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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:41 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameProstaglandin E1
DescriptionProstaglandin 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.
(+)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acidHMDB
(-)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acidHMDB
(-)-Prostaglandin e1HMDB
(13E)-(15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acidHMDB
(13E)-(15S)-11-alpha,15-Dihydroxy-9-oxoprost-13-enoic acidHMDB
(13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acidHMDB
11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acidHMDB
11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid (acd/name 4.0)HMDB
3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acidHMDB
Alprostadil prostoglandin e1HMDB
L-Prostaglandin e1HMDB
Prostin VRHMDB
Chemical FormulaC20H34O5
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
IUPAC Name7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
Traditional Namealprostadil
CAS Registry Number745-65-3
InChI Identifier
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty alcohol
  • Carbocyclic fatty acid
  • Cyclopentanol
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
StatusDetected and Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Component of Prostaglandin and leukotriene metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
Experimental Properties
Melting Point115 - 116 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.20AVDEEF,A ET AL. (1995)
Predicted Properties
Water Solubility0.079 mg/mLALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity98.32 m3·mol-1ChemAxon
Polarizability41.88 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Artery
  • Fibroblasts
  • Kidney
  • Liver
  • Nerve Cells
  • Placenta
  • Platelet
  • Skin
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified<0.0001 uMAdult (>18 years old)Both
BloodDetected and Quantified0.0000037 (0.0000034-0.0000051) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified<0.0001 uMAdult (>18 years old)Both
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022625
KNApSAcK IDNot Available
Chemspider ID4444306
KEGG Compound IDC04741
BiGG ID44455
Wikipedia LinkAlprostadil
NuGOwiki LinkHMDB01442
Metagene LinkHMDB01442
PubChem Compound5280723
PDB IDNot Available
ChEBI ID15544
Synthesis ReferenceLiang, Yong-tao; Wei, Feng-ping; Li, Gui-ying; Wang, En-si. Chemoenzymic synthesis of prostaglandin E1. Jilin Daxue Ziran Kexue Xuebao (2001), (2), 77-80.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Borsick M, Rajkhowa T, Taub M: Evidence for post-transcriptional regulation of Na,K-ATPase by prostaglandin E1. Biochem Biophys Res Commun. 2006 Jun 30;345(2):739-45. Epub 2006 May 5. [16701566 ]
  2. Weiss T, Fischer D, Hausmann D, Weiss C: Endothelial function in patients with peripheral vascular disease: influence of prostaglandin E1. Prostaglandins Leukot Essent Fatty Acids. 2002 Nov;67(5):277-81. [12445486 ]
  3. Thum J, Caspary L, Creutzig A, Alexander K: Intra-arterial and intravenous administration of prostaglandin E1 cause different changes to skin microcirculation in patients with peripheral arterial occlusive disease. Vasa. 1998 May;27(2):100-5. [9612114 ]
  4. Foldvari M, Oguejiofor CJ: Metabolism studies on transdermal prostaglandin E1 in human foreskin in vitro. Eur J Drug Metab Pharmacokinet. 1997 Apr-Jun;22(2):111-20. [9248778 ]
  5. Kornberg A, Schotte U, Kupper B, Hommann M, Scheele J: Impact of selective prostaglandin E1 treatment on graft perfusion and function after liver transplantation. Hepatogastroenterology. 2004 Mar-Apr;51(56):526-31. [15086195 ]
  6. Sato Y, Suzuki N, Adachi H, Hisasue S, Horita H, Tsukamoto T: Evaluation of the alleviative action of neurotropin for penile pain associated with intracavernous injection of prostaglandin E1 assessed using the visual analogue scale. Int J Impot Res. 1998 Mar;10(1):1-3. [9542683 ]
  7. Kikura M, Kazama T, Ikeda T, Sato S: Disaggregatory effects of prostaglandin E1, amrinone and milrinone on platelet aggregation in human whole blood. Platelets. 2000 Dec;11(8):446-58. [11177444 ]
  8. Rady-Pentek P, Mueller R, Tang BK, Kalow W: Interindividual variation in the enzymatic 15-keto-reduction of 13,14-dihydro-15-keto-prostaglandin E1 in human liver and in human erythrocytes. Eur J Clin Pharmacol. 1997;52(2):147-53. [9174685 ]
  9. Kunimoto F, Arai K, Isa Y, Koyano T, Kadoi Y, Saito S, Goto F: A comparative study of the vasodilator effects of prostaglandin E1 in patients with pulmonary hypertension after mitral valve replacement and with adult respiratory distress syndrome. Anesth Analg. 1997 Sep;85(3):507-13. [9296401 ]
  10. Sinzinger H, Kritz H, Virgolini I, Schmid P, Rogatti W: Prostaglandin E1 increases binding of 123I-low-density lipoprotein to the human liver in vivo. Eur J Clin Pharmacol. 1996;49(6):515-20. [8706779 ]
  11. Fabbri A, Magalotti D, Marchesini G, Brizi M, Bianchi G, Zoli M: Effects of systemic prostaglandin E1 on splanchnic and peripheral haemodynamics in control subjects and in patients with cirrhosis. Prostaglandins Other Lipid Mediat. 1998 Mar;55(4):209-18. [9644112 ]
  12. Fabbri A, Bianchi G, Brizi M, Bugianesi E, Magalotti D, Zoli M, Marchesini G: Effects of systemic prostaglandin E1 on hepatic amino acid-nitrogen metabolism in patients with cirrhosis. Hepatology. 1998 Mar;27(3):815-21. [9500712 ]
  13. Hawker RJ, Turner VS, Mitchell SG: Use of prostaglandin E1 during preparation of platelet concentrates. Transfus Med. 1996 Sep;6(3):249-54. [8885155 ]
  14. Foldvari M, Oguejiofor CJ, Wilson TW, Afridi SK, Kudel TA: Transcutaneous delivery of prostaglandin E1: in vitro and laser doppler flowmetry study. J Pharm Sci. 1998 Jun;87(6):721-5. [9607949 ]
  15. Liu XL, Fan DM: Protective effects of prostaglandin E1 on hepatocytes. World J Gastroenterol. 2000 Jun;6(3):326-329. [11819590 ]
  16. Masoodi M, Nicolaou A: Lipidomic analysis of twenty-seven prostanoids and isoprostanes by liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(20):3023-9. [16986207 ]


General function:
Involved in oxidoreductase activity
Specific function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:
Uniprot ID:
Molecular weight: