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Namespace Prefixes

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Statements

Subject Item
n2:DB01242
rdf:type
n3:Drug
n3:description
Clomipramine, the 3-chloro analog of imipramine, 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, clomipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, clomipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as clomipramine, 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. See toxicity section below for a complete listing of side effects. Clomipramine may be used to treat obsessive-compulsive disorder and disorders with an obsessive-compulsive component (e.g. depression, schizophrenia, Tourette’s disorder). Unlabeled indications include panic disorder, chronic pain (e.g. central pain, idiopathic pain disorder, tension headache, diabetic peripheral neuropathy, neuropathic pain), cataplexy and associated narcolepsy, autistic disorder, trichotillomania, onchophagia, stuttering, premature ejaculation, and premenstrual syndrome. Clomipramine is rapidly absorbed from the gastrointestinal tract and demethylated in the liver to its primary active metabolite, desmethylclomipramine.
n3:dosage
n27:271B5E02-363D-11E5-9242-09173F13E4C5 n27:271B5E03-363D-11E5-9242-09173F13E4C5 n27:271B5E04-363D-11E5-9242-09173F13E4C5 n27:271B5E05-363D-11E5-9242-09173F13E4C5 n27:271B5E06-363D-11E5-9242-09173F13E4C5 n27:271B5E07-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# FDA label
n3:group
approved
n3:halfLife
Following oral administration of a single 150 mg dose of clomipramine, the average elimination half-life of clomipramine was 32 hours (range: 19-37 hours) and of desmethylclomipramine was 69 hours (range: 54-77 hours). Elimination half-life may vary substantially with different doses due to saturable kinetics (i.e. metabolism).
n3:indication
May be used to treat obsessive-compulsive disorder and disorders with an obsessive-compulsive component (e.g. depression, schizophrenia, Tourette’s disorder). Unlabeled indications include: depression, panic disorder, chronic pain (e.g. central pain, idiopathic pain disorder, tension headache, diabetic peripheral neuropathy, neuropathic pain), cataplexy and associated narcolepsy (limited evidence), autistic disorder (limited evidence), trichotillomania (limited evidence), onchophagia (limited evidence), stuttering (limited evidence), premature ejaculation, and premenstrual syndrome.
owl:sameAs
n11:DB01242 n31:DB01242
dcterms:title
Clomipramine
adms:identifier
n16:DB01242 n17:50021927 n18:47780 n21:Clomipramine n22:D00811 n23:PA449048 n24:0781-2027-31 n25:CXX n26:2398 n28:C06918 n29:2398
n3:mechanismOfAction
Clomipramine is a strong, but not completely selective serotonin reuptake inhibitor (SRI), as the active main metabolite desmethyclomipramine acts preferably as an inhibitor of noradrenaline reuptake. &alpha;<sub>1</sub>-receptor blockage and &beta;-down-regulation have been noted and most likely play a role in the short term effects of clomipramine. A blockade of sodium-channels and NDMA-receptors might, as with other tricyclics, account for its effect in chronic pain, in particular the neuropathic type.
n3:packager
n4:271B5DEE-363D-11E5-9242-09173F13E4C5 n4:271B5DEB-363D-11E5-9242-09173F13E4C5 n4:271B5DEC-363D-11E5-9242-09173F13E4C5 n4:271B5DDA-363D-11E5-9242-09173F13E4C5 n4:271B5DDD-363D-11E5-9242-09173F13E4C5 n4:271B5DDE-363D-11E5-9242-09173F13E4C5 n4:271B5DDB-363D-11E5-9242-09173F13E4C5 n4:271B5DDC-363D-11E5-9242-09173F13E4C5 n4:271B5DE1-363D-11E5-9242-09173F13E4C5 n4:271B5DE2-363D-11E5-9242-09173F13E4C5 n4:271B5DDF-363D-11E5-9242-09173F13E4C5 n4:271B5DE0-363D-11E5-9242-09173F13E4C5 n4:271B5DE5-363D-11E5-9242-09173F13E4C5 n4:271B5DE6-363D-11E5-9242-09173F13E4C5 n4:271B5DE3-363D-11E5-9242-09173F13E4C5 n4:271B5DE4-363D-11E5-9242-09173F13E4C5 n4:271B5DE9-363D-11E5-9242-09173F13E4C5 n4:271B5DEA-363D-11E5-9242-09173F13E4C5 n4:271B5DE7-363D-11E5-9242-09173F13E4C5 n4:271B5DE8-363D-11E5-9242-09173F13E4C5 n4:271B5DED-363D-11E5-9242-09173F13E4C5
n3:routeOfElimination
Urine (51-60%) and feces via biliary elimination (24-32%)
n3:synonym
Clomipraminum Monochlorimipramine 3-(3-CHLORO-5H-dibenzo[b,F]azepin-5-yl)-N,N-dimethylpropan-1-amine 3-(3-chloro-10,11-dihydro-5H-Dibenzo[b,F]azepin-5-yl)-N,N-dimethyl-1-propanamine Clomipramina Clomipramine g 34586 3-Chloroimipramine Chlorimipramine
n3:toxicity
Signs and symptoms vary in severity depending upon factors such as the amount of drug absorbed, the age of the patient, and the time elapsed since drug ingestion. Critical manifestations of overdose include cardiac dysrhythmias, severe hypotension, convulsions, and CNS depression including coma. Changes in the electrocardiogram, particularly in QRS axis or width, are clinically significant indicators of tricyclic toxicity. In U.S. clinical trials, 2 deaths occurred in 12 reported cases of acute overdosage with Anafranil either alone or in combination with other drugs. One death involved a patient suspected of ingesting a dose of 7000 mg. The second death involved a patient suspected of ingesting a dose of 5750 mg. Side effects include: sedation, hypotension, blurred vision, dry mouth, constipation, urinary retention, postural hypotension, tachycardia, hypertension, ECG changes, heart failure, impaired memory and delirium, and precipitation of hypomanic or manic episodes in bipolar depression. Withdrawal symptoms include gastrointestinal disturbances, anxiety, and insomnia.
n3:volumeOfDistribution
~ 17 L/kg (range: 9-25 L/kg). Clomipramine is capable of distributing into the cerebrospinal fluid, the brain, and into breast milk.
n12:hasAHFSCode
n19:28-16-04-28
n3:foodInteraction
Grapefruit and grapefruit juice should be avoided throughout treatment, grapefruit can modify serum levels of clomipramine and its metabolite desmethyl-clomipramine. Take with food to reduce irritation. Avoid alcohol.
n3:proteinBinding
Clomipramine is approximately 97-98% bound to plasma proteins, principally to albumin and possibly to &alpha;<sub>1</sub>-acid glycoprotein. Desmethylclomipramine is 97-99% bound to plasma proteins.
n3:salt
n3:synthesisReference
Schindler, W. and Dietrich, H.; US. Patent 3,515,785; June 2,1970; assigned to Geigy Chemical Corp.
n7:hasConcept
n8:M0004598
foaf:page
n6:ana1020.shtml n9:clomipr.htm n32:clomipramine.html
n3:IUPAC-Name
n14:271B5E0C-363D-11E5-9242-09173F13E4C5
n3:InChI
n14:271B5E12-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n14:271B5E11-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n14:271B5E0E-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n14:271B5E0F-363D-11E5-9242-09173F13E4C5
n3:SMILES
n14:271B5E10-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n14:271B5E21-363D-11E5-9242-09173F13E4C5 n14:271B5E0A-363D-11E5-9242-09173F13E4C5
n3:logP
n14:271B5E24-363D-11E5-9242-09173F13E4C5 n14:271B5E08-363D-11E5-9242-09173F13E4C5 n14:271B5E0B-363D-11E5-9242-09173F13E4C5
n3:logS
n14:271B5E09-363D-11E5-9242-09173F13E4C5
n12:hasATCCode
n13:N06AA04
n3:H-Bond-Acceptor-Count
n14:271B5E18-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n14:271B5E19-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n14:271B5E13-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n14:271B5E14-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n14:271B5E16-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n14:271B5E15-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n14:271B5E17-363D-11E5-9242-09173F13E4C5
n3:absorption
Well absorbed from the GI tract following oral administration. Bioavailability is approximately 50% orally due to extensive first-pass metabolism. Bioavailability is not affected by food. Peak plasma concentrations occurred 2-6 hours following oral administration of a single 50 mg dose. The peak plasma concentration ranged from 56 ng/mL to 154 mg/mL (mean, 92 ng/mL). There are large interindividual variations in plasma concentrations occur, partly due to genetic differences in clomipramine metabolism. On average, steady state plasma concentrations are achieved in 1-2 weeks following multiple dose oral administration. Smoking appears to lower the steady-state plasma concentration of clomipramine, but not its active metabolite desmethylclomipramine.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
303-49-1
n3:category
n3:containedIn
n20:271B5DF9-363D-11E5-9242-09173F13E4C5 n20:271B5DFA-363D-11E5-9242-09173F13E4C5 n20:271B5DF7-363D-11E5-9242-09173F13E4C5 n20:271B5DF8-363D-11E5-9242-09173F13E4C5 n20:271B5DFD-363D-11E5-9242-09173F13E4C5 n20:271B5DFE-363D-11E5-9242-09173F13E4C5 n20:271B5DFB-363D-11E5-9242-09173F13E4C5 n20:271B5DFC-363D-11E5-9242-09173F13E4C5 n20:271B5E01-363D-11E5-9242-09173F13E4C5 n20:271B5DFF-363D-11E5-9242-09173F13E4C5 n20:271B5E00-363D-11E5-9242-09173F13E4C5 n20:271B5DEF-363D-11E5-9242-09173F13E4C5 n20:271B5DF0-363D-11E5-9242-09173F13E4C5 n20:271B5DF3-363D-11E5-9242-09173F13E4C5 n20:271B5DF4-363D-11E5-9242-09173F13E4C5 n20:271B5DF6-363D-11E5-9242-09173F13E4C5 n20:271B5DF5-363D-11E5-9242-09173F13E4C5 n20:271B5DF1-363D-11E5-9242-09173F13E4C5 n20:271B5DF2-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n14:271B5E1D-363D-11E5-9242-09173F13E4C5
n3:Boiling-Point
n14:271B5E23-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n14:271B5E1F-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n14:271B5E20-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n14:271B5E22-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n14:271B5E1C-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n14:271B5E1B-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n14:271B5E1E-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n14:271B5E0D-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n14:271B5E1A-363D-11E5-9242-09173F13E4C5