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QuickView for Imipramine (compound)

Name: Imipramine
PubChem Compound ID: 25379
Description: The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.
Molecular formula: C20H26ClN
Molecular weight: 315.88 g/mol
CHEBI:5882; LU 3-070; Antideprin hydrochloride; N,N-Dimethyl-10,11-dihydro-5H-dibenzo(a,d)cycloheptene-5-propylamine hydrochloride; 10563-68-5; VUFB2793; 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine hydrochloride; Imipramine hydrochloride; 5H-DIBENZO(a,d)CYCLOHEPTENE-5-PROPYLAMINE, 10,11-DIHYDRO-N,N-DIMETHYL-, HYDROCHL; 5H-Dibenzo(a,d)cycloheptene-5-propylamine, 10,11-dihydro-N,N-dimethyl-, hydrochloride.
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Name: Imipramine
Name (isomeric): DB00458
Drug Type: small molecule
Description: The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.
Brand: Surplix, Prazepine, Tipramine, Presamine, Psychoforin, Intalpram, Iramil, Janimine, Antideprin, Imiprin, Tofranil-PM (imipramine pamoate), Sk-Pramine, Timolet, Melipramine, Impramine, Censtin, Imipramina, DPID, Censtim, Nelipramin, Eupramin, Tofraniln A, Imavate, Berkomine, Dynaprin, Norfranil, Trimipramine Maleate, Dyna-Zina, Imipramine Hcl, IM, Pramine, Dimipressin, Imidobenzyle, Imizin, Irmin, Imizine, Promiben, Estraldine, Imizinum, Declomipramine, Melipramin, Tofranil, Base
Category: Norepinephrine-Reuptake Inhibitors, Adrenergic Uptake Inhibitors, Antidepressive Agents, Tricyclic
CAS number: 50-49-7
Indication: For the relief of symptoms of depression and as temporary adjunctive therapy in reducing enuresis in children aged 6 years and older. May also be used to manage panic disorders, with or without agoraphobia, as a second line agent in ADHD, management of eating disorders, for short-term management of acute depressive episodes in bipolar disorder and schizophrenia, and for symptomatic treatment of postherpetic neuralgia.
Imipramine is a tricyclic antidepressant with general pharmacological properties similar to those of structurally related tricyclic antidepressant drugs such as amitriptyline and doxepin. A tertiary amine, imipramine inhibits the reuptake of serotonin more so than most secondary amine tricyclics, meaning that it blocks the reuptake of neurotransmit...
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Mechanism of Action:
Imipramine works by inhibiting the neuronal reuptake of the neurotransmitters norepinephrine and serotonin. It binds the sodium-dependent serotonin transporter and sodium-dependent norepinephrine transporter preventing or reducing the reuptake of norepinephrine and serotonin by nerve cells. Depression has been linked to a lack of stimulation of the...
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Absorption: Rapidly and well absorbed after oral administration. Bioavailability is approximately 43%. Peak plasma concentrations usually attained 1 - 2 hours following oral administration. Absorption is unaffected by food.
Protein binding: 60-95%
Biotransformation: Exclusively metabolized by the liver. Imipramine is converted in the liver by various CYP isoenzymes (e.g. CYP1A2, CYP2D6, CYP3A4, CYP2C9) to active metabolites desipramine and 2-hydroxydesipramine.
Route of elimination: Approximately 40% of an orally administered dose is eliminated in urine within 24 hours, 70% in 72 hours. Small amounts are eliminated in feces via the biliary elimination.
Half Life: Imipramine - 8-20 hours; Desipramine (active metabolite) - up to 125 hours
Toxicity: Oral, rat LD50: 355 to 682 mg/kg. Toxic signs proceed progressively from depression, irregular respiration and ataxia to convulsions and death. Antagonism of the histamine H1 and α1 receptors can lead to sedation and hypotension. Antimuscarinic and anticholinergic side effects such as blurred vision, dry mouth, constipation and urine retention may occur. Cardiotoxicity may occur with high doses of imipramine. Cardiovascular side effects in postural hypotension, tachycardia, hypertension, ECG changes and congestive heart failure. Psychotoxic effects include impaired memory and delirium. Induction of hypomanic or manic episodes may occur in patients with a history of bipolar disorder. Withdrawal symptoms include GI disturbances (e.g. nausea, vomiting, abdominal pain, diarrhea), anxiety, insomnia, nervousness, headache and malaise.
Affected organisms: Humans and other mammals
Food interaction:
Avoid St.John's Wort.
Avoid alcohol.
Avoid excessive quantities of coffee or tea (caffeine).
Do not take fibers at the same time.
Take with food.
Drug interaction:
GrepafloxacinIncreased risk of cardiotoxicity and arrhythmias
TacrineThe therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Imipramine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
DuloxetinePossible increase in the levels of this agent when used with duloxetine
RifabutinThe rifamycin, rifabutin, may decrease the effect of the tricyclic antidepressant, imipramine, by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of imipramine if rifabutin is initiated, discontinued or dose changed.
SparfloxacinIncreased risk of cardiotoxicity and arrhythmias
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