AH6809
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MedKoo CAT#: 531431

CAS#: 33458-93-4

Description: AH6809 is a DP/EP prostanoid receptor antagonist.

Chemical Structure

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AH6809
CAS# 33458-93-4
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 531431
Name: AH6809
CAS#: 33458-93-4
Chemical Formula: C17H14O5
Exact Mass: 298.08
Molecular Weight: 298.294
Elemental Analysis: C, 68.45; H, 4.73; O, 26.82

Price and Availability

Size Price Availability Quantity
25mg USD 450 2 Weeks
50mg USD 750 2 Weeks
100mg USD 1250 2 Weeks
200mg USD 1950 2 Weeks
500mg USD 2950 2 Weeks
1g USD 4250 2 Weeks
2g USD 6850 2 Weeks
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Synonym: AH6809; AH-6809; AH 6809;

IUPAC/Chemical Name: 9-oxo-6-propan-2-yloxyxanthene-2-carboxylic acid

InChi Key: AQFFXPQJLZFABJ-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H14O5/c1-9(2)21-11-4-5-12-15(8-11)22-14-6-3-10(17(19)20)7-13(14)16(12)18/h3-9H,1-2H3,(H,19,20)

SMILES Code: O=C(C1=CC(C2=O)=C(OC3=C2C=CC(OC(C)C)=C3)C=C1)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: AH 6809 is an antagonist at prostaglandin EP1 (pA2 = 6.8) and EP2 (Ki = 350 nM) receptors. Also weakly inhibits DP receptors (pA2 = 4.45).
In vitro activity: 2. All prostanoids tested were active in non-pregnant human myometrium either as stimulators and/or inhibitors of spontaneous activity or both. Biphasic responses to PGE2 indicate that at least two receptor types of the EP-receptor exist, one mediating relaxation and the other mediating contraction. 3. Further evidence for the EP-receptor mediating excitation and relaxation was provided by the action of the EP2-/EP3-receptor selective prostanoids rioprostil, AY23626 and misoprostol, and the EP1-/EP2-receptor selective agonist 16,16-dimethylprostaglandin E2. 4. Butaprost, an EP2-receptor selective agonist, produced potent inhibition of spontaneous activity in the tissue which was generally longer-lasting than that evoked by the natural prostanoid PGE2. 5. The EP1-/EP3-receptor selective agonist sulprostone and the EP3-receptor agonist enprostil produced potent contractile responses supporting the presence of contractile EP3-receptors in the non-pregnant human myometrium in vitro. 6. The EP1-/IP-receptor selective agonist, iloprost, produced mixed responses in non-pregnant human myometrium. The contractile response was inhibited by the EP1-receptor antagonist AH6809. However, responses to the EP1-/EP3-receptor selective agonist sulprostone were unaffected by AH6809 which may indicate that only a small population of EP1-receptors is present. 7. Therefore it would seem that a heterogeneous population of EP-receptors is present in the non-pregnant human myometrium. Reference: Senior J, Marshall K, Sangha R, Baxter GS, Clayton JK. In vitro characterization of prostanoid EP-receptors in the non-pregnant human myometrium. Br J Pharmacol. 1991 Mar;102(3):747-53. doi: 10.1111/j.1476-5381.1991.tb12244.x. PMID: 1285399; PMCID: PMC1917944.
In vivo activity: The antagonism of the anti-aggregatory activity of PGD2 by AH6809 was concentration-related and could be overcome by increasing the concentration of PGD2. Analysis of the data yielded an apparent pA2 for AH6809 of 5.35. 4. At approximately 10 fold higher concentrations than those required to antagonize the action of PGD2, AH6809 also antagonized the aggregatory effect of U-46619 in whole blood (pA2 = 4.45). However, concentrations of AH6809 up to 300 microM were without effect upon either ADP- or platelet activating factor (Paf)-induced aggregation (pA2 less than 3.5). 5. The potency of AH6809 against PGD2 and U-46619 was increased in a resuspended platelet preparation suggesting that the drug is extensively bound to plasma proteins. However, in resuspended platelets the specificity of AH6809 relative to that seen in whole blood was reduced since aggregation by ADP and Paf was also slightly antagonized. 6. In conclusion, AH6809 appears to be a weak but specific DP-receptor blocking drug on human platelets and should prove to be a useful drug tool for defining the involvement of endogenous PGD2 in platelet aggregation and classifying the mode of action of anti-aggregatory prostanoids. Reference: Keery RJ, Lumley P. AH6809, a prostaglandin DP-receptor blocking drug on human platelets. Br J Pharmacol. 1988 Jul;94(3):745-54. doi: 10.1111/j.1476-5381.1988.tb11584.x. PMID: 2460179; PMCID: PMC1854016.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 1.0 3.35
0.1 M Na2CO3 4.0 13.41
DMF 8.0 26.82
Ethanol 5.0 16.76
PBS (pH 7.2) 0.3 1.14

Preparing Stock Solutions

The following data is based on the product molecular weight 298.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: Senior J, Marshall K, Sangha R, Baxter GS, Clayton JK. In vitro characterization of prostanoid EP-receptors in the non-pregnant human myometrium. Br J Pharmacol. 1991 Mar;102(3):747-53. doi: 10.1111/j.1476-5381.1991.tb12244.x. PMID: 1285399; PMCID: PMC1917944.
In vitro protocol: Senior J, Marshall K, Sangha R, Baxter GS, Clayton JK. In vitro characterization of prostanoid EP-receptors in the non-pregnant human myometrium. Br J Pharmacol. 1991 Mar;102(3):747-53. doi: 10.1111/j.1476-5381.1991.tb12244.x. PMID: 1285399; PMCID: PMC1917944.
In vivo protocol: Keery RJ, Lumley P. AH6809, a prostaglandin DP-receptor blocking drug on human platelets. Br J Pharmacol. 1988 Jul;94(3):745-54. doi: 10.1111/j.1476-5381.1988.tb11584.x. PMID: 2460179; PMCID: PMC1854016.

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1: Wang R, Zhang W, Dong Z, Qi Y, Hultström M, Zhou X, Lai EY. c-Jun N-terminal Kinase mediates prostaglandin-induced sympathoexcitation in rats with chronic heart failure by reducing GAD1 and GABRA1 expression. Acta Physiol (Oxf). 2016 Jul 20. doi: 10.1111/apha.12758. [Epub ahead of print] PubMed PMID: 27439062.

2: Liu M, Gong Y, Wei JY, Xie D, Wang J, Yu YH, Quan S. [Media of rat macrophage NR8383 cells with prostaglandins E2-induced VEGF over-expression promotes migration and tube formation of human umbilical vein endothelial cells]. Nan Fang Yi Ke Da Xue Xue Bao. 2016 Jun 20;36(7):936-40. Chinese. PubMed PMID: 27435772.

3: Abdel-Ghany R, Rabia I, El-Ahwany E, Saber S, Gamal R, Nagy F, Mahmoud O, Hamad RS, Barakat W. BLOCKADE OF PGE2, PGD2 RECEPTORS CONFERS PROTECTION AGAINST PREPATENT SCHISTOSOMIASIS MANSONI IN MICE. J Egypt Soc Parasitol. 2015 Dec;45(3):511-20. PubMed PMID: 26939228.

4: Ma Y, Matsuwaki T, Yamanouchi K, Nishihara M. Glucocorticoids Suppress the Protective Effect of Cyclooxygenase-2-Related Signaling on Hippocampal Neurogenesis Under Acute Immune Stress. Mol Neurobiol. 2016 Feb 24. [Epub ahead of print] PubMed PMID: 26910812.

5: Zoccal KF, Sorgi CA, Hori JI, Paula-Silva FW, Arantes EC, Serezani CH, Zamboni DS, Faccioli LH. Opposing roles of LTB4 and PGE2 in regulating the inflammasome-dependent scorpion venom-induced mortality. Nat Commun. 2016 Feb 23;7:10760. doi: 10.1038/ncomms10760. PubMed PMID: 26907476; PubMed Central PMCID: PMC4766425.

6: Gu H, Fang YJ, Liu DD, Chen P, Mei YA. cAMP/PKA Pathways and S56 Phosphorylation Are Involved in AA/PGE2-Induced Increases in rNaV1.4 Current. PLoS One. 2015 Oct 20;10(10):e0140715. doi: 10.1371/journal.pone.0140715. PubMed PMID: 26485043; PubMed Central PMCID: PMC4618696.

7: Preising C, Schneider R, Bucher M, Gekle M, Sauvant C. Regulation of Expression of Renal Organic Anion Transporters OAT1 and OAT3 in a Model of Ischemia/Reperfusion Injury. Cell Physiol Biochem. 2015;37(1):1-13. doi: 10.1159/000430328. PubMed PMID: 26277839.

8: Arosh JA, Lee J, Balasubbramanian D, Stanley JA, Long CR, Meagher MW, Osteen KG, Bruner-Tran KL, Burghardt RC, Starzinski-Powitz A, Banu SK. Molecular and preclinical basis to inhibit PGE2 receptors EP2 and EP4 as a novel nonsteroidal therapy for endometriosis. Proc Natl Acad Sci U S A. 2015 Aug 4;112(31):9716-21. doi: 10.1073/pnas.1507931112. PubMed PMID: 26199416; PubMed Central PMCID: PMC4534219.

9: Hoang KG, Allison S, Murray M, Petrovic N. Prostanoids regulate angiogenesis acting primarily on IP and EP4 receptors. Microvasc Res. 2015 Sep;101:127-34. doi: 10.1016/j.mvr.2015.07.004. PubMed PMID: 26188701.

10: Chen D, Zhao J, Wang H, An N, Zhou Y, Fan J, Luo J, Su W, Liu C, Li J. Oxytocin evokes a pulsatile PGE2 release from ileum mucosa and is required for repair of intestinal epithelium after injury. Sci Rep. 2015 Jul 10;5:11731. doi: 10.1038/srep11731. PubMed PMID: 26159321; PubMed Central PMCID: PMC4498177.

11: Simplicio JA, Resstel LB, Tirapelli DP, D'Orléans-Juste P, Tirapelli CR. Contribution of oxidative stress and prostanoids in endothelial dysfunction induced by chronic fluoxetine treatment. Vascul Pharmacol. 2015 Oct;73:124-37. doi: 10.1016/j.vph.2015.06.015. PubMed PMID: 26141931.

12: Shen L, Liu Y. Prostaglandin E2 blockade enhances the pulmonary anti-Cryptococcus neoformans immune reaction via the induction of TLR-4. Int Immunopharmacol. 2015 Sep;28(1):376-81. doi: 10.1016/j.intimp.2015.06.026. PubMed PMID: 26122137.

13: Amadio P, Baldassarre D, Tarantino E, Zacchi E, Gianellini S, Squellerio I, Amato M, Weksler BB, Tremoli E, Barbieri SS. Production of prostaglandin E2 induced by cigarette smoke modulates tissue factor expression and activity in endothelial cells. FASEB J. 2015 Sep;29(9):4001-10. doi: 10.1096/fj.14-268383. PubMed PMID: 26065856.

14: Zhang T, Gong X, Hu G, Wang X. EP2-PKA signaling is suppressed by triptolide in lipopolysaccharide-induced microglia activation. J Neuroinflammation. 2015 Mar 14;12:50. doi: 10.1186/s12974-015-0275-y. PubMed PMID: 25880276; PubMed Central PMCID: PMC4364339.

15: Arosh JA, Lee J, Starzinski-Powitz A, Banu SK. Selective inhibition of prostaglandin E2 receptors EP2 and EP4 modulates DNA methylation and histone modification machinery proteins in human endometriotic cells. Mol Cell Endocrinol. 2015 Jul 5;409:51-8. doi: 10.1016/j.mce.2015.03.023. PubMed PMID: 25843056.

16: Serra-Pages M, Torres R, Plaza J, Herrerias A, Costa-Farré C, Marco A, Jiménez M, Maurer M, Picado C, de Mora F. Activation of the Prostaglandin E2 receptor EP2 prevents house dust mite-induced airway hyperresponsiveness and inflammation by restraining mast cells' activity. Clin Exp Allergy. 2015 Oct;45(10):1590-600. doi: 10.1111/cea.12542. PubMed PMID: 25823713.

17: Takahashi T, Uehara H, Ogawa H, Umemoto H, Bando Y, Izumi K. Inhibition of EP2/EP4 signaling abrogates IGF-1R-mediated cancer cell growth: involvement of protein kinase C-θ activation. Oncotarget. 2015 Mar 10;6(7):4829-44. PubMed PMID: 25638159; PubMed Central PMCID: PMC4467118.

18: Li S, Xu X, Jiang M, Bi Y, Xu J, Han M. Lipopolysaccharide induces inflammation and facilitates lung metastasis in a breast cancer model via the prostaglandin E2-EP2 pathway. Mol Med Rep. 2015 Jun;11(6):4454-62. doi: 10.3892/mmr.2015.3258. PubMed PMID: 25625500.

19: Kim S, Jin Z, Lee G, Park YS, Park CS, Jin YH. Prostaglandin potentiates 5-HT responses in stomach and ileum innervating visceral afferent sensory neurons. Biochem Biophys Res Commun. 2015 Jan 2;456(1):167-72. doi: 10.1016/j.bbrc.2014.11.053. PubMed PMID: 25446121.

20: Shehzad A, Ul Islam S, Lee J, Lee YS. Prostaglandin E2 reverses curcumin-induced inhibition of survival signal pathways in human colorectal carcinoma (HCT-15) cell lines. Mol Cells. 2014 Dec 31;37(12):899-906. doi: 10.14348/molcells.2014.0212. PubMed PMID: 25431425; PubMed Central PMCID: PMC4275707.