Desipramine

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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)
Not to be confused with depramine.

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[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] Any overdose or suspected overdose of desipramine is considered to be a medical emergency and can result in death without prompt medical intervention. If an overdose is confirmed or suspected the local poison control should be contacted (1-800-222-1222 in the U.S.; 111 in the UK) immediately, and the victim should be taken to the nearest emergency room as soon as possible. The victim should not attempt to transport themselves to a medical facility, if no other person is available to transport the victim 911 (in the U.S. and Canada; 999 in the UK) should be called to arrange for an ambulance to take the victim to the closest emergency room for overdose management as quickly as possible. Do not wait until overdose symptoms have presented, regardless of whether or not the overdose is confirmed, as symptoms can escalate quickly after they appear and at this point it may not be possible to reach a medical facility in time to prevent death.

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 (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. 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[edit]