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MedKoo Cat#: 573267 | Name: Arglabin
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Description:

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

Arglabin is a sesquiterpene lactone that attenuates inflammation by inhibiting NLRP3. Arglabin also protects pancreatic β-Cells from apoptosis and may help prevent Type 2 Diabetes Mellitus.

Chemical Structure

Arglabin
CAS#84692-91-1

Theoretical Analysis

MedKoo Cat#: 573267

Name: Arglabin

CAS#: 84692-91-1

Chemical Formula: C15H18O3

Exact Mass: 246.1256

Molecular Weight: 246.31

Elemental Analysis: C, 73.15; H, 7.37; O, 19.49

Price and Availability

Size Price Availability Quantity
5mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
(+)-Arglabin, Arglabin
IUPAC/Chemical Name
3H-Oxireno(8,8a)azuleno(4,5-b)furan-8(4aH)-one, 5,6,6a,7,9a,9b-hexahydro-1,4a-dimethyl-7-methylene-
InChi Key
UVJYAKBJSGRTHA-CUZKYEQNSA-N
InChi Code
1S/C15H18O3/c1-8-4-7-15-11(8)12-10(9(2)13(16)17-12)5-6-14(15,3)18-15/h4,10-12H,2,5-7H2,1,3H3/t10-,11+,12-,14-,15+/m0/s1
SMILES Code
CC1=CC[C@@]23[C@H]1[C@@H]4[C@@H](CC[C@@]2(O3)C)C(=C)C(=O)O4
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

Preparing Stock Solutions

The following data is based on the product molecular weight 246.31 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
1: Manayi A, Nabavi SM, Khayatkashani M, Habtemariam S, Khayat Kashani HR. Arglabin could target inflammasome-induced ARDS and cytokine storm associated with COVID-19. Mol Biol Rep. 2021 Dec;48(12):8221-8225. doi: 10.1007/s11033-021-06827-7. Epub 2021 Oct 15. PMID: 34655016; PMCID: PMC8519322. 2: Lone SH, Bhat KA, Khuroo MA. Arglabin: From isolation to antitumor evaluation. Chem Biol Interact. 2015 Oct 5;240:180-98. doi: 10.1016/j.cbi.2015.08.015. Epub 2015 Aug 29. PMID: 26327249. 3: El Gaafary M, Morad SAF, Schmiech M, Syrovets T, Simmet T. Arglabin, an EGFR receptor tyrosine kinase inhibitor, suppresses proliferation and induces apoptosis in prostate cancer cells. Biomed Pharmacother. 2022 Dec;156:113873. doi: 10.1016/j.biopha.2022.113873. Epub 2022 Oct 19. PMID: 36272260. 4: Adekenov SM, Shamilova ST, Khabarov IA. Analysis of arglabin and its derivatives using high-performance liquid chromatography. Phytochem Anal. 2021 Sep;32(5):780-784. doi: 10.1002/pca.3023. Epub 2021 Jan 6. PMID: 33410214. 5: Adekenov SM. Chemical modification of arglabin and biological activity of its new derivatives. Fitoterapia. 2016 Apr;110:196-205. doi: 10.1016/j.fitote.2015.11.018. Epub 2015 Nov 25. PMID: 26625839. 6: Ren Z, Yu P, Li D, Li Z, Liao Y, Wang Y, Zhou B, Wang L. Single-Cell Reconstruction of Progression Trajectory Reveals Intervention Principles in Pathological Cardiac Hypertrophy. Circulation. 2020 May 26;141(21):1704-1719. doi: 10.1161/CIRCULATIONAHA.119.043053. Epub 2020 Feb 26. PMID: 32098504. 7: Yang Y, Guo L, Wang J, Li W, Zhou X, Zhang C, Han C. Arglabin regulates microglia polarization to relieve neuroinflammation in Alzheimer's disease. J Biochem Mol Toxicol. 2022 Jun;36(6):e23045. doi: 10.1002/jbt.23045. Epub 2022 Mar 15. PMID: 35289014. 8: He W, Lai R, Lin Q, Huang Y, Wang L. Arglabin is a plant sesquiterpene lactone that exerts potent anticancer effects on human oral squamous cancer cells via mitochondrial apoptosis and downregulation of the mTOR/PI3K/Akt signaling pathway to inhibit tumor growth in vivo. J BUON. 2018 Nov- Dec;23(6):1679-1685. PMID: 30610794. 9: Adekenov S, Zhumakayeva A, Perminov V, Bekmanov B, Rakhimov K. Neoadjuvant Therapy with Drug Arglabin for Breast Cancer with Expression of H-Ras Oncoproteins. Asian Pac J Cancer Prev. 2020 Nov 1;21(11):3441-3447. doi: 10.31557/APJCP.2020.21.11.3441. PMID: 33247707; PMCID: PMC8033125. 10: Freeman TL, Swartz TH. Targeting the NLRP3 Inflammasome in Severe COVID-19. Front Immunol. 2020 Jun 23;11:1518. doi: 10.3389/fimmu.2020.01518. PMID: 32655582; PMCID: PMC7324760. 11: Shaikenov TE, Adekenov SM, Williams RM, Prashad N, Baker FL, Madden TL, Newman R. Arglabin-DMA, a plant derived sesquiterpene, inhibits farnesyltransferase. Oncol Rep. 2001 Jan-Feb;8(1):173-9. doi: 10.3892/or.8.1.173. PMID: 11115593. 12: Kalidindi S, Jeong WB, Schall A, Bandichhor R, Nosse B, Reiser O. Enantioselective synthesis of arglabin. Angew Chem Int Ed Engl. 2007;46(33):6361-3. doi: 10.1002/anie.200701584. PMID: 17634992. 13: Zhai JD, Li D, Long J, Zhang HL, Lin JP, Qiu CJ, Zhang Q, Chen Y. Biomimetic semisynthesis of arglabin from parthenolide. J Org Chem. 2012 Aug 17;77(16):7103-7. doi: 10.1021/jo300888s. Epub 2012 Aug 9. PMID: 22849854. 14: Hafiane A, Daskalopoulou SS. Targeting the residual cardiovascular risk by specific anti-inflammatory interventions as a therapeutic strategy in atherosclerosis. Pharmacol Res. 2022 Apr;178:106157. doi: 10.1016/j.phrs.2022.106157. Epub 2022 Mar 4. PMID: 35257900. 15: Zhumakayeva A, Rakhimov K, Sirota V, Arystan L, Madiyarov A, Adekenov S. LONG-TERM RESULTS OF COMBINATION THERAPY FOR LOCALLY ADVANCED BREAST CANCER. Georgian Med News. 2018 Sep;(282):30-35. PMID: 30358536. 16: Abderrazak A, El Hadri K, Bosc E, Blondeau B, Slimane MN, Büchele B, Simmet T, Couchie D, Rouis M. Inhibition of the Inflammasome NLRP3 by Arglabin Attenuates Inflammation, Protects Pancreatic β-Cells from Apoptosis, and Prevents Type 2 Diabetes Mellitus Development in ApoE2Ki Mice on a Chronic High- Fat Diet. J Pharmacol Exp Ther. 2016 Jun;357(3):487-94. doi: 10.1124/jpet.116.232934. Epub 2016 Apr 4. PMID: 27044804. 17: Abderrazak A, Couchie D, Mahmood DF, Elhage R, Vindis C, Laffargue M, Matéo V, Büchele B, Ayala MR, El Gaafary M, Syrovets T, Slimane MN, Friguet B, Fulop T, Simmet T, El Hadri K, Rouis M. Anti-inflammatory and antiatherogenic effects of the NLRP3 inflammasome inhibitor arglabin in ApoE2.Ki mice fed a high-fat diet. Circulation. 2015 Mar 24;131(12):1061-70. doi: 10.1161/CIRCULATIONAHA.114.013730. Epub 2015 Jan 22. PMID: 25613820. 18: Schepetkin IA, Kirpotina LN, Mitchell PT, Kishkentaeva АS, Shaimerdenova ZR, Atazhanova GA, Adekenov SM, Quinn MT. The natural sesquiterpene lactones arglabin, grosheimin, agracin, parthenolide, and estafiatin inhibit T cell receptor (TCR) activation. Phytochemistry. 2018 Feb;146:36-46. doi: 10.1016/j.phytochem.2017.11.010. Epub 2017 Dec 22. PMID: 29216473; PMCID: PMC5750123. 19: Csuk R, Heinold A, Siewert B, Schwarz S, Barthel A, Kluge R, Ströhl D. Synthesis and biological evaluation of antitumor-active arglabin derivatives. Arch Pharm (Weinheim). 2012 Mar;345(3):215-22. doi: 10.1002/ardp.201100065. Epub 2011 Oct 14. Erratum in: Arch Pharm (Weinheim). 2012 Dec;345(12):1001. PMID: 21997763. 20: Kalyieva S, Minakova N, Yukhnevich-Nassonova Y. Cost-Effectiveness Analysis of the Original Drug Arglabin. Value Health. 2014 Nov;17(7):A734-5. doi: 10.1016/j.jval.2014.08.103. Epub 2014 Oct 26. PMID: 27202629.