Clozapine hydrochlorideProduct ingredient for Clozapine
- Name
- Clozapine hydrochloride
- Drug Entry
- Clozapine
Clozapine is a tricyclic dibenzodiazepine, classified as an atypical antipsychotic agent.23 Clozapine displays affinity to various neuroreceptors with a particularly low affinity to the dopamine receptors, thus breaking the mold of first-generation antipsychotics and deeming it "atypical".26. This low affinity to dopamine receptors results in fewer extrapyramidal side effects, especially tardive dyskinesia.21 However, its promiscuity toward the muscarinic and adrenergic receptors can result in other side effects, notably gastrointestinal hypomotility and orthostatic hypotension. 27,8. Despite its effectiveness in treating both positive and negative symptoms of schizophrenia, clozapine was briefly removed from the market in various jurisdictions in 1970 due to severe agranulocytosis.24,25 However, continued evidence of its effectiveness led to clozapine's eventual reintroduction, although with a reluctance to prescribe it.25
Clozapine was approved by the FDA in 1989 for treatment-resistant schizophrenia under the brand CLOZARIL.27 Due to its severe adverse effects profile, clozapine is only available through a restricted program under a Risk Evaluation Mitigation Strategy (REMS) called the Clozapine REMS Program.27
- Accession Number
- DBSALT002286
- Structure
- Synonyms
- Not Available
- UNII
- 80862U56A3
- CAS Number
- 54241-01-9
- Weight
- Average: 363.29
Monoisotopic: 362.1065021 - Chemical Formula
- C18H20Cl2N4
- InChI Key
- ARWPDHKDEREYEE-UHFFFAOYSA-N
- InChI
- InChI=1S/C18H19ClN4.ClH/c1-22-8-10-23(11-9-22)18-14-4-2-3-5-15(14)20-16-7-6-13(19)12-17(16)21-18;/h2-7,12,20H,8-11H2,1H3;1H
- IUPAC Name
- 6-chloro-10-(4-methylpiperazin-1-yl)-2,9-diazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,9,12,14-heptaene hydrochloride
- SMILES
- Cl.CN1CCN(CC1)C1=NC2=CC(Cl)=CC=C2NC2=C1C=CC=C2
- External Links
- ChemSpider
- 15171283
- ChEMBL
- CHEMBL538973
- Predicted Properties
Property Value Source Water Solubility 0.186 mg/mL ALOGPS logP 3.67 ALOGPS logP 3.4 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 15.9 Chemaxon pKa (Strongest Basic) 7.35 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 30.87 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 97.36 m3·mol-1 Chemaxon Polarizability 35.7 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon