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Merck

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
Assay:
≥95% (TLC)
Form:
solid
Quality level:
100
Storage condition:
OK to freeze, protect from light

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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

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.

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

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.

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.

Legal Information

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

Disclaimer

Toxicity: Carcinogenic / Teratogenic (D)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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