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20-September-2008 09:55:49 - Prostacyclin Prostacyclin Systematic IUPAC name 5-7-hydroxy-8- 3-hydroxyoct-1-enyl -4-oxabicyclo3.3.0oct-3-ylidene pentanoic acid Identifiers CAS number 35121-78-9 ATC code B01AC09 PubChem 114805 DrugBank APRD00949 Chemical data Formula C20H32O5 Mol. mass 352.465 g/mol SMILES eMolecules PubChem Pharmacokinetic data Bioavailability ? Metabolism ? Half life ? Excretion ? Therapeutic considerations Pregnancy cat. ? Legal status Routes ? Prostacyclin or PGI2 is a member of the family of lipid molecules known as eicosanoids. Contents 1 Production 2 Degradation 3 Mode of action 4 Function 5 Pharmacology 6 References 7 See also Production Eicosanoid synthesis. Prostacyclin near bottom center. Eicosanoid synthesis. Prostacyclin near bottom center. It is produced in endothelial cells from prostaglandin H2 PGH2 by the action of the enzyme prostacyclin synthase. Although prostacyclin is considered an independent mediator, it is called PGI2 prostaglandin I2 in eicosanoid nomenclature, and is a member of the prostanoids together with the prostaglandins and thromboxane. The series-3 prostaglandin PGH3 also follows the prostacyclin synthase pathway, yielding another prostacyclin, PGI3.Fischer, 1985 The unqualified term 'prostacyclin' usually refers to PGI2. PGI2 is derived from the ω-6 arachidonic acid. PGI3 is derived from the ω-3 EPA. Degradation Prostacyclin, which has a half-life of seconds, is broken down into 6-keto-PGF1 which is a much weaker vasodilator. Mode of action Prostacyclin PGI2 is released by healthy endothelial cells and performs its function through a paracrine signaling cascade that involves G protein-coupled receptors on nearby platelets and endothelial cells. The platelet Gs protein-coupled receptor prostacyclin receptor is activated when it binds to PGI2. This activation, in turn, signals adenylyl cyclase to produce cAMP. cAMP goes on to inhibit any undue platelet activation in order to promote circulation and also counteracts any increase in cytosolic calcium levels which would result from thromboxane A2 TXA2 binding leading to platelet activation and subsequent coagulation. PGI2 also binds to endothelial prostacyclin receptors and in the same manner raise cAMP levels in the cytosol. This cAMP then goes on to activate protein kinase A PKA. PKA then continues the cascade by activating myosin light-chain kinase which leads to smooth muscle relaxation and vasodilation. Notably, PGI2 and TXA2 work as antagonists. Function Prostacyclin PGI2 chiefly prevents formation of the platelet plug involved in primary hemostasis a part of blood clot formation. It is also an effective vasodilator. Prostacyclin's interactions in contrast to thromboxane TXA2, another eicosanoid, strongly suggest a mechanism of cardiovascular homeostasis between the two hormones in relation to vascular damage. Pharmacology Synthetic prostacyclin analogues iloprost, cisaprost are used intravenously, subcutaneously or by inhalation: as a vasodilator in severe Raynaud's phenomenon or ischemia of a limb; in pulmonary hypertension. Its production is inhibited indirectly by NSAIDs, which inhibit the cyclooxygenase enzymes COX1 and COX2. These convert arachidonic acid to prostaglandin H2 PGH2, the immediate precursor of prostacyclin. Since thromboxane an eicosanoid stimulator of platelet aggregation is also downstream of COX enzymes, one would think that the effect of NSAIDs would balance out. However, prostacyclin concentrations recover much faster than thromboxane levels, so aspirin administration initially has little to no effect but eventually prevents platelet aggregation the effect of thromboxane predominates. This is explained by understanding the cells that produce each molecule, TXA2 and PGI2. Since PGI2 is primarily produced in a nucleated endothelial cell the COX inhibition by NSAID can be overcome with time by increased COX gene activation and subsequent production of more COX enzymes to catalyze the formation of PGI2. In contrast, TXA2 is primarily released by anucleated plateles which are unable to respond to NSAID COX inhibition with additional transcription of the COX gene because they lack DNA material necessary to perform such a task. This allows NSAIDs to result in PGI2 dominance that promotes circulation and retards thrombosis. References Dorlands Medical Dictionary. epoprostenol. Retrieved on February 10, 2006. Fischer S, Weber PC 1985. Thromboxane TXA3 and prostaglandin PGI3 are formed in man after dietary eicosapentaenoic acid: identification and quantification by capillary gas chromatography-electron impact mass spectrometry. Biomed. Mass Spectrom. 12 9: 470-6. doi:10.1002/bms.1200120905. PMID 2996649. See also Essential fatty acid v d e Antithrombotics thrombolytics, anticoagulants and antiplatelet drugs B01 Antiplatelet drugs Glycoprotein IIb/IIIa inhibitors Abciximab Eptifibatide Tirofiban ADP receptor/P2Y12 inhibitors Clopidogrel Ticlopidine Prasugrel Prostaglandin analogue PGI2 Beraprost Prostacyclin Iloprost Treprostinil COX inhibitors Acetylsalicylic acid/Aspirin Aloxiprin Carbasalate calcium Other Ditazole Cloricromen Dipyridamole Indobufen Picotamide Triflusal Anticoagulants Vitamin K antagonists inhibit II, VII, IX, X Acenocoumarol Clorindione Coumatetralyl Dicoumarol Dicumarol Diphenadione Ethyl biscoumacetate Phenprocoumon Phenindione Tioclomarol Warfarin Heparin group Antithrombin III Danaparoid Sulodexide low molecular weight heparin Bemiparin, Dalteparin, Enoxaparin, Nadroparin, Parnaparin, Reviparin, Tinzaparin Direct thrombin II inhibitors Argatroban Bivalirudin Dabigatran Desirudin Hirudin Lepirudin Melagatran Ximelagatran Factor Xa inhibitors Apixaban Otamixaban Rivaroxaban oligosaccharides Fondaparinux, Idraparinux Other Defibrotide Dermatan sulfate Ramatroban Thrombolytic drugs/ fibrinolytics plasminogen activators: TPA Alteplase, Reteplase, Tenecteplase UPA Urokinase, Saruplase Streptokinase Anistreplase Monteplase other serine endopeptidases: Ancrod Drotrecogin alfa/Protein C Fibrinolysin Brinase Non-medicinal Citrate EDTA Oxalate v d e Medications used in the management of pulmonary arterial hypertension B01, C02 Prostacyclin analogues Beraprost, Epoprostenol, Iloprost, Treprostinil Endothelin receptor antagonists Ambrisentan, Bosentan, Sitaxsentan PDE5 inhibitors Sildenafil, Tadalafil Adjunctive therapy Calcium channel blockers, Diuretics, Digoxin, Oxygen therapy, Warfarin v d e Eicosanoids: prostaglandins Endogenous/series 2 D2 - E2 Dinoprostone - F2 Dinoprost - H2 - I2 Prostacyclin Prostaglandin analogues E: Alprostadil - Enprostil - Misoprostol F: Bimatoprost - Carboprost - Latanoprost - Travoprost I: Beraprost - Epoprostenol - Iloprost - Treprostinil Retrieved from http://en..org/wiki/Prostacyclin Categories: Prostaglandins | Gilead Sciences Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages БългарÑ?ки Deutsch Español Français Polski This page was last modified on 21 June 2008, at 22:45
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