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MedKoo Cat#: 571158 | Name: Docebenone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Docebenone is an inhibitor of 5-lipoxygenase (5-LO; IC50 = 0.8 µM). It is greater than 100-fold selective for 5-LO over 12-LO and cyclooxygenase (COX). Docebenone inhibits the production of 5-HETE and leukotriene B4 (LTB4) induced by A23187 with IC50 values of 0.03 and 0.08 µM, respectively, in isolated rat peritoneal macrophages. It reduces paw edema, pleurisy, and cell infiltration induced by carrageenan in rats when administered at a dose of 80 mg/kg. Docebenone (20 mg/kg) reduces ovalbumin-induced bronchoconstriction in an ovalbumin-sensitized guinea pig model of experimental allergic asthma.

Chemical Structure

Docebenone
Docebenone
CAS#80809-81-0

Theoretical Analysis

MedKoo Cat#: 571158

Name: Docebenone

CAS#: 80809-81-0

Chemical Formula: C21H26O3

Exact Mass: 326.1882

Molecular Weight: 326.44

Elemental Analysis: C, 77.27; H, 8.03; O, 14.70

Price and Availability

Size Price Availability Quantity
5mg USD 750.00 2 Weeks
10mg USD 1,100.00 2 Weeks
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Related CAS #
No Data
Synonym
Docebenone; Docebenona; Docebenonum; A61589; A-61589; A 61589; AA 861; AA-861; AA861;
IUPAC/Chemical Name
2,5-Cyclohexadiene-1,4-dione, 2-(12-hydroxy-5,10-dodecadiynyl)-3,5,6-trimethyl-
InChi Key
WDEABJKSGGRCQA-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H26O3/c1-16-17(2)21(24)19(18(3)20(16)23)14-12-10-8-6-4-5-7-9-11-13-15-22/h22H,5,7-10,12,14-15H2,1-3H3
SMILES Code
O=C1C(CCCCC#CCCCC#CCO)=C(C)C(C(C)=C1C)=O
Appearance
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
Solvent mg/mL mM
Solubility
DMSO, sonicated 250.0 765.84
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 326.44 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
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Dexmedetomidine-induced contraction involves c-Jun NH2 -terminal kinase phosphorylation through activation of the 5-lipoxygenase pathway in the isolated endothelium-denuded rat aorta. Clin Exp Pharmacol Physiol. 2014 Dec;41(12):1014-22. doi: 10.1111/1440-1681.12307. PMID: 25224579. 7: Siddiqui T, Lively S, Ferreira R, Wong R, Schlichter LC. Expression and contributions of TRPM7 and KCa2.3/SK3 channels to the increased migration and invasion of microglia in anti-inflammatory activation states. PLoS One. 2014 Aug 22;9(8):e106087. doi: 10.1371/journal.pone.0106087. PMID: 25148577; PMCID: PMC4141841. 8: Huang Y, Tan Q, Wu Y, Zhu H, Xiong M, Hu J. RNA Interference Protects Against 5-Lipoxygenase-Induced Cocarcinogen, Benzidine, Oxidation and Cytotoxicity in Human Tracheobronchial Epithelial Cells. Int J Toxicol. 2014 Jul;33(4):297-306. doi: 10.1177/1091581814542030. Epub 2014 Jul 7. PMID: 25001243. 9: Li L, Liu YR, Gao S, Li JF, Li SS, Zhang DD, Liu S, Bai L, Zheng SJ, Duan ZP, Qi M, Chen Y. Inhibition of 5-lipoxygenase pathway attenuates acute liver failure by inhibiting macrophage activation. J Immunol Res. 2014;2014:697560. doi: 10.1155/2014/697560. Epub 2014 Jun 1. PMID: 24987711; PMCID: PMC4058580. 10: Gouix E, Buisson A, Nieoullon A, Kerkerian-Le Goff L, Tauskela JS, Blondeau N, Had-Aissouni L. Oxygen glucose deprivation-induced astrocyte dysfunction provokes neuronal death through oxidative stress. Pharmacol Res. 2014 Sep;87:8-17. doi: 10.1016/j.phrs.2014.06.002. Epub 2014 Jun 11. PMID: 24928737. 11: Chaves MM, Marques-da-Silva C, Monteiro AP, Canetti C, Coutinho-Silva R. Leukotriene B4 modulates P2X7 receptor-mediated Leishmania amazonensis elimination in murine macrophages. J Immunol. 2014 May 15;192(10):4765-73. doi: 10.4049/jimmunol.1301058. Epub 2014 Apr 11. PMID: 24729618. 12: Magi S, Takemoto Y, Kobayashi H, Kasamatsu M, Akita T, Tanaka A, Takano K, Tashiro E, Igarashi Y, Imoto M. 5-Lipoxygenase and cysteinyl leukotriene receptor 1 regulate epidermal growth factor-induced cell migration through Tiam1 upregulation and Rac1 activation. Cancer Sci. 2014 Mar;105(3):290-6. doi: 10.1111/cas.12340. Epub 2014 Jan 28. PMID: 24350867; PMCID: PMC4317946. 13: Chen CK, Huang Y, Wu Y, Wang J, Hu JA. [Study on activation of benzo(a)pyrene and DNA damage mediated by lipoxygenase in human bronchial epithelial cells]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2013 Sep;31(9):641-8. Chinese. PMID: 24064117. 14: Lee HM, Ok SH, Sung HJ, Eun SY, Kim HJ, Lee SH, Kang S, Shin IW, Lee HK, Chung YK, Choi MJ, Bae SI, Sohn JT. Mepivacaine-induced contraction involves phosphorylation of extracellular signal-regulated kinase through activation of the lipoxygenase pathway in isolated rat aortic smooth muscle. Can J Physiol Pharmacol. 2013 Apr;91(4):285-94. doi: 10.1139/cjpp-2012-0197. Epub 2013 Jan 2. PMID: 23627840. 15: Nguyen MV, Lardy B, Rousset F, Hazane-Puch F, Zhang L, Trocmé C, Serrander L, Krause KH, Morel F. Quinone compounds regulate the level of ROS production by the NADPH oxidase Nox4. Biochem Pharmacol. 2013 Jun 1;85(11):1644-54. doi: 10.1016/j.bcp.2013.03.023. Epub 2013 Apr 9. PMID: 23583257. 16: Gregus AM, Dumlao DS, Wei SC, Norris PC, Catella LC, Meyerstein FG, Buczynski MW, Steinauer JJ, Fitzsimmons BL, Yaksh TL, Dennis EA. Systematic analysis of rat 12/15-lipoxygenase enzymes reveals critical role for spinal eLOX3 hepoxilin synthase activity in inflammatory hyperalgesia. FASEB J. 2013 May;27(5):1939-49. doi: 10.1096/fj.12-217414. Epub 2013 Feb 4. PMID: 23382512; PMCID: PMC3633813. 17: Romero D, Sanabria-Valentín E, Vlamakis H, Kolter R. Biofilm inhibitors that target amyloid proteins. Chem Biol. 2013 Jan 24;20(1):102-10. doi: 10.1016/j.chembiol.2012.10.021. PMID: 23352144; PMCID: PMC3559003. 18: Czapski GA, Czubowicz K, Strosznajder RP. Evaluation of the antioxidative properties of lipoxygenase inhibitors. Pharmacol Rep. 2012;64(5):1179-88. doi: 10.1016/s1734-1140(12)70914-3. PMID: 23238474. 19: Wylam ME, Xue A, Sieck GC. Mechanisms of intrinsic force in small human airways. Respir Physiol Neurobiol. 2012 Apr 15;181(1):99-108. doi: 10.1016/j.resp.2012.01.011. Epub 2012 Feb 2. PMID: 22322114; PMCID: PMC4066449. 20: Sunaga T, Oh N, Hosoya K, Takagi S, Okumura M. Pro-apoptotic effects of tepoxalin, a cyclooxygenase/lipoxygenase dual inhibitor, on canine synovial fibroblasts. J Vet Med Sci. 2012 Jun;74(6):745-50. doi: 10.1292/jvms.11-0435. Epub 2012 Jan 12. PMID: 22240988.