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
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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Pharmacodynamics

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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Toxicity

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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Product Ingredients
IngredientUNIICASInChI Key
Mitoquinone mesylate6E01CG547T845959-50-4GVZFUVXPTPGOQT-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
  1. Tauskela JS: MitoQ--a mitochondria-targeted antioxidant. IDrugs. 2007 Jun;10(6):399-412. [Article]
PubChem Substance
347909923
ChemSpider
9563240
ChEMBL
CHEMBL1229093

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
2CompletedTreatmentParkinson's Disease (PD)1
2Not Yet RecruitingTreatmentDilated Cardiomyopathy (DCM)1
2TerminatedTreatmentFatty Liver, Non-alcoholic Fatty Liver Disease, NAFLD1
1RecruitingBasic ScienceChronic Obstructive Pulmonary Disease (COPD) / Heart Failure / High Blood Pressure (Hypertension) / Pulmonary Arterial Hypertension (PAH)1
1RecruitingTreatmentAsthma / Obesity1
1, 2CompletedTreatmentFatigue / Multiple Sclerosis1
1, 2RecruitingPreventionAntiviral Treatment / Coronavirus Disease 2019 (COVID‑19) / Viral Respiratory Tract Infection1
1, 2RecruitingTreatmentCoronavirus Disease 2019 (COVID‑19) / Fatigue / Multiple Sclerosis1
Not AvailableCompletedTreatmentAging1

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
PropertyValueSource
Water Solubility1.09e-05 mg/mLALOGPS
logP7.82ALOGPS
logP8.71ChemAxon
logS-7.8ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity175.48 m3·mol-1ChemAxon
Polarizability67.49 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Drug created at October 21, 2007 22:23 / Updated at May 10, 2021 12:42