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HCID 2801Erstellt: 4. November 2026

Clomipramin

CLOMIPRAMINE HCL · ANAFRANIL · CHLORIMIPRAMINE · CIM · g34586 · G34596 · 5H-Dibe · G 34586

https://huagongshe.com/de/chemical/2801

Molekülstruktur von Clomipramin

Identifikatoren & physikalische Daten

CAS No.303-49-1
SummenformelC19H23ClN2
Durchschnittliche Molmasse314,9 g/mol
Monoisotopische Masse314,1549764 g/mol
SMILESCN(C)CCCN1c2ccccc2CCc2ccc(Cl)cc21
InChIKeyGDLIGKIOYRNHDA-UHFFFAOYSA-N
PubChem CID2801
ChEMBLCHEMBL415
ChEBICHEBI:47780
EC No.206-144-2
DTXSIDDTXSID6022844
Lokaler NameClomipramin

Chemische & physikalische Eigenschaften

XLogP5,2
Polarare Oberfläche (TPSA)6,5
H-Brücken-Donoren0
H-Brücken-Akzeptoren2
Frei drehbare Bindungen4
Schwere Atome22
Formalladung0
Komplexität346
ArzneimittelPharmaceuticals -> Tricyclic Antidepressants (TCAs)Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Used in Switzerland
LogP (Verteilungskoeffizient)log Kow = 5.194.5
Löslichkeit1.44e-02 g/LH2O: 25 mg/mL
Human DrugsBreast FeedingLactationMilk, HumanAntidepressive AgentsAntidepressive Agents, TricyclicPharmaceuticalsMedicines for obsessive compulsive disorders
Animal DrugsEMA approved medicines: Veterinary medicine
Siedepunkt160-170 °C at 3.00E-01 mm Hg160-170 °C at 0.3 mm Hgbp0.3 160-170°
Schmelzpunkt191.5-192189.5 °C189.5°C
Physical DescriptionSolid
Dissociation Constants9.389.1
Collision Cross Section174.5 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID3042633]174.3 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)]174.4 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated]160.44 Ų [M+H-H2O]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
Other Experimental PropertiesCrystals from acetone-ether/methanol-ether. MW 351.31. MP 189-190 °C ...also reported as crystals from acetonemp 191-5-192 °C... Freely soluble in water, methanol, methylene chloridepractically insoluble in ethyl ether, benzene /Clomipramine hydrochloride/
Dichte1.0568 (rough estimate)
Brechungsindex1.5749 (estimate)
LagerbedingungenSealed in dry,Room Temperature
Aggregatzustandpowder
pKa (Säurekonstante)pKa 9.38(H2O) (Uncertain)
Farbewhite to off-white
CAS Datenbank303-49-1(CAS DataBase Reference)
NIST chemische InformationenClomipramine(303-49-1)

Sicherheit & Vorschriften

GHS-EinstufungWarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 2 notifications to the ECHA C&L Inventory.
Regulatorische InformationenREACH registered substance: Clomipramine (EC: 206-144-2)5H-Dibenzb,fazepine-5-propanamine, 3-chloro-10,11-dihydro-N,N-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard
FDA-AnforderungenClomipramine tablets. ... Indications for use /in dogs/. For use as part of a comprehensive behavioral management program to treat separation anxiety in dogs greater than 6 months of age. ... Limitations: Federal law restricts this drug to use by or on the order of a licensed veterinarian.The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl clomipramine hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Clomipramine hydrochloride/The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Clomipramine hydrochloride is included on this list. /Clomipramine hydrochloride/
Hazard Classes and CategoriesAcute Tox. 4 (100%)
LagerbedingungenClomipramine hydrochloride capsules should be stored in tight containers at a temperature of 20-25 °C and protected from moisture. When stored as directed, the capsules have an expiration date of 3 years following the date of manufacture.
EntsorgungsverfahrenSRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Anwendungen & Verwendung

Verwenden

Antidepressan.

Treatment
Obtain an ECG and immediately initiate cardiac monitoring. Protect the patient's airway, establish an intravenous line, and initiate gastric decontamination. A minimum of 6 hours of observation with cardiac monitoring and observation for signs of CNS or respiratory depression, hypotension, cardiac dysrhythmias and/or conduction blocks, and seizures is necessary. If signs of toxicity occur at any time during this period, extended monitoring is required. (L1712)
WechselwirkungenLimited data suggest that demethylation of clomipramine may be reduced with chronic alcohol consumption. In one study, the clearance of clomipramine via demethylation was decreased substantially and the ratio of blood clomipramine to desmethylclomipramine concentrations at steady state was higher in recently detoxified alcoholic patients (abstinence periods ranged from 4-20 weeks) compared with a control group of patients with no history of alcoholism.The plasma concentration of clomipramine has been reported to be increased by the concomitant administration of haloperidolplasma levels of several closely related tricyclic antidepressants have been reported to be increased by the concomitant administration of methylphenidate or hepatic enzyme inhibitors (eg, cimetidine, fluoxetine) and decreased by the concomitant administration of hepatic enzyme inducers (eg, barbiturates, phenytoin), and such an effect may be anticipated with clomipramine as well. Administration of clomipramine has been reported to increase the plasma levels of phenobarbital, if given concomitantly.Several tricyclic antidepressants have been reported to block the pharmacologic effects of guanethidine, clonidine, or similar agents, and such an effect may be anticipated with clomipramine because of its structural similarity to other tricyclic antidepressants.Close supervision and careful adjustment of dosage are required when clomipramine is administered with anticholinergic or sympathomimetic drugs.For more Interactions (Complete) data for Clomipramine (11 total), please visit the HSDB record page.
HepatotoxicityLiver test abnormalities have been reported to occur in up to 16% of patients being treated with tricyclic antidepressants, but elevations are uncommonly above 3 times the upper limit of normal. Serum aminotransferase elevations during clomipramine therapy are reported in 1% to 3% of patients and the abnormalities were usually mild, asymptomatic and transient, reversing even with continuation of medication. As with many tricyclic antidepressants, rare instances of clinically apparent acute liver injury have been reported in patients taking clomipramine. The clinical features of cases of drug induced liver disease from clomipramine have not been well defined. The acute liver injury caused by tricyclic antidepressants typically arises within 1 to 4 weeks of starting the medication and presents with fatigue followed by dark urine and jaundice. Both hepatocellular and cholestatic patterns of injury have been described. The injury is usually mild-to-moderate in severity and recovery is rapid when the tricyclic is discontinued. Immunoallergic features such as rash, fever and eosinophilia are not common and autoantibodies are generally not detected. Fatal cases are extremely rare.
Unerwünschte WirkungenThe adverse effects of clomipramine include nausea, weight gain, increased appetite, sedation, dry mouth, constipation, urinary retention, blurred vision, headache, dizziness, fatigue, hypotension, anxiety, restlessness, sweating, blue-green urine, and sexual dysfunction. Life-threatening adverse effects include arrhythmia, tachycardia, QTc prolongation, orthostasis, seizures, paralytic ileus, hyperthermia, hepatic failure, increased intraocular pressure, mania induction, and activation of suicidality.
ExpositionspfadeWell 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.
Milk Concentrations... Four clomipramine-treated breastfeeding mother-infant pairs were assessed for serum concentrations of clomipramine, N-desmethylclomipramine, and corresponding 8-hydroxymetabolites. Although the mothers exhibited a wide range of serum concentrations, the parent drug and metabolites were either nondetectable or below the quantifiable limit in the sera of all infants. ...
ToxizitätsübersichtSigns and Symptoms of OverdoseClomipramine 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.
Signs and SymptomsSigns 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.
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ ... Four clomipramine-treated breastfeeding mother-infant pairs were assessed for serum concentrations of clomipramine, N-desmethylclomipramine, and corresponding 8-hydroxymetabolites. Although the mothers exhibited a wide range of serum concentrations, the parent drug and metabolites were either nondetectable or below the quantifiable limit in the sera of all infants. No adverse clinical effects were observed. .../SIGNS AND SYMPTOMS/ 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. Other CNS manifestations may include drowsiness, stupor, ataxia, restlessness, agitation, delirium, severe perspiration, hyperactive reflexes, muscle rigidity, athetoid and choreiform movements. Cardiac abnormalities may include tachycardia, signs of congestive heart failure, and in very rare cases, cardiac arrest. Respiratory depression, cyanosis, shock, vomiting, hyperpyrexia, mydriasis, and oliguria or anuria may also be present./SIGNS AND SYMPTOMS/ Abrupt or gradual discontinuation of tricyclic antidepressants may precipitate withdrawal symptoms. The most common of these are general somatic or gastrointestinal distress, anxiety and agitation, sleep disturbance, akathisia, parkinsonism, paradoxical behavioral activation and mania. There are very few reports of withdrawal reactions following discontinuation of clomipramine .../CASE REPORTS/ In U.S. clinical trials, 2 deaths occurred in 12 reported cases of acute overdosage with clomipramine 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. The 10 nonfatal cases involved doses of up to 5000 mg, accompanied by plasma levels of up to 1010 ng/mL. All 10 patients completely recovered.For more Human Toxicity Excerpts (Complete) data for Clomipramine (25 total), please visit the HSDB record page.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver InjuryDrug-Induced Liver Injury Severity and Toxicity (DILIst)clomipramineDILI PositiveOralDOI:10.1016/j.drudis.2019.09.022
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ To determine the effects of clomipramine hydrochloride on heart rate and rhythm in 17 healthy Beagles. In experiment 1, 8 dogs received placebo or clomipramine (20 mg/kg of body weight, q 24 hr, po) for 7 days in a 2-way crossover design. In experiment 2, 9 dogs were evaluated for 48 hours before and 24 hours after oral administration of clomipramine (4 or 12 mg/kg) in a 2-way crossover design. Electrocardiogram and heart rate were monitored continuously by use of telemetry. A significant diurnal rhythm in heart rate was detectedminimum values were recorded at night. Administration of 20 mg of clomipramine/kg induced a significant reduction in heart rate, with peak effect achieved approximately 12 hours after dosing. Administration of 4 or 12 mg of clomipramine/kg did not result in significant changes in heart rate. Sinoatrial and second-degree atrioventricular block and ventricular escape beats were observed during periods of slow heart rate in more dogs that received clomipramine (3 to 4 of 8 dogs), compared with dogs that received placebo (1 to 2 of 8 dogs), but this difference was not significant. Short-term administration of clomipramine induced benign cardiovascular effects in dogs rather than the potentially dangerous arrhythmias or tachycardia reported following administration of tricyclic antidepressants to humans./LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ The authors studied the effect of daily administration of a single dose of either clomipramine or desipramine, two monoamine-reuptake-inhibitors with preferential serotonergic and noradrenergic profiles, respectively, during 15 days, on the visuo-spatial memory of adults rats measured through their performance in an eight-arm radial maze. Rats receiving 10 mg/kg i.p. daily of clomipramine or desipramine, 30 min before testing, committed a significantly greater number of errors than saline-treated control rats throughout the duration of the test (5 sessions, 15 days), excepting for session one (after 3 days of testing) where there were no differences between the 3 groups of rats. Results indicated that both serotonergic and noradrenergic antidepressants could impair long-term visuo-spatial memory in the rat, whereas inducing no changes in working memory, effects that are likely related to changes in brain monoamine metabolism .../LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ No evidence of carcinogenecity was found in two 2 year bioassays in rats at doses up to 100 mg/kg, which is 24 and 4 times the maximum recommended human daily dose (MRHD) on a mg/kg and mg/sq m basis, respectively, or in a 2 year bioassay in mice at doses up to 80 mg/kg, which is 20 and 1.5 times the MRHD on a mg/kg and mg/sq m basis, respectively./LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ No teratogenic effects were observed in studies performed in rats and mice at doses up to 100 mg/kg, which is 24 times the maximum recommended human daily dose (MRHD) on a mg/kg basis and 4 times (rats) and 2 times (mice) the MRHD on a mg/sq m basis. Slight nonspecific embryo/fetotoxic effects were seen in the offspring of treated rats given 50 and 100 mg/kg and of treated mice given 100 mg/kg.For more Non-Human Toxicity Excerpts (Complete) data for Clomipramine (7 total), please visit the HSDB record page.
Wassergefährdungsklasse (WGK)3
RTECS-Nr.HN9055000
R-Sätze (R)20/21/22
GefahrensymboleXn
Sicherheitshinweise (S)36
Gefahrstoffdaten303-49-1(Hazardous Substances Data)