1.02011-09-21 00:15:53 UTC2015-07-21 06:57:15 UTCFDB022560Prostaglandin I2Prostaglandin I2 or prostacyclin (or PGI2) is a member of the family of lipid molecules known as eicosanoids. It is produced in endothelial cells from prostaglandin H2 (PGH2) by the action of the enzyme prostacyclin synthase. It is a powerful vasodilator and inhibits platelet aggregation. Prostaglandin I2 is the main prostaglandin synthesized by the blood vessel wall. This suggests that it may play an important role in limiting platelet-mediated thrombosis. In particular, prostacyclin (PGI2) chiefly prevents formation of the platelet plug involved in primary hemostasis (a part of blood clot formation). The sodium salt (known as epoprostenol) has been used to treat primary pulmonary hypertension. 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 inhibiting myosin light-chain kinase which leads to smooth muscle relaxation and vasodilation. Notably, PGI2 and TXA2 work as antagonists. PGI2 is stable in basic buffers (pH=8), but it is rapidly hydrolyzed to 6-keto PGF1alpha in neutral or acidic solutions. The half-life is short both in vivo and in vitro, ranging from 30 seconds to a few minutes. PGI2 is administered by continuous infusion in humans for the treatment of idiopathic pulmonary hypertension.
Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. [HMDB](5Z,13E,15S)-6,9a-epoxy-11a,15-dihydroxyprosta-5,13-dienoate(5Z,13E,15S)-6,9a-epoxy-11a,15-dihydroxyprosta-5,13-dienoic acid(5Z,13E)-(15S)-6,9-alpha-epoxy-11-alpha,15-dihydroxyprosta-5,13-dienoate(5Z,13E)-(15S)-6,9-alpha-epoxy-11-alpha,15-dihydroxyprosta-5,13-dienoic acid(5Z,13E)-(15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dienoate(5Z,13E)-(15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dienoic acid(5Z,13e)-(15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoate(5Z,13e)-(15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoic acid(5Z,13E)-(15S)-6,9alpha-Epoxy-11alpha,15-dihydroxyprosta-5,13-dienoate(5Z,13E)-(15S)-6,9alpha-Epoxy-11alpha,15-dihydroxyprosta-5,13-dienoic acid(5Z,13e)-(15S)-6,9α-epoxy-11α,15-dihydroxyprosta-5,13-dienoate(5Z,13e)-(15S)-6,9α-epoxy-11α,15-dihydroxyprosta-5,13-dienoic acid(5Z,9a,11a,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oate(5Z,9a,11a,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oic acid(5Z,9alpha,11alpha,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oate(5Z,9alpha,11alpha,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oic acid(5Z,9α,11α,13e,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oate(5Z,9α,11α,13e,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oic acidEpoprostenolFlolanPGI2PGXprostacyclinprostacyclineProstaglandin I2Prostaglandin XVasocyclinC20H32O5352.4651352.2249741345-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acidepoprostenol35121-78-9[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@]1([H])CC(O2)=CCCCC(O)=OInChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8?/t14-,16+,17+,18+,19-/m0/s1KAQKFAOMNZTLHT-VVUHWYTRSA-N belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.Prostaglandins and related compoundsOrganic compoundsLipids and lipid-like moleculesFatty AcylsEicosanoidsAliphatic heteropolycyclic compoundsCarbonyl compoundsCarboxylic acidsCyclic alcohols and derivativesFatty alcoholsHeterocyclic fatty acidsHydrocarbon derivativesHydroxy fatty acidsMedium-chain fatty acidsMedium-chain hydroxy acids and derivativesMonocarboxylic acids and derivativesOrganic oxidesOxacyclic compoundsSecondary alcoholsTetrahydrofuransAlcoholAliphatic heteropolycyclic compoundCarbonyl groupCarboxylic acidCarboxylic acid derivativeCyclic alcoholFatty alcoholHeterocyclic fatty acidHydrocarbon derivativeHydroxy fatty acidMedium-chain fatty acidMedium-chain hydroxy acidMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacycleProstaglandin skeletonSecondary alcoholTetrahydrofuranSolidlogp3.83logs-3.41solubility1.36e-01 g/llogp2.42pka_strongest_acidic4.43pka_strongest_basic-1.6iupac5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acidaverage_mass352.4651mono_mass352.224974134smiles[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@]1([H])CC(O2)=CCCCC(O)=OformulaC20H32O5inchiInChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8?/t14-,16+,17+,18+,19-/m0/s1inchikeyKAQKFAOMNZTLHT-VVUHWYTRSA-Npolar_surface_area86.99refractivity99.01polarizability41.59rotatable_bond_count10acceptor_count5donor_count3physiological_charge-1formal_charge0Arachidonic Acid MetabolismSMP00075map00590Specdb::MsMs262275Specdb::MsMs262276Specdb::MsMs262277Specdb::MsMs282207Specdb::MsMs282208Specdb::MsMs282209HMDB0133515552#<Reference:0x00005556758489a8>#<Reference:0x00005556758487f0>#<Reference:0x0000555675848638>#<Reference:0x0000555675848480>#<Reference:0x00005556758482c8>#<Reference:0x0000555675848110>#<Reference:0x0000555675847f08>#<Reference:0x0000555675847d50>#<Reference:0x0000555675847b98>#<Reference:0x00005556758479e0>#<Reference:0x0000555675847828>#<Reference:0x0000555675847670>#<Reference:0x00005556758474b8>#<Reference:0x0000555675847300>#<Reference:0x0000555675847148>#<Reference:0x0000555675846f90>#<Reference:0x0000555675846dd8>#<Reference:0x0000555675846c20>#<Reference:0x0000555675846a68>#<Reference:0x00005556758468b0>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823Prostacyclin receptorP43119PTGIR