Lofepramine

Lofepramine

Systematic (IUPAC) name
N-(4-chlorobenzoylmethyl)-3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-methylpropan-1-amine
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	℞ Prescription only
Routes	Oral
Pharmacokinetic data
Half-life	4-6 hours (lofepramine - prodrug); 21-23 hours (desipramine - active metabolite)
Identifiers
CAS number	23047-25-8 N
ATC code	N06AA07
PubChem	CID 3947
ChemSpider	3810 Y
UNII	OCA4JT7PAW Y
KEGG	D08140 Y
ChEBI	CHEBI:47782 Y
ChEMBL	CHEMBL87708 Y
Chemical data
Formula	C26H27ClN2O
Mol. mass	418.958 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C26H27ClN2O/c1-28(19-26(30)22-13-15-23(27)16-14-22)17-6-18-29-24-9-4-2-7-20(24)11-12-21-8-3-5-10-25(21)29/h2-5,7-10,13-16H,6,11-12,17-19H2,1H3 Y Key:SAPNXPWPAUFAJU-UHFFFAOYSA-N Y
N(what is this?)  (verify)

Lofepramine (Gamanil, Tymelyt, Lomont) is a third Generation tricyclic antidepressant which was introduced in 1983 for the treatment of depressive disorders. It is partially converted to its active metabolite desipramine in vivo. However, it is unlikely this property plays a substantial role in its overall effects as lofepramine exhibits lower toxicity and anticholinergic side effects relative to desipramine while retaining equivalent antidepressant efficacy.

Indications

In the United Kingdom, lofepramine is licensed for the treatment of depression.

Description: An antidepressant administered orally (as tablets). It has fewer sedative properties than many of the products used to treat depressive illnesses and is suited to patients whose symptoms tend towards withdrawal and apathy, rather than restlessness and agitation.

It is commonly prescribed for major depressive disorder, anxiety, insomnia, neuropathic/chronic pain, and treatment resistant depression.

Side effects

Delusions, headache, nightmares, facial oedema, general feeling of being unwell, bleeding from skin, excitement/anxiety, nausea, inflammation of mucous membranes, loss of taste, parasthesia, skin rash, psychiatric problems such as self harm, drowsiness, dry mouth, pins and needles, heartbeat irregularities, sweating, low blood pressure, constipation, blurred vision palpatations, dizziness and urinary retention. Can cause confusion in elderly patients or behavioural disturbance in the young. May produce weight gain or cause changes in the levels of blood sugar. Some patients report muscular discomfort, particularly in the shoulders. However, lofepramine is less sedating than, for instance, amitriptyline, and is safer in overdose than older tricyclics.

Warnings

To be used with caution for epileptic patients or those with glaucoma or psychosis. Lofepramine should not be given to people who have suffered liver failure or heart disease. Not advisable for use in pregnant women.

Availability

In the United Kingdom, lofepramine is marketed (as the hydrochloride salt) in the form of 70 mg tablets and 5ml oral suspension as the generic Lomont.

See also

• Tricyclic antidepressant