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Details

Stereochemistry ACHIRAL
Molecular Formula C26H27ClN2O.ClH
Molecular Weight 455.419
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOFEPRAMINE HYDROCHLORIDE

SMILES

Cl.CN(CCCN1C2=C(CCC3=C1C=CC=C3)C=CC=C2)CC(=O)C4=CC=C(Cl)C=C4

InChI

InChIKey=ZWZIQPOLMDPIQM-UHFFFAOYSA-N
InChI=1S/C26H27ClN2O.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C26H27ClN2O
Molecular Weight 418.958
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Lofepramine is a tricyclic antidepressant that is structurally similar to imipramine and is extensively metabolised to desipramine. In the absence of other major pharmacological effects it appears that its antidepressant activity stems from the facilitation of noradrenergic neurotransmission by uptake inhibition, and possibly by the additional facilitation of serotoninergic neurotransmission. The overall therapeutic efficacy of lofepramine is comparable to that of imipramine, amitriptyline, clomipramine, maprotiline and mianserin in patients with depression of varying severity, and coexisting anxiety. Lofepramine is a strong inhibitor of norepinephrine reuptake (Ki=5.4 nM) and a moderate inhibitor of serotonin reuptake (Ki=70 nM). It is a weak-intermediate level antagonist of the muscarinic acetylcholine receptors.Lofepramine is licensed for the treatment of depression in the United Kingdom.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Lofepramine

Approved Use

Lofepramine Tablets are used to treat the symptoms of depression. Common symptoms include feelings of worthlessness or deep sadness, difficulty with everyday tasks, sleeping too much or not being able to sleep, and feeling anxious.
PubMed

PubMed

TitleDatePubMed
Pharmacological profile of antidepressants and related compounds at human monoamine transporters.
1997 Dec 11
Comparison of the effects of antidepressants and their metabolites on reuptake of biogenic amines and on receptor binding.
1999 Aug
Meta-analytical studies on new antidepressants.
2001
MRI changes in multiple sclerosis following treatment with lofepramine and L-phenylalanine.
2001 Jul 3
Antidepressants as risk factor for ischaemic heart disease: case-control study in primary care.
2001 Sep 22
Simultaneous determination of seven tricyclic antidepressant drugs in human plasma by direct-injection HPLC-APCI-MS-MS with an ion trap detector.
2002 Aug
The effect of lofepramine and other related agents on the motility of Tetrahymena pyriformis.
2002 Mar 10
Managing MS. While a cure is sought, people with MS can help themselves.
2002 Nov
Treatment of multiple sclerosis with lofepramine, L-phenylalanine and vitamin B(12): mechanism of action and clinical importance: roles of the locus coeruleus and central noradrenergic systems.
2002 Nov
Nonpharmacological treatments for anxiety disorders.
2002 Sep
A randomised placebo controlled exploratory study of vitamin B-12, lofepramine, and L-phenylalanine (the "Cari Loder regime") in the treatment of multiple sclerosis.
2002 Sep
Determination of selected human pharmaceutical compounds in effluent and surface water samples by high-performance liquid chromatography-electrospray tandem mass spectrometry.
2003 Oct 10
The promises and pitfalls of reboxetine.
2003 Winter
Current use of selective serotonin reuptake inhibitors and risk of acute myocardial infarction.
2004
Risk of fetal exposure to tricyclic antidepressants.
2004 Oct
The occurrence of selected human pharmaceutical compounds in UK estuaries.
2004 Sep
Cutaneous adverse drug reaction to oral chlorphenamine detected with patch testing.
2005 Jan
Enhancing central noradrenergic function in depression: is there still a place for a new antidepressant?
2005 Mar
A randomised controlled trial to compare the cost-effectiveness of tricyclic antidepressants, selective serotonin reuptake inhibitors and lofepramine.
2005 May
Cost-effectiveness and cost-utility of tricyclic antidepressants, selective serotonin reuptake inhibitors and lofepramine: randomised controlled trial.
2006 Apr
Solid-phase extraction and analysis of 20 antidepressant drugs in human plasma by LC/MS with SSI method.
2006 Oct 16
Neuropsychiatric manifestations of depression in multiple sclerosis: neuroinflammatory, neuroendocrine, and neurotrophic mechanisms in the pathogenesis of immune-mediated depression.
2007
Is untargeted educational outreach visiting delivered by pharmaceutical advisers effective in primary care? A pragmatic randomized controlled trial.
2007 Jul 26
Inflammatory multiple-sclerosis plaques generate characteristic metabolic profiles in cerebrospinal fluid.
2007 Jul 4
Folate augmentation of treatment - evaluation for depression (FolATED): protocol of a randomised controlled trial.
2007 Nov 15
Treating bipolar disorder in patients with renal failure having haemodialysis: two case reports.
2008 Jul 26
Community-based randomised controlled trial evaluating falls and osteoporosis risk management strategies.
2008 Nov 4
Effect of educational outreach on general practice prescribing of antibiotics and antidepressants: a two-year randomised controlled trial.
2009
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
Tryptophan, Neurodegeneration and HIV-Associated Neurocognitive Disorder.
2010
Trazodone effects on [H]-paroxetine and alpha(2)-adrenoreceptors in platelets of patients with major depression.
2010 May 25
Tricyclic antidepressants and headaches: systematic review and meta-analysis.
2010 Oct 20
Psychosocial issues in palliative care: a review of five cases.
2010 Sep
Patents

Sample Use Guides

The recommended dose for adults is one tablet to be taken 2 or 3 times a day
Route of Administration: Oral
In Vitro Use Guide
The mean value for the inhibition constant (Ki) for lofepramine in human parotid gland was 285 nM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:17:30 GMT 2023
Edited
by admin
on Fri Dec 15 15:17:30 GMT 2023
Record UNII
Z24K96F991
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOFEPRAMINE HYDROCHLORIDE
JAN   MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
4'-CHLORO-2-((3-(10,11-DIHYDRO-5H-DIBENZ(B,F)AZEPIN-5-YL)PROPYL)METHYLAMINO)ACETOPHENONE MONOHYDROCHLORIDE
Systematic Name English
Lofepramine hydrochloride [WHO-DD]
Common Name English
LOFEPRAMINE HYDROCHLORIDE [MART.]
Common Name English
LOFEPRAMINE HYDROCHLORIDE [USAN]
Common Name English
ETHANONE, 1-(4-CHLOROPHENYL)-2-((3-(10,11-DIHYDRO-5H-DIBENZ(B,F)AZEPIN-5-YL)PROPYL)METHYLAMINO)-, MONOHYDROCHLORIDE
Common Name English
LOFEPRAMINE HCL
Common Name English
4'-CHLORO-2-((3-(10,11-DIHYDRO-5H-DIBENZ(B,F)AZEPIN-5-YL)PROPYL)METHYLAMINO)ACETOPHENONE HYDROCHLORIDE
Systematic Name English
AMPLIT
Brand Name English
LOFEPRAMINE HYDROCHLORIDE [MI]
Common Name English
WHR-2908A
Code English
LOFEPRAMINE HYDROCHLORIDE [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C265
Created by admin on Fri Dec 15 15:17:30 GMT 2023 , Edited by admin on Fri Dec 15 15:17:30 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C87616
Created by admin on Fri Dec 15 15:17:30 GMT 2023 , Edited by admin on Fri Dec 15 15:17:30 GMT 2023
PRIMARY
ECHA (EC/EINECS)
248-002-2
Created by admin on Fri Dec 15 15:17:30 GMT 2023 , Edited by admin on Fri Dec 15 15:17:30 GMT 2023
PRIMARY
SMS_ID
100000087617
Created by admin on Fri Dec 15 15:17:30 GMT 2023 , Edited by admin on Fri Dec 15 15:17:30 GMT 2023
PRIMARY
MERCK INDEX
m6884
Created by admin on Fri Dec 15 15:17:30 GMT 2023 , Edited by admin on Fri Dec 15 15:17:30 GMT 2023
PRIMARY Merck Index
CHEBI
31780
Created by admin on Fri Dec 15 15:17:30 GMT 2023 , Edited by admin on Fri Dec 15 15:17:30 GMT 2023
PRIMARY
USAN
Y-39
Created by admin on Fri Dec 15 15:17:30 GMT 2023 , Edited by admin on Fri Dec 15 15:17:30 GMT 2023
PRIMARY
FDA UNII
Z24K96F991
Created by admin on Fri Dec 15 15:17:30 GMT 2023 , Edited by admin on Fri Dec 15 15:17:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID9047833
Created by admin on Fri Dec 15 15:17:30 GMT 2023 , Edited by admin on Fri Dec 15 15:17:30 GMT 2023
PRIMARY
RXCUI
6294
Created by admin on Fri Dec 15 15:17:30 GMT 2023 , Edited by admin on Fri Dec 15 15:17:30 GMT 2023
PRIMARY RxNorm
CAS
26786-32-3
Created by admin on Fri Dec 15 15:17:30 GMT 2023 , Edited by admin on Fri Dec 15 15:17:30 GMT 2023
PRIMARY
PUBCHEM
33611
Created by admin on Fri Dec 15 15:17:30 GMT 2023 , Edited by admin on Fri Dec 15 15:17:30 GMT 2023
PRIMARY
ChEMBL
CHEMBL87708
Created by admin on Fri Dec 15 15:17:30 GMT 2023 , Edited by admin on Fri Dec 15 15:17:30 GMT 2023
PRIMARY
EVMPD
SUB02965MIG
Created by admin on Fri Dec 15 15:17:30 GMT 2023 , Edited by admin on Fri Dec 15 15:17:30 GMT 2023
PRIMARY
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