Prostaglandin E1

Prostaglandin E1
Clinical data
Trade namesCaverject, Muse, others
AHFS/Drugs.comMonograph
MedlinePlusa695022
License data
Routes of
administration		Intravenous, intracavernous
ATC code
Legal status
Legal status
Identifiers
IUPAC name
  • 7-[(1R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.010.925
Chemical and physical data
FormulaC20H34O5
Molar mass354.487 g·mol−1
3D model (JSmol)
SMILES
  • CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)O)O)O
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)/b13-12+/t15-,16+,17+,19+/m0/s1 N
  • Key:GMVPRGQOIOIIMI-DWKJAMRDSA-N N
 NY (what is this?)  (verify)

Prostaglandin E1 (PGE1) is a naturally occurring prostaglandin with various medical uses. Alprostadil and misoprostol are synthetic forms of prostaglandin E1 used as medications. Lubiprostone, a derivative of prostaglandin E1, is also used as a medication.[3][4] Prostaglandin E1 is a vasodilator. It has various effects in the body that include opening blood vessels, relaxing smooth muscle, inhibiting clotting, and causing uterine contractions.[3][5]

In infants with certain congenital heart defects, alprostadil is delivered by slow injection into a vein to maintain a patent ductus arteriosus until surgery can be carried out.[5] By injection into the penis or placement in the urethra, alprostadil is used to treat erectile dysfunction.[6] Common side effects when given to babies include decreased breathing, fever, and low blood pressure.[3] When injected into the penis for erectile dysfunction; side effects may include penile pain, bleeding at the site of injection, and prolonged erection (priapism).[3] Prostaglandin E1 was isolated in 1957 and approved for medical use in the United States in 1981.[3][7]

Misoprostol has various obstetric uses. It is used to induce abortion, to completely empty the uterus after a miscarriage, to induce labor, and to prevent and treat postpartum hemorrhage. The medication is available through many routes. It can be swallowed, dissolved in the mouth, placed in the vagina, or placed in the rectum. Misoprostol can also be used to manage duodenal ulcers and peptic ulcer disease when other medications are not effective.[8] It is on the World Health Organization's List of Essential Medicines for its obstetric uses.[9]

Lubiprostone is a PGE1 derivative used to treat chronic constipation. It is taken orally.[10] Common side effects include diarrhea, vomiting, and abdominal pain.[11]

  1. ^ "Neupedix alprostadil 500 microgram/1 mL solution for injection ampoule (446011)". Therapeutic Goods Administration (TGA). Retrieved 9 May 2025.
  2. ^ "Neupedix 500 micrograms/ml concentrate for solution for infusion". electronic medicines compendium (emc). 7 May 2025. Retrieved 9 May 2025.
  3. ^ a b c d e "Alprostadil". The American Society of Health-System Pharmacists. Archived from the original on 16 January 2017. Retrieved 8 January 2017.
  4. ^ Hew MR, Gerriets V (3 April 2023). "Prostaglandin E1". StatPearls. PMID 31536236 – via National Library of Medicine.
  5. ^ a b Northern Neonatal Network (208). Neonatal Formulary: Drug Use in Pregnancy and the First Year of Life (5 ed.). John Wiley & Sons. p. 2010. ISBN 9780470750353. Archived from the original on 13 January 2017. {{cite book}}: ISBN / Date incompatibility (help)
  6. ^ British National Formulary (BNF) (69th ed.). British Medical Association. 2015. p. 569. ISBN 9780857111562.
  7. ^ Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 185. ISBN 9780470015520. Archived from the original on 13 January 2017.
  8. ^ Dudzinski DM, Serhan CN (2017). "Pharmacology of Eicosanoids". In Golan DE, Armstrong EJ, Armstrong AW (eds.). Principles of Pharmacology: The Pathophysiologic Basis of Drug Therapy (4th ed.). Wolters Kluwer. ISBN 9781451191004.
  9. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  10. ^ Dietrich E, Rubin D (2023). "Anti-Inflammatory, Antipyretic, and Analgesic Agents". In Whalen K, Lerchenfeldt S, Giordano C (eds.). Pharmacology (8th ed.). Wolters Kluwer. pp. 613–633. ISBN 9781975170554.
  11. ^ "Lubiprostone: Drug Information". UpToDate Lexidrug. Wolters Kluwer. 2025.
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