Structure via PubChem · Public domain (PubChem)
lofepramine
Sign in to saveAlso known as Gamanil ®, Lomont ®, WHR-2908A, Lopramine, 4'-Chlor-2-((3-(10,11-dihydro-5H-dibenz(b,f)azepin-5-yl)propyl)methylamino)acetophenon, 4'-chloro-2-((3-(10,11-dihydro-5H-dibenz(b,f)azepin5-yl)propyl)methylamino)acetophenone, 1-(4-chlorophenyl)-2-{[3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl]methylamino}ethanone
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
In the Vinony graph
Vinony's link graph records 1,099 inbound references to lofepramine, and connects out to amine, heart arrhythmia and histamine antagonist.
It sits within the topics 4-Chlorophenyl compounds, Alpha-1 blockers and Amines.
Vinony links it to 7 Wikipedia language editions.
Chemical data
- Formula
- C26H27ClN2O
- Molecular weight
- 419 g/mol
- IUPAC name
- 1-(4-chlorophenyl)-2-[3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl-methylamino]ethanone
- SMILES
- CN(CCCN1C2=CC=CC=C2CCC3=CC=CC=C31)CC(=O)C4=CC=C(C=C4)Cl
- InChIKey
- SAPNXPWPAUFAJU-UHFFFAOYSA-N
- XLogP
- 6.8
- Polar surface area
- 23.6 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- Indications
- major depressive disorder
via ChEMBL · EBI
Research
169 papers- Lofepramine overdosage.Pharmacopsychiatry · 1990
- Lofepramine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in depressive illness.Drugs · 1989
- Dose equivalents of antidepressants: Evidence-based recommendations from randomized controlled trials.Journal of affective disorders · 2015
- Lofepramine in the elderly.International clinical psychopharmacology · 1988
- Lofepramine and psychomotor function.International clinical psychopharmacology · 1988
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 418.181191
- Has use
- medication
Show 5 more facts
- chemical formula
- C₂₆H₂₇ClN₂O
- Commons category
- Lofepramine
- canonical SMILES
- CN(CCCN1C2=CC=CC=C2CCC3=CC=CC=C31)CC(=O)C4=CC=C(C=C4)Cl
- subject has role
- tricyclic antidepressant
- physically interacts with
- solute carrier family 6 member 4
Sources (2)
via Wikidata · CC0
~11 min read
Encyclopedic overview
19 sectionsContents
- Depression
- Contraindications
- Pregnancy and lactation
- Side effects
- Withdrawal
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Generic names
- Brand names
- Availability
- Research
- Fatigue
- References
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.
Excerpted from Wikipedia’s “lofepramine” article, available under the CC BY-SA 4.0 licence.