SEA0400
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MedKoo CAT#: 526678

CAS#: 223104-29-8

Description: SEA0400 is a Na+/Ca2+ exchanger 1 inhibitor. SEA0400 prevents dopaminergic neurotoxicity in an MPTP mouse model of Parkinson's disease. SEA0400 reduces calcium overload induced by ischemia and reperfusion in mouse ventricular myocytes. SEA0400 attenuates sodium nitroprusside-induced apoptosis in cultured rat microglia. SEA0400, preserves cardiac function and high-energy phosphates against ischemia/reperfusion injury.


Chemical Structure

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SEA0400
CAS# 223104-29-8

Theoretical Analysis

MedKoo Cat#: 526678
Name: SEA0400
CAS#: 223104-29-8
Chemical Formula: C21H19F2NO3
Exact Mass: 371.13
Molecular Weight: 371.380
Elemental Analysis: C, 67.92; H, 5.16; F, 10.23; N, 3.77; O, 12.92

Price and Availability

Size Price Availability Quantity
50mg USD 450
100mg USD 750
200mg USD 1250
500mg USD 2650 2 Weeks
1g USD 3850 2 Weeks
2g USD 6450 2 Weeks
Bulk inquiry

Synonym: SEA0400; SEA-0400; SEA 0400.

IUPAC/Chemical Name: 2-[4-[(2,5-difluorophenyl)methoxy]phenoxy]-5-ethoxyaniline

InChi Key: YSUBLPUJDOWYDP-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H19F2NO3/c1-2-25-18-8-10-21(20(24)12-18)27-17-6-4-16(5-7-17)26-13-14-11-15(22)3-9-19(14)23/h3-12H,2,13,24H2,1H3

SMILES Code: NC1=CC(OCC)=CC=C1OC2=CC=C(OCC3=CC(F)=CC=C3F)C=C2

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, DMF, and ethanol

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:

Product Data:
Biological target: SEA0400 is a selective inhibitor of the Na+/Ca2+ exchanger (IC50s = 5, 8.3, and 33 nM for inhibiting Na+-dependent Ca2+ uptake in rat astrocyte, microglia, and cortical neuron cell lines, respectively).
In vitro activity: SEA0400 exhibits renoprotective effects in a hypoxic injury model using porcine renal tubular cells expressing wild-type NCX1 but not SEA0400-insensitive mutants. SEA0400 demonstrates preferential inhibition of (45)Ca(2+) uptake by NCX1 compared to NCX2, NCX3, and NCKX2 in NCX-transfected fibroblasts. Reference: J Biol Chem. 2004 Feb 27;279(9):7544-53. https://pubmed.ncbi.nlm.nih.gov/14660663/
In vivo activity: The results of this study suggest that SEA0400's antiarrhythmic effects on IKr blocker-induced TdP may be multifaceted, depending on the severity of proarrhythmogenic conditions, distinguishing it from the effects of verapamil. SEA0400 has the potential to inhibit low-dose nifekalant-induced TdP by suppressing the MAP-prolonging action of nifekalant. In animals treated with high-dose nifekalant, SEA0400 inhibited TdP without affecting the MAP-prolonging action of nifekalant. Reference: Biol Pharm Bull. 2023;46(8):1120-1127. https://pubmed.ncbi.nlm.nih.gov/37532563/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 1.0 2.69
DMSO 2.0 5.39
Ethanol 0.3 0.67

Preparing Stock Solutions

The following data is based on the product molecular weight 371.38 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: 1. Nashida T, Takuma K, Fukuda S, Kawasaki T, Takahashi T, Baba A, Ago Y, Matsuda T. The specific Na(+)/Ca(2+) exchange inhibitor SEA0400 prevents nitric oxide-induced cytotoxicity in SH-SY5Y cells. Neurochem Int. 2011 Aug;59(1):51-8. doi: 10.1016/j.neuint.2011.03.026. Epub 2011 Jun 6. PMID: 21672583. 2. Iwamoto T, Kita S, Uehara A, Imanaga I, Matsuda T, Baba A, Katsuragi T. Molecular determinants of Na+/Ca2+ exchange (NCX1) inhibition by SEA0400. J Biol Chem. 2004 Feb 27;279(9):7544-53. doi: 10.1074/jbc.M310491200. Epub 2003 Dec 5. PMID: 14660663. 3. Kawakami S, Takada K, Aimoto M, Nagasawa Y, Kusakabe T, Kato K, Takahara A. The Antiarrhythmic Action of the Na+/Ca2+ Exchanger Inhibitor SEA0400 on Drug-Induced Long QT Syndrome Depends on the Severity of Proarrhythmic Conditions in Anesthetized Atrioventricular Block Rabbits. Biol Pharm Bull. 2023;46(8):1120-1127. doi: 10.1248/bpb.b23-00202. PMID: 37532563. 4. Bögeholz N, Schulte JS, Kaese S, Bauer BK, Pauls P, Dechering DG, Frommeyer G, Goldhaber JI, Kirchhefer U, Eckardt L, Pott C, Müller FU. The Effects of SEA0400 on Ca2+ Transient Amplitude and Proarrhythmia Depend on the Na+/Ca2+ Exchanger Expression Level in Murine Models. Front Pharmacol. 2017 Sep 21;8:649. doi: 10.3389/fphar.2017.00649. PMID: 28983248; PMCID: PMC5613119.
In vitro protocol: 1. Nashida T, Takuma K, Fukuda S, Kawasaki T, Takahashi T, Baba A, Ago Y, Matsuda T. The specific Na(+)/Ca(2+) exchange inhibitor SEA0400 prevents nitric oxide-induced cytotoxicity in SH-SY5Y cells. Neurochem Int. 2011 Aug;59(1):51-8. doi: 10.1016/j.neuint.2011.03.026. Epub 2011 Jun 6. PMID: 21672583. 2. Iwamoto T, Kita S, Uehara A, Imanaga I, Matsuda T, Baba A, Katsuragi T. Molecular determinants of Na+/Ca2+ exchange (NCX1) inhibition by SEA0400. J Biol Chem. 2004 Feb 27;279(9):7544-53. doi: 10.1074/jbc.M310491200. Epub 2003 Dec 5. PMID: 14660663.
In vivo protocol: 1. Kawakami S, Takada K, Aimoto M, Nagasawa Y, Kusakabe T, Kato K, Takahara A. The Antiarrhythmic Action of the Na+/Ca2+ Exchanger Inhibitor SEA0400 on Drug-Induced Long QT Syndrome Depends on the Severity of Proarrhythmic Conditions in Anesthetized Atrioventricular Block Rabbits. Biol Pharm Bull. 2023;46(8):1120-1127. doi: 10.1248/bpb.b23-00202. PMID: 37532563. 2. Bögeholz N, Schulte JS, Kaese S, Bauer BK, Pauls P, Dechering DG, Frommeyer G, Goldhaber JI, Kirchhefer U, Eckardt L, Pott C, Müller FU. The Effects of SEA0400 on Ca2+ Transient Amplitude and Proarrhythmia Depend on the Na+/Ca2+ Exchanger Expression Level in Murine Models. Front Pharmacol. 2017 Sep 21;8:649. doi: 10.3389/fphar.2017.00649. PMID: 28983248; PMCID: PMC5613119.

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1: Yatabe MS, Yatabe J, Takano K, Sanada H, Kimura J, Watanabe T. Effects of renal Na+/Ca2+ exchanger 1 inhibitor (SEA0400) treatment on electrolytes, renal function and hemodynamics in rats. Clin Exp Nephrol. 2015 Aug;19(4):585-90. doi: 10.1007/s10157-014-1053-3. Epub 2014 Nov 20. PubMed PMID: 25410661.

2: Egar J, Ali A, Howlett SE, Friesen CH, O'Blenes S. The Na+/Ca2+ exchange inhibitor SEA0400 limits intracellular Ca2+ accumulation and improves recovery of ventricular function when added to cardioplegia. J Cardiothorac Surg. 2014 Jan 8;9:11. doi: 10.1186/1749-8090-9-11. PubMed PMID: 24401610; PubMed Central PMCID: PMC3914709.

3: Chou CC, Chang PC, Wen MS, Lee HL, Chu Y, Baba A, Matsuda T, Yeh SJ, Wu D. Effects of SEA0400 on arrhythmogenicity in a Langendorff-perfused 1-month myocardial infarction rabbit model. Pacing Clin Electrophysiol. 2013 May;36(5):596-606. doi: 10.1111/pace.12091. Epub 2013 Feb 4. PubMed PMID: 23380010.

4: Chen Y, Payne K, Perara VS, Huang S, Baba A, Matsuda T, Yu X. Inhibition of the sodium-calcium exchanger via SEA0400 altered manganese-induced T1 changes in isolated perfused rat hearts. NMR Biomed. 2012 Nov;25(11):1280-5. doi: 10.1002/nbm.2799. Epub 2012 Mar 21. PubMed PMID: 22434695; PubMed Central PMCID: PMC3522749.

5: Ago Y, Kawasaki T, Nashida T, Ota Y, Cong Y, Kitamoto M, Takahashi T, Takuma K, Matsuda T. SEA0400, a specific Na+/Ca2+ exchange inhibitor, prevents dopaminergic neurotoxicity in an MPTP mouse model of Parkinson's disease. Neuropharmacology. 2011 Dec;61(8):1441-51. doi: 10.1016/j.neuropharm.2011.08.041. Epub 2011 Sep 2. PubMed PMID: 21903118.

6: Nashida T, Takuma K, Fukuda S, Kawasaki T, Takahashi T, Baba A, Ago Y, Matsuda T. The specific Na(+)/Ca(2+) exchange inhibitor SEA0400 prevents nitric oxide-induced cytotoxicity in SH-SY5Y cells. Neurochem Int. 2011 Aug;59(1):51-8. doi: 10.1016/j.neuint.2011.03.026. Epub 2011 Jun 6. PubMed PMID: 21672583.

7: Waghorn B, Yang Y, Baba A, Matsuda T, Schumacher A, Yanasak N, Hu TC. Assessing manganese efflux using SEA0400 and cardiac T1-mapping manganese-enhanced MRI in a murine model. NMR Biomed. 2009 Oct;22(8):874-81. doi: 10.1002/nbm.1414. PubMed PMID: 19593760.

8: Namekata I, Tsuneoka Y, Takahara A, Shimada H, Sugimoto T, Takeda K, Nagaharu M, Shigenobu K, Kawanishi T, Tanaka H. Involvement of the Na(+)/Ca(2+) exchanger in the automaticity of guinea-pig pulmonary vein myocardium as revealed by SEA0400. J Pharmacol Sci. 2009 May;110(1):111-6. Epub 2009 May 8. PubMed PMID: 19423954.

9: Szentandrássy N, Birinyi P, Szigeti G, Farkas A, Magyar J, Tóth A, Csernoch L, Varró A, Nánási PP. SEA0400 fails to alter the magnitude of intracellular Ca2+ transients and contractions in Langendorff-perfused guinea pig heart. Naunyn Schmiedebergs Arch Pharmacol. 2008 Jul;378(1):65-71. doi: 10.1007/s00210-008-0296-5. Epub 2008 May 6. PubMed PMID: 18458877.

10: Birinyi P, Tóth A, Jóna I, Acsai K, Almássy J, Nagy N, Prorok J, Gherasim I, Papp Z, Hertelendi Z, Szentandrássy N, Bányász T, Fülöp F, Papp JG, Varró A, Nánási PP, Magyar J. The Na+/Ca2+ exchange blocker SEA0400 fails to enhance cytosolic Ca2+ transient and contractility in canine ventricular cardiomyocytes. Cardiovasc Res. 2008 Jun 1;78(3):476-84. doi: 10.1093/cvr/cvn031. Epub 2008 Feb 5. PubMed PMID: 18252759.

11: Tanaka H, Shimada H, Namekata I, Kawanishi T, Iida-Tanaka N, Shigenobu K. Involvement of the Na+/Ca2+ exchanger in ouabain-induced inotropy and arrhythmogenesis in guinea-pig myocardium as revealed by SEA0400. J Pharmacol Sci. 2007 Feb;103(2):241-6. PubMed PMID: 17310075.

12: Soma S, Kuwashima H, Matsumura C, Kimura T. Inhibition by SEA0400, a selective inhibitor of Na+/Ca2+ exchanger, of Na+ -dependent Ca2+ uptake and catecholamine release in bovine adrenal chromaffin cells. J Pharmacol Sci. 2006 Sep;102(1):88-95. Epub 2006 Sep 8. PubMed PMID: 16960421.

13: Namekata I, Shimada H, Kawanishi T, Tanaka H, Shigenobu K. Reduction by SEA0400 of myocardial ischemia-induced cytoplasmic and mitochondrial Ca2+ overload. Eur J Pharmacol. 2006 Aug 14;543(1-3):108-15. Epub 2006 Jun 14. PubMed PMID: 16842776.

14: Wang J, Zhang Z, Hu Y, Hou X, Cui Q, Zang Y, Wang C. SEA0400, a novel Na+/Ca2+ exchanger inhibitor, reduces calcium overload induced by ischemia and reperfusion in mouse ventricular myocytes. Physiol Res. 2007;56(1):17-23. Epub 2006 Feb 23. PubMed PMID: 16497099.

15: Feng NC, Satoh H, Urushida T, Katoh H, Terada H, Watanabe Y, Hayashi H. A selective inhibitor of Na+/Ca2+ exchanger, SEA0400, preserves cardiac function and high-energy phosphates against ischemia/reperfusion injury. J Cardiovasc Pharmacol. 2006 Feb;47(2):263-70. PubMed PMID: 16495765.

16: Birinyi P, Acsai K, Bányász T, Tóth A, Horváth B, Virág L, Szentandrássy N, Magyar J, Varró A, Fülöp F, Nánási PP. Effects of SEA0400 and KB-R7943 on Na+/Ca2+ exchange current and L-type Ca2+ current in canine ventricular cardiomyocytes. Naunyn Schmiedebergs Arch Pharmacol. 2005 Jul;372(1):63-70. Epub 2005 Aug 6. PubMed PMID: 16086157.

17: Tanaka H, Namekata I, Takeda K, Kazama A, Shimizu Y, Moriwaki R, Hirayama W, Sato A, Kawanishi T, Shigenobu K. Unique excitation-contraction characteristics of mouse myocardium as revealed by SEA0400, a specific inhibitor of Na+-Ca2+ exchanger. Naunyn Schmiedebergs Arch Pharmacol. 2005 Jun;371(6):526-34. Epub 2005 Jul 8. PubMed PMID: 16003546.

18: Namekata I, Nakamura H, Shimada H, Tanaka H, Shigenobu K. Cardioprotection without cardiosuppression by SEA0400, a novel inhibitor of Na+-Ca2+ exchanger, during ischemia and reperfusion in guinea-pig myocardium. Life Sci. 2005 Jun 3;77(3):312-24. Epub 2005 Feb 9. PubMed PMID: 15878358.

19: Matsuda T, Koyama Y, Baba A. Functional proteins involved in regulation of intracellular Ca(2+) for drug development: pharmacology of SEA0400, a specific inhibitor of the Na(+)-Ca(2+) exchanger. J Pharmacol Sci. 2005 Mar;97(3):339-43. Epub 2005 Mar 12. Review. PubMed PMID: 15764845.

20: Nagano T, Osakada M, Ago Y, Koyama Y, Baba A, Maeda S, Takemura M, Matsuda T. SEA0400, a specific inhibitor of the Na+-Ca2+ exchanger, attenuates sodium nitroprusside-induced apoptosis in cultured rat microglia. Br J Pharmacol. 2005 Mar;144(5):669-79. PubMed PMID: 15678087; PubMed Central PMCID: PMC1576047.