Desipramine

Not to be confused with depramine.
Desipramine
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
  • US: C (Risk not ruled out)
Oral
Pharmacokinetic data
Bioavailability 73-92%[1]
Metabolism Hepatic (CYP2D6)[1]
Half-life 21-125 hours[1]
Excretion Urine (70%)
Identifiers
50-47-5 Yes
N06AA01
PubChem CID 2995
IUPHAR ligand 2399
DrugBank DB01151 Yes
ChemSpider 2888 Yes
UNII TG537D343B Yes
KEGG D07791 Yes
ChEBI CHEBI:47781 Yes
ChEMBL CHEMBL72 Yes
Chemical data
Formula C18H22N2
266.381 g/mol
 Yes (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 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]

It has also been tried, albeit with little evidence of efficacy, in the treatment of cocaine dependence.[5] Evidence for usefulness in neuropathic pain is also poor.[6]

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.[7]

Genotoxicity

Desipramine has been shown to be genotoxic in fruit flies;[8] 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.[9] 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. ↑ 1.0 1.1 1.2 Sallee, FR; Pollock, BG (May 1990). "Clinical pharmacokinetics of imipramine and desipramine.". Clinical Pharmacokinetics 18 (5): 346–64. doi:10.2165/00003088-199018050-00002. PMID 2185906.
  2. ↑ 2.0 2.1 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. doi:10.2174/15748863113089990029. PMID 23914752.
  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. doi:10.1002/14651858.CD006997.pub2. PMID 25238582.
  5. ↑ 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. doi:10.1002/14651858.CD002950.pub3. PMID 22161371.
  6. ↑ 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. doi:10.1002/14651858.CD011003.pub2. PMID 25246131.
  7. ↑ "Desipramine Hydrochloride". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. 13 December 2013. Retrieved 17 July 2014.
  8. ↑ 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. doi:10.1016/0165-1218(91)90085-Z. PMID 1902910.
  9. ↑ 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. doi:10.1007/BF03161207. PMC 3550116. PMID 19031375.

External links