Ziprasidone mesylate trihydrateProduct ingredient for Ziprasidone

Name
Ziprasidone mesylate trihydrate
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
DBSALT000811
Structure
Synonyms
Ziprasidon mesilate trihydrate / Ziprasidone mesylate
External IDs
CP-88, 059-27 / CP-88,059-27
UNII
3X6SAX83JZ
CAS Number
199191-69-0
Weight
Average: 563.087
Monoisotopic: 562.132268453
Chemical Formula
C22H31ClN4O7S2
InChI Key
WLQZEFFFIUHSJB-UHFFFAOYSA-N
InChI
InChI=1S/C21H21ClN4OS.CH4O3S.3H2O/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;1-5(2,3)4;;;/h1-4,11,13H,5-10,12H2,(H,23,27);1H3,(H,2,3,4);3*1H2
IUPAC Name
5-{2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl}-6-chloro-3H-indol-2-ol methanesulfonic acid trihydrate
SMILES
O.O.O.CS(O)(=O)=O.OC1=NC2=C(C1)C=C(CCN1CCN(CC1)C1=NSC3=CC=CC=C13)C(Cl)=C2
PubChem Compound
656685
ChemSpider
571025
ChEBI
53757
ChEMBL
CHEMBL3989833
Predicted Properties
PropertyValueSource
Water Solubility0.013 mg/mLALOGPS
logP4.42ALOGPS
logP2.6Chemaxon
logS-4.5ALOGPS
pKa (Strongest Acidic)4.33Chemaxon
pKa (Strongest Basic)7.18Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area51.96 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity117.48 m3·mol-1Chemaxon
Polarizability44.78 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon