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MedKoo Cat#: 326757 | Name: Tonabersat
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Description:

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

Tonabersat, also known as SB-220453, is gap-junction modulator for the prevention of migraine. Migraine is a common, recurrent, primary headache disorder associated with significant morbidity as well as high direct and indirect costs.

Chemical Structure

Tonabersat
Tonabersat
CAS#175013-84-0

Theoretical Analysis

MedKoo Cat#: 326757

Name: Tonabersat

CAS#: 175013-84-0

Chemical Formula: C20H19ClFNO4

Exact Mass: 391.0987

Molecular Weight: 391.82

Elemental Analysis: C, 61.31; H, 4.89; Cl, 9.05; F, 4.85; N, 3.57; O, 16.33

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 550.00 2 Weeks
25mg USD 1,250.00 2 Weeks
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Related CAS #
No Data
Synonym
SB-220453; SB 220453; SB220453; Tonabersat
IUPAC/Chemical Name
N-((3S,4S)-6-Acetyl-3-hydroxy-2,2-dimethylchroman-4-yl)-3-chloro-4-fluorobenzamide
InChi Key
XLIIRNOPGJTBJD-ROUUACIJSA-N
InChi Code
InChI=1S/C20H19ClFNO4/c1-10(24)11-5-7-16-13(8-11)17(18(25)20(2,3)27-16)23-19(26)12-4-6-15(22)14(21)9-12/h4-9,17-18,25H,1-3H3,(H,23,26)/t17-,18-/m0/s1
SMILES Code
O=C(N[C@@H]1[C@H](O)C(C)(C)OC2=C1C=C(C(C)=O)C=C2)C3=CC=C(F)C(Cl)=C3
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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 391.82 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
1: Schmidt ENC, Evert BO, Pregler BEF, Melhem A, Hsieh MC, Raspe M, Strobel H, Roos J, Pietsch T, Schuss P, Fischer-Posovszky P, Westhoff MA, Hölzel M, Herrlinger U, Vatter H, Waha A, Schneider M, Potthoff AL. Tonabersat enhances temozolomide-mediated cytotoxicity in glioblastoma by disrupting intercellular connectivity through connexin 43 inhibition. Mol Oncol. 2024 Dec 16. doi: 10.1002/1878-0261.13786. Epub ahead of print. PMID: 39680504. 2: Bhujbal S, Rupenthal ID, Agarwal P. Development and validation of a stability-indicating HPLC method for assay of tonabersat in pharmaceutical formulations. Methods. 2024 Nov;231:178-185. doi: 10.1016/j.ymeth.2024.10.001. Epub 2024 Oct 3. PMID: 39368764. 3: Cliff CL, Squires PE, Hills CE. Tonabersat suppresses priming/activation of the NOD-like receptor protein-3 (NLRP3) inflammasome and decreases renal tubular epithelial-to-macrophage crosstalk in a model of diabetic kidney disease. Cell Commun Signal. 2024 Jul 5;22(1):351. doi: 10.1186/s12964-024-01728-1. PMID: 38970061; PMCID: PMC11225428. 4: Zoteva V, De Meulenaere V, Vanhove C, Leybaert L, Raedt R, Pieters L, Vral A, Boterberg T, Deblaere K. Integrating and optimizing tonabersat in standard glioblastoma therapy: A preclinical study. PLoS One. 2024 Mar 15;19(3):e0300552. doi: 10.1371/journal.pone.0300552. PMID: 38489314; PMCID: PMC10942024. 5: Kwakowsky A, Chawdhary B, de Souza A, Meyer E, Kaye AH, Green CR, Stylli SS, Danesh-Meyer H. Tonabersat Significantly Reduces Disease Progression in an Experimental Mouse Model of Multiple Sclerosis. Int J Mol Sci. 2023 Dec 14;24(24):17454. doi: 10.3390/ijms242417454. PMID: 38139284; PMCID: PMC10744318. 6: McDouall A, Wassink G, Ranasinghe S, Zhou KQ, Karunasinghe RN, Dean JM, Davidson JO. Blockade of connexin hemichannels with tonabersat protects against mild hypoxic ischemic brain injury in neonatal rats. Exp Neurol. 2024 Jan;371:114611. doi: 10.1016/j.expneurol.2023.114611. Epub 2023 Nov 8. PMID: 37944882. 7: Mugisho OO, Aryal J, Shome A, Lyon H, Acosta ML, Green CR, Rupenthal ID. Orally Delivered Connexin43 Hemichannel Blocker, Tonabersat, Inhibits Vascular Breakdown and Inflammasome Activation in a Mouse Model of Diabetic Retinopathy. Int J Mol Sci. 2023 Feb 15;24(4):3876. doi: 10.3390/ijms24043876. PMID: 36835288; PMCID: PMC9961562. 8: Williams BM, Cliff CL, Demirel I, Squires PE, Hills CE. Blocking connexin 43 hemichannel-mediated ATP release reduces communication within and between tubular epithelial cells and medullary fibroblasts in a model of diabetic nephropathy. Diabet Med. 2022 Dec;39(12):e14963. doi: 10.1111/dme.14963. Epub 2022 Oct 25. PMID: 36256487; PMCID: PMC9828766. 9: Almad AA, Taga A, Joseph J, Gross SK, Welsh C, Patankar A, Richard JP, Rust K, Pokharel A, Plott C, Lillo M, Dastgheyb R, Eggan K, Haughey N, Contreras JE, Maragakis NJ. Cx43 hemichannels contribute to astrocyte-mediated toxicity in sporadic and familial ALS. Proc Natl Acad Sci U S A. 2022 Mar 29;119(13):e2107391119. doi: 10.1073/pnas.2107391119. Epub 2022 Mar 21. PMID: 35312356; PMCID: PMC9060483. 10: Lyon H, Yin N, Rupenthal ID, Green CR, Mugisho OO. Blocking connexin43 hemichannels prevents TGF-β2 upregulation and epithelial-mesenchymal transition in retinal pigment epithelial cells. Cell Biol Int. 2022 Feb;46(2):323-330. doi: 10.1002/cbin.11718. Epub 2021 Nov 9. PMID: 34719065. 11: Mat Nor MN, Rupenthal ID, Green CR, Acosta ML. Differential Action of Connexin Hemichannel and Pannexin Channel Therapeutics for Potential Treatment of Retinal Diseases. Int J Mol Sci. 2021 Feb 10;22(4):1755. doi: 10.3390/ijms22041755. PMID: 33578721; PMCID: PMC7916454. 12: Lyon H, Shome A, Rupenthal ID, Green CR, Mugisho OO. Tonabersat Inhibits Connexin43 Hemichannel Opening and Inflammasome Activation in an In Vitro Retinal Epithelial Cell Model of Diabetic Retinopathy. Int J Mol Sci. 2020 Dec 30;22(1):298. doi: 10.3390/ijms22010298. PMID: 33396676; PMCID: PMC7794685. 13: Louie HH, Shome A, Kuo CY, Rupenthal ID, Green CR, Mugisho OO. Connexin43 hemichannel block inhibits NLRP3 inflammasome activation in a human retinal explant model of diabetic retinopathy. Exp Eye Res. 2021 Jan;202:108384. doi: 10.1016/j.exer.2020.108384. Epub 2020 Dec 5. PMID: 33285185. 14: Acosta ML, Mat Nor MN, Guo CX, Mugisho OO, Coutinho FP, Rupenthal ID, Green CR. Connexin therapeutics: blocking connexin hemichannel pores is distinct from blocking pannexin channels or gap junctions. Neural Regen Res. 2021 Mar;16(3):482-488. doi: 10.4103/1673-5374.290097. PMID: 32985469; PMCID: PMC7996017. 15: Mat Nor MN, Rupenthal ID, Green CR, Acosta ML. Connexin Hemichannel Block Using Orally Delivered Tonabersat Improves Outcomes in Animal Models of Retinal Disease. Neurotherapeutics. 2020 Jan;17(1):371-387. doi: 10.1007/s13311-019-00786-5. PMID: 31637594; PMCID: PMC7007471. 16: De Meulenaere V, Bonte E, Verhoeven J, Kalala Okito JP, Pieters L, Vral A, De Wever O, Leybaert L, Goethals I, Vanhove C, Descamps B, Deblaere K. Adjuvant therapeutic potential of tonabersat in the standard treatment of glioblastoma: A preclinical F98 glioblastoma rat model study. PLoS One. 2019 Oct 21;14(10):e0224130. doi: 10.1371/journal.pone.0224130. PMID: 31634381; PMCID: PMC6802836. 17: Mugisho OO, Rupenthal ID, Paquet-Durand F, Acosta ML, Green CR. Targeting connexin hemichannels to control the inflammasome: the correlation between connexin43 and NLRP3 expression in chronic eye disease. Expert Opin Ther Targets. 2019 Oct;23(10):855-863. doi: 10.1080/14728222.2019.1673368. Epub 2019 Oct 11. PMID: 31554417. 18: Gava F, Rigal L, Mondesert O, Pesce E, Ducommun B, Lobjois V. Gap junctions contribute to anchorage-independent clustering of breast cancer cells. BMC Cancer. 2018 Feb 27;18(1):221. doi: 10.1186/s12885-018-4148-5. PMID: 29482519; PMCID: PMC5828067. 19: Younus I, Reddy DS. A resurging boom in new drugs for epilepsy and brain disorders. Expert Rev Clin Pharmacol. 2018 Jan;11(1):27-45. doi: 10.1080/17512433.2018.1386553. Epub 2017 Oct 23. PMID: 28956955. 20: Kim Y, Griffin JM, Nor MNM, Zhang J, Freestone PS, Danesh-Meyer HV, Rupenthal ID, Acosta M, Nicholson LFB, O'Carroll SJ, Green CR. Tonabersat Prevents Inflammatory Damage in the Central Nervous System by Blocking Connexin43 Hemichannels. Neurotherapeutics. 2017 Oct;14(4):1148-1165. doi: 10.1007/s13311-017-0536-9. PMID: 28560708; PMCID: PMC5722754.