Ziprasidone hydrochlorideProduct ingredient for Ziprasidone

Name
Ziprasidone hydrochloride
Drug Entry
Ziprasidone

Disorders such as schizophrenia and bipolar disorder can significantly impair mood, cognition, and behavior.6 These mental illnesses can often be accompanied by comorbidities such as depression and substance abuse, and can significantly impact the quality of life of patients and caregivers.6 Luckily, several treatment options for psychotic disorders have been introduced to market since the realization of chlorpromazine's antipsychotic properties in 1952.6

Second generation antipsychotics (commonly referred to as atypical antipsychotics) include clozapine, quetiapine, olanzapine, aripiprazole and ziprasidone among others, and are generally thought to be as efficacious as first generation antipsychotics but differ in their adverse effect profiles.6,7 First generation antipsychotics are associated with extrapyramidal adverse effects while atypical antipsychotics are linked to weight gain, impaired glucose tolerance and metabolic syndrome.7,8

Ziprasidone is used to treat schizophrenia and bipolar disorder.5 It can effectively reduce the rate and time of relapses in schizophrenia, and can be used to treat manic episodes in bipolar disorder although the mechanism of action is unknown.5 Although ziprasidone is classified as an atypical antipsychotic, it appears to have a lower incidence of metabolic adverse effects compared to other medications in the same class.6

Accession Number
DBSALT000810
Structure
Synonyms
Ziprasidone HCl / Ziprasidone hydrochloride / Ziprasidone hydrochloride monohydrate
External IDs
CP-88,059-1
UNII
216X081ORU
CAS Number
138982-67-9
Weight
Average: 467.41
Monoisotopic: 466.0997026
Chemical Formula
C21H24Cl2N4O2S
InChI Key
ZCBZSCBNOOIHFP-UHFFFAOYSA-N
InChI
InChI=1S/C21H21ClN4OS.ClH.H2O/c22-17-13-18-15(12-20(27)23-18)11-14(17)5-6-25-7-9-26(10-8-25)21-16-3-1-2-4-19(16)28-24-21;;/h1-4,11,13H,5-10,12H2,(H,23,27);1H;1H2
IUPAC Name
5-{2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl}-6-chloro-2,3-dihydro-1H-indol-2-one hydrate hydrochloride
SMILES
O.Cl.ClC1=C(CCN2CCN(CC2)C2=NSC3=CC=CC=C23)C=C2CC(=O)NC2=C1
PubChem Compound
60853
ChemSpider
54840
ChEBI
32314
ChEMBL
CHEMBL1375743
Wikipedia
Ziprasidone
Predicted Properties
PropertyValueSource
Water Solubility0.00718 mg/mLALOGPS
logP4.64ALOGPS
logP4.3Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)12.21Chemaxon
pKa (Strongest Basic)7.09Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area48.47 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity116.72 m3·mol-1Chemaxon
Polarizability44.44 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon