Desipramine

Desipramine.svg

Tricyclic antidepressant medication

Desipramine
Trade names	Norpramin, Pertofrane
Chemical nomenclature
IUPAC name	(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-methylpropan-1-amine)
Routes	Oral
Pregnancy category	N
Bioavailability	60-70%
Metabolism	Hepatic
Half-life	12-54 hours
Excretion	Renal
Legal status	Rx-only
Identifiers
CAS Number	50-47-5
PubChem	2995
DrugBank	DB01151
ChemSpider	2888
UNII	TG537D343B
KEGG	D03630
ChEMBL	717
Chemical data
Chemical formula	C18H22N2
SMILES	CNCCC1=CC=CC2=C1C3=C(CC2)N(C)CC3
InChI	1S/C18H22N2/c1-19-12-11-15-6-2-3-7-17-16-8-4-5-9-18(16)20(17)10-14(15)13-19/h2-3,6-7,14H,4-5,8-13H2,1H3
InChIKey	HSJDBSCOQWCQNR-UHFFFAOYSA-N

Desipramine is a tricyclic antidepressant (TCA) used primarily in the treatment of depression. It is also sometimes used to treat anxiety disorders, chronic pain, and attention deficit hyperactivity disorder (ADHD). Desipramine is marketed under the brand names Norpramin and Pertofrane.

Medical uses

Desipramine is primarily used to treat major depressive disorder. It is also prescribed for anxiety disorders, chronic pain conditions such as neuropathic pain, and attention deficit hyperactivity disorder (ADHD).

Mechanism of action

Desipramine works by inhibiting the reuptake of norepinephrine and, to a lesser extent, serotonin, thereby increasing the levels of these neurotransmitters in the brain. This action helps to alleviate symptoms of depression and anxiety.

Side effects

Common side effects of desipramine include dry mouth, constipation, urinary retention, blurred vision, and drowsiness. Serious side effects can include cardiac arrhythmias, seizures, and orthostatic hypotension.

Contraindications

Desipramine should not be used in individuals with a history of myocardial infarction, arrhythmias, or bipolar disorder without careful monitoring. It is also contraindicated in patients who are taking monoamine oxidase inhibitors (MAOIs).

Pharmacokinetics

Desipramine is well absorbed from the gastrointestinal tract and has a bioavailability of 60-70%. It is highly protein-bound (90%) and is metabolized in the liver. The elimination half-life of desipramine ranges from 12 to 54 hours, and it is excreted primarily through the kidneys.

History

Desipramine was first introduced in the 1960s and has been used extensively since then for the treatment of depression and other conditions.

See also

• Tricyclic antidepressant
• Major depressive disorder
• Anxiety disorder
• Chronic pain
• Attention deficit hyperactivity disorder