84692-91-1

Basic information

• Product Name: arglabin
• Synonyms: arglabin;(3aR,4aS)-1,4aα-Dimethyl-7-methylene-4a,5,6,6aα,9aβ,9bα-hexahydro-3H-oxireno[8,8a]azuleno[4,5-b]furan-8(7H)-one;(3aS)-2,3,3aβ,4,5β,6,6a,7,9aβ,9bα-Decahydro-6α,6aα-epoxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2-one;3H-Oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one, 5,6,6a,7,9a,9b-hexahydro-1,4a-diMethyl-7-Methylene-, [4aS-(3aS*,4aα,6aα,9aβ,9bα)]-;Arglabine;(3aR,4aS,6aS,9aS,9bR)-5,6,6a,7,9a,9b-Hexahydro-1,4a-dimethyl-7-methylene-3H-oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one;3H-Oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one,5,6,6a,7,9a,9b-hexahydro-1,4a-dimethyl-7-methylene-, (3aR,4aS,6aS,9aS,9bR)
• CAS NO: 84692-91-1
• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.304
• Mol File: 84692-91-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 100-102 °C
• Boiling Point: 404.6°C at 760 mmHg
• Flash Point: 171.3°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 9.34E-07mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly)
• CAS DataBase Reference: arglabin(CAS DataBase Reference)
• NIST Chemistry Reference: arglabin(84692-91-1)
• EPA Substance Registry System: arglabin(84692-91-1)

Safety Data

• Hazardous Substances Data: 84692-91-1(Hazardous Substances Data)

Usage

Description

Arglabin is a new antineoplastic agent launched in Russia for the treatment of a variety of cancers. It is a sesquiterpene gamma-lactone extracted from Artemisia glabella, a plant from Kazakstan; it was first developed in Kazakstan followed by US and other countries as an ethical pharmaceutical. Arglabin can be obtained by resin extraction from A.glabella, purification by chromatography and finally recrystallization. Arglabin is a potent and selective inhibitor of farnesyl transferase, an enzyme critical to the function of the Ras oncogene in cancer cell reproduction. It showed a strong Inhibitory effect against tumor cells proliferation in in vitro models of transformed mouse hepatocytes and splenocytes. This cytotoxic effect against tumor cells was 50-100 times higher than that on intact cells. In many patients with various cancers, Arglabin was shown to stop or inhibit the tumour development, alone or in combination with other anticancer agents, and was reportedly well tolerated with few sideeffects. Promising response rates were also reported with Arglabin after treating other 《difficult-to-treat cancers》 such as breast, ovarian, lung or colon cancers.

Originator

NuOncology Labs (Kazakstan)

Uses

Arglabin is a sesquiterpene lactone used in the inhibition of glucose induced NF-kB activation and MCP-1/TGF-β1 expression treating diabetic nephropathy. Cytocoxic.

Definition

ChEBI: An organic heterotetracyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-dimethyl-1,3a,4,5,6,7-hexahydroazulen-5-yl group in which the double bond in the 7-membered ring has been epoxidised and in which the hydroxy group and the carboxy group have undergone formal condensation to give the corresponding gamma-lactone. It is found in Artemisia glabella. Arglabin-DMA HCl, the hydrochloride salt of the add ct resulting from the conjugate addition of dimethylamine to the ene-lactone moiety, has been successfully used in Khazakhstan for the treatment of breast, colon, ovarian and lung cancers.

InChI:InChI=1/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

Upstream product

• 68370-47-8 (3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylene-3a,4,5,7,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2(3H)-one 
• 81066-45-7 kauniolide 
• 503551-53-9 parthenolide 
• 1343403-10-0 (1R,3aR,4aS,6aS,9aS,9bS)-1-hydroxy-1,4a-dimethyl-7-methyleneoctahydro-1H-oxireno[2',3':8,8a]azuleno[4,5-b]furan-8(4aH)-one 

Downstream Products

• 1370045-04-7 2-({[(3aR,4aS,6aS,7S,9aS,9bR)-1,4a-dimethyl-8-oxo-4a,5,6,6a,7,8,9a,9b-octahydro-3H-oxireno[8,8a]azuleno[4,5-b]furan-7-yl]methyl}thio)benzoic acid 
• 6831-14-7 arborescin 
• 36416-50-9 3α,4α-epoxyarglabin 
• 36416-50-9 3β,4β-epoxyarglabin 

Relevant articles and documents

Chamomile lactone derivative as well as preparation method and application thereof (by machine translation)

The invention relates to the technical field of organic synthesis, in particular to a small white chrysanthemum lactone derivative and a preparation method and application thereof. To the invention, small white chrysanthemum is used as the original main raw material, 11 small white chrysanthemum lactone derivatives are synthesized through a series of chemical reactions, and the derivatives have certain anti-proliferative activity on glioblastoma cells. The invention also proves that the deuterated derivative DMAPAPAPAPAPT-D6 can significantly induce accumulation of active oxygen of glioblastoma cells, thereby leading DNA damage in glioblastoma cells. Furthermore, DMAPAPAPAPAPT-D6 promotes exogenous apoptosis mediated by the death receptor of caspase, indicating DNA damage induced by DMAPAPAPAPAPT-D6 inducible glioblastoma apoptosis. , ROS accumulation caused by DMAPAPAPAPAPT-D6 treatment leads DNA damage and death receptor-mediated apoptosis, which indicates that DMAPAPAPAPAPT-D6 with novel ingredients has therapeutic potential for treating glioblastoma and can be applied to preparation of drugs for treating glioblastoma. (by machine translation)

USES OF SESQUITERPENE LACTONE COMPOUNDS AND THEIR DERIVATIVES IN DRUGS PREPARATION

The present invention relates to the uses of sesquiterpene lactone compounds and their derivatives in preparing drugs. It belongs to the field of drug technology, specifically relates to the uses of the compounds of Formula (I) in preparing the drugs, especially the uses in preparing the drugs to treat rheumatoid arthritis and treat cancers through inhibiting cancer stem cells.

Sesquiterpene lactones and their derivatives inhibit high glucose-induced NF-κB activation and MCP-1 and TGF-β1 expression in rat mesangial cells

Diabetic nephropathy (DN) is one of the most common and serious chronic complications of diabetes mellitus, however, no efficient clinical drugs exist for the treatment of DN. We selected and synthesized several sesquiterpene lactones (SLs), and then used the MTT assay to detect rat mesangial cells (MCs) proliferation, ELISA to measure the expression level of monocyte chemoattractant protein-1 (MCP-1), transforming growth factor beta (TGF-β1) and fibronectin(FN), real-time fluorescent quantitative PCR analysis to measure the MCP-1 and TGF-β1 gene expression, western blot to detect the level of IκBα protein and EMSA to measure the activation of nuclear factor kappa B (NF-κB). We discovered that SLs, including parthenolide (PTL), micheliolide (MCL), arglabin, and isoalantolactone (IAL), as well as several synthetic analogs of these molecules, could effectively attenuate the high glucose-stimulated activation of NF-κB, the degradation of IκBα, and the expression of MCP-1, TGF-β1 and FN in rat mesangial cells (MCs). These findings suggest that SLs and their derivatives have potential as candidate drugs for the treatment of DN.