ChemicalBook--->CAS DataBase List--->84692-91-1

84692-91-1

84692-91-1 Structure

84692-91-1 Structure
IdentificationBack Directory
[Name]

arglabin
[CAS]

84692-91-1
[Synonyms]

CS-1320
arglabin
Arglabine
Arglabin, BR
(+)-Arglabin
Arglabin 84692-91-1
Arglabin ((+)-Arglabin)
(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
(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
(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)
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)]-
[Molecular Formula]

C15H18O3
[MDL Number]

MFCD11519463
[MOL File]

84692-91-1.mol
[Molecular Weight]

246.3
Chemical PropertiesBack Directory
[Melting point ]

100-102 °C
[Boiling point ]

404.6±45.0 °C(Predicted)
[density ]

1.22±0.1 g/cm3(Predicted)
[storage temp. ]

Amber Vial, -20°C Freezer, Under inert atmosphere
[solubility ]

Chloroform (Slightly)
[form ]

Solid
[color ]

Off-White
[biological source]

semisynthetic (from parthenolide)
Hazard InformationBack Directory
[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.
[storage]

Store at -20°C
Spectrum DetailBack Directory
[Spectrum Detail]

arglabin(84692-91-1)1HNMR
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