct
[(11)C]PE2I: a highly selective radioligand for PET examination of the dopamine transporter in monkey and human brain.
2003 Sep
The promises and pitfalls of reboxetine.
2003 Winter
[Placebo to antidepressant effects ratio by electroencephalographic data].
2004
Current use of selective serotonin reuptake inhibitors and risk of acute myocardial infarction.
2004
Increased subcutaneous abdominal tissue norepinephrine levels in patients with anorexia nervosa: an in vivo microdialysis study.
2004
Is dopamine a limiting factor of the antidepressant-like effect in the mouse forced swimming test?
2004 Dec
Human liver aldehyde oxidase: inhibition by 239 drugs.
2004 Jan
Effect of the antidepressant maprotiline on Ca2+ movement and proliferation in human prostate cancer cells.
2004 Jul
Effect of maprotiline on Ca(2+) movement in human neuroblastoma cells.
2004 Jul 16
[Determination of amitriptyline and maprotiline in health foods by GC-MS].
2004 May
[Comparative observation on efficacy of jieyu pill and maprotiline in treating depression].
2004 May
Serotonin syndrome due to association of venlafaxine, maprotiline and reboxetine.
2004 Nov
Risk of fetal exposure to tricyclic antidepressants.
2004 Oct
Serotonin and noradrenaline reuptake inhibitors in animal models of pain.
2004 Oct
Clinical study on electro-acupuncture treatment for 30 cases of mental depression.
2004 Sep
Tricyclic antidepressants, QT interval prolongation, and torsade de pointes.
2004 Sep-Oct
Contribution of sleep research to the development of new antidepressants.
2005
Dose-response relationship of recent antidepressants in the short-term treatment of depression.
2005
The AGNP-TDM Expert Group Consensus Guidelines: focus on therapeutic monitoring of antidepressants.
2005
Screening antidepressants in the chick separation-stress paradigm.
2005 Aug
Synthesis and C-11 labeling of three potent norepinephrine transporter selective ligands ((R)-nisoxetine, lortalamine, and oxaprotiline) for comparative PET studies in baboons.
2005 Aug 1
Reduction of Submissive Behavior Model for antidepressant drug activity testing: study using a video-tracking system.
2005 Dec
[(11)C]MADAM, a new serotonin transporter radioligand characterized in the monkey brain by PET.
2005 Dec 1
Development of a solid phase extraction for 13 'new' generation antidepressants and their active metabolites for gas chromatographic-mass spectrometric analysis.
2005 Dec 9
Analgesic therapy in postherpetic neuralgia: a quantitative systematic review.
2005 Jul
Effect of long-term administration of antidepressants on the lipid composition of brain plasma membranes.
2005 Jun
Effect of pharmacologically selective antidepressants on serotonin uptake in rat platelets.
2005 Mar
[Detection of maprotiline and proserine in forensic medical examination of cadaver].
2005 Mar-Apr
The monoamine-mediated antiallodynic effects of intrathecally administered milnacipran, a serotonin noradrenaline reuptake inhibitor, in a rat model of neuropathic pain.
2005 May
Changes in AMPA subunit expression in the mouse brain after chronic treatment with the antidepressant maprotiline: a link between noradrenergic and glutamatergic function?
2006 Apr
A fully automated turbulent-flow liquid chromatography-tandem mass spectrometry technique for monitoring antidepressants in human serum.
2006 Feb
Inhibition of cardiac HERG potassium channels by antidepressant maprotiline.
2006 Feb 15
Dopamine release in human neocortical slices: characterization of inhibitory autoreceptors and of nicotinic acetylcholine receptor-evoked release.
2006 Jan 30
Are the effects of the antidepressants amitriptyline, maprotiline, and fluoxetine on inhibitory avoidance state-dependent?
2006 Jan 6
Increasing synaptic noradrenaline, serotonin and histamine enhances in vivo binding of phosphodiesterase-4 inhibitor (R)-[11C]rolipram in rat brain, lung and heart.
2006 Jun 20
Age-dependent interactive changes in serotonergic and noradrenergic cortical axon terminals in F344 rats.
2006 Mar
Phosducin-like protein levels in leukocytes of patients with major depression and in rat cortex: the effect of chronic treatment with antidepressants.
2006 Mar 30
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Initial Adult Dosage: 75 mg daily is suggested for outpatients with mild to moderate depression. However, in some patients, particularly the elderly, an initial dosage of 25 mg daily may be used. Because of the long half-life of maprotiline, the initial dosage should be maintained for 2 weeks. The dosage may then be increased gradually in 25 mg increments as required and tolerated. In most outpatients a maximum dose of 150 mg daily More severely depressed, hospitalized patients should be given an initial daily dose of 100 mg to 150 mg which may be gradually increased as required and tolerated. Most hospitalized patients with moderate to severe depression respond to a daily dose of 150 mg although dosages as high as 225 mg may be re quired in some cases. Daily dosage of 225 mg should not be exceeded. Elderly Patients: In general, lower dosages are recommended for patients over 60 years of age. Dosages of 50 mg to 75 mg daily are usually satisfactory as maintenance therapy for elderly patients who do not tolerate higher amounts.
Route of Administration: Oral
In Vitro Use Guide
Maprotiline inhibited hERG currents with an IC(50) of 8.2 micromol/l in HEK cells and 29.2 micromol/l in Xenopus oocytes
Name Type Language
MAPROTILINE
INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
N-METHYL-9,10-ETHANOANTHRACENE-9(10H)-PROPYLAMINE
Systematic Name English
BA-34,276 FREE BASE
Code English
MAPROTILINE [MART.]
Common Name English
MAPROTILINE [WHO-DD]
Common Name English
MAPROTILINE [INN]
Common Name English
MAPROTILINE [MI]
Common Name English
MAPROTILINE [USAN]
Common Name English
BA-34276 FREE BASE
Code English
9,10-ETHANOANTHRACENE-9(10H)-PROPANAMINE, N-METHYL-
Systematic Name English
MAPROTILINE [VANDF]
Common Name English
Classification Tree Code System Code
LIVERTOX 581
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
WHO-ATC N06AA21
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
WHO-VATC QN06AA21
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
NCI_THESAURUS C265
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
Code System Code Type Description
EPA CompTox
10262-69-8
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
PRIMARY
NCI_THESAURUS
C61824
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
PRIMARY
ECHA (EC/EINECS)
233-599-4
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
PRIMARY
DRUG BANK
DB00934
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
PRIMARY
MERCK INDEX
M7083
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
PRIMARY Merck Index
CAS
10262-69-8
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
PRIMARY
ChEMBL
CHEMBL21731
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
PRIMARY
INN
2763
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
PRIMARY
EVMPD
SUB08647MIG
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
PRIMARY
WIKIPEDIA
MAPROTILINE
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
PRIMARY
LactMed
10262-69-8
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
PRIMARY
PUBCHEM
4011
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
PRIMARY
RXCUI
6646
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
PRIMARY RxNorm
IUPHAR
2402
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
PRIMARY
MESH
D008376
Created by admin on Tue Oct 22 00:34:10 UTC 2019 , Edited by admin on Tue Oct 22 00:34:10 UTC 2019
PRIMARY