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33458-93-4,MFCD08056083
Catalog No.:AA00BXW7

33458-93-4 | Ah 6809

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1mg
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5mg
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10mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00BXW7
Chemical Name:
Ah 6809
CAS Number:
33458-93-4
Molecular Formula:
C17H14O5
Molecular Weight:
298.2901
MDL Number:
MFCD08056083
SMILES:
CC(Oc1ccc2c(c1)oc1c(c2=O)cc(cc1)C(=O)O)C
Properties
Properties
 
Form:
Solid  

Computed Properties
 
Complexity:
446  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
3  
XLogP3:
3.9  

Literature

Title: Leptin induces CREB-dependent aromatase activation through COX-2 expression in breast cancer cells.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20170801

Title: Role of hypoxia-inducible factor 1, α subunit and cAMP-response element binding protein 1 in synergistic release of interleukin 8 by prostaglandin E2 and nickel in lung fibroblasts.

Journal: American journal of respiratory cell and molecular biology 20130701

Title: Murine corneal stroma cells suppress bone marrow-derived dendritic cells maturation in vitro.

Journal: Chinese medical journal 20120601

Title: The cyclooxygenase-2 pathway via the PGE₂ EP2 receptor contributes to oligodendrocytes apoptosis in cuprizone-induced demyelination.

Journal: Journal of neurochemistry 20120501

Title: Prostaglandin E2 blocks menadione-induced apoptosis through the Ras/Raf/Erk signaling pathway in promonocytic leukemia cell lines.

Journal: Molecules and cells 20120430

Title: Prostaglandin E2 restrains macrophage maturation via E prostanoid receptor 2/protein kinase A signaling.

Journal: Blood 20120308

Title: Influence of influenza A infection on capsaicin-induced responses in murine airways.

Journal: The Journal of pharmacology and experimental therapeutics 20120201

Title: Prostaglandin E2 induces spontaneous rhythmic activity in mouse urinary bladder independently of efferent nerves.

Journal: British journal of pharmacology 20120101

Title: Acute effects of prostaglandin E1 and E2 on vascular reactivity and blood flow in situ in the chick chorioallantoic membrane.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20120101

Title: Primary human airway epithelial cell-dependent inhibition of human lung mast cell degranulation.

Journal: PloS one 20120101

Title: PGE(2)-induced CXCL12 production and CXCR4 expression controls the accumulation of human MDSCs in ovarian cancer environment.

Journal: Cancer research 20111215

Title: EP4 receptor as a new target for bronchodilator therapy.

Journal: Thorax 20111201

Title: SO(2)-induced neurotoxicity is mediated by cyclooxygenases-2-derived prostaglandin E(2) and its downstream signaling pathway in rat hippocampal neurons.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20111201

Title: Thromboxane and isoprostane share the same prostanoid receptors to increase human placental tone.

Journal: Placenta 20111201

Title: Thromboxane prostanoid receptor activation amplifies airway stretch-activated contractions assessed in perfused intact bovine bronchial segments.

Journal: The Journal of pharmacology and experimental therapeutics 20111001

Title: Suppressive effect of aqueous humor on lipopolysaccharide-induced dendritic cell maturation.

Journal: Japanese journal of ophthalmology 20110901

Title: Tumor-secreted PGE2 inhibits CCL5 production in activated macrophages through cAMP/PKA signaling pathway.

Journal: The Journal of biological chemistry 20110121

Title: Cyclooxygenase-2 up-regulates vascular endothelial growth factor via a protein kinase C pathway in non-small cell lung cancer.

Journal: Journal of experimental & clinical cancer research : CR 20110101

Title: Inhibitory influence of protease-activated receptor 2 and E-prostanoid receptor stimulants in lipopolysaccharide models of acute airway inflammation.

Journal: The Journal of pharmacology and experimental therapeutics 20101101

Title: The role of cyclooxygenase-2-dependent signaling via cyclic AMP response element activation on aromatase up-regulation by o,p'-DDT in human breast cancer cells.

Journal: Toxicology letters 20101020

Title: Jack bean urease alters serotonin-induced effects on Rhodnius prolixus anterior midgut.

Journal: Journal of insect physiology 20100901

Title: Functional and molecular characterization of prostaglandin E2 dilatory receptors in the rat craniovascular system in relevance to migraine.

Journal: Cephalalgia : an international journal of headache 20100901

Title: Inducible cyclooxygenase released prostaglandin E2 modulates the severity of infection caused by Streptococcus pyogenes.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20100815

Title: Selective blockade of prostaglandin E2 receptors EP2 and EP4 signaling inhibits proliferation of human endometriotic epithelial cells and stromal cells through distinct cell cycle arrest.

Journal: Fertility and sterility 20100515

Title: Prostaglandin E2 induces CYP1B1 expression via ligand-independent activation of the ERalpha pathway in human breast cancer cells.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20100401

Title: Human papillomavirus type 16 E5 protein inhibits hydrogen-peroxide-induced apoptosis by stimulating ubiquitin-proteasome-mediated degradation of Bax in human cervical cancer cells.

Journal: Carcinogenesis 20100301

Title: Age-related changes in isoprostane-mediated relaxation of piglet blood vessels.

Journal: Frontiers in bioscience (Elite edition) 20100101

Title: Expression of cyclooxygenase-1/-2, microsomal prostaglandin-E synthase-1 and E-prostanoid receptor 2 and regulation of inflammatory mediators by PGE(2) in the amoeboid microglia in hypoxic postnatal rats and murine BV-2 cells.

Journal: Neuroscience 20091215

Title: Role of prostanoid production and receptors in the regulation of retinal endogenous amino acid neurotransmitters by 8-isoprostaglandin E2, ex vivo.

Journal: Neurochemical research 20091201

Title: Differential afferent sensitivity to mucosal lipopolysaccharide from Salmonella typhimurium and Escherichia coli in the rat jejunum.

Journal: Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20091201

Title: Involvement of cyclooxygenase-2 in carbachol-induced positive inotropic response in mouse isolated left atrium.

Journal: The Journal of pharmacology and experimental therapeutics 20091201

Title: Prostaglandin E2 mediates cough via the EP3 receptor: implications for future disease therapy.

Journal: American journal of respiratory and critical care medicine 20091115

Title: Chronic methionine load-induced hyperhomocysteinemia impairs the relaxation induced by bradykinin in the isolated rat carotid.

Journal: Amino acids 20091001

Title: The EP1 subtype of prostaglandin E2 receptor: role in keratinocyte differentiation and expression in non-melanoma skin cancer.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20091001

Title: Regulation of ANP secretion from isolated atria by prostaglandins and cyclooxygenase-2.

Journal: Peptides 20090901

Title: Ketamine inhibits the phagocytic responses of canine peripheral blood polymorphonuclear cells through the upregulation of prostaglandin E2 in peripheral blood mononuclear cells in vitro.

Journal: Research in veterinary science 20090801

Title: Activation of prostaglandin E2 EP1 receptor increases arteriolar tone and blood pressure in mice with type 2 diabetes.

Journal: Cardiovascular research 20090701

Title: Prostaglandin E2 released from activated microglia enhances astrocyte proliferation in vitro.

Journal: Toxicology and applied pharmacology 20090701

Title: Prostaglandin E2 signaling through E prostanoid receptor 2 impairs proliferative response of double negative regulatory T cells.

Journal: International immunopharmacology 20090501

Title: Developmental changes in the effects of prostaglandin E2 in the chicken ductus arteriosus.

Journal: Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology 20090201

Title: Prostaglandin E2 and its cognate EP receptors control human adult articular cartilage homeostasis and are linked to the pathophysiology of osteoarthritis.

Journal: Arthritis and rheumatism 20090201

Title: Effect of prostaglandin E2 on urokinase-type plasminogen activator production by human lung fibroblasts.

Journal: Scandinavian journal of clinical and laboratory investigation 20090101

Title: Roles of cyclooxygenase-2 in microvascular endothelial cell proliferation induced by basic fibroblast growth factor.

Journal: Chinese medical journal 20081220

Title: 15d-PGJ2 upregulates synthesis of IL-8 in endothelial cells through induction of oxidative stress.

Journal: Antioxidants & redox signaling 20081201

Title: Engagement of the EP2 prostanoid receptor closes the K+ channel KCa3.1 in human lung mast cells and attenuates their migration.

Journal: European journal of immunology 20080901

Title: The effects of cyclooxygenase2-prostaglandinE2 pathway on Helicobacter pylori-induced urokinase-type plasminogen activator system in the gastric cancer cells.

Journal: Helicobacter 20080601

Title: The role of prostaglandin E and thromboxane-prostanoid receptors in the response to prostaglandin E2 in the aorta of Wistar Kyoto rats and spontaneously hypertensive rats.

Journal: Cardiovascular research 20080401

Title: Prostaglandin E2 glycerol ester, an endogenous COX-2 metabolite of 2-arachidonoylglycerol, induces hyperalgesia and modulates NFkappaB activity.

Journal: British journal of pharmacology 20080401

Title: Prostaglandin E2 and F2alpha activate the FP receptor and up-regulate cyclooxygenase-2 expression via the cyclic AMP response element.

Journal: Molecular and cellular endocrinology 20080326

Title: PTGER1 and PTGER2 receptors mediate regulation of progesterone synthesis and type 1 11beta-hydroxysteroid dehydrogenase activity by prostaglandin E2 in human granulosa lutein cells.

Journal: The Journal of endocrinology 20070901

Title: Prostaglandin E2 enhances acetylcholine-induced, Ca2+-dependent ionic currents in swine tracheal mucous gland cells.

Journal: The Journal of pharmacology and experimental therapeutics 20070801

Title: Prostaglandin E2 enhances the sensitizing effect of hyperthermia on pulmonary C-fibers in rats.

Journal: Respiratory physiology & neurobiology 20070615

Title: Development and validation of a liquid chromatography/tandem mass spectrometry method for the determination of DMXAA in human and mouse plasma.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070601

Title: TNF-alpha modulates hepatic Na+-K+ ATPase activity via PGE2 and EP2 receptors.

Journal: Prostaglandins & other lipid mediators 20070601

Title: Functional characterization of the mechanisms underlying bradykinin-induced relaxation in the isolated rat carotid artery.

Journal: Life sciences 20070417

Title: Iloprost-induced desensitization of the prostacyclin receptor in isolated rabbit lungs.

Journal: Respiratory research 20070101

Title: Involvement of cyclooxygenase-2--prostaglandin E2 pathway in interleukin-8 production in gastric cancer cells.

Journal: Digestive diseases and sciences 20061201

Title: Prostaglandin E2 promotes cell survival of glomerular epithelial cells via the EP4 receptor.

Journal: American journal of physiology. Renal physiology 20060601

Title: Identification of prostaglandin E2 receptor subtype 2 as a receptor activated by OxPAPC.

Journal: Circulation research 20060317

Title: Early changes in prostaglandins precede bone formation in a rabbit model of heterotopic ossification.

Journal: Bone 20060301

Title: Involvement of EP1 and EP2 receptors in the regulation of the Na,K-ATPase by prostaglandins in MDCK cells.

Journal: Prostaglandins & other lipid mediators 20060301

Title: Role of periaqueductal grey prostaglandin receptors in formalin-induced hyperalgesia.

Journal: European journal of pharmacology 20060113

Title: Prostaglandin E2 drives cyclooxygenase-2 expression via cyclic AMP response element activation in human pancreatic cancer cells.

Journal: Cancer biology & therapy 20051101

Title: Lipopolysaccharide-induced changes in mesenteric afferent sensitivity of rat jejunum in vitro: role of prostaglandins.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20050801

Title: Sensitization of mesenteric afferents to chemical and mechanical stimuli following systemic bacterial lipopolysaccharide.

Journal: Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20050201

Title: EP1- and EP3-receptors mediate prostaglandin E2-induced constriction of porcine large cerebral arteries.

Journal: Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20041201

Title: Implication of prostaglandin E(2) in TNF-alpha-induced release of m-calpain from HCS-2/8 chondrocytes. Inhibition of m-calpain release by NSAIDs.

Journal: Osteoarthritis and cartilage 20041101

Title: Prostacyclin release and receptor activation: differential control of human pulmonary venous and arterial tone.

Journal: British journal of pharmacology 20040601

Title: Prostaglandin E2 regulates amyloid precursor protein expression via the EP2 receptor in cultured rat microglia.

Journal: Neuroscience letters 20040520

Title: Identification in human airways smooth muscle cells of the prostanoid receptor and signalling pathway through which PGE2 inhibits the release of GM-CSF.

Journal: British journal of pharmacology 20040401

Title: E-ring 8-isoprostanes inhibit ACh release from parasympathetic nerves innervating guinea-pig trachea through agonism of prostanoid receptors of the EP3-subtype.

Journal: British journal of pharmacology 20040201

Title: Inhibition of human glioma cell growth by a PHS-2 inhibitor, NS398, and a prostaglandin E receptor subtype EP1-selective antagonist, SC51089.

Journal: Journal of neuro-oncology 20040201

Title: Glutamate-mediated cytosolic calcium oscillations regulate a pulsatile prostaglandin release from cultured rat astrocytes.

Journal: The Journal of physiology 20031201

Title: Effects of mechanical strain on the function of Gap junctions in osteocytes are mediated through the prostaglandin EP2 receptor.

Journal: The Journal of biological chemistry 20031031

Title: Role of prostaglandin E2 receptors in migration of murine and human breast cancer cells.

Journal: Experimental cell research 20031001

Title: Leukotriene D4-induced adhesion of Caco-2 cells is mediated by prostaglandin E2 and upregulation of alpha2beta1-integrin.

Journal: Experimental cell research 20031001

Title: Modulation of guinea pig intrinsic cardiac neurons by prostaglandins.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20030901

Title: Effects of PGE2 in guinea pig colonic myenteric ganglia.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20021201

Title: Differential peristaltic motor effects of prostanoid (DP, EP, IP, TP) and leukotriene receptor agonists in the guinea-pig isolated small intestine.

Journal: British journal of pharmacology 20021201

Title: PGD(2) modulates fibroblast-mediated native collagen gel contraction.

Journal: American journal of respiratory cell and molecular biology 20020901

Title: AH6809 antagonizes non-small cell lung cancer prostaglandin receptors.

Journal: Lung cancer (Amsterdam, Netherlands) 20020401

Title: Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques.

Journal: The Journal of pharmacy and pharmacology 20020401

Title: Role of EP(1) and EP(4) PGE(2) subtype receptors in serum-induced 3T6 fibroblast cycle progression and proliferation.

Journal: American journal of physiology. Cell physiology 20020201

Title: Trophic effects of the cyclooxygenase-2 product prostaglandin E(2) in cardiac myocytes.

Journal: Hypertension (Dallas, Tex. : 1979) 20020201

Title: Prostanoid EP(1)- and TP-receptors involved in the contraction of human pulmonary veins.

Journal: British journal of pharmacology 20011201

Title: Prostanoids stimulate K secretion and Cl secretion in guinea pig distal colon via distinct pathways.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20011001

Title: Human granulosa-lutein cells express functional EP1 and EP2 prostaglandin receptors.

Journal: Biochemical and biophysical research communications 20010803

Title: Characterization of PGE2 receptors in fetal and newborn lamb ductus arteriosus.

Journal: American journal of physiology. Heart and circulatory physiology 20010501

Title: EP(4) receptors mediate prostaglandin E(2)-stimulated glycosaminoglycan synthesis in human cervical fibroblasts in culture.

Journal: Molecular human reproduction 20010401

Title: Role of PGE(2) in protease-activated receptor-1, -2 and -4 mediated relaxation in the mouse isolated trachea.

Journal: British journal of pharmacology 20010101

Title: The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.

Journal: Biochimica et biophysica acta 20000117

Title: Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes.

Journal: European journal of pharmacology 19971211

Title: Characterization of the prostanoid receptor(s) on human blood monocytes at which prostaglandin E2 inhibits lipopolysaccharide-induced tumour necrosis factor-alpha generation.

Journal: British journal of pharmacology 19970901

Title: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.

Journal: British journal of pharmacology 19970901

Title: 6-Isopropoxy-9-oxoxanthene-2-carboxylic acid (AH 6809), a human EP2 receptor antagonist.

Journal: Biochemical pharmacology 19951109

Title: Nociceptive effects induced by intrathecal administration of prostaglandin D2, E2, or F2 alpha to conscious mice.

Journal: Brain research 19900226

Title: Selective inhibition of prostaglandin E2 receptors EP2 and EP4 induces apoptosis of human endometriotic cells through suppression of ERK1/2, AKT, NFkappaB, and beta-catenin pathways and activation of intrinsic apoptotic mechanisms.

Journal: Molecular endocrinology (Baltimore, Md.)

Title: Estrogen receptor-related receptor alpha mediates up-regulation of aromatase expression by prostaglandin E2 in prostate stromal cells.

Journal: Molecular endocrinology (Baltimore, Md.)

Title: Abramovitz M, et, al. The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. Biochim Biophys Acta. 2000 Jan 17;1483(2):285-93.

Title: Kiriyama M, et, al. Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol. 1997 Sep;122(2):217-24.

Title: Woodward DF, et, al. 6-Isopropoxy-9-oxoxanthene-2-carboxylic acid (AH 6809), a human EP2 receptor antagonist. Biochem Pharmacol. 1995 Nov 9;50(10):1731-3.

Title: Zoccal KF, et, al. Opposing roles of LTB4 and PGE2 in regulating the inflammasome-dependent scorpion venom-induced mortality. Nat Commun. 2016 Feb 23;7:10760.

Title: Keery RJ, et, al. AH6809, a prostaglandin DP-receptor blocking drug on human platelets. Br J Pharmacol. 1988 Jul;94(3):745-54.

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