Desipramine

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Not to be confused with depramine.
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.
Legal status
Routes Oral
Pharmacokinetic data
Bioavailability 73-92%[1]
Metabolism Hepatic (CYP2D6)[1]
Half-life 21-125 hours[1]
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.[2]

Medical uses[edit]

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[edit]

It 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[edit]

Desipramine has been shown to be genotoxic in fruit flies and associated with an increased risk of breast cancer in women.[8]

Overdose[edit]

Desipramine is particularly toxic in cases of overdose, compared to other antidepressants.[9]

Pharmacology and mechanism[edit]

Receptor Binding Affinity (Ki [nM]) Action
α1 Agonist
α2 Agonist
5-HT1A Agonist
5-HT2A Agonist
5-HT2B Agonist
5-HT2C Agonist

See also[edit]

References[edit]

  1. ^ a b c 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. ^ a b Brunton, L; Chabner, B; Knollman, B (2010). Goodman and Gilman's The Pharmacological Basis of Therapeutics (in English) (12th ed.). New York: McGraw-Hill Professional. ISBN 978-0-07-162442-8.  edit
  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. 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. 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. PMID 19031375. 

External links[edit]