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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB00458
rdf:type
n4:Drug
n4:description
Imipramine, the prototypical tricyclic antidepressant (TCA), is a dibenzazepine-derivative TCA. TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, imipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, imipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as imipramine and amitriptyline, are more potent inhibitors of serotonin reuptake than secondary amine TCAs, such as nortriptyline and desipramine. TCAs also down-regulate cerebral cortical &beta;-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine H<sub>1</sub> receptors, &alpha;<sub>1</sub>-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. Imipramine has less sedative and anticholinergic effects than the tertiary amine TCAs, amitriptyline and clomipramine. See toxicity section below for a complete listing of side effects. Imipramine may be used to treat depression and nocturnal enuresis in children. Unlabeled indications include chronic and neuropathic pain (including diabetic neuropathy), panic disorder, attention-deficit/hyperactivity disorder (ADHD), and post-traumatic stress disorder (PTSD).
n4:dosage
n12:271B554B-363D-11E5-9242-09173F13E4C5 n12:271B554C-363D-11E5-9242-09173F13E4C5 n12:271B554D-363D-11E5-9242-09173F13E4C5 n12:271B554E-363D-11E5-9242-09173F13E4C5 n12:271B554F-363D-11E5-9242-09173F13E4C5 n12:271B5558-363D-11E5-9242-09173F13E4C5 n12:271B5550-363D-11E5-9242-09173F13E4C5 n12:271B5551-363D-11E5-9242-09173F13E4C5 n12:271B5552-363D-11E5-9242-09173F13E4C5 n12:271B5553-363D-11E5-9242-09173F13E4C5 n12:271B5554-363D-11E5-9242-09173F13E4C5 n12:271B5555-363D-11E5-9242-09173F13E4C5 n12:271B5556-363D-11E5-9242-09173F13E4C5 n12:271B5557-363D-11E5-9242-09173F13E4C5
n4:group
approved
n4:halfLife
Imipramine - 8-20 hours; Desipramine (active metabolite) - up to 125 hours
n4: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.
n4:manufacturer
n5:271B5516-363D-11E5-9242-09173F13E4C5 n5:271B5517-363D-11E5-9242-09173F13E4C5 n5:271B5514-363D-11E5-9242-09173F13E4C5 n5:271B5515-363D-11E5-9242-09173F13E4C5 n5:271B5512-363D-11E5-9242-09173F13E4C5 n5:271B5513-363D-11E5-9242-09173F13E4C5 n5:271B5510-363D-11E5-9242-09173F13E4C5 n5:271B5511-363D-11E5-9242-09173F13E4C5 n5:271B5521-363D-11E5-9242-09173F13E4C5 n5:271B551F-363D-11E5-9242-09173F13E4C5 n5:271B5520-363D-11E5-9242-09173F13E4C5 n5:271B551D-363D-11E5-9242-09173F13E4C5 n5:271B551E-363D-11E5-9242-09173F13E4C5 n5:271B551B-363D-11E5-9242-09173F13E4C5 n5:271B551C-363D-11E5-9242-09173F13E4C5 n5:271B5519-363D-11E5-9242-09173F13E4C5 n5:271B551A-363D-11E5-9242-09173F13E4C5 n5:271B5518-363D-11E5-9242-09173F13E4C5
owl:sameAs
n19:DB00458 n25:DB00458
dcterms:title
Imipramine
adms:identifier
n14:Imipramine n20:3696 n21:46507351 n22:IXX n23:PA449969 n24:C07049 n26:53489-330-07 n27:357 n28:357 n29:DB00458 n30:5881 n31:3568
n4:mechanismOfAction
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 post-synaptic neuron by norepinephrine and serotonin. Slowing the reuptake of these neurotransmitters increases their concentration in the synaptic cleft, which is thought to contribute to relieving symptoms of depression. In addition to acutely inhibiting neurotransmitter re-uptake, imipramine causes down-regulation of cerebral cortical beta-adrenergic receptors and sensitization of post-synaptic serotonergic receptors with chronic use. This leads to enhanced serotonergic transmission.
n4:packager
n5:271B5504-363D-11E5-9242-09173F13E4C5 n5:271B5505-363D-11E5-9242-09173F13E4C5 n5:271B5502-363D-11E5-9242-09173F13E4C5 n5:271B5503-363D-11E5-9242-09173F13E4C5 n5:271B5508-363D-11E5-9242-09173F13E4C5 n5:271B5509-363D-11E5-9242-09173F13E4C5 n5:271B5506-363D-11E5-9242-09173F13E4C5 n5:271B5507-363D-11E5-9242-09173F13E4C5 n5:271B550C-363D-11E5-9242-09173F13E4C5 n5:271B550D-363D-11E5-9242-09173F13E4C5 n5:271B550A-363D-11E5-9242-09173F13E4C5 n5:271B550B-363D-11E5-9242-09173F13E4C5 n5:271B54FB-363D-11E5-9242-09173F13E4C5 n5:271B54F9-363D-11E5-9242-09173F13E4C5 n5:271B54FA-363D-11E5-9242-09173F13E4C5 n5:271B54E5-363D-11E5-9242-09173F13E4C5 n5:271B54E6-363D-11E5-9242-09173F13E4C5 n5:271B54F1-363D-11E5-9242-09173F13E4C5 n5:271B54E3-363D-11E5-9242-09173F13E4C5 n5:271B54F2-363D-11E5-9242-09173F13E4C5 n5:271B54E4-363D-11E5-9242-09173F13E4C5 n5:271B54EF-363D-11E5-9242-09173F13E4C5 n5:271B54E9-363D-11E5-9242-09173F13E4C5 n5:271B54F0-363D-11E5-9242-09173F13E4C5 n5:271B54EA-363D-11E5-9242-09173F13E4C5 n5:271B54E7-363D-11E5-9242-09173F13E4C5 n5:271B54F5-363D-11E5-9242-09173F13E4C5 n5:271B54FC-363D-11E5-9242-09173F13E4C5 n5:271B54E8-363D-11E5-9242-09173F13E4C5 n5:271B54F3-363D-11E5-9242-09173F13E4C5 n5:271B54ED-363D-11E5-9242-09173F13E4C5 n5:271B54F4-363D-11E5-9242-09173F13E4C5 n5:271B54EE-363D-11E5-9242-09173F13E4C5 n5:271B54EB-363D-11E5-9242-09173F13E4C5 n5:271B54FF-363D-11E5-9242-09173F13E4C5 n5:271B5500-363D-11E5-9242-09173F13E4C5 n5:271B54EC-363D-11E5-9242-09173F13E4C5 n5:271B54FD-363D-11E5-9242-09173F13E4C5 n5:271B54FE-363D-11E5-9242-09173F13E4C5 n5:271B5501-363D-11E5-9242-09173F13E4C5 n5:271B550F-363D-11E5-9242-09173F13E4C5 n5:271B54F7-363D-11E5-9242-09173F13E4C5 n5:271B54F8-363D-11E5-9242-09173F13E4C5 n5:271B54F6-363D-11E5-9242-09173F13E4C5 n5:271B550E-363D-11E5-9242-09173F13E4C5
n4:routeOfElimination
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.
n4:synonym
3-(5H-DIBENZO[b,F]azepin-5-yl)-N,N-dimethylpropan-1-amine N-(γ-dimethylaminopropyl)iminodibenzyl Antideprin 5-[3-(dimethylamino)Propyl]-10,11-dihydro-5H-dibenz[b,F]azepine Irmin N-(gamma-Dimethylaminopropyl)iminodibenzyl Imizine Melipramine 10,11-dihydro-N,N-Dimethyl-5H-dibenz[b,F]azepine-5-propanamine Imipraminum Imipramin Imipramine
n4:toxicity
Oral, rat LD<sub>50</sub>: 355 to 682 mg/kg. Toxic signs proceed progressively from depression, irregular respiration and ataxia to convulsions and death. Antagonism of the histamine H<sub>1</sub> and &alpha;<sub>1</sub> 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.
n9:hasAHFSCode
n11:28-16-04-28
n4:foodInteraction
Avoid alcohol. Take with food. Avoid St.John's Wort. Do not take fibers at the same time. Avoid excessive quantities of coffee or tea (caffeine).
n4:proteinBinding
60-95%
n4:salt
n4:synthesisReference
U.S. Patent 2,554,736.
foaf:page
n8:tof1448.shtml n16:imip.htm n17:imipramine.html
n4:IUPAC-Name
n6:271B555D-363D-11E5-9242-09173F13E4C5
n4:InChI
n6:271B5563-363D-11E5-9242-09173F13E4C5
n4:Molecular-Formula
n6:271B5562-363D-11E5-9242-09173F13E4C5
n4:Molecular-Weight
n6:271B555F-363D-11E5-9242-09173F13E4C5
n4:Monoisotopic-Weight
n6:271B5560-363D-11E5-9242-09173F13E4C5
n4:SMILES
n6:271B5561-363D-11E5-9242-09173F13E4C5
n4:Water-Solubility
n6:271B5572-363D-11E5-9242-09173F13E4C5 n6:271B555B-363D-11E5-9242-09173F13E4C5
n4:logP
n6:271B5575-363D-11E5-9242-09173F13E4C5 n6:271B5559-363D-11E5-9242-09173F13E4C5 n6:271B555C-363D-11E5-9242-09173F13E4C5
n4:logS
n6:271B5576-363D-11E5-9242-09173F13E4C5 n6:271B555A-363D-11E5-9242-09173F13E4C5
n4:pKa
n6:271B5578-363D-11E5-9242-09173F13E4C5
n9:hasATCCode
n10:N06AA02
n4:H-Bond-Acceptor-Count
n6:271B5569-363D-11E5-9242-09173F13E4C5
n4:H-Bond-Donor-Count
n6:271B556A-363D-11E5-9242-09173F13E4C5
n4:InChIKey
n6:271B5564-363D-11E5-9242-09173F13E4C5
n4:Polar-Surface-Area--PSA-
n6:271B5565-363D-11E5-9242-09173F13E4C5
n4:Polarizability
n6:271B5567-363D-11E5-9242-09173F13E4C5
n4:Refractivity
n6:271B5566-363D-11E5-9242-09173F13E4C5
n4:Rotatable-Bond-Count
n6:271B5568-363D-11E5-9242-09173F13E4C5
n4: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.
n4:affectedOrganism
Humans and other mammals
n4:caco2-Permeability
n6:271B5577-363D-11E5-9242-09173F13E4C5
n4:casRegistryNumber
50-49-7
n4:category
n4:containedIn
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n4:Bioavailability
n6:271B556E-363D-11E5-9242-09173F13E4C5
n4:Boiling-Point
n6:271B5574-363D-11E5-9242-09173F13E4C5
n4:Ghose-Filter
n6:271B5570-363D-11E5-9242-09173F13E4C5
n4:MDDR-Like-Rule
n6:271B5571-363D-11E5-9242-09173F13E4C5
n4:Melting-Point
n6:271B5573-363D-11E5-9242-09173F13E4C5
n4:Number-of-Rings
n6:271B556D-363D-11E5-9242-09173F13E4C5
n4:Physiological-Charge
n6:271B556C-363D-11E5-9242-09173F13E4C5
n4:Rule-of-Five
n6:271B556F-363D-11E5-9242-09173F13E4C5
n4:Traditional-IUPAC-Name
n6:271B555E-363D-11E5-9242-09173F13E4C5
n4:pKa--strongest-basic-
n6:271B556B-363D-11E5-9242-09173F13E4C5