Enpatoran | CAS#2101938-42-3 | Toll-Like receptor antagonist

MedKoo Cat#: 463650 | Name: Enpatoran free base

Description:

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

Enpatoran, also known as M5049, is a novel potent and selective TLR7/8 inhibitor for treatment of autoimmunity. M5049 showed potent and selective activity in a range of cellular assays for inhibition of TLR7/8 and block synthetic ligands and natural endogenous RNA ligands such as microRNA and Alu RNA. M5049 was found to be potent in vivo as TLR7/8 inhibition efficaciously treated disease in several murine lupus models. M5049 had greater potency in disease models than expected based on its in vitro potency and pharmacokinetic/pharmacodynamic properties. M5049 may be efficacious in treating autoimmunity and has the potential to provide benefit to a variety of patients with varying disease pathogenesis.

Chemical Structure

Enpatoran free base

CAS#2101938-42-3 (free base)

Theoretical Analysis

MedKoo Cat#: 463650

Name: Enpatoran free base

CAS#: 2101938-42-3 (free base)

Chemical Formula: C16H15F3N4

Exact Mass: 320.1249

Molecular Weight: 320.32

Elemental Analysis: C, 60.00; H, 4.72; F, 17.79; N, 17.49

Price and Availability

Size	Price	Availability
25mg	USD 650.00	2 Weeks
50mg	USD 1,050.00	2 Weeks
100mg	USD 1,850.00	2 Weeks
200mg	USD 2,850.00	2 Weeks

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Related CAS #

2101945-93-9 (HCl) 2409589-21-3 (2HCl) 2101938-42-3 (free base) 2409588-96-9 (TFA)

Synonym

Enpatoran; M 5049; M5049; M-5049;

IUPAC/Chemical Name

5-((3R,5S)-3-amino-5-(trifluoromethyl)piperidin-1-yl)quinoline-8-carbonitrile

InChi Key

BJXYHBKEQFQVES-PIJUOVFKSA-N

InChi Code

InChI=1S/C16H15F3N4/c17-16(18,19)11-6-12(21)9-23(8-11)14-4-3-10(7-20)15-13(14)2-1-5-22-15/h1-5,11-12H,6,8-9,21H2/t11?,12-/m1/s1

SMILES Code

N[C@]1([H])C[C@]([H])(C(F)(F)F)CN(C2=CC=C(C#N)C3=C2C=CC=N3)C1

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

>3 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 320.32 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.

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

1: Razak NA, Abu N, Ho WY, Zamberi NR, Tan SW, Alitheen NB, Long K, Yeap SK. Cytotoxicity of eupatorin in MCF-7 and MDA-MB-231 human breast cancer cells via cell cycle arrest, anti-angiogenesis and induction of apoptosis. Sci Rep. 2019 Feb 6;9(1):1514. doi: 10.1038/s41598-018-37796-w. PMID: 30728391; PMCID: PMC6365513. 2: Abd Razak N, Yeap SK, Alitheen NB, Ho WY, Yong CY, Tan SW, Tan WS, Long K. Eupatorin Suppressed Tumor Progression and Enhanced Immunity in a 4T1 Murine Breast Cancer Model. Integr Cancer Ther. 2020 Jan-Dec;19:1534735420935625. doi: 10.1177/1534735420935625. PMID: 32830560; PMCID: PMC7448146. 3: Ali Z, Radhakrishnan S, Avula B, Chittiboyina AG, Li J, Wu C, Khan IA. Eupatorin 3'-O-glucopyranoside, a trimethoxyflavonoid glucoside from the aerial parts of Salvia mellifera. Nat Prod Res. 2023 Jan;37(2):269-276. doi: 10.1080/14786419.2021.1969565. Epub 2021 Aug 26. PMID: 34435528. 4: González-Cortazar M, Salinas-Sánchez DO, Herrera-Ruiz M, Román-Ramos DC, Zamilpa A, Jiménez-Ferrer E, Ble-González EA, Álvarez-Fitz P, Castrejón-Salgado R, Pérez-García MD. Eupatorin and Salviandulin-A, with Antimicrobial and Anti- Inflammatory Effects from Salvia lavanduloides Kunth Leaves. Plants (Basel). 2022 Jun 30;11(13):1739. doi: 10.3390/plants11131739. PMID: 35807691; PMCID: PMC9269164. 5: Laavola M, Nieminen R, Yam MF, Sadikun A, Asmawi MZ, Basir R, Welling J, Vapaatalo H, Korhonen R, Moilanen E. Flavonoids eupatorin and sinensetin present in Orthosiphon stamineus leaves inhibit inflammatory gene expression and STAT1 activation. Planta Med. 2012 May;78(8):779-86. doi: 10.1055/s-0031-1298458. Epub 2012 Apr 19. PMID: 22516932. 6: Yam MF, Tan CS, Ahmad M, Shibao R. Mechanism of vasorelaxation induced by eupatorin in the rats aortic ring. Eur J Pharmacol. 2016 Oct 15;789:27-36. doi: 10.1016/j.ejphar.2016.06.047. Epub 2016 Jun 28. PMID: 27370961. 7: Salmela AL, Pouwels J, Kukkonen-Macchi A, Waris S, Toivonen P, Jaakkola K, Mäki-Jouppila J, Kallio L, Kallio MJ. The flavonoid eupatorin inactivates the mitotic checkpoint leading to polyploidy and apoptosis. Exp Cell Res. 2012 Mar 10;318(5):578-92. doi: 10.1016/j.yexcr.2011.12.014. Epub 2011 Dec 29. PMID: 22227008. 8: Rizou AEI, Nasi GI, Paikopoulos Y, Bezantakou DS, Vraila KD, Spatharas PM, Dimaki VD, Papandreou NC, Lamari FN, Chondrogianni N, Iconomidou VA. A Multilevel Study of Eupatorin and Scutellarein as Anti-Amyloid Agents in Alzheimer's Disease. Biomedicines. 2023 May 4;11(5):1357. doi: 10.3390/biomedicines11051357. PMID: 37239029; PMCID: PMC10216506. 9: Li L, Chen Y, Feng X, Yin J, Li S, Sun Y, Zhang L. Identification of Metabolites of Eupatorin in Vivo and in Vitro Based on UHPLC-Q-TOF-MS/MS. Molecules. 2019 Jul 23;24(14):2658. doi: 10.3390/molecules24142658. PMID: 31340434; PMCID: PMC6680898. 10: Adams JH, Lewis JR. Eupatorin, a constituent of Merrillia caloxylon. Planta Med. 1977 Aug;32(1):86-7. doi: 10.1055/s-0028-1097564. PMID: 905420. 11: Estévez S, Marrero MT, Quintana J, Estévez F. Eupatorin-induced cell death in human leukemia cells is dependent on caspases and activates the mitogen- activated protein kinase pathway. PLoS One. 2014 Nov 12;9(11):e112536. doi: 10.1371/journal.pone.0112536. PMID: 25390937; PMCID: PMC4229185. 12: Sahid EDN, Claudino JC, Oda FB, Carvalho FA, Santos AGD, Graminha MAS, Clementino LDC. Baccharis trimera (Less.) DC leaf derivatives and eupatorin activities against Leishmania amazonensis. Nat Prod Res. 2022 Mar;36(6):1599-1603. doi: 10.1080/14786419.2021.1887175. Epub 2021 Feb 13. PMID: 33586545. 13: Dolečková I, Rárová L, Grúz J, Vondrusová M, Strnad M, Kryštof V. Antiproliferative and antiangiogenic effects of flavone eupatorin, an active constituent of chloroform extract of Orthosiphon stamineus leaves. Fitoterapia. 2012 Sep;83(6):1000-7. doi: 10.1016/j.fitote.2012.06.002. Epub 2012 Jun 12. PMID: 22698713. 14: Feng R, Li L, Zhang X, Zhang Y, Chen Y, Feng X, Zhang L, Zhang G. Assessment of a developed HPLC-MS/MS approach for determining plasma eupatorin in rats and its application in pharmacokinetics analysis. RSC Adv. 2020 Aug 28;10(53):32020-32026. doi: 10.1039/d0ra03350b. PMID: 35518153; PMCID: PMC9056642. 15: Tousi MS, Sepehri H, Khoee S, Farimani MM, Delphi L, Mansourizadeh F. Evaluation of apoptotic effects of mPEG-b-PLGA coated iron oxide nanoparticles as a eupatorin carrier on DU-145 and LNCaP human prostate cancer cell lines. J Pharm Anal. 2021 Feb;11(1):108-121. doi: 10.1016/j.jpha.2020.04.002. Epub 2020 Apr 18. PMID: 33717617; PMCID: PMC7930876. 16: Xu H, Yao N, Xu H, Wang T, Li G, Li Z. Characterization of the interaction between eupatorin and bovine serum albumin by spectroscopic and molecular modeling methods. Int J Mol Sci. 2013 Jul 9;14(7):14185-203. doi: 10.3390/ijms140714185. PMID: 23839090; PMCID: PMC3742238. 17: Namazi Sarvestani N, Sepehri H, Delphi L, Moridi Farimani M. Eupatorin and Salvigenin Potentiate Doxorubicin-Induced Apoptosis and Cell Cycle Arrest in HT-29 and SW948 Human Colon Cancer Cells. Asian Pac J Cancer Prev. 2018 Jan 27;19(1):131-139. doi: 10.22034/APJCP.2018.19.1.131. PMID: 29373904; PMCID: PMC5844607. 18: Androutsopoulos V, Arroo RR, Hall JF, Surichan S, Potter GA. Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1-mediated metabolism. Breast Cancer Res. 2008;10(3):R39. doi: 10.1186/bcr2090. Epub 2008 May 2. PMID: 18454852; PMCID: PMC2481486. 19: Hong F, Zhao M, Xue LL, Ma X, Liu L, Cai XY, Zhang RJ, Li N, Wang L, Ni HF, Wu WS, Ye HY, Chen LJ. The ethanolic extract of Artemisia anomala exerts anti- inflammatory effects via inhibition of NLRP3 inflammasome. Phytomedicine. 2022 Jul 20;102:154163. doi: 10.1016/j.phymed.2022.154163. Epub 2022 May 10. PMID: 35597027. 20: Yam MF, Mohamed EA, Ang LF, Pei L, Darwis Y, Mahmud R, Asmawi MZ, Basir R, Ahmad M. A simple isocratic HPLC method for the simultaneous determination of sinensetin, eupatorin, and 3'-hydroxy-5,6,7,4'-tetramethoxyflavone in Orthosiphon stamineus extracts. J Acupunct Meridian Stud. 2012 Aug;5(4):176-82. doi: 10.1016/j.jams.2012.05.005. Epub 2012 Jun 15. PMID: 22898066.

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