Mitoquinone mesylate

Mitoquinone mesylate (MitoQ) is a synthetic analogue of coenzyme Q10 which has antioxidant effects. It was first developed in New Zealand in the late 1990s.^[1] It has significantly improved bioavailability and improved mitochondrial penetration compared to coenzyme Q10,^[2][3] and has shown potential in a number of medical indications,^[4][5][6][7] being widely sold as a dietary supplement.^[8][9]

Mitoquinone mesylate

Clinical data
Trade names	MitoQ
Identifiers
IUPAC name 10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)decyl-triphenylphosphanium methanesulfonate
CAS Number	845959-50-4
PubChem CID	11388331
ChemSpider	9563239
UNII	6E01CG547T
ChEMBL	ChEMBL4074884
CompTox Dashboard (EPA)	DTXSID00233573
Chemical and physical data
Formula	C38H47O7PS
Molar mass	678.82 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=C(C(=O)C(=C(C1=O)OC)OC)CCCCCCCCCC[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.CS(=O)(=O)[O-]
InChI InChI=1S/C37H44O4P.CH4O3S/c1-29-33(35(39)37(41-3)36(40-2)34(29)38)27-19-8-6-4-5-7-9-20-28-42(30-21-13-10-14-22-30,31-23-15-11-16-24-31)32-25-17-12-18-26-32;1-5(2,3)4/h10-18,21-26H,4-9,19-20,27-28H2,1-3H3;1H3,(H,2,3,4)/q+1;/p-1 Key:GVZFUVXPTPGOQT-UHFFFAOYSA-M

A 2014 review found insufficient evidence for the use of mitoquinone mesylate in Parkinson's disease and other movement disorders.^[10]

See also

• Idebenone
• Nicotinamide mononucleotide
• Pyrroloquinoline quinone

References

1. US abandoned 20060229278, Taylor K, Smith R, "Mitoquinone derivatives used as mitochondrially targeted antioxidants.", published 12 October 2006, assigned to Antipodean Pharmaceuticals Inc
2. Battogtokh G, Choi YS, Kang DS, Park SJ, Shim MS, Huh KM, et al. (October 2018). "Mitochondria-targeting drug conjugates for cytotoxic, anti-oxidizing and sensing purposes: current strategies and future perspectives". Acta Pharmaceutica Sinica B. 8 (6): 862–880. doi:10.1016/j.apsb.2018.05.006. PMC 6251809. PMID 30505656.
3. Gutierrez-Mariscal FM, Arenas-de Larriva AP, Limia-Perez L, Romero-Cabrera JL, Yubero-Serrano EM, López-Miranda J (October 2020). "Coenzyme Q₁₀ Supplementation for the Reduction of Oxidative Stress: Clinical Implications in the Treatment of Chronic Diseases". International Journal of Molecular Sciences. 21 (21): 7870. doi:10.3390/ijms21217870. PMC 7660335. PMID 33114148.
4. Silva FS, Simoes RF, Couto R, Oliveira PJ (2016). "Targeting Mitochondria in Cardiovascular Diseases". Current Pharmaceutical Design. 22 (37): 5698–5717. doi:10.2174/1381612822666160822150243. PMID 27549376.
5. Kezic A, Spasojevic I, Lezaic V, Bajcetic M (2016). "Mitochondria-Targeted Antioxidants: Future Perspectives in Kidney Ischemia Reperfusion Injury". Oxidative Medicine and Cellular Longevity. 2016: 2950503. doi:10.1155/2016/2950503. PMC 4894993. PMID 27313826.
6. Oliver DM, Reddy PH (April 2019). "Small molecules as therapeutic drugs for Alzheimer's disease". Molecular and Cellular Neurosciences. 96: 47–62. doi:10.1016/j.mcn.2019.03.001. PMC 6510253. PMID 30877034.
7. Ismail H, Shakkour Z, Tabet M, Abdelhady S, Kobaisi A, Abedi R, et al. (October 2020). "Traumatic Brain Injury: Oxidative Stress and Novel Anti-Oxidants Such as Mitoquinone and Edaravone". Antioxidants. 9 (10): 943. doi:10.3390/antiox9100943. PMC 7601591. PMID 33019512.
8. Braakhuis AJ, Nagulan R, Somerville V (2018). "The Effect of MitoQ on Aging-Related Biomarkers: A Systematic Review and Meta-Analysis". Oxidative Medicine and Cellular Longevity. 2018: 8575263. doi:10.1155/2018/8575263. PMC 6079400. PMID 30116495.
9. Thoma A, Akter-Miah T, Reade RL, Lightfoot AP (August 2020). "Targeting reactive oxygen species (ROS) to combat the age-related loss of muscle mass and function". Biogerontology. 21 (4): 475–484. doi:10.1007/s10522-020-09883-x. PMC 7347670. PMID 32447556.
10. Liu J, Wang LN (January 2014). "Mitochondrial enhancement for neurodegenerative movement disorders: a systematic review of trials involving creatine, coenzyme Q10, idebenone and mitoquinone". CNS Drugs. 28 (1): 63–8. doi:10.1007/s40263-013-0124-4. PMID 24242074. S2CID 207486107.