Desipramine

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Desipramine
Skeletal formula of desipramine
Ball-and-stick model of the desipramine molecule
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
category
  • US: C (Risk not ruled out)
Legal status
Routes of
administration
Oral
Pharmacokinetic data
Bioavailability 73-92%[1]
Metabolism Hepatic (CYP2D6)[1]
Biological half-life 21-125 hours[1]
Excretion Urine (70%)
Identifiers
CAS Number 50-47-5 YesY
ATC code N06AA01 (WHO)
PubChem CID: 2995
IUPHAR/BPS 2399
DrugBank DB01151 YesY
ChemSpider 2888 YesY
UNII TG537D343B YesY
KEGG D07791 YesY
ChEBI CHEBI:47781 YesY
ChEMBL CHEMBL72 YesY
Chemical data
Formula C18H22N2
Molecular mass 266.381 g/mol
  • c1cc3c(cc1)CCc2c(cccc2)N3CCCNC
  • InChI=1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3 YesY
  • Key:HCYAFALTSJYZDH-UHFFFAOYSA-N YesY
  (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 Norpramin, and Pertofrane.[2]

Medical uses

It is primarily used for the treatment of depression.[2] It may also be useful to treat symptoms of attention deficit hyperactivity disorder.[3] Evidence of benefit is only in the short term and with concerns of side effects its overall usefulness is not clear.[4] Desipramine at very low doses is also used to help reduce the pain associated with functional dyspepsia. [5]

It has also been tried, albeit with little evidence of efficacy, in the treatment of cocaine dependence.[6] Evidence for usefulness in neuropathic pain is also poor.[7]

Adverse effects

Desipramine tends to be less sedating than other TCAs and tends to produce fewer anticholinergic effects like dry mouth, urinary retention, blurred vision, memory impairment and constipation.[8]

Genotoxicity

Desipramine has been shown to be genotoxic in fruit flies;[9] and it is associated with an increased risk of breast cancer in women.[medical citation needed]

Overdose

Desipramine is particularly toxic in cases of overdose, compared to other antidepressants.[10] Any overdose or suspected overdose of desipramine is considered to be a medical emergency and can result in death without prompt medical intervention.

References

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  5. http://www.uptodate.com/contents/upset-stomach-functional-dyspepsia-in-adults-beyond-the-basics
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External links