Ziprasidone

Names

[ Name ]:
Ziprasidone

[Synonym ]:
5-{2-4-(1,2-benzothiazol-3-yl)piperazin-1-ylethyl}-6-chloro-1,3-dihydro-2H-indol-2-one
5-{2-[4-(1,2-Benzisothiazol-3-yl)piperazin-1-yl]ethyl}-6-chloro-1,3-dihydro-2H-indol-2-one
ziprasidonum
Ziprasidone
UNII-6UKA5VEJ6X
5-{2-[4-(1,2-Benzothiazol-3-yl)piperazin-1-yl]ethyl}-6-chloro-1,3-dihydro-2H-indol-2-one
ziprasidona
EINECS 203-794-9
5-{2-[4-(1,2-Benzisothiazol-3-yl)piperazin-1-yl]ethyl}-6-chlor-1,3-dihydro-2H-indol-2-on
Zipwell
MFCD00866661
2H-Indol-2-one, 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-
2H-indol-2-one, 5-2-4-(1,2-benzisothiazol-3-yl)-1-piperazinylethyl-6-chloro-1,3-dihydro-
5-{2-[4-(1,2-Benzothiazol-3-yl)-1-piperazinyl]ethyl}-6-chloro-1,3-dihydro-2H-indol-2-one
ziprazidone
Ziprasidone [INN:BAN]
Geodon
Zeldox
5-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-6-chloro-1,3-dihydroindol-2-one

Biological Activity

[Description]:

Ziprasidone(CP88059) is a combined 5-HT (serotonin) and dopamine receptor antagonist which exhibits potent effects of antipsychotic activity.IC50 value:Target: 5-HT receptor; Dopamine receptorZiprasidone possesses an in vitro 5-HT2A/dopamine D2 receptor affinity ratio higher than any clinically available antipsychotic agent. In vivo, ziprasidone antagonizes 5-HT2A receptor-induced head twitch with 6-fold higher potency than for blockade of d-amphetamine-induced hyperactivity, a measure of central dopamine D2 receptor antagonism. Ziprasidone also has high affinity for the 5-HT1A, 5-HT1D and 5-HT2C receptor subtypes, which may further enhance its therapeutic potential [1]. Ziprasidone sulfoxide and sulfone were the major metabolites in human serum. The affinities of the sulfoxide and sulfone metabolites for 5-HT2 and D2 receptors are low with respect to ziprasidone, and are thus unlikely to contribute to its antipsychotic effects [2]. Ziprasidone was associated with significant differential adverse effects relative to placebo in BPM, BPD, and schizophrenia with no significant difference in weight gain in all 3 groups. Self-reported somnolence was increased across the 3 conditions. Subjects with BPM were more vulnerable to EPS than those with BPD or schizophrenia [3].Clinical indications: Bipolar I disorder; Bipolar disorder; Mania; SchizophreniaFDA Approved Date: February 2001

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor

Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor

Research Areas >> Neurological Disease

[References]

[1]. Seeger, T.F., et al., Ziprasidone (CP-88,059): a new antipsychotic with combined dopamine and serotonin receptor antagonist activity. J Pharmacol Exp Ther, 1995. 275(1): p. 101-13.

[2]. Prakash, C., et al., Metabolism and excretion of a new antipsychotic drug, ziprasidone, in humans. Drug Metab Dispos, 1997. 25(7): p. 863-72.

[3]. Gao, K., et al., Risk for adverse events and discontinuation due to adverse events of ziprasidone monotherapy relative to placebo in the acute treatment of bipolar depression, mania, and schizophrenia. J Clin Psychopharmacol, 2013. 33(3): p. 425-31.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
554.8±50.0 °C at 760 mmHg

[ Melting Point ]:
213-215°C

[ Molecular Formula ]:
C₂₁H₂₁ClN₄OS

[ Molecular Weight ]:
412.94

[ Flash Point ]:
289.3±30.1 °C

[ PSA ]:
76.71000

[ LogP ]:
4.00

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.681

[ Storage condition ]:
Refrigerator

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS02, GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H315-H360FD

[ Supplemental HS ]:
May form explosive peroxides.

[ Precautionary Statements ]:
P201-P210-P308 + P313-P403 + P235

[ Hazard Codes ]:
C,N

[ Risk Phrases ]:
R22:Harmful if swallowed. R34:Causes burns. R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .

[ Safety Phrases ]:
S26-S36/37/39-S45-S60-S61

[ RIDADR ]:
UN 3259 8/PG 3

[ WGK Germany ]:
2

[ RTECS ]:
JR6475000

[ Packaging Group ]:
II

[ Hazard Class ]:
8

[ HS Code ]:
29211980

Customs

[ HS Code ]: 29211980

Articles

Gingival pain: an unusual side effect of ziprasidone.

BMJ Case Rep. 2013 , doi:10.1136/bcr-2012-007577, (2013)

The patient is a 52-year-old man with schizophrenia who developed severe, unremitting gingival pain after his ziprasidone dosage was increased from 80 to 120 mg. His physical examination and laborator...

A thorough QTc study of 3 doses of iloperidone including metabolic inhibition via CYP2D6 and/or CYP3A4 and a comparison to quetiapine and ziprasidone.

J. Clin. Psychopharmacol. 33(1) , 3-10, (2013)

The potential for iloperidone, a D2/5-HT2A antipsychotic, to affect the heart rate-corrected QT interval (QTc) was assessed in the absence and presence of metabolic inhibitors in a randomized, open-la...

Association between second-generation antipsychotics and changes in body mass index in adolescents.

J. Adolesc. Health 52(3) , 336-43, (2013)

To assess the association of second-generation antipsychotics (SGAs) with changes in body mass index (BMI) among adolescents compared with a matched untreated comparison group.A retrospective cohort s...