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Merck
CN

172060

Andrographolide

A bicyclic diterpenoid lactone that displays anti-viral, anti-inflammatory, anti-apoptotic, and anti-hyperglycemic properties.

Synonym(s):

Andrographolide, Andro

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About This Item

Empirical Formula (Hill Notation):
C20H30O5
CAS Number:
5508-58-7
Molecular Weight:
350.45
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD07778082

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Product Name

Andrographolide, A bicyclic diterpenoid lactone that displays anti-viral, anti-inflammatory, anti-apoptotic, and anti-hyperglycemic properties.

SMILES string

O1CC(\C(=C/C[C@H]2[C@]3(C(C(C(CC3)O)(CO)C)CCC2=C)C)\C1=O)O

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-ZJFCSBQFSA-N

description

Merck USA index - 14, 633

assay

≥95% (TLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

off-white

solubility

chloroform: methanol (1:1): 10 mg/mL
DMSO: 15 mg/mL (Use only fresh DMSO.)

shipped in

ambient

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Cell permeable: no
Primary Target
NF-κB and AP-1 activation
Product does not compete with ATP.
Reversible: no
Target IC50: ≤ 15 µM against NF-κB and AP-1 activation

Disclaimer

Toxicity: Carcinogenic / Teratogenic (D)

General description

A bicyclic diterpenoid lactone that displays anti-viral, anti-inflammatory, anti-apoptotic, and anti-hyperglycemic properties. Acts as an irreversible antagonist of NF-κB and AP-1 (IC50 ≤ 15 µM) activation, and prevents in vitro and in vivo T cell activation. Exerts no effect on IκBα degradation, p50 and p65 nuclear translocation. Inhibits iNOS and Mac-1 expressions and ROS production, and prevents endotoxin shock in mouse model. Further, reported to activate PI 3K/Akt pathway.
An irreversible blocker of NF-κB and AP-1 (IC50 ≤ 15 µM) activation that displays anti-viral, anti-inflammatory, anti-apoptotic, and anti-hyperglycemic properties. Exerts no effect on IκBα degradation of nuclear translocation p50 and p65. Inhibits iNOS and Mac-1 expressions and ROS production, and prevents endotoxin shock in a mouse model. Reported to supress Cytochrome C release and apoptosis by activating the PI 3-K/Akt pathway.

Other Notes

Xia, Y.F., et al. 2004. J. Immunol.173, 4207.
Chen, J.H., et al. 2004. Biochem. Pharmacol.67, 1337.
Yu, B.C., et al. 2003. Planta Med.69, 1075.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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