Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H30O5 |
Molecular Weight | 338.4385 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(OC)C(=O)C(CCCCCCCCCCO)=C(C)C1=O
InChI
InChIKey=JGPMMRGNQUBGND-UHFFFAOYSA-N
InChI=1S/C19H30O5/c1-14-15(12-10-8-6-4-5-7-9-11-13-20)17(22)19(24-3)18(23-2)16(14)21/h20H,4-13H2,1-3H3
DescriptionSources: http://www.drugbank.ca/drugs/DB09081Curator's Comment: Description was created based on several resources including http://www.ncbi.nlm.nih.gov/pubmed/19283347 and https://www.drugs.com/uk/raxone.html
Sources: http://www.drugbank.ca/drugs/DB09081
Curator's Comment: Description was created based on several resources including http://www.ncbi.nlm.nih.gov/pubmed/19283347 and https://www.drugs.com/uk/raxone.html
Idebenone is a synthetic short-chain benzoquinone and a substrate for the enzyme NAD(P)H:quinone oxidoreductase (NQO1) capable of stimulating mitochondrial electron transport and supplementing cellular energy levels. Idebenone was initially developed by Takeda Pharmaceutical Company for the treatment of Alzheimer’s disease and other cognitive defects. This has been met with limited success. The Swiss company Santhera Pharmaceuticals has started to investigate it for the treatment of neuromuscular diseases. In 2010, early clinical trials for the treatment of Friedreich’s ataxia and Duchenne muscular dystrophy have been completed. In clinical trials, Idebenone (Raxone/Catena) had a positive impact on a measurement of respiratory function (Peak Expiratory Flow, or PEF) in non-ambulatory Duchenne muscular dystrophy patients who were not taking steroids. As of December 2013 the drug is not approved for these indications in North America or Europe. It is approved for the treatment of Leber's hereditary optic neuropathy (LHON) in Europe. Idebenone (Raxone) is indicated for the treatment of visual impairment in adolescent and adult patients with Leber’s Hereditary Optic Neuropathy (LHON). Because the number of patients with Leber's hereditary optic neuropathy is low, the disease is considered ‘rare’, and Raxone was designated an ‘orphan medicine’ on 15 February 2007. Idebenone is thought to help improve production of energy by restoring mitochondrial function, thereby preventing the cellular damage and the loss of sight seen in LHON. Idebenone is a rapidly absorbed, safe and well-tolerated drug and is currently the only clinically proven treatment option for Leber's hereditary optic neuropathy (LHON) patients.
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pubmed/7586900
Curator's Comment: Idebenone is an active CNS drug that inhibits lipid peroxidation and attenuates glutathione depletion via its antioxidant activity http://www.jpharmsci.org/article/S0022-3549(16)31541-6/pdf
Originator
Sources: http://www.ncbi.nlm.nih.gov/pubmed/19283347
Curator's Comment: Initially developed by Takeda Pharmaceuticals Company Ltd. (Takeda) for the treatment of patients with cognitive disorders and Alzheimer’s disease and was approved in Japan in 1986. # Takeda Pharmaceuticals Company Ltd. (Takeda)
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: map04210 Sources: http://www.ncbi.nlm.nih.gov/pubmed/23661043 |
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Target ID: WP408 Sources: http://www.ncbi.nlm.nih.gov/pubmed/23661043 |
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Target ID: CHEMBL614865 Sources: http://www.ncbi.nlm.nih.gov/pubmed/23473946 |
5.8 µM [IC50] | ||
Target ID: NADH oxidase activity (complexes I, III and IV) Sources: http://www.ncbi.nlm.nih.gov/pubmed/23473946 |
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Target ID: reactive oxygen species Sources: http://www.ncbi.nlm.nih.gov/pubmed/23473946 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Raxone Approved UseEuropean Medicines Agency approved Raxone in June 2015 Launch Date2015 |
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Primary | Catena Approved UseFor the treatment of Friedreich’s Ataxia Launch Date2008 |
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Primary | Avan Approved UseFor the improvement of cerebral metabolism and psychiatric symptoms in Alzheimer's disease. Launch Date1985 |
Sample Use Guides
The recommended dose is 900 mg/day idebenone (300 mg, 3 times a day).
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/23661043
Pretreatment with 10 uM idebenone led to an increase in viability of ONHA (optic nerve head astrocytes) after H2O2 treatment.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
N06BX13
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FDA ORPHAN DRUG |
232006
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FDA ORPHAN DRUG |
281909
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DSLD |
1468 (Number of products:13)
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EU-Orphan Drug |
EU/3/07/434
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FDA ORPHAN DRUG |
178303
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FDA ORPHAN DRUG |
231906
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EMA ASSESSMENT REPORTS |
SOVRIMA (REFUSED: FRIEDREICH ATAXIA)
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NCI_THESAURUS |
C275
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WHO-VATC |
QN06BX13
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EMA ASSESSMENT REPORTS |
RAXONE (AUTHORIZED: OPTIC ATROPHY, HEREDITARY, LEBER)
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Idebenone
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100000092647
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3686
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31687
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HB6PN45W4J
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DB09081
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51296
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m6199
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FG-11
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5465
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C74158
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SUB08114MIG
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HB6PN45W4J
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CHEMBL252556
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C036619
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759228
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58186-27-9
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1416
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DTXSID0040678
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ACTIVE MOIETY