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Namespace Prefixes

PrefixIRI
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n14http://linked.opendata.cz/ontology/sukl/drug/

Statements

Subject Item
n2:DB01151
rdf:type
n3:Drug
n3:description
Desipramine hydrochloride is a dibenzazepine-derivative tricyclic antidepressant (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, desipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, desipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Secondary amine TCAs, such as desipramine and nortriptyline, are more potent inhibitors of norepinephrine reuptake than tertiary amine TCAs, such as amitriptyline and doxepine. 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. See toxicity section below for a complete listing of side effects. Desipramine exerts less anticholinergic and sedative side effects compared to tertiary amine TCAs, such as amitriptyline and clomipramine. Desipramine may be used to treat depression, neuropathic pain (unlabeled use), agitation and insomnia (unlabeled use) and attention-deficit hyperactivity disorder (unlabeled use).
n3:dosage
n12:271B4A24-363D-11E5-9242-09173F13E4C5 n12:271B4A25-363D-11E5-9242-09173F13E4C5 n12:271B4A26-363D-11E5-9242-09173F13E4C5 n12:271B4A27-363D-11E5-9242-09173F13E4C5 n12:271B4A22-363D-11E5-9242-09173F13E4C5 n12:271B4A23-363D-11E5-9242-09173F13E4C5 n12:271B4A2A-363D-11E5-9242-09173F13E4C5 n12:271B4A2B-363D-11E5-9242-09173F13E4C5 n12:271B4A2C-363D-11E5-9242-09173F13E4C5 n12:271B4A2D-363D-11E5-9242-09173F13E4C5 n12:271B4A2E-363D-11E5-9242-09173F13E4C5 n12:271B4A2F-363D-11E5-9242-09173F13E4C5 n12:271B4A30-363D-11E5-9242-09173F13E4C5 n12:271B4A28-363D-11E5-9242-09173F13E4C5 n12:271B4A29-363D-11E5-9242-09173F13E4C5
n3:group
approved
n3:halfLife
7-60+ hours; 70% eliminated renally
n3:indication
For relief of symptoms in various depressive syndromes, especially endogenous depression. It has also been used to manage chronic peripheral neuropathic pain, as a second line agent for the management of anxiety disorders (e.g. panic disorder, generalized anxiety disorder), and as a second or third line agent in the ADHD management.
owl:sameAs
n5:DB01151 n11:DB01151
dcterms:title
Desipramine
adms:identifier
n7:D07791 n10:Desipramine n16:46504624 n18:PA449233 n19:2995 n20:0781-1971-01 n21:DSM n22:2399 n23:C06943 n24:2399 n25:2888 n26:DB01151 n27:35229 n28:47781
n3:mechanismOfAction
Desipramine is a tricyclic antidepressant (TCA) that selectively blocks reuptake of norepinephrine (noradrenaline) from the neuronal synapse. It also inhibits serotonin reuptake, but to a lesser extent compared to tertiary amine TCAs such as imipramine. Inhibition of neurotransmitter reuptake increases stimulation of the post-synaptic neuron. Chronic use of desipramine also leads to down-regulation of beta-adrenergic receptors in the cerebral cortex and sensitization of serotonergic receptors. An overall increase in serotonergic transmission likely confers desipramine its antidepressant effects. Desipramine also possesses minor anticholinergic activity, through its affinity for muscarinic receptors. TCAs are believed to act by restoring normal levels of neurotransmitters via synaptic reuptake inhibition and by increasing serotonergic neurotransmission via serotonergic receptor sensitization in the central nervous system.
n3:packager
n17:271B49F7-363D-11E5-9242-09173F13E4C5 n17:271B49F8-363D-11E5-9242-09173F13E4C5 n17:271B49F5-363D-11E5-9242-09173F13E4C5 n17:271B49F6-363D-11E5-9242-09173F13E4C5 n17:271B49F9-363D-11E5-9242-09173F13E4C5 n17:271B4A02-363D-11E5-9242-09173F13E4C5 n17:271B4A05-363D-11E5-9242-09173F13E4C5 n17:271B4A00-363D-11E5-9242-09173F13E4C5 n17:271B4A01-363D-11E5-9242-09173F13E4C5 n17:271B4A08-363D-11E5-9242-09173F13E4C5 n17:271B4A09-363D-11E5-9242-09173F13E4C5 n17:271B4A06-363D-11E5-9242-09173F13E4C5 n17:271B4A07-363D-11E5-9242-09173F13E4C5 n17:271B4A0A-363D-11E5-9242-09173F13E4C5 n17:271B4A04-363D-11E5-9242-09173F13E4C5 n17:271B4A03-363D-11E5-9242-09173F13E4C5 n17:271B49FA-363D-11E5-9242-09173F13E4C5 n17:271B49FB-363D-11E5-9242-09173F13E4C5 n17:271B49EF-363D-11E5-9242-09173F13E4C5 n17:271B49F0-363D-11E5-9242-09173F13E4C5 n17:271B49FE-363D-11E5-9242-09173F13E4C5 n17:271B49EE-363D-11E5-9242-09173F13E4C5 n17:271B49FF-363D-11E5-9242-09173F13E4C5 n17:271B49F3-363D-11E5-9242-09173F13E4C5 n17:271B49FC-363D-11E5-9242-09173F13E4C5 n17:271B49F4-363D-11E5-9242-09173F13E4C5 n17:271B49F1-363D-11E5-9242-09173F13E4C5 n17:271B49FD-363D-11E5-9242-09173F13E4C5 n17:271B49F2-363D-11E5-9242-09173F13E4C5
n3:routeOfElimination
Desipramine is metabolized in the liver, and approximately 70% is excreted in the urine.
n3:synonym
Desipraminum Desipramine DMI 5-(gamma-Methylaminopropyl)iminodibenzyl Norimipramine Desipramina N-(3-methylaminopropyl)iminobibenzyl 3-(10,11-DIHYDRO-5H-dibenzo[b,F]azepin-5-yl)-N-methylpropan-1-amine Monodemethylimipramine 5-(γ-methylaminopropyl)iminodibenzyl Desipramin Desmethylimipramine Déméthylimipramine
n3:toxicity
Male mice: LD50 = 290 mg/kg, female rats: LD50 = 320 mg/kg. Antagonism of the histamine H<sub>1</sub> and &alpha;<sub>1</sub> receptors can lead to sedation and hypotension. Antimuscarinic activity confers anticholinergic side effects such as blurred vision, dry mouth, constipation and urine retention may occur. Cardiotoxicity may occur with high doses of desipramine. 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.
n14:hasAHFSCode
n15:28-16-04-28
n3:foodInteraction
Take with food to reduce irritation, limit caffeine intake. Avoid alcohol.
n3:proteinBinding
73-92% bound to plasma proteins
n3:salt
n3:synthesisReference
Biel, J.H.and Judd, C.I.; US. Patent 3,454,554; July 8,1969; assigned to Colgate Palmolive Co.
n8:hasConcept
n9:M0006074
foaf:page
n30:desipramine.html n34:desipram.htm
n3:IUPAC-Name
n13:271B4A35-363D-11E5-9242-09173F13E4C5
n3:InChI
n13:271B4A3B-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n13:271B4A3A-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n13:271B4A37-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n13:271B4A38-363D-11E5-9242-09173F13E4C5
n3:SMILES
n13:271B4A39-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n13:271B4A4A-363D-11E5-9242-09173F13E4C5 n13:271B4A33-363D-11E5-9242-09173F13E4C5
n3:logP
n13:271B4A4C-363D-11E5-9242-09173F13E4C5 n13:271B4A31-363D-11E5-9242-09173F13E4C5 n13:271B4A34-363D-11E5-9242-09173F13E4C5
n3:logS
n13:271B4A4D-363D-11E5-9242-09173F13E4C5 n13:271B4A32-363D-11E5-9242-09173F13E4C5
n3:pKa
n13:271B4A4F-363D-11E5-9242-09173F13E4C5
n14:hasATCCode
n31:N06AA01
n3:H-Bond-Acceptor-Count
n13:271B4A41-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n13:271B4A42-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n13:271B4A3C-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n13:271B4A3D-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n13:271B4A3F-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n13:271B4A3E-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n13:271B4A40-363D-11E5-9242-09173F13E4C5
n3:absorption
Desipramine hydrochloride is rapidly and almost completely absorbed from the gastrointestinal tract. It undergoes extensive first-pass metabolism. Peak plasma concentrations are attained 4 - 6 hours following oral administration.
n3:affectedOrganism
Humans and other mammals
n3:caco2-Permeability
n13:271B4A4E-363D-11E5-9242-09173F13E4C5
n3:casRegistryNumber
50-47-5
n3:category
n3:containedIn
n32:271B4A1D-363D-11E5-9242-09173F13E4C5 n32:271B4A1E-363D-11E5-9242-09173F13E4C5 n32:271B4A1B-363D-11E5-9242-09173F13E4C5 n32:271B4A1C-363D-11E5-9242-09173F13E4C5 n32:271B4A21-363D-11E5-9242-09173F13E4C5 n32:271B4A1F-363D-11E5-9242-09173F13E4C5 n32:271B4A20-363D-11E5-9242-09173F13E4C5 n32:271B4A0D-363D-11E5-9242-09173F13E4C5 n32:271B4A0E-363D-11E5-9242-09173F13E4C5 n32:271B4A0B-363D-11E5-9242-09173F13E4C5 n32:271B4A0C-363D-11E5-9242-09173F13E4C5 n32:271B4A11-363D-11E5-9242-09173F13E4C5 n32:271B4A12-363D-11E5-9242-09173F13E4C5 n32:271B4A0F-363D-11E5-9242-09173F13E4C5 n32:271B4A10-363D-11E5-9242-09173F13E4C5 n32:271B4A15-363D-11E5-9242-09173F13E4C5 n32:271B4A16-363D-11E5-9242-09173F13E4C5 n32:271B4A13-363D-11E5-9242-09173F13E4C5 n32:271B4A14-363D-11E5-9242-09173F13E4C5 n32:271B4A19-363D-11E5-9242-09173F13E4C5 n32:271B4A1A-363D-11E5-9242-09173F13E4C5 n32:271B4A17-363D-11E5-9242-09173F13E4C5 n32:271B4A18-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n13:271B4A46-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n13:271B4A48-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n13:271B4A49-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n13:271B4A4B-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n13:271B4A45-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n13:271B4A44-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n13:271B4A47-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n13:271B4A36-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n13:271B4A43-363D-11E5-9242-09173F13E4C5