Lofepramine

Structural formula
General
Non-proprietary name	Lofepramine
other names	1- (4-Chlorophenyl) -2 - {[3- (10,11-dihydro-5 H -dibenz [ b , f ] azepin-5-yl) propyl] methylamino} ethanone; 4'-chloro-2 - {[3- (10,11-dihydro-5 H -dibenz [ b , f ] azepin-5-yl) propyl] methylamino} acetophenone; Lopramine;
Molecular formula	C 26 H 27 ClN 2 O
External identifiers / databases
ECHA InfoCard	100.041.254
PubChem	3947
Wikidata	Q368941
Drug information
ATC code	N06 AA07
Drug class	Antidepressants
properties
Molar mass	418.96 g · mol -1
Physical state	firmly
Melting point	104-106 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-335-413
	P: 261
Toxicological data	920 mg kg −1 ( LD 50 , mouse , ip ) ; > 5000 mg kg −1 ( LD 50 , rat , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Lofepramine is a chemical from the dibenzazepine class that is used as a drug to treat depression . It belongs to the group of active substances called tricyclic antidepressants .

The drug was patented in 1970 and 1972 by the Swedish stock corporation Leo ( Leo Läkemedel AB ) and was on the market in Germany under the trade name Gamonil ^® from Merck .

Presentation and extraction

The synthesis starts from the drug desipramine from, the secondary amine structure with 2-bromo-4'-chloroacetophenone alkylated is.

Clinical information

The mean daily dose of lofepramine is between 70 and 210 mg.

Pharmacological properties

Lofepramine is structurally a derivative of imipramine , which is metabolized to the active metabolite desipramine . The drug is used in the form of its hydrochloride .

The substance inhibits the reuptake of norepinephrine from the synaptic cleft to a much greater extent than that of serotonin . Lofepramine also acts as a FIASMA (functional inhibitor of acid sphingomyelinase ).

literature

Harald Schmidt (Ed.), Founded by Claus-Jürgen Estler: Pharmacology and Toxicology. 6th edition Schattauer, Stuttgart a. New York 2007. p. 241 u. 245.

Individual evidence

^ Römpp Lexikon Chemie. 10 ed. Thieme, Stuttgart a. New York 1996-1999. P. 2441.
↑ ^a ^b Lofepramine hydrochloride data sheet from Sigma-Aldrich , accessed on February 1, 2013 ( PDF ).

↑ ^a ^b Entry on lofepramine in the ChemIDplus database of the United States National Library of Medicine (NLM) .

^ A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2001) Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 .

↑ Ernst Mutschler: drug effects. 7th edition. Wissenschaftliche Verlagsgesellschaft, Stuttgart 1996. p. 156.

↑ Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, Mühle C, Terfloth L, Groemer T, Spitzer G, Liedl K, Gulbins E, Tripal P: Identification of novel functional inhibitors of acid sphingomyelinase . In: PLoS ONE . 6, No. 8, 2011, p. E23852. doi : 10.1371 / journal.pone.0023852 .

[1] Römpp Lexikon Chemie. 10 ed. Thieme, Stuttgart a. New York 1996-1999. P. 2441.

[Sigma-2] Lofepramine hydrochloride data sheet from Sigma-Aldrich , accessed on February 1, 2013 ( PDF ).

[ChemIDplus-3] Entry on lofepramine in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Kleemann-4] A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2001) Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 .

[5] Ernst Mutschler: drug effects. 7th edition. Wissenschaftliche Verlagsgesellschaft, Stuttgart 1996. p. 156.

[pmid18504571-6] Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, Mühle C, Terfloth L, Groemer T, Spitzer G, Liedl K, Gulbins E, Tripal P: Identification of novel functional inhibitors of acid sphingomyelinase . In: PLoS ONE . 6, No. 8, 2011, p. E23852. doi : 10.1371 / journal.pone.0023852 .