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MedKoo Cat#: 318996 | Name: Ziprasidone free base
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Ziprasidone free base
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: 412.1125

Molecular Weight: 412.94

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 190.00 Ready to ship
500mg USD 350.00 Ready to ship
1g USD 550.00 Ready to ship
2g USD 950.00 Ready to ship
5g USD 2,050.00 Ready to ship
10g USD 3,650.00 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
Solvent mg/mL mM
Solubility
DMSO 13.5 32.69
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.
1: Engel J, Jeridi L, Auerbach L, Zolk O, Greiner T, Heinze M, Buspavanich P, Schneider M. Sexual dysfunctions associated with antipsychotic drug intake: a retrospective analysis of the FDA adverse events reporting system (FAERS). Naunyn Schmiedebergs Arch Pharmacol. 2025 Jan 11. doi: 10.1007/s00210-024-03763-8. Epub ahead of print. PMID: 39797988. 2: Cho H, Jo H, Jeong YD, Jang W, Park J, Yim Y, Lee K, Lee H, Lee S, Fond G, Boyer L, Pizzol D, Jung J, Yon DK. Antipsychotic use during pregnancy and outcomes in pregnant individuals and newborns. J Affect Disord. 2025 Jan 2;373:495-504. doi: 10.1016/j.jad.2024.12.102. Epub ahead of print. PMID: 39755128. 3: Gasparini S, Senese S, Scuma E, Parodi F, Gianfredi A, Ciabattini S, Loddo V, Peroni G, Porcedda G, Pisano T. Cardiac safety of antipsychotic medications in pediatric and adolescent population: a systematic review and pathways for future research. Eur J Pediatr. 2024 Nov 16;184(1):20. doi: 10.1007/s00431-024-05885-w. PMID: 39549076. 4: Wang E, Liu Y, Wang Y, Han X, Zhou Y, Zhang L, Tang Y. Comparative Safety of Antipsychotic Medications and Mood Stabilizers During Pregnancy: A Systematic Review and Network Meta-analysis of Congenital Malformations and Prenatal Outcomes. CNS Drugs. 2025 Jan;39(1):1-22. doi: 10.1007/s40263-024-01131-x. Epub 2024 Nov 11. PMID: 39528870; PMCID: PMC11695384. 5: Mari J, Dieckmann LHJ, Prates-Baldez D, Haddad M, Rodrigues da Silva N, Kapczinski F. The efficacy of valproate in acute mania, bipolar depression and maintenance therapy for bipolar disorder: an overview of systematic reviews with meta-analyses. BMJ Open. 2024 Nov 5;14(11):e087999. doi: 10.1136/bmjopen-2024-087999. PMID: 39500601; PMCID: PMC11552594. 6: Wu SN, Chen XD, Yan D, Wang YQ, Wang SP, Guan WY, Huang C, Hu J, Liu Z. Drug- associated glaucoma: A real-world study based on the Food and Drug Administration adverse event reporting system database. Clin Exp Ophthalmol. 2024 Oct 25. doi: 10.1111/ceo.14454. Epub ahead of print. PMID: 39460378. 7: Huang L, Wei C, Qin Q. Effects of six antipsychotic drug treatment regimens on short-term heart rate variability in patients with schizophrenia. Int J Psychiatry Med. 2024 Oct 25:912174241293650. doi: 10.1177/00912174241293650. Epub ahead of print. PMID: 39455903. 8: Izat N, Bolleddula J, Carione P, Huertas Valentin L, Jones RS, Kulkarni P, Moss D, Peterkin VC, Tian DD, Treyer A, Venkatakrishnan K, Zientek MA, Barber J, Houston JB, Galetin A, Scotcher D. Establishing a physiologically based pharmacokinetic framework for aldehyde oxidase and dual aldehyde oxidase-CYP substrates. CPT Pharmacometrics Syst Pharmacol. 2025 Jan;14(1):164-178. doi: 10.1002/psp4.13255. Epub 2024 Oct 23. PMID: 39444174; PMCID: PMC11706420. 9: Song M, Li D, Peng J, Wang N, Zhang M, Ren XL. A disproportionality analysis of antipsychotic-induced hyperprolactinemia based on FDA adverse event reporting system. Int J Clin Pharmacol Ther. 2024 Dec;62(12):543-552. doi: 10.5414/CP204518. PMID: 39380546. 10: Griffiths K, Velichkova N, Quadt L, Berni J. Can atypical antipsychotics alleviate Deficits in psychosocial impairments in patients with a diagnosis of Borderline Personality? A systematic review and meta-analysis. Psychiatry Res Commun. 2024 Sep;4(3):None. doi: 10.1016/j.psycom.2024.100187. PMID: 39309544; PMCID: PMC11413517. 11: Lam LK, Poon LY, Xu PL, Xie PC, Xie T, Xiao Y, Chen LG. Efficacy and safety of a Chinese medicine formula Diankuang Mengxing Decoction combined with antipsychotics in the treatment of schizophrenia: A meta-analysis of randomized controlled trials. Medicine (Baltimore). 2024 Sep 6;103(36):e39489. doi: 10.1097/MD.0000000000039489. PMID: 39252273; PMCID: PMC11384066. 12: He S, Chen B, Li C. Drug-induced liver injury associated with atypical generation antipsychotics from the FDA Adverse Event Reporting System (FAERS). BMC Pharmacol Toxicol. 2024 Aug 30;25(1):59. doi: 10.1186/s40360-024-00782-2. PMID: 39215339; PMCID: PMC11363531. 13: Huang W, He S, Liu M, Xu J. Comparative efficacy, safety, and tolerability of pharmacotherapies for acute mania in adults: a systematic review and network meta-analysis of randomized controlled trials. Mol Psychiatry. 2024 Aug 27. doi: 10.1038/s41380-024-02705-3. Epub ahead of print. PMID: 39191865. 14: Mu C, Chen L. Characteristics of eye disorders induced by atypical antipsychotics: a real-world study from 2016 to 2022 based on Food and Drug Administration Adverse Event Reporting System. Front Psychiatry. 2024 Aug 2;15:1322939. doi: 10.3389/fpsyt.2024.1322939. PMID: 39156610; PMCID: PMC11327930. 15: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Ziprasidone. 2024 Aug 15. PMID: 30000199. 16: Wang F, Wang F, Tao X, Ni W, Li W, Lin J. Evaluation of Clinical Correlation between Insulin Resistance and Antipsychotic Drug Therapy in Patients with Schizophrenia. Actas Esp Psiquiatr. 2024 Aug;52(4):412-419. doi: 10.62641/aep.v52i4.1681. PMID: 39129685; PMCID: PMC11319756. 17: Vita G, Nöhles VB, Ostuzzi G, Barbui C, Tedeschi F, Heuer FH, Keller A, DelBello MP, Welge JA, Blom TJ, Kowatch RA, Correll CU. Systematic Review and Network Meta-Analysis: Efficacy and Safety of Antipsychotics vs Antiepileptics or Lithium for Acute Mania in Children and Adolescents. J Am Acad Child Adolesc Psychiatry. 2024 Aug 9:S0890-8567(24)01316-9. doi: 10.1016/j.jaac.2024.07.920. Epub ahead of print. PMID: 39128561. 18: Melo L, Pillai A, Kompella R, Patail H, Aronow WS. An Updated Safety Review of the Relationship Between Atypical Antipsychotic Drugs, the QTc Interval and Torsades de Pointe As: Implications for Clinical Use. Expert Opin Drug Saf. 2024 Sep;23(9):1127-1134. doi: 10.1080/14740338.2024.2392002. Epub 2024 Aug 13. 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