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Clomipraminhydrochlorid
ANAFRANIL · Clomicalm · anaphranil · Chlomipramine · CLOMIPRAMINE HCL · Clomipramine hydroch · Chloroimipram-ine HCl · ANAFRANIL HYDROCHLORIDE
Identifikatoren & physikalische Daten
| CAS No. | 17321-77-6 |
|---|---|
| Summenformel | C19H24Cl2N2 |
| Durchschnittliche Molmasse | 351,3 g/mol |
| Monoisotopische Masse | 350,1316542 g/mol |
| SMILES | CN(C)CCCN1c2ccccc2CCc2ccc(Cl)cc21.Cl |
| InChIKey | WIMWMKZEIBHDTH-UHFFFAOYSA-N |
| PubChem CID | 68539 |
| ChEMBL | CHEMBL1200710 |
| ChEBI | CHEBI:3755 |
| EC No. | 241-344-3 |
| DTXSID | DTXSID3042633 |
| Lokaler Name | Clomipraminhydrochlorid |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 6,5 |
|---|---|
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 23 |
| Formalladung | 0 |
| Komplexität | 346 |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Animal Drugs | EMA approved medicines: Veterinary medicineFDA approved animal drugs -> Active ingredient |
| Collision Cross Section | 173.2 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Schmelzpunkt | 189-190°C |
| Flammpunkt | 9℃ |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | H2O: 25 mg/mL |
| Aggregatzustand | powder |
| Farbe | white to off-white |
| pH | 3.5~5.0(100g/l,25℃) |
| BCS Class | 3/1 |
| Hauptanwendungen | pharmaceutical (small molecule) |
| InChI | InChI=1S/C19H23ClN2.ClH/c1-21(2)12-5-13-22-18-7-4-3-6-15(18)8-9-16-10-11-17(20)14-19(16)22/h3-4,6-7,10-11,14H,5,8-9,12-13H2,1-2H31H |
| InChIKey | WIMWMKZEIBHDTH-UHFFFAOYSA-N |
| SMILES | N1(CCCN(C)C)C2C=CC=CC=2CCC2C=CC(Cl)=CC1=2.Cl |
| CAS Datenbank | 17321-77-6(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 61 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Hazard Traits - BioaccumulationEnvironmental PersistenceREACH registered substance: Clomipramine hydrochloride (EC: 241-344-3)Clomipramine hydrochloride: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 5H-Dibenz[b,f]azepine-5-propanamine, 3-chloro-10,11-dihydro-N,N-dimethyl-, monohydrochloride: Human health tier I assessment |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| 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) |
| Expositionspfade | 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. |
| Toxizitätsübersicht | 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. |
| 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. 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. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Clomipramine hydrochloridevMost-DILI-concern8Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015 |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | 3249 |
| Zollcode | 2933996100 |
| RTECS-Nr. | HN9055000 |
| R-Sätze (R) | 20/21/22-39/23/24/25-23/24/25-11-36/37/38 |
| Gefahrensymbole | Xn,T,F |
| Sicherheitshinweise (S) | 36-45-36/37-16-7-62-38-36/37/39-28-26-24/25-22-20/21-13 |
| Gefahrenklasse | 6.1(b)Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1STOT SE 1STOT SE 3 |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Beschreibung
Clomipramine is a tricyclic antidepressant, the 3-chlorinated derivative of imipramine . Like imipramine, clomipramine potently inhibits serotonin and norepinephrine reuptake (Kis = 7.4 and 96 nM, respectively). It also is an antagonist at histamine, muscarinic acetylcholine, α1-adrenergic, and dopamine receptors (Kds = 31, 37, 38, and 190 nM for H1, M1, α1, and D2, respectively).
Verwenden
Serotonin reuptake inhibitor. Antidepressant; antiobsessional agent