Desipramine

Desipramine

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	N06AA01 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	73-92%
Metabolism	Hepatic (CYP2D6)
Biological half-life	21-125 hours
Excretion	Urine (70%)
Identifiers
IUPAC name 3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-methylpropan-1-amine
CAS Number	50-47-5 Y
PubChem CID	2995
IUPHAR/BPS	2399
DrugBank	DB01151 Y
ChemSpider	2888 Y
UNII	TG537D343B
KEGG	D07791 Y
ChEBI	CHEBI:47781 Y
ChEMBL	CHEMBL72 Y
ECHA InfoCard	100.000.037
Chemical and physical data
Formula	C18H22N2
Molar mass	266.381 g/mol
3D model (Jmol)	Interactive image
SMILES c1cc3c(cc1)CCc2c(cccc2)N3CCCNC
InChI InChI=1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3 Y Key:HCYAFALTSJYZDH-UHFFFAOYSA-N Y

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.

It is primarily used for the treatment of depression. It may also be useful to treat symptoms of attention deficit hyperactivity disorder. Evidence of benefit is only in the short term and with concerns of side effects its overall usefulness is not clear. Desipramine at very low doses is also used to help reduce the pain associated with functional dyspepsia.

It is used effectively in the treatment of post herpetic neuralgia, a sequelae to Herpes Zoster infections.

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

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.

Desipramine has been shown to be genotoxic in fruit flies; and it is associated with an increased risk of breast cancer in women.

Desipramine is particularly toxic in cases of overdose, compared to other antidepressants. Any overdose or suspected overdose of desipramine is considered to be a medical emergency and can result in death without prompt medical intervention.