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. C (US)
Legal status -only (US)
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]

Its primary therapeutic use is in the treatment of depression.[2] Along with other tricyclics, desipramine has found use in treating neuropathic pain.[3] 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.[4] It has also been tried, albeit with little evidence of efficacy, in the treatment of cocaine dependence.[5]

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

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.[6]

Genotoxicity[edit]

Desipramine has been shown to be genotoxic in fruit flies and associated with an increased risk of breast cancer in women.[7]

Overdose[edit]

Desipramine is particularly toxic in cases of overdose, compared to other antidepressants.[8]

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. ^ O'Connor, AB; Noyes, K; Holloway, RG (August 2007). "A cost-effectiveness comparison of desipramine, gabapentin, and pregabalin for treating postherpetic neuralgia.". Journal of the American Geriatrics Society 55 (8): 1176–84. doi:10.1111/j.1532-5415.2007.01246.x. PMID 17661955. 
  4. ^ 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. 
  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. ^ "Desipramine Hydrochloride". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. 13 December 2013. Retrieved 17 July 2014. 
  7. ^ 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. 
  8. ^ 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]