Lofepramine

Lofepramine
Clinical data
Trade namesGamanil, Lomont, Tymelyt, others
Other namesLopramine; DB-2182; Leo-460; WHR-2908A[1][2][3][4]
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability7%[5]
Protein binding99%[6]
MetabolismHepatic (via cytochrome P450, including CYP2D6)[7]
MetabolitesDesipramine (major)
Elimination half-lifeUp to 5 hours;[1] 12–24 hours (active metabolites)
ExcretionUrine, feces (mostly as metabolites)
Identifiers
  • N-(4-chlorobenzoylmethyl)-3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-methylpropan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.041.254 Edit this at Wikidata
Chemical and physical data
FormulaC26H27ClN2O
Molar mass418.97 g·mol−1
3D model (JSmol)
  • Clc1ccc(cc1)C(=O)CN(C)CCCN4c2ccccc2CCc3c4cccc3
  • 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 checkY
  • Key:SAPNXPWPAUFAJU-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Lofepramine, sold under the brand names Gamanil, Lomont, and Tymelyt among others, is a tricyclic antidepressant (TCA) which is used to treat depression.[7][3][8] 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.[7] 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.[9]

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.[1]

  1. ^ a b c "Lofepramine Hydrochloride". Martindale: The Complete Drug Reference. The Pharmaceutical Press. Retrieved 3 August 2017.
  2. ^ Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
  3. ^ a b Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 614–. ISBN 978-3-88763-075-1.
  4. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  5. ^ Lancaster SG, Gonzalez JP (February 1989). "Lofepramine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in depressive illness". Drugs. 37 (2): 123–140. doi:10.2165/00003495-198937020-00003. PMID 2649353. S2CID 195693275.
  6. ^ "Lofepramine 70mg tablets - Summary of Product Characteristics (SPC)". electronic Medicines Compendium. Merck Serono. 18 November 2010. Archived from the original on 2 December 2013. Retrieved 21 November 2013.
  7. ^ a b c Cite error: The named reference EMC was invoked but never defined (see the help page).
  8. ^ Leonard BE (October 1987). "A comparison of the pharmacological properties of the novel tricyclic antidepressant lofepramine with its major metabolite, desipramine: a review". International Clinical Psychopharmacology. 2 (4): 281–297. doi:10.1097/00004850-198710000-00001. PMID 2891742.
  9. ^ "SAFC Commercial Life Science Products & Services | Sigma-Aldrich". Safcglobal.com. 2015-05-12. Retrieved 2016-02-24.