Vatiquinone

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

MedKoo CAT#: 319685

CAS#: 1213269-98-7

Description: Vatiquinone, also known as EPI 743, is an orally bioavailable para-benzoquinone being developed for inherited mitochondrial diseases. The mechanism of action of EPI-743 involves augmenting the synthesis of glutathione, optimizing metabolic control, enhancing the expression of genetic elements critical for cellular management of oxidative stress, and acting at the mitochondria to regulate electron transport.


Price and Availability

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1g
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2g
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5g
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Vatiquinone is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319685
Name: Vatiquinone
CAS#: 1213269-98-7
Chemical Formula: C29H44O3
Exact Mass: 440.329
Molecular Weight: 440.668
Elemental Analysis: C, 79.04; H, 10.06; O, 10.89


Synonym: EPI743; EPI-743; EPI 743; Vatiquinone; alpha-Tocotrienol quinone. ATQ3;

IUPAC/Chemical Name: 2-((R,6E,10E)-3-hydroxy-3,7,11,15-tetramethylhexadeca-6,10,14-trien-1-yl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione

InChi Key: LNOVHERIIMJMDG-XZXLULOTSA-N

InChi Code: InChI=1S/C29H44O3/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8,32)19-17-26-25(7)27(30)23(5)24(6)28(26)31/h12,14,16,32H,9-11,13,15,17-19H2,1-8H3/b21-14+,22-16+/t29-/m1/s1

SMILES Code: O=C1C(CC[C@](C)(O)CC/C=C(C)/CC/C=C(C)/CC/C=C(C)\C)=C(C)C(C(C)=C1C)=O


Technical Data

Appearance:
White to off-white 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).

Harmonized System Code:
2934.99.90.01


Additional Information

Edison Pharmaceuticals is developing vatiquinone, which was awarded Fast Track status for Friedreich's ataxia in March 2014.


References

1: Peragallo JH, Newman NJ. Is there treatment for Leber hereditary optic neuropathy? Curr Opin Ophthalmol. 2015 Nov;26(6):450-7. doi: 10.1097/ICU.0000000000000212. PubMed PMID: 26448041; PubMed Central PMCID: PMC4618295.

2: Miller DK, Menezes MJ, Simons C, Riley LG, Cooper ST, Grimmond SM, Thorburn DR, Christodoulou J, Taft RJ. Rapid identification of a novel complex I MT-ND3 m.10134C>A mutation in a Leigh syndrome patient. PLoS One. 2014 Aug 12;9(8):e104879. doi: 10.1371/journal.pone.0104879. eCollection 2014. PubMed PMID: 25118196; PubMed Central PMCID: PMC4130626.

3: Strawser CJ, Schadt KA, Lynch DR. Therapeutic approaches for the treatment of Friedreich's ataxia. Expert Rev Neurother. 2014 Aug;14(8):949-57. doi: 10.1586/14737175.2014.939173. Epub 2014 Jul 18. PubMed PMID: 25034024.

4: Enns GM. Treatment of mitochondrial disorders: antioxidants and beyond. J Child Neurol. 2014 Sep;29(9):1235-40. doi: 10.1177/0883073814538509. Epub 2014 Jun 30. PubMed PMID: 24985754.

5: Avula S, Parikh S, Demarest S, Kurz J, Gropman A. Treatment of mitochondrial disorders. Curr Treat Options Neurol. 2014 Jun;16(6):292. doi: 10.1007/s11940-014-0292-7. PubMed PMID: 24700433; PubMed Central PMCID: PMC4067597.

6: Hargreaves IP. Coenzyme Q10 as a therapy for mitochondrial disease. Int J Biochem Cell Biol. 2014 Apr;49:105-11. doi: 10.1016/j.biocel.2014.01.020. Epub 2014 Feb 2. Review. PubMed PMID: 24495877.

7: Chicani CF, Chu ER, Miller G, Kelman SE, Sadun AA. Comparing EPI-743 treatment in siblings with Leber's hereditary optic neuropathy mt14484 mutation. Can J Ophthalmol. 2013 Oct;48(5):e130-3. doi: 10.1016/j.jcjo.2013.05.011. PubMed PMID: 24093206.

8: Pastore A, Petrillo S, Tozzi G, Carrozzo R, Martinelli D, Dionisi-Vici C, Di Giovamberardino G, Ceravolo F, Klein MB, Miller G, Enns GM, Bertini E, Piemonte F. Glutathione: a redox signature in monitoring EPI-743 therapy in children with mitochondrial encephalomyopathies. Mol Genet Metab. 2013 Jun;109(2):208-14. doi: 10.1016/j.ymgme.2013.03.011. Epub 2013 Mar 24. PubMed PMID: 23583222.

9: Sadun AA, La Morgia C, Carelli V. Mitochondrial optic neuropathies: our travels from bench to bedside and back again. Clin Experiment Ophthalmol. 2013 Sep-Oct;41(7):702-12. doi: 10.1111/ceo.12086. Epub 2013 Apr 11. Review. PubMed PMID: 23433229.

10: Kerr DS. Review of clinical trials for mitochondrial disorders: 1997-2012. Neurotherapeutics. 2013 Apr;10(2):307-19. doi: 10.1007/s13311-013-0176-7. Review. PubMed PMID: 23361264; PubMed Central PMCID: PMC3625388.

11: Blankenberg FG, Kinsman SL, Cohen BH, Goris ML, Spicer KM, Perlman SL, Krane EJ, Kheifets V, Thoolen M, Miller G, Enns GM. Brain uptake of Tc99m-HMPAO correlates with clinical response to the novel redox modulating agent EPI-743 in patients with mitochondrial disease. Mol Genet Metab. 2012 Dec;107(4):690-9. doi: 10.1016/j.ymgme.2012.09.023. Epub 2012 Sep 28. PubMed PMID: 23084792.

12: Martinelli D, Catteruccia M, Piemonte F, Pastore A, Tozzi G, Dionisi-Vici C, Pontrelli G, Corsetti T, Livadiotti S, Kheifets V, Hinman A, Shrader WD, Thoolen M, Klein MB, Bertini E, Miller G. EPI-743 reverses the progression of the pediatric mitochondrial disease--genetically defined Leigh Syndrome. Mol Genet Metab. 2012 Nov;107(3):383-8. doi: 10.1016/j.ymgme.2012.09.007. Epub 2012 Sep 10. PubMed PMID: 23010433.

13: Büsing A, Drotleff AM, Ternes W. Identification of α-tocotrienolquinone epoxides and development of an efficient molecular distillation procedure for quantitation of α-tocotrienol oxidation products in food matrices by high-performance liquid chromatography with diode array and fluorescence detection. J Agric Food Chem. 2012 Aug 29;60(34):8302-13. doi: 10.1021/jf301137b. Epub 2012 Aug 16. PubMed PMID: 22747466.

14: Sadun AA, Chicani CF, Ross-Cisneros FN, Barboni P, Thoolen M, Shrader WD, Kubis K, Carelli V, Miller G. Effect of EPI-743 on the clinical course of the mitochondrial disease Leber hereditary optic neuropathy. Arch Neurol. 2012 Mar;69(3):331-8. doi: 10.1001/archneurol.2011.2972. PubMed PMID: 22410442.

15: Enns GM, Kinsman SL, Perlman SL, Spicer KM, Abdenur JE, Cohen BH, Amagata A, Barnes A, Kheifets V, Shrader WD, Thoolen M, Blankenberg F, Miller G. Initial experience in the treatment of inherited mitochondrial disease with EPI-743. Mol Genet Metab. 2012 Jan;105(1):91-102. doi: 10.1016/j.ymgme.2011.10.009. Epub 2011 Oct 21. PubMed PMID: 22115768.

16: Shrader WD, Amagata A, Barnes A, Enns GM, Hinman A, Jankowski O, Kheifets V, Komatsuzaki R, Lee E, Mollard P, Murase K, Sadun AA, Thoolen M, Wesson K, Miller G. α-Tocotrienol quinone modulates oxidative stress response and the biochemistry of aging. Bioorg Med Chem Lett. 2011 Jun 15;21(12):3693-8. doi: 10.1016/j.bmcl.2011.04.085. Epub 2011 Apr 24. PubMed PMID: 21600768.

17: Gagnon KT. HD Therapeutics - CHDI Fifth Annual Conference. IDrugs. 2010 Apr;13(4):219-23. PubMed PMID: 20373247.

18: Bidichandani SI, Delatycki MB. Friedreich Ataxia. 1998 Dec 18 [updated 2014 Jul 24]. In: Pagon RA, Adam MP, Ardinger HH, Wallace SE, Amemiya A, Bean LJH, Bird TD, Fong CT, Mefford HC, Smith RJH, Stephens K, editors. GeneReviews® [Internet]. Seattle (WA): University of Washington, Seattle; 1993-2016. Available from http://www.ncbi.nlm.nih.gov/books/NBK1281/ PubMed PMID: 20301458.

19: Yu-Wai-Man P, Chinnery PF. Leber Hereditary Optic Neuropathy. 2000 Oct 26 [updated 2013 Sep 19]. In: Pagon RA, Adam MP, Ardinger HH, Wallace SE, Amemiya A, Bean LJH, Bird TD, Fong CT, Mefford HC, Smith RJH, Stephens K, editors. GeneReviews® [Internet]. Seattle (WA): University of Washington, Seattle; 1993-2016. Available from http://www.ncbi.nlm.nih.gov/books/NBK1174/ PubMed PMID: 20301353.