Desipramine

Desipramine
Skeletal formula of desipramine
Ball-and-stick model of the desipramine molecule
Clinical data
Trade names Norpramin
AHFS/Drugs.com Monograph
MedlinePlus a682387
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration		 Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 73-92%[1]
Metabolism Hepatic (CYP2D6)[1]
Biological half-life 21-125 hours[1]
Excretion Urine (70%)
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.000.037
Chemical and physical data
Formula C18H22N2
Molar mass 266.381 g/mol
3D model (JSmol)
  (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.

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

  1. 1 2 3 Sallee, FR; Pollock, BG (May 1990). "Clinical pharmacokinetics of imipramine and desipramine.". Clinical Pharmacokinetics. 18 (5): 346–64. PMID 2185906. doi:10.2165/00003088-199018050-00002.
  2. 1 2 Brunton, L; Chabner, B; Knollman, B (2010). Goodman and Gilman's The Pharmacological Basis of Therapeutics (12th ed.). New York: McGraw-Hill Professional. ISBN 978-0-07-162442-8.
  3. ↑ Ghanizadeh, A (July 2013). "A systematic review of the efficacy and safety of desipramine for treating ADHD.". Current Drug Safety. 8 (3): 169–74. PMID 23914752. doi:10.2174/15748863113089990029.
  4. ↑ Otasowie, J; Castells, X; Ehimare, UP; Smith, CH (Sep 19, 2014). "Tricyclic antidepressants for attention deficit hyperactivity disorder (ADHD) in children and adolescents.". The Cochrane database of systematic reviews. 9: CD006997. PMID 25238582. doi:10.1002/14651858.CD006997.pub2.
  5. ↑ http://www.uptodate.com/contents/upset-stomach-functional-dyspepsia-in-adults-beyond-the-basics
  6. ↑ Pani, PP; Trogu, E; Vecchi, S; Amato, L (December 2011). "Antidepressants for cocaine dependence and problematic cocaine use.". The Cochrane Database of Systematic Reviews (12): CD002950. PMID 22161371. doi:10.1002/14651858.CD002950.pub3.
  7. ↑ Hearn, L; Moore, RA; Derry, S; Wiffen, PJ; Phillips, T (Sep 23, 2014). "Desipramine for neuropathic pain in adults.". The Cochrane database of systematic reviews. 9: CD011003. PMID 25246131. doi:10.1002/14651858.CD011003.pub2.
  8. ↑ "Desipramine Hydrochloride". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. 13 December 2013. Retrieved 17 July 2014.
  9. ↑ van Schaik, N; Graf, U (May 1991). "Genotoxicity evaluation of five tricyclic antidepressants in the wing somatic mutation and recombination test in Drosophila melanogaster.". Mutation Research. 260 (1): 99–104. PMID 1902910. doi:10.1016/0165-1218(91)90085-Z.
  10. ↑ White, N; Litovitz, T; Clancy, C (December 2008). "Suicidal antidepressant overdoses: a comparative analysis by antidepressant type.". Journal of Medical Toxicology. 4 (4): 238–50. PMC 3550116 Freely accessible. PMID 19031375. doi:10.1007/BF03161207.
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