| IUPAC name | (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one |
| inchi | InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1 |
| inchi key | BOJKULTULYSRAS-OTESTREVSA-N |
| molecular formula | C20H30O5 |
| synonyms | Andrographolide5508-58-7CHEBI:65408HMPL004UNII-410105JHGR |
| Compound Description | Andrographolide is a labdane diterpenoid isolated from the leaves and roots of Andrographis paniculata that exhibits anti-HIV, anti-inflammatory and antineoplastic properties. It has a role as a metabolite, an anti-inflammatory drug, an anti-HIV agent and an antineoplastic agent. It is a gamma-lactone, a primary alcohol, a secondary alcohol, a labdane diterpenoid and a carbobicyclic compound.Andrographolide is a botanical product extracted from a herb that occurs naturally in China. The herb has an extensive history of use in TCM for the treatment of upper respiratory tract infections and other inflammatory and infectious diseases.Andrographolide has been reported in Andrographis paniculata, Cymbopogon schoenanthus, and Ginkgo biloba with data available.Andrographolide is a labdane diterpenoid that is produced by the Andrographis paniculata plant, which has a broad range of therapeutic applications including anti-inflammatory and anti-platelet aggregation activities and potential antineoplastic properties. Since andrographolide has multiple therapeutic activities there are several proposed mechanisms of action for this agent. The anti-inflammatory effects of this agent appear to be related to the inhibition of nitric oxide production by macrophages. This agent may activate the NO/cyclic GMP pathway and inhibit both the phospholipase C gamma 2 /protein kinase C and PI3K/AKT-MAPK signaling pathways in activated platelets to inhibit platelet aggregation. In activated platelets, these three signaling pathways are downstream of integrin activation mediated by collagen binding and influence the association of fibrinogen with its receptors. Additionally, andrographolide may exert its anti-cancer activity through the induction of cell cycle arrest at G0/G1 phase and the stimulation of lymphocyte proliferation and activation. These processes could result in decreased proliferation of and increased immunocytotoxicity against tumor cells.ANDROGRAPHOLIDE is a small molecule drug with a maximum clinical trial phase of III and has 4 investigational indications. |
