Maprotiline

Maprotiline

Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a682158
Pregnancy category	US: B3[in US?]
Routes of administration	oral, intramuscular, intravenous (infusion)
ATC code	N06AA21 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	66–70%
Protein binding	88%
Metabolism	hepatic
Onset of action	6 hours
Biological half-life	27–58 hours
Excretion	biliar (30%) and urine (57%) as glucuronides, 3–4% as unchanged drug
Identifiers
IUPAC name N-Methyl-9,10-ethanoanthracene-9(10H)-propanamine
CAS Number	10262-69-8 Y
PubChem (CID)	4011
IUPHAR/BPS	2402
DrugBank	DB00934 Y
ChemSpider	23719117 N
UNII	2U1W68TROF Y
KEGG	D02566 Y
ChEMBL	CHEMBL21731 Y
ECHA InfoCard	100.030.532
Chemical and physical data
Formula	C20H23N
Molar mass	277.403 g/mol
3D model (Jmol)	Interactive image
SMILES CNCCC[C@@]12C3=CC=CC=C3[C@@H](C4=CC=CC=C14)CC2
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+ N Key:QSLMDECMDJKHMQ-GSXCWMCISA-N N
NY (what is this?)

Maprotiline (sold as Deprilept, Ludiomil, Psymion) is a medication that belongs to tetracyclic antidepressants (TeCA), a specific group of antidepressants.

Maprotiline was developed and has been marketed by the Swiss manufacturer Geigy (now operated by Novartis) since the early 1980s under the brand name Ludiomil. Generics are widely available.

After oral use absorption is good. It binds to plasma proteins 80–90%. Maximal plasma concentration is reached 6 hours after use. The mean time to peak is 12 hours. The half-life of elimination averages 51 hours.

Maprotiline exhibits strong effects as a norepinephrine reuptake inhibitor with only weak actions the reuptake of serotonin and dopamine. It is also a strong antagonist of the H₁ receptor, a moderate antagonist of the 5-HT₂ and α₁-adrenergic receptors, and a weak antagonist of the D₂ and maCh receptors.

Maprotiline has also more recently been identified as a potent antagonist of the 5-HT₇ receptor, with this action potentially playing an important role in its antidepressant effectiveness.

The pharmacological profile of maprotiline explains its antidepressant, sedative, anxiolytic, and sympathomimetic activities. In accordance to the pharmacological characteristics it is used in the treatment of depression, such as depression associated with agitation or anxiety. Additionally, it shows strong antagonism against reserpine-induced effects in animal studies, as do the other 'classical' antidepressants. Although maprotiline behaves in most regards as a 'first-generation antidepressant' it is commonly referred to as 'second-generation antidepressant'.