Identification
- Generic Name
- Mitoquinone
- DrugBank Accession Number
- DB05063
- Background
Mitoquinone is based on a novel technology, targeted lipophilic cations, that transport and concentrate antioxidants into the mitochondria -- organelles inside cells that provide energy for life processes -- where they accumulate up to a thousand fold. In 2004, a genomic study of hereditary early-onset Parkinson's disease demonstrated a direct molecular link between mitochondrial dysfunction and the pathogenesis of Parkinson's disease. Mitochondrial dysfunction also has been shown to represent an early critical event in the pathogenesis of the sporadic form of Parkinson's disease. Clinical studies by the Parkinson's Study Group show that very high doses of an antioxidant called Coenzyme Q (which Mitoquinone effectively targets into mitochondria) appear to slow the progression of Parkinson's disease symptoms.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Mitoquinone (DB05063)
- Weight
- Average: 583.728
Monoisotopic: 583.297173315 - Chemical Formula
- C37H44O4P
- Synonyms
- Mitoquinone cation
- Mitoquinone ion
Pharmacology
- Indication
Investigated for use/treatment in hepatitis (viral, C) and parkinson's disease.
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Mitoquinone may help to prevent the nerve cell damage that leads to Parkinson's disease. It aims to slow or halt Parkinson's disease at its cause by tackling cell damage caused when mitochondria cease to function normally. It is anticipated that MitoQ will slow or arrest the progression of Parkinson's disease symptoms. Hepatits C virus can directly alter mitochondrial function, leading to increased reactive oxygen species (free-radical) production that can lead to scarring of the liver and cirrhosis. Mitoquinone could be used to halt or decrease liver inflammation and fibrosis progression, even in the absence of sustained virologic response. Mitoquinone directly affects the mitochondria in two steps: a targeting component directs the drug to the mitochondria; and an antioxidant component helps to prevent cell damage.
- Mechanism of action
Mitoquinone is targeted to mitochondria by covalent attachment to a lipophilic triphenylphosphonium cation. Because of the large mitochondria membrane potential, the cations accumulate within cellular mitochondria up to 1,000 fold, compared to non-targeted antioxidants such as Coenzyme Q or its analogues, enabling the antioxidant moiety to block lipid peroxidation and protect mitochondria from oxidative damage. By selectively blocking mitochondrial oxidative damage, it prevents cell death.
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Mitoquinone mesylate 6E01CG547T 845959-50-4 GVZFUVXPTPGOQT-UHFFFAOYSA-M - International/Other Brands
- MitoQ
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 47BYS17IY0
- CAS number
- 444890-41-9
- InChI Key
- OIIMUKXVVLRCAF-UHFFFAOYSA-N
- InChI
- InChI=1S/C37H44O4P/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/h10-18,21-26H,4-9,19-20,27-28H2,1-3H3/q+1
- IUPAC Name
- [10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)decyl]triphenylphosphanium
- SMILES
- COC1=C(OC)C(=O)C(CCCCCCCCCC[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C(C)C1=O
References
- General References
- Tauskela JS: MitoQ--a mitochondria-targeted antioxidant. IDrugs. 2007 Jun;10(6):399-412. [Article]
- External Links
- PubChem Substance
- 347909923
- ChemSpider
- 9563240
- ChEMBL
- CHEMBL1229093
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Chronic Hepatitis C Virus (HCV) Infection 1 2 Completed Treatment Parkinson's Disease (PD) 1 2 Not Yet Recruiting Treatment Aging / Mild Cognitive Impairment (MCI) / Senescence 1 2 Recruiting Treatment Coronavirus Disease 2019 (COVID‑19) / Seasonal Allergic Rhinitis 1 2 Recruiting Treatment Dilated Cardiomyopathy (DCM) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 1.09e-05 mg/mL ALOGPS logP 7.82 ALOGPS logP 8.71 Chemaxon logS -7.8 ALOGPS pKa (Strongest Basic) -4.7 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 52.6 Å2 Chemaxon Rotatable Bond Count 16 Chemaxon Refractivity 175.48 m3·mol-1 Chemaxon Polarizability 67.49 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Drug created at October 21, 2007 22:23 / Updated at May 10, 2021 12:42