Lofepramine

Lofepramine
Clinical data
Trade names	Gamanil, Lomont, Tymelyt, others
Other names	Lopramine; DB-2182; Leo-460; WHR-2908A
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	N06AA07 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only);
Pharmacokinetic data
Bioavailability	7%
Protein binding	99%
Metabolism	Hepatic (via cytochrome P450, including CYP2D6)
Metabolites	Desipramine (major)
Elimination half-life	Up to 5 hours; 12–24 hours (active metabolites)
Excretion	Urine, feces (mostly as metabolites)
Identifiers
	IUPAC name N-(4-chlorobenzoylmethyl)-3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-methylpropan-1-amine;
CAS Number	23047-25-8 ; 26786-32-3 (hydrochloride);
PubChem CID	3947;
IUPHAR/BPS	7551;
ChemSpider	3810 ;
UNII	OCA4JT7PAW;
KEGG	D08140 ;
ChEBI	CHEBI:47782 ;
ChEMBL	ChEMBL87708 ;
CompTox Dashboard (EPA)	DTXSID2023220 ;
ECHA InfoCard	100.041.254
Chemical and physical data
Formula	C26H27ClN2O
Molar mass	418.97 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1ccc(cc1)C(=O)CN(C)CCCN4c2ccccc2CCc3c4cccc3;
	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 ; Key:SAPNXPWPAUFAJU-UHFFFAOYSA-N ;
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Lofepramine, sold under the brand names Gamanil, Lomont, and Tymelyt among others, is a tricyclic antidepressant (TCA) which is used to treat depression. The TCAs are so named as they share the common property of having three rings in their chemical structure. Like most TCAs lofepramine is believed to work in relieving depression by increasing concentrations of the neurotransmitters norepinephrine and serotonin in the synapse, by inhibiting their reuptake. It is usually considered a third-generation TCA, as unlike the first- and second-generation TCAs it is relatively safe in overdose and has milder and less frequent side effects.

Lofepramine is not available in the United States, Canada, Australia or New Zealand, although it is available in Ireland, Japan, South Africa and the United Kingdom, among other countries.