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AH 6809 is an EP and DP receptor antagonist with nearly equal affinity for the cloned human EP1, EP2, EP3-III, and DP1 receptors.1 AH 6809 blocks the PGE2-induced accumulation of cAMP in COS cells transfected with the human EP2 receptor.2 It also blocks the accumulation of Ca2+ in Xenopus oocytes expressing the human EP1 receptor.3 In the human and guinea pig, the activity profile of AH 6809 is similar to that of SC-19220, but it is somewhat more potent.4 In the mouse, AH 6809 has the highest affinity for the EP2 receptor, but also acts as a weak ligand at the murine EP1 and DP1 receptors.5 In whole human platelets, AH 6809 is an effective antagonist of the antiaggregatory actions of PGD2, but not PGI2, with an EC50 of about 5 x 10−5 M.6
1
Abramovitz, M., Adam, M., Boie, Y., et al. The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. Biochim Biophys Acta1483285-293(2000).
2
Woodward, D.F., Pepperl, D.J., Burkey, T.H., et al. 6-Isopropoxy-9-oxoxanthene-2-carboxylic acid (AH 6809), a human EP2 receptor antagonist. Biochem Pharmacol501731-1733(1995).
3
Funk, C.D., Furci, L., Fitzgerald, G.A., et al. Cloning and expression of a cDNA for the human prostaglandin E receptor EP1 subtype. J Biol Chem26826767-26772(1993).
4
Coleman, R.A., Kennedy, I., and Sheldrick, R.L.G. AH6809, a prostanoid EP1 receptor blocking drug. Br J Pharmacol85273P(1985).
5
Kiriyama, M., Ushikubi, F., Kobayashi, T., et al. Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol122217-224(1997).
6
Keery, R.J., and Lumley, P. AH6809, a prostaglandin DP-receptor blocking drug on human platelets. Br J Pharmacol94745-754(1988).
Formal Name
6-isopropoxy-9-oxoxanthene-2-carboxylic acid
CAS Number
33458-93-4
Molecular Formula
C17H14O5
Formula Weight
298.3
Formulation
A crystalline solid
Purity
≥98%
λmax
244, 305 nm
Stability
2 years
Storage
4°C
Shipping
Wet ice
in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CC(OC1=CC(OC2=CC=C(C(O)=O)C=C2C3=O)=C3C=C1)C
Background Reading
Abramovitz, M., Adam, M., Boie, Y., et al. The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. Biochim Biophys Acta1483285-293(2000).
Woodward, D.F., Pepperl, D.J., Burkey, T.H., et al. 6-Isopropoxy-9-oxoxanthene-2-carboxylic acid (AH 6809), a human EP2 receptor antagonist. Biochem Pharmacol501731-1733(1995).
Coleman, R.A., Kennedy, I., and Sheldrick, R.L.G. AH6809, a prostanoid EP1 receptor blocking drug. Br J Pharmacol85273P(1985).
Keery, R.J., and Lumley, P. AH6809, a prostaglandin DP-receptor blocking drug on human platelets. Br J Pharmacol94745-754(1988).
Kiriyama, M., Ushikubi, F., Kobayashi, T., et al. Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol122217-224(1997).
Funk, C.D., Furci, L., Fitzgerald, G.A., et al. Cloning and expression of a cDNA for the human prostaglandin E receptor EP1 subtype. J Biol Chem26826767-26772(1993).