Ziprasidone free base
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MedKoo CAT#: 318996

CAS#: 146939-27-7 (free base)

Description: Ziprazidone is approved for the treatment of schizophrenia, and acute mania and mixed states associated with bipolar disorder. Its intramuscular injection form is approved for acute agitation in schizophrenic patients for whom treatment with just ziprasidone is appropriate. The mechanism of action of ziprasidone, as with other drugs having efficacy in schizophrenia, is unknown. However, it has been proposed that this drug's efficacy in schizophrenia is mediated through a combination of dopamine type 2 (D2) and serotonin type 2 (5HT2) antagonism. As with other drugs having efficacy in bipolar disorder, the mechanism of action of ziprasidone in bipolar disorder is unknown.


Chemical Structure

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Ziprasidone free base
CAS# 146939-27-7 (free base)

Theoretical Analysis

MedKoo Cat#: 318996
Name: Ziprasidone free base
CAS#: 146939-27-7 (free base)
Chemical Formula: C21H21ClN4OS
Exact Mass: 412.11
Molecular Weight: 412.940
Elemental Analysis: C, 61.08; H, 5.13; Cl, 8.58; N, 13.57; O, 3.87; S, 7.76

Price and Availability

Size Price Availability Quantity
200mg USD 190 Ready to ship
500mg USD 350 Ready to ship
1g USD 550 Ready to ship
2g USD 950 Ready to ship
5g USD 2050 Ready to ship
10g USD 3650 Ready to ship
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Related CAS #: 199191-69-0 (mesylate trihydrate)   122883-93-6 (HCl)   138982-67-9 (HCl hydrate)   146939-27-7 (free base)    

Synonym: CP88059; CP-88059; CP 88059; CP-88,059; CP-88,059-01; CP88059 hydrochloride; Ziprasidone HCl, brand name: Geodon; Zeldox; Zipwell.

IUPAC/Chemical Name: 5-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-6-chloro-1,3-dihydroindol-2-one

InChi Key: MVWVFYHBGMAFLY-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H21ClN4OS/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)

SMILES Code: O=C1NC2=C(C=C(CCN3CCN(C4=NSC5=CC=CC=C45)CC3)C(Cl)=C2)C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: Related CAS# 146939-27-7 (Ziprasidone free base); 122883-93-6 (Ziprasidone HCl salt); 138982-67-9 (Ziprasidone HCl hydrate); 199191-69-0 (Ziprasidone Mesylate Trihydrate)

Biological target: Ziprasidone, an antipsychotic agent, is a combined 5-HT (serotonin) and dopamine receptor antagonist. Ziprasidone has high affinity for rat (Ki: 3.4 nM)/human (2.5 nM) 5-HT1A receptors, 5-HT2A (0.42 nM), and dopamine D2 receptors (4.8 nM).
In vitro activity: The effect of ziprasidone, a widely used treatment for schizophrenia, on voltage-dependent K+ (Kv) channels of coronary arterial smooth muscle cells was investigated using the patch-clamp technique. Ziprasidone dose-dependently inhibited Kv channels with an IC50 value of 0.39 ± 0.06 μM and a Hill coefficient of 0.62 ± 0.03. Although ziprasidone had no effect on the steady-state inactivation kinetics of the Kv channels, the steady-state activation curve shifted towards a more positive potential. These results suggest that ziprasidone inhibits Kv channels by targeting their voltage sensors. The recovery time constant of Kv channel inactivation was increased in the presence of ziprasidone. Furthermore, application of train steps (of 1 and 2 Hz) in the presence of ziprasidone led to a progressive increase in the blockade of Kv currents, suggesting that ziprasidone-induced inhibition of Kv channels is use (state)-dependent. Pretreatment with Kv1.5, Kv2.1, and Kv7 subtype inhibitors partially suppressed the ziprasidone-induced inhibition of Kv currents. These results suggest that ziprasidone inhibits vascular Kv channels through its effect on gating properties. The Kv channel-inhibiting action of ziprasidone is concentration- and use (state)-depedent. Reference: Biochem Biophys Res Commun. 2020 Aug 20;529(2):191-197. https://linkinghub.elsevier.com/retrieve/pii/S0006-291X(20)31245-6
In vivo activity: The effects of ziprasidone on resting energy expenditure, physical activity, thermogenesis, food intake, and weight gain was examined in female Sprague-Dawley rats. Ziprasidone (20 mg/kg) or vehicle was administered once daily for 7 weeks; and body weight, food intake, resting energy expenditure, locomotor activity, colonic temperature on cold exposure, and abdominal fat were measured. Compared with control animals, ziprasidone-treated rats gained significantly less weight (P = .031), had a lower level of physical activity (P = .016), showed a higher resting energy expenditure (P < .001), and displayed a greater capacity for thermogenesis when subjected to cold (P < .001). In addition, ziprasidone-treated rats had a lower level of abdominal fat than did controls, although the difference was not significant. Ziprasidone had no effect on food intake. These results indicate that, in female Sprague-Dawley rats, a 7-week treatment regimen of ziprasidone induces a significant decrease in weight gain by increasing resting energy expenditure without decreasing food intake and even with a lower level of physical activity. Further studies are needed to elucidate the precise mechanism of lower propensity of weight gain of ziprasidone. Reference: Metabolism. 2012 Jun;61(6):787-93. https://linkinghub.elsevier.com/retrieve/pii/S0026-0495(11)00350-7

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 13.5 32.69

Preparing Stock Solutions

The following data is based on the product molecular weight 412.94 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol: 1. An JR, Seo MS, Jung HS, Heo R, Kang M, Ha KS, Park H, Park WS. The inhibitory effect of ziprasidone on voltage-dependent K+ channels in coronary arterial smooth muscle cells. Biochem Biophys Res Commun. 2020 Aug 20;529(2):191-197. doi: 10.1016/j.bbrc.2020.06.038. Epub 2020 Jun 22. PMID: 32703410.
In vivo protocol: 1. Park S, Kim MS, Namkoong C, Park MH, Hong JP. The effect of ziprasidone on body weight and energy expenditure in female rats. Metabolism. 2012 Jun;61(6):787-93. doi: 10.1016/j.metabol.2011.10.011. Epub 2011 Dec 28. PMID: 22209671.

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1: Bouchette D, Pellegrini MV. Ziprasidone. 2017 Oct 9. StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2017 Jun-. Available from http://www.ncbi.nlm.nih.gov/books/NBK448157/ PubMed PMID: 28846230.

2: Mandrioli R, Protti M, Mercolini L. Evaluation of the pharmacokinetics, safety and clinical efficacy of ziprasidone for the treatment of schizophrenia and bipolar disorder. Expert Opin Drug Metab Toxicol. 2015 Jan;11(1):149-74. doi: 10.1517/17425255.2015.991713. Epub 2014 Dec 6. Review. PubMed PMID: 25483358.

3: Lee HB, Yoon BH, Kwon YJ, Woo YS, Lee JG, Kim MD, Bahk WM. The efficacy and safety of switching to ziprasidone from olanzapine in patients with bipolar I disorder: an 8-week, multicenter, open-label study. Clin Drug Investig. 2013 Oct;33(10):743-53. doi: 10.1007/s40261-013-0120-y. Review. PubMed PMID: 23990283.

4: Andrade C. Antidepressant action of atypical antipsychotics: focus on ziprasidone monotherapy, with a few twists in the tale. J Clin Psychiatry. 2013 Mar;74(3):e193-6. doi: 10.4088/JCP.13f08410. Review. PubMed PMID: 23561239.

5: Pappadopulos E, Newcomer JW, Kolluri S. Changes in weight, plasma lipids, and glucose in adults treated with ziprasidone: a comprehensive analysis of pfizer-initiated clinical trials. J Clin Psychiatry. 2012 Jun;73(6):e742-8. doi: 10.4088/JCP.10r06802. Review. PubMed PMID: 22795213.

6: Stip E, Zhornitsky S, Moteshafi H, Létourneau G, Stikarovska I, Potvin S, Tourjman V. Ziprasidone for psychotic disorders: a meta-analysis and systematic review of the relationship between pharmacokinetics, pharmacodynamics, and clinical profile. Clin Ther. 2011 Dec;33(12):1853-67. doi: 10.1016/j.clinthera.2011.10.027. Epub 2011 Dec 1. Review. PubMed PMID: 22133697.

7: Sacchetti E, Galluzzo A, Valsecchi P. Oral ziprasidone in the treatment of patients with bipolar disorders: a critical review. Expert Rev Clin Pharmacol. 2011 Mar;4(2):163-79. doi: 10.1586/ecp.10.139. Review. PubMed PMID: 22115400.

8: Cañas F, Correll CU, Fagiolini A, Larmo I, Levy P, Papageorgiou G, Rossi A, Zink M, Montes JM. Practical guidance for prescribing ziprasidone in acute manic or mixed episodes of bipolar I disorder. Expert Opin Pharmacother. 2011 Oct;12(14):2245-63. doi: 10.1517/14656566.2011.605787. Epub 2011 Jul 30. Review. PubMed PMID: 21801083.

9: Ochedzan D, Jarema M. [Practical aspects of the use of ziprasidone in schizophrenia]. Psychiatr Pol. 2010 Nov-Dec;44(6):881-93. Review. Polish. PubMed PMID: 21449170.

10: Citrome L. Drug safety evaluation of ziprasidone. Expert Opin Drug Saf. 2011 May;10(3):437-48. doi: 10.1517/14740338.2011.560114. Epub 2011 Feb 19. Review. PubMed PMID: 21332416.

11: Fagiolini A, Cañas F, Gallhofer B, Larmo I, Levy P, Montes JM, Papageorgiou G, Zink M, Rossi A. Strategies for successful clinical management of schizophrenia with ziprasidone. Expert Opin Pharmacother. 2010 Sep;11(13):2199-220. doi: 10.1517/14656566.2010.507630. Review. PubMed PMID: 20658947.

12: Citrome L. Ziprasidone HCl capsules for the adjunctive maintenance treatment of bipolar disorder in adults. Expert Rev Neurother. 2010 Jul;10(7):1031-7. doi: 10.1586/ern.10.66. Review. PubMed PMID: 20586686.

13: Khan AA, Strawn JR, Croarkin PE. Emerging treatment options in bipolar disorder in adolescents: focus on ziprasidone. Adolesc Health Med Ther. 2010 Oct 11;1:137-43. doi: 10.2147/AHMT.S7586. eCollection 2010. Review. PubMed PMID: 24600269; PubMed Central PMCID: PMC3915792.

14: Komossa K, Rummel-Kluge C, Hunger H, Schwarz S, Bhoopathi PS, Kissling W, Leucht S. Ziprasidone versus other atypical antipsychotics for schizophrenia. Cochrane Database Syst Rev. 2009 Oct 7;(4):CD006627. doi: 10.1002/14651858.CD006627.pub2. Review. PubMed PMID: 19821380; PubMed Central PMCID: PMC4164848.

15: Citrome L. Using oral ziprasidone effectively: the food effect and dose-response. Adv Ther. 2009 Aug;26(8):739-48. doi: 10.1007/s12325-009-0055-0. Epub 2009 Aug 8. Review. PubMed PMID: 19669631.

16: Rosa AR, Franco C, Torrent C, Comes M, Cruz N, Horga G, Benabarre A, Vieta E. Ziprasidone in the treatment of affective disorders: a review. CNS Neurosci Ther. 2008 Winter;14(4):278-86. doi: 10.1111/j.1755-5949.2008.00056.x. Review. PubMed PMID: 19040553.

17: Durán-Ferreras E, Alvarez-López M, García-Moreno JM, Chacón J. [Ziprasidone in Parkinsonian dopamine psychosis]. Rev Neurol. 2008 Apr 16-30;46(8):476-80. Review. Spanish. PubMed PMID: 18428105.

18: Preskorn SH. Clinical relevance of relative receptor binding affinity: quetiapine and ziprasidone as examples. J Psychiatr Pract. 2007 Nov;13(6):393-8. Review. PubMed PMID: 18032984.

19: Warrington L, Lombardo I, Loebel A, Ice K. Ziprasidone for the treatment of acute manic or mixed episodes associated with bipolar disorder. CNS Drugs. 2007;21(10):835-49. Review. PubMed PMID: 17850172.

20: Greenberg WM, Citrome L. Ziprasidone for schizophrenia and bipolar disorder: a review of the clinical trials. CNS Drug Rev. 2007 Summer;13(2):137-77. Review. PubMed PMID: 17627670.