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Ziprasidone Hydrochloride Monohydrate

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CP-88059; 5-(2-(4-(1,2-Benzisothiazol-3-yl)piperazinyl)ethyl)-6-chlorooxindole · HCl · H2O
146939-27-7 (net), 138982-67-9 (hydrochloride monohydrate)
Molecular Formula
Ziprasidone hydrochloride monohydrate is approved by the U.S. Food and Drug Administration (FDA) for the treatment of schizophrenia, acute mania and mixed states associated with bipolar disorder. Ziprasidone is also used off-label for depression, bipolar maintenance and PTSD.
Ziprasidone (marketed as Geodon, Zeldox and Zipwell) was the fifth atypical antipsychotic to gain approval (February 2001) in the United States.
Areas of Interest
Bipolar disorder Schizophrenia
  • Background
  • Related Products
  • References

Ziprasidone hydrochloride monohydrate is an atypical antipsychotic that displays combined SR-2A and D2DR inhibition. Ziprasidone displays high affinity at SR-2A receptors with a SR-2A/D2DR affinity ratio greater than any other clinically available atypical antipsychotics.

CAS: 616-91-1
Sequence: Ac-Cys-OH
M.W: 163.2
Molecular Formula: ---
CAS: 75921-69-6 (net)
Sequence: Ac-Ser-Tyr-Ser-Nle-Glu-His-D-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2 acetate salt
M.W: 1646.85
Molecular Formula: C78H111N21O19
CAS: 79561-22-1
Sequence: Pyr-His-Trp-Ser-Tyr-D-Ala-Leu-Arg-Pro-NHEt
M.W: 1167.3
Molecular Formula: C56H78N16O12
CAS: 128270-60-0 (net)
Sequence: H-D-Phe-Pro-Arg-Pro-Gly-Gly-Gly-Gly-Asn-Gly-Asp-Phe-Glu-Glu-Ile-Pro-Glu-Glu-Tyr-Leu-OH trifluoroacetate salt
M.W: 2108.3
Molecular Formula: C98H138N24O33
CAS: 269062-93-3
Sequence: L-Lysinamide,L-isoleucyl-L-leucyl-L-arginyl-L-tryptophyl-L-prolyl-L-tryptophyl-L-tryptophyl-L-prolyl-L-tryptophyl-L-arginyl-L-arginyl-,hydrochloride (1:5)
M.W: 1961.45
Molecular Formula: C90H127N27O12·5HCl

In the current work the kinetics of dehydration of ziprasidone hydrochloride monohydrate was studied by nonisothermal thermogravimetry. Ziprasidone hydrochloride monohydrate was heated from 30 to 150° with a heating rate of 5° per min under nitrogen gas atmosphere and weight loss data were collected. Powder X-ray difraction was used to characterize the solid before and after dehydration. The well accepted Coats-Redfern model fitting approach was applied to the thermogravimetry data for the kinetic analysis. Thirteen solid state reaction models were studied; among them one-dimensional diffusion model was found to be the best fit model for this reaction with an excellent correlation 0.9994. The Arrhenius parameters, activation energy, and pre-exponential factor were determined, the values were found to be 28 k.cal/mol and 9.53×1013 sec-1, respectively.

Ravikiran, A., Arthanareeswari, M., Kamaraj, P., & Praveen, C. (2013). Nonisothermal kinetics analysis of the dehydration of ziprasidone hydrochloride monohydrate by thermogravimetry. Indian journal of pharmaceutical sciences, 75(3), 361.

The findings of this study indicate that mild-to-moderate impairment of renal function does not result in clinically significant alteration of ziprasidone pharmacokinetics and therefore does not necessitate dose adjustment.

Aweeka, F., Jayesekara, D., Horton, M., Swan, S., Lambrecht, L., Wilner, K. D., ... & Turncliff, R. Z. (2000). The pharmacokinetics of ziprasidone in subjects with normal and impaired renal function. British journal of clinical pharmacology, 49(S1), 27-33.

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