Idebenone
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MedKoo CAT#: 329671

CAS#: 58186-27-9

Description: Idebenone, also known as CV 2619, ss a drug that was initially developed by Takeda Pharmaceutical Company for the treatment of Alzheimer's disease and other cognitive defects. As of December 2013 the drug is not approved for these indications in North America or Europe, but it is approved for the treatment of Leber's hereditary optic neuropathy (LHON) in Europe.

Chemical Structure

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Idebenone
CAS# 58186-27-9
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329671
Name: Idebenone
CAS#: 58186-27-9
Chemical Formula: C19H30O5
Exact Mass: 338.21
Molecular Weight: 338.444
Elemental Analysis: C, 67.43; H, 8.94; O, 23.64

Price and Availability

Size Price Availability Quantity
1g USD 150 Ready to ship
2g USD 250 Ready to ship
5g USD 450 2 weeks
10g USD 750 2 Weeks
25g USD 1450 2 weeks
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Synonym: Idebenone; CV 2619; CV-2619; CV2619; Catena, Raxone, Sovrima

IUPAC/Chemical Name: 2-(10-Hydroxydecyl)-5,6-dimethoxy-3-methyl-p-benzoquinone

InChi Key: JGPMMRGNQUBGND-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: O=C(C(OC)=C1OC)C(C)=C(CCCCCCCCCCO)C1=O

Appearance: Orange 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

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).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Certificate of Analysis:
View CoA: current batch, Lot#T7L09C22
Safety Data Sheet (SDS):
View Safety Data Sheet (SDS)
Instruction:
View handling instruction
Biological target: Idebenone (CV-2619) is a synthetic analog of coenzyme Q10 (CoQ10) and a brain stimulant.
In vitro activity: To detect the potential cytotoxicity of idebenone, the dose-dependent effects of idebenone (1, 2.5, 5, 7.5, 10, and 20 μM) on the survival of BV2 microglial cells was analyzed. The result demonstrated that idebenone was not cytotoxic to BV2 microglial cells at 1, 2.5, or 5 μM (Figure 1A). Activated microglia release various proinflammatory cytokines, NO and superoxide (Shao et al., 2013). The effects of idebenone on LPS-activated BV2 cells was then investigated. The data showed that idebenone (1, 2.5, and 5 μM) dose-dependently decreased the LPS-stimulated production of NO (p < 0.01; Figure 1B) and suppressed the mRNA expression of IL-6, IL-1β, TNF-α, and iNOS in LPS-stimulated BV2 cells (p < 0.05; Figure 1C). As shown in Figure 1, the most inhibition was observed at the concentration of 5 μM. Idebenone had little impact on microglia polarization in resting state, while it could suppress the expression of M1 markers (p < 0.05; Figure 2A) and promote activated microglia to alternatively M2 phenotype in conditions of inflammatory stimulation, as demonstrated by the increased expression of Arg-1, CD206, and YM (M2 markers) (p < 0.05; Figure 2B). Reference: Front Cell Neurosci. 2019 Jan 9;12:529. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30687016/
In vivo activity: Experimentation was conducted to identify whether idebenone treatment affected MPTP-induced dopaminergic neuronal death and neurobehavioral deficits. Mice received idebenone showed no visible disorders such as reduced appetite, infection, or inhibition of motor activity. The open field test and pole test are useful methods for evaluating the motor dysfunction caused by PD. For open field test, the mice’s paths on the 3rd and 7th days were mapped, which were recorded as the total distance mice traveled in 5 min. MPTP-treated mice that were pretreated with corn oil moved around the arena very little, compared with MPTP-treated mice that received idebenone (3 days: p < 0.01; 7 days: p < 0.001; Figures 5A,B). Corn oil-MPTP-treated mice demonstrated decreased locomotor activity, crossing fewer lines than corn oil-saline-treated mice (3 days: p < 0.001; 7 days: p < 0.001; Figures 5A,C). Idebenone-MPTP treated mice crossed more lines than corn oil-MPTP-treated mice (3 days: p < 0.01; 7 days: p < 0.01; Figures 5A,C). For the pole test, the time to descend for the corn oil-MPTP group was markedly prolonged compared with the corn oil-saline group (3 days: p < 0.001; 7 days: p < 0.01; Figure 5D). However, the time to descend of the idebenone-MPTP group was shortened to 8.69 ± 0.64 s (3 days, p < 0.01; Figure 5D), and 6.97 ± 0.54 s (7 days, p < 0.05; Figure 5D) compared with the corn oil-MPTP group. Reference: Front Cell Neurosci. 2019 Jan 9;12:529. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30687016/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 68.0 200.92
Ethanol 68.0 200.92

Preparing Stock Solutions

The following data is based on the product molecular weight 338.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol: 1. Yan A, Liu Z, Song L, Wang X, Zhang Y, Wu N, Lin J, Liu Y, Liu Z. Idebenone Alleviates Neuroinflammation and Modulates Microglial Polarization in LPS-Stimulated BV2 Cells and MPTP-Induced Parkinson's Disease Mice. Front Cell Neurosci. 2019 Jan 9;12:529. doi: 10.3389/fncel.2018.00529. PMID: 30687016; PMCID: PMC6333870. 2. Peng J, Wang H, Gong Z, Li X, He L, Shen Q, Pan J, Peng Y. Idebenone attenuates cerebral inflammatory injury in ischemia and reperfusion via dampening NLRP3 inflammasome activity. Mol Immunol. 2020 Jul;123:74-87. doi: 10.1016/j.molimm.2020.04.013. Epub 2020 May 18. PMID: 32438202.
In vivo protocol: 1. Yan A, Liu Z, Song L, Wang X, Zhang Y, Wu N, Lin J, Liu Y, Liu Z. Idebenone Alleviates Neuroinflammation and Modulates Microglial Polarization in LPS-Stimulated BV2 Cells and MPTP-Induced Parkinson's Disease Mice. Front Cell Neurosci. 2019 Jan 9;12:529. doi: 10.3389/fncel.2018.00529. PMID: 30687016; PMCID: PMC6333870. 2. Peng J, Wang H, Gong Z, Li X, He L, Shen Q, Pan J, Peng Y. Idebenone attenuates cerebral inflammatory injury in ischemia and reperfusion via dampening NLRP3 inflammasome activity. Mol Immunol. 2020 Jul;123:74-87. doi: 10.1016/j.molimm.2020.04.013. Epub 2020 May 18. PMID: 32438202.

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1: Montenegro L, Modica MN, Salerno L, Panico AM, Crascì L, Puglisi G, Romeo G. In Vitro Antioxidant Activity of Idebenone Derivative-Loaded Solid Lipid Nanoparticles. Molecules. 2017 May 27;22(6). pii: E887. doi: 10.3390/molecules22060887. PubMed PMID: 28555014.

2: Yu-Wai-Man P, Soiferman D, Moore DG, Burté F, Saada A. Evaluating the therapeutic potential of idebenone and related quinone analogues in Leber hereditary optic neuropathy. Mitochondrion. 2017 Jan 16. pii: S1567-7249(17)30012-0. doi: 10.1016/j.mito.2017.01.004. [Epub ahead of print] PubMed PMID: 28093355.

3: Contin M, Buontempo F, García Becerra C, Dobrecky C, Lucangioli S, Tripodi V. New Micellar Electrokinetic Chromatographic Method for Analyzing Idebenone in Pediatric Formulations. J Chromatogr Sci. 2017 Mar 1;55(3):351-357. doi: 10.1093/chromsci/bmw172. PubMed PMID: 27881490.

4: Schlatter J, Bourguignon E, Majoul E, Kabiche S, Balde IB, Cisternino S, Fontan JE. Stability study of oral pediatric idebenone suspensions. Pharm Dev Technol. 2017 Mar;22(2):296-299. doi: 10.1080/10837450.2016.1231811. Epub 2016 Sep 21. PubMed PMID: 27583702.

5: Buyse GM, Voit T, Schara U, Straathof CS, D'Angelo MG, Bernert G, Cuisset JM, Finkel RS, Goemans N, Rummey C, Leinonen M, Mayer OH, Spagnolo P, Meier T, McDonald CM; DELOS Study Group. Treatment effect of idebenone on inspiratory function in patients with Duchenne muscular dystrophy. Pediatr Pulmonol. 2017 Apr;52(4):508-515. doi: 10.1002/ppul.23547. Epub 2016 Aug 29. PubMed PMID: 27571420; PubMed Central PMCID: PMC5396356.

6: Guan Y, Li J, Zhan T, Wang JW, Yu JB, Yang L. Idebenone Maintains Survival of Mutant Myocilin Cells by Inhibiting Apoptosis. Chin Med J (Engl). 2016 Aug 20;129(16):2001-4. doi: 10.4103/0366-6999.187856. PubMed PMID: 27503028; PubMed Central PMCID: PMC4989434.

7: Lauro F, Ilari S, Giancotti LA, Ventura CA, Morabito C, Gliozzi M, Malafoglia V, Palma E, Paolino D, Mollace V, Muscoli C. Pharmacological effect of a new idebenone formulation in a model of carrageenan-induced inflammatory pain. Pharmacol Res. 2016 Sep;111:767-73. doi: 10.1016/j.phrs.2016.07.043. Epub 2016 Jul 29. PubMed PMID: 27480201.

8: Gómez-Murcia V, Torrecillas A, deGodos AM, Corbalán-García S, Gómez-Fernández JC. X-ray diffraction and NMR data for the study of the location of idebenone and idebenol in model membranes. Data Brief. 2016 Mar 24;7:981-9. doi: 10.1016/j.dib.2016.03.064. eCollection 2016 Jun. PubMed PMID: 27408910; PubMed Central PMCID: PMC4927974.

9: McDonald CM, Meier T, Voit T, Schara U, Straathof CS, D'Angelo MG, Bernert G, Cuisset JM, Finkel RS, Goemans N, Rummey C, Leinonen M, Spagnolo P, Buyse GM; DELOS Study Group. Idebenone reduces respiratory complications in patients with Duchenne muscular dystrophy. Neuromuscul Disord. 2016 Aug;26(8):473-80. doi: 10.1016/j.nmd.2016.05.008. Epub 2016 May 12. PubMed PMID: 27238057.

10: Gueven N. Idebenone for Leber's hereditary optic neuropathy. Drugs Today (Barc). 2016 Mar;52(3):173-81. doi: 10.1358/dot.2016.52.3.2463564. Review. PubMed PMID: 27186591.

11: Schiff M, Rustin P. Idebenone in Friedreich ataxia and Leber's hereditary optic neuropathy: close mechanisms, similar therapy? Brain. 2016 Jul;139(Pt 7):e39. doi: 10.1093/brain/aww085. Epub 2016 Apr 19. PubMed PMID: 27095078.

12: Lyseng-Williamson KA. Idebenone: A Review in Leber's Hereditary Optic Neuropathy. Drugs. 2016 May;76(7):805-13. doi: 10.1007/s40265-016-0574-3. PubMed PMID: 27071925.

13: Gómez-Murcia V, Torrecillas A, de Godos AM, Corbalán-García S, Gómez-Fernández JC. Both idebenone and idebenol are localized near the lipid-water interface of the membrane and increase its fluidity. Biochim Biophys Acta. 2016 Jun;1858(6):1071-81. doi: 10.1016/j.bbamem.2016.02.034. Epub 2016 Feb 27. PubMed PMID: 26926421.

14: Smith TG, Seto S, Ganne P, Votruba M. A randomized, placebo-controlled trial of the benzoquinone idebenone in a mouse model of OPA1-related dominant optic atrophy reveals a limited therapeutic effect on retinal ganglion cell dendropathy and visual function. Neuroscience. 2016 Apr 5;319:92-106. doi: 10.1016/j.neuroscience.2016.01.042. Epub 2016 Jan 25. PubMed PMID: 26820596.

15: Kombath S, Balde IB, Carret S, Kabiche S, Cisternino S, Fontan JE, Schlatter J. Stability-Indicating HPLC Assay for Determination of Idebenone in Pharmaceutical Forms. J Anal Methods Chem. 2015;2015:835986. doi: 10.1155/2015/835986. Epub 2015 Oct 29. PubMed PMID: 26605105; PubMed Central PMCID: PMC4641926.

16: Lauro MR, Carbone C, Sansone F, Ruozi B, Chillemi R, Sciuto S, Aquino RP, Puglisi G. Innovative oral spray-dried Idebenone systems to improve patient compliance. Drug Dev Ind Pharm. 2016;42(7):1127-36. doi: 10.3109/03639045.2015.1115870. Epub 2015 Dec 1. PubMed PMID: 26556126.

17: Lin P, Liu J, Ren M, Ji K, Li L, Zhang B, Gong Y, Yan C. Idebenone protects against oxidized low density lipoprotein induced mitochondrial dysfunction in vascular endothelial cells via GSK3β/β-catenin signalling pathways. Biochem Biophys Res Commun. 2015 Sep 25;465(3):548-55. doi: 10.1016/j.bbrc.2015.08.058. Epub 2015 Aug 15. PubMed PMID: 26284974.

18: Seo Y, Park J, Kim M, Lee HK, Kim JH, Jeong JH, Namkung W. Inhibition of ANO1/TMEM16A Chloride Channel by Idebenone and Its Cytotoxicity to Cancer Cell Lines. PLoS One. 2015 Jul 21;10(7):e0133656. doi: 10.1371/journal.pone.0133656. eCollection 2015. PubMed PMID: 26196390; PubMed Central PMCID: PMC4511415.

19: Arend N, Wertheimer C, Laubichler P, Wolf A, Kampik A, Kernt M. Idebenone Prevents Oxidative Stress, Cell Death and Senescence of Retinal Pigment Epithelium Cells by Stabilizing BAX/Bcl-2 Ratio. Ophthalmologica. 2015;234(2):73-82. doi: 10.1159/000381726. Epub 2015 Jun 4. PubMed PMID: 26044821.

20: Mercuri E, Muntoni F. Efficacy of idebenone in Duchenne muscular dystrophy. Lancet. 2015 May 2;385(9979):1704-6. doi: 10.1016/S0140-6736(15)60758-9. Epub 2015 Apr 20. PubMed PMID: 25907159.