1.0 2011-09-21 00:17:03 UTC 2015-10-09 22:33:18 UTC FDB022625 Prostaglandin E1 Prostaglandin E1 (PGE1) is a potent endogenous vasodilator agent that increases peripheral blood flow. It inhibits platelet aggregation and has many other biological effects such as bronchodilation, mediation of inflammation, and various protective functions. The protective action of PGE1 has been shown on both experimental animal models of liver injury and patients with fulminant viral hepatitis. PGE1-treated cirrhotic rats had less hepatosplenomegaly, lower serum alanine aminotransferase levels, and portal pressures and higher arterial pressure than placebo-treated cirrhotic rats. Mechanisms of hepatic cytopotection of PGE1: inhibitory effects on T-cell mediated cytotoxicity, enhance DNA synthesis of injured liver after partial hepatectomy by stimulating cyclic AMP production and increasing ATP level in hepatic tissue, and could accelerate the recovery of mitochondrial respiratory functio n after reperfusion, stabilization of membrane microviscosity. PGE1 is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). (PMID: 11819590, 16986207) 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] (-)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoate (-)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoic acid (-)-Prostaglandin E1 (+)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoate (+)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoic acid (11a,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oate (11a,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid (11alpha,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oate (11alpha,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid (11α,13e,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-Oate (11α,13e,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-Oic acid (13E)-(15S)-11-alpha,15-dihydroxy-9-oxoprost-13-enoate (13E)-(15S)-11-alpha,15-dihydroxy-9-oxoprost-13-enoic acid (13E)-(15S)-11,15-dihydroxy-9-oxoprost-13-enoate (13E)-(15S)-11,15-dihydroxy-9-oxoprost-13-enoic acid (13e)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoate (13e)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acid (13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoate (13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoic acid (13e)-(15S)-11α,15-dihydroxy-9-oxoprost-13-enoate (13e)-(15S)-11α,15-dihydroxy-9-oxoprost-13-enoic acid 11,15-Dihydroxy-9-oxoprost-13-en-1-oate 11,15-Dihydroxy-9-oxoprost-13-en-1-oic acid 11,15-dihydroxy-9-oxoprost-13-en-1-oic acid (ACD/Name 4.0) 11a,15a-Dihydroxy-9-oxo-13-trans-prostenoate 11a,15a-Dihydroxy-9-oxo-13-trans-prostenoic acid 11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoate 11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoic acid 11α,15α-dihydroxy-9-oxo-13-trans-prostenoate 11α,15α-dihydroxy-9-oxo-13-trans-prostenoic acid 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid Alprostadil Alprostadil Prostoglandin E1 Alprostadil(usan) Alprostadilum Befar Befar (TN) Caverject EDEX l-Prostaglandin E1 MUSE PGE-1 PGE1 Prink Prink (TN) prostaglandin E1 Prostin VR C20H34O5 354.481 354.240624198 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid alprostadil 745-65-3 CCCCC[C@H](O)C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/t15-,16+,17+,19+/m0/s1 GMVPRGQOIOIIMI-DODZYUBVSA-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 compounds Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic homomonocyclic compounds Carboxylic acids Cyclic alcohols and derivatives Cyclic ketones Cyclopentanols Fatty alcohols Hydrocarbon derivatives Hydroxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Alcohol Aliphatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Cyclic ketone Cyclopentanol Fatty alcohol Hydrocarbon derivative Hydroxy fatty acid Ketone Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Prostaglandin skeleton Secondary alcohol Solid logp 3.04 ALOGPS logs -3.65 ALOGPS solubility 7.88e-02 g/l ALOGPS logp 3.59 ChemAxon pka_strongest_acidic 4.35 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid ChemAxon average_mass 354.481 ChemAxon mono_mass 354.240624198 ChemAxon smiles CCCCC[C@H](O)C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O ChemAxon formula C20H34O5 ChemAxon inchi InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/t15-,16+,17+,19+/m0/s1 ChemAxon inchikey GMVPRGQOIOIIMI-DODZYUBVSA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 98.32 ChemAxon polarizability 42.35 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 14567 Specdb::CMs 38076 Specdb::MsMs 245637 Specdb::MsMs 245638 Specdb::MsMs 245639 Specdb::MsMs 265584 Specdb::MsMs 265585 Specdb::MsMs 265586 HMDB01442 15544 #<Reference:0x000055ce3324e670> #<Reference:0x000055ce3324e4b8> #<Reference:0x000055ce3324e2b0> #<Reference:0x000055ce3324e0f8> #<Reference:0x000055ce3324df40> #<Reference:0x000055ce3324dd38> #<Reference:0x000055ce3324db80> #<Reference:0x000055ce3324d9c8> #<Reference:0x000055ce3324d7c0> #<Reference:0x000055ce3324d608> #<Reference:0x000055ce3324d428> #<Reference:0x000055ce3324d270> #<Reference:0x000055ce3324d0b8> #<Reference:0x000055ce3324ce88> #<Reference:0x000055ce3324ccd0> #<Reference:0x000055ce3324cb18> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Carbonyl reductase [NADPH] 1 P16152 CBR1