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Record Information
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-04-23 20:52:11 UTC
Secondary Accession Numbers
  • HMDB01442
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. There are several mechanisms of PGE1 hepatic cytoprotection: inhibiting T-cell mediated cytotoxicity, enhancing DNA synthesis of the injured liver after partial hepatectomy by stimulating cyclic AMP production, increasing ATP level in hepatic tissue to accelerate the recovery of mitochondrial respiratory function after reperfusion, and stabilizing membrane microviscosity. PGE1 is a prostanoid. The term prostanoid collectively describes prostaglandins, prostacyclins, and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They are derived from C-20 polyunsaturated fatty acids, mainly dihomo-γ-linolenic (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 and are 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 signalling pathways.
(11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acidChEBI
11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoic acidChEBI
Prostin VRChEBI
Prostin VR pediatricKegg
(11a,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acidGenerator
(11Α,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-Oic acidGenerator
(13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acidGenerator
(13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acidGenerator
(13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoic acidGenerator
11a,15a-Dihydroxy-9-oxo-13-trans-prostenoic acidGenerator
11Α,15α-dihydroxy-9-oxo-13-trans-prostenoic acidGenerator
Caverject impulseHMDB
(+)-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
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
Lipo pge1HMDB
Prostaglandin e1alphaHMDB
Prostine VRHMDB
Abbott brand OF alprostadilHMDB
Paladin brand OF alprostadilHMDB
Schwarz pharma brand OF alprostadilHMDB
Astra brand OF alprostadilHMDB
Hoyer brand OF alprostadilHMDB
Allphar brand OF alprostadilHMDB
AstraZeneca brand OF alprostadilHMDB
Janssen brand OF alprostadilHMDB
Pharmacia brand 1 OF alprostadilHMDB
Pharmacia brand 2 OF alprostadilHMDB
Schwarz brand OF alprostadilHMDB
Vivus brand OF alprostadilHMDB
Prostaglandin e1MeSH, KEGG
Chemical FormulaC20H34O5
Average Molecular Weight354.487
Monoisotopic Molecular Weight354.240624195
IUPAC Name7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
Traditional Namealprostadil
CAS Registry Number745-65-3
InChI Identifier
Chemical Taxonomy
Description 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
  • Fatty alcohol
  • Hydroxy fatty acid
  • Cyclopentanol
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors

Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Biological role:

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 g/LALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity98.32 m³·mol⁻¹ChemAxon
Polarizability42.13 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-67bf705be88aef628788Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0k9l-2159000000-ea5fde7ba374a4b745acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9420000000-64831d7733e0f1578bc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-8df8823c74db989620bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0673-4297000000-470e93d0689f9efe2bf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06du-9120000000-617b73c4fa8e71daf174Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Epidermis
  • Fibroblasts
  • Kidney
  • Liver
  • Neuron
  • Placenta
  • Platelet
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
Phenol Explorer Compound IDNot Available
FooDB IDFDB022625
KNApSAcK IDNot Available
Chemspider ID4444306
KEGG Compound IDC04741
BioCyc IDNot Available
BiGG ID44455
Wikipedia LinkProstaglandin_E1
PubChem Compound5280723
PDB IDNot Available
ChEBI ID15544
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:9607949 ]
  15. Liu XL, Fan DM: Protective effects of prostaglandin E1 on hepatocytes. World J Gastroenterol. 2000 Jun;6(3):326-329. [PubMed: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. [PubMed: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: