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
ChemSpider
15171283
ChEMBL
CHEMBL538973
Predicted Properties
PropertyValueSource
Water Solubility0.186 mg/mLALOGPS
logP3.67ALOGPS
logP3.4Chemaxon
logS-3.2ALOGPS
pKa (Strongest Acidic)15.9Chemaxon
pKa (Strongest Basic)7.35Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area30.87 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity97.36 m3·mol-1Chemaxon
Polarizability35.7 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon