Tonabersat | SB-220453 | CAS#175013-84-0 | gap-junction modulator

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

MedKoo CAT#: 326757

CAS#: 175013-84-0

Description: 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

CAS# 175013-84-0

Instruction

Theoretical Analysis

MedKoo Cat#: 326757
Name: Tonabersat
CAS#: 175013-84-0
Chemical Formula: C20H19ClFNO4
Exact Mass: 391.10
Molecular Weight: 391.823
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
5mg	USD 350	2 Weeks
10mg	USD 550	2 Weeks
25mg	USD 1250	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

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.

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:
In vivo protocol:

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1: Chen Q, Boire A, Jin X, Valiente M, Er EE, Lopez-Soto A, Jacob LS, Patwa R, Shah H, Xu K, Cross JR, Massagué J. Carcinoma-astrocyte gap junctions promote brain metastasis by cGAMP transfer. Nature. 2016 May 18;533(7604):493-8. doi: 10.1038/nature18268. PubMed PMID: 27225120.

2: Diener HC, Charles A, Goadsby PJ, Holle D. New therapeutic approaches for the prevention and treatment of migraine. Lancet Neurol. 2015 Oct;14(10):1010-22. doi: 10.1016/S1474-4422(15)00198-2. Review. PubMed PMID: 26376968.

3: Sarrouilhe D, Dejean C, Mesnil M. Involvement of gap junction channels in the pathophysiology of migraine with aura. Front Physiol. 2014 Feb 25;5:78. doi: 10.3389/fphys.2014.00078. eCollection 2014. Review. PubMed PMID: 24611055; PubMed Central PMCID: PMC3933780.

4: Cao Y, Zheng OJ. Tonabersat for migraine prophylaxis: a systematic review. Pain Physician. 2014 Jan-Feb;17(1):1-8. Review. PubMed PMID: 24452641.

5: Costa C, Tozzi A, Rainero I, Cupini LM, Calabresi P, Ayata C, Sarchielli P. Cortical spreading depression as a target for anti-migraine agents. J Headache Pain. 2013 Jul 23;14:62. doi: 10.1186/1129-2377-14-62. Review. PubMed PMID: 23879550; PubMed Central PMCID: PMC3728002.

6: Bialer M, Johannessen SI, Levy RH, Perucca E, Tomson T, White HS. Progress report on new antiepileptic drugs: a summary of the Eleventh Eilat Conference (EILAT XI). Epilepsy Res. 2013 Jan;103(1):2-30. doi: 10.1016/j.eplepsyres.2012.10.001. Epub 2012 Dec 4. Review. PubMed PMID: 23219031.

7: Lionetto L, Negro A, Palmisani S, Gentile G, Del Fiore MR, Mercieri M, Simmaco M, Smith T, Al-Kaisy A, Arcioni R, Martelletti P. Emerging treatment for chronic migraine and refractory chronic migraine. Expert Opin Emerg Drugs. 2012 Sep;17(3):393-406. doi: 10.1517/14728214.2012.709846. Epub 2012 Aug 3. Review. PubMed PMID: 22862686.

8: Barbanti P, Aurilia C, Egeo G, Fofi L. Future trends in drugs for migraine prophylaxis. Neurol Sci. 2012 May;33 Suppl 1:S137-40. doi: 10.1007/s10072-012-1058-1. Review. PubMed PMID: 22644189.

9: Sarrouilhe D, Dejean C. [Gap junctional intercellular communication: a new mechanism in pathophysiology of migraine with aura. Therapeutic applications]. Pathol Biol (Paris). 2012 Dec;60(6):392-8. doi: 10.1016/j.patbio.2012.04.002. Epub 2012 May 25. Review. French. PubMed PMID: 22633071.

10: Barbanti P, Aurilia C, Egeo G, Fofi L. Migraine prophylaxis: what is new and what we need? Neurol Sci. 2011 May;32 Suppl 1:S111-5. doi: 10.1007/s10072-011-0526-3. Review. PubMed PMID: 21533725.

11: Olesen J, Ashina M. Emerging migraine treatments and drug targets. Trends Pharmacol Sci. 2011 Jun;32(6):352-9. doi: 10.1016/j.tips.2011.02.016. Epub 2011 Apr 2. Review. PubMed PMID: 21459461.

12: Shimizu T, Shibata M, Suzuki N. [Migraine: advances in the pathophysiology and treatment]. Rinsho Shinkeigaku. 2011 Feb;51(2):103-9. Review. Japanese. PubMed PMID: 21404609.

13: Hauge AW, Hougaard A, Olesen J. On the methodology of drug trials in migraine with aura. Cephalalgia. 2010 Sep;30(9):1041-8. doi: 10.1177/0333102409359091. Epub 2010 Apr 27. PubMed PMID: 20713554.

14: Loder E. Design considerations in migraine with aura trials: learning from experience. Cephalalgia. 2010 Sep;30(9):1027-8. doi: 10.1177/0333102410368441. Epub 2010 Apr 26. PubMed PMID: 20713552.

15: Garza I. Tonabersat: a cortical spreading depression inhibitor as potential pharmacologic prophylaxis in migraine with aura. Curr Neurol Neurosci Rep. 2010 Jan;10(1):7-9. doi: 10.1007/s11910-009-0083-9. PubMed PMID: 20425219.

16: Silberstein SD. Tonabersat, a novel gap-junction modulator for the prevention of migraine. Cephalalgia. 2009 Nov;29 Suppl 2:28-35. doi: 10.1111/j.1468-2982.2009.01973.x. Review. PubMed PMID: 19723123.

17: Silberstein SD, Schoenen J, Göbel H, Diener HC, Elkind AH, Klapper JA, Howard RA. Tonabersat, a gap-junction modulator: efficacy and safety in two randomized, placebo-controlled, dose-ranging studies of acute migraine. Cephalalgia. 2009 Nov;29 Suppl 2:17-27. doi: 10.1111/j.1468-2982.2009.01974.x. PubMed PMID: 19723122.

18: Dahlöf CG, Hauge AW, Olesen J. Efficacy and safety of tonabersat, a gap-junction modulator, in the acute treatment of migraine: a double-blind, parallel-group, randomized study. Cephalalgia. 2009 Nov;29 Suppl 2:7-16. doi: 10.1111/j.1468-2982.2009.01975.x. PubMed PMID: 19723121.

19: Durham PL, Garrett FG. Neurological mechanisms of migraine: potential of the gap-junction modulator tonabersat in prevention of migraine. Cephalalgia. 2009 Nov;29 Suppl 2:1-6. doi: 10.1111/j.1468-2982.2009.01976.x. Review. PubMed PMID: 19723120; PubMed Central PMCID: PMC3142555.

20: Dodick DW. Tonabersat for migraine prevention: new life or last gasp? Lancet Neurol. 2009 Aug;8(8):693-5. doi: 10.1016/S1474-4422(09)70174-7. Epub 2009 Jun 29. PubMed PMID: 19570718.

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