Desipramine

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Desipramine
Desipramine.svg
Systematic (IUPAC) name
3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-methylpropan-1-amine
Clinical data
Trade names Norpramin
AHFS/Drugs.com monograph
MedlinePlus a682387
Pregnancy cat. C (US)
Legal status -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability 73-92%
Metabolism Hepatic (CYP2D6)
Half-life 15-24 hours
Excretion Urine (70%)
Identifiers
CAS number 50-47-5 YesY
ATC code N06AA01
PubChem CID 2995
IUPHAR ligand 2399
DrugBank DB01151
ChemSpider 2888 YesY
UNII TG537D343B YesY
KEGG D07791 YesY
ChEBI CHEBI:47781 YesY
ChEMBL CHEMBL72 YesY
Chemical data
Formula C18H22N2 
Mol. mass 266.381 g/mol
 YesY (what is this?)  (verify)

Desipramine (also known as desmethylimipramine) is a tricyclic antidepressant (TCA). It inhibits the reuptake of norepinephrine and to a minor extent serotonin. It is used to treat depression, but not considered a first line treatment since the introduction of SSRI antidepressants. Desipramine is an active metabolite of imipramine. It is sold under the brand names Treyzafagit, Norpramin and Pertofrane.

Along with other tricyclics, desipramine has found use in treating neuropathic pain. The mechanism of action seems to involve the activation, through norepinephrine reuptake inhibition, of descending pathways in the spinal cord that block pain signals from ascending to the brain. Desipramine is one of the most potent and selective medications in this respect. It may also be used to treat symptoms of Attention Deficit Hyperactivity Disorder, as the underproduction of norepinephrine has been increasingly linked to symptoms associated with Attention Deficit Disorder[citation needed]. It may also be used to treat symptoms of cocaine withdrawal.[citation needed]

Cardiac arrhythmia[edit]

On December 2, 2009, the US Food and Drug Administration (FDA) and Sanofi-Aventis are warning healthcare professionals to use caution when prescribing the antidepressant desipramine hydrochloride (Norpramin) in patients with a family history of dysrhythmias or sudden cardiac death.

"The new safety information states that extreme caution should be used when this drug is given to patients who have a family history of sudden death, cardiac dysrhythmias, and cardiac conduction disturbances," according to an alert sent today from MedWatch, the FDA's safety information and adverse event reporting program.

The FDA and the manufacturer also warn that some patients may have seizures before cardiac dysrhythmias and death. Desipramine overdose is more likely to result in death than overdose with other tricyclic antidepressants, notes a company letter sent to healthcare professionals.[1]

The "warnings" and "overdosage" sections of the drug's labeling are being changed to reflect these potential adverse events.

Genotoxicity[edit]

Desipramine has been shown to be genotoxic in fruit flies and associated with an increased risk of breast cancer in women.[2]

Overdose[edit]

As tricyclic antidepressants have a relatively narrow therapeutic index, the likelihood of overdose (both accidental and intentional) is fairly high and should be considered carefully by the prescribing physician prior to patient use. Symptoms of overdose are similar to those of other tricyclic antidepressants, with cardiac toxicity (due to inhibition of sodium and calcium channels) generally occurring before the threshold for serotonin syndrome is reached. Due to this risk, tricyclic antidepressants are rarely selected as the first line treatment for depression. Desipramine overdose should always be considered a medical emergency. In the event of a suspected or known overdose, a poison control center (in the U.S. 1-800-222-1222), or 911 (999 in the UK) should be contacted immediately. The victim should be brought to the nearest hospital when/where phone services are not available.

See also[edit]

References[edit]

  1. ^ http://www.medscape.com/viewarticle/713305?sssdmh=dm1.563907&src=ddd&uac=122237BK
  2. ^ British Journal of Cancer 2002: volume 86, pages 92-97

External links[edit]