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Prostaglandin E1 information



Prostaglandin E1
Clinical data
Trade namesCaverject, Muse, others
AHFS/Drugs.comMonograph
MedlinePlusa695022
License data
  • US DailyMed: Alprostadil
Routes of
administration
Intravenous
ATC code
  • C01EA01 (WHO) G04BE01 (WHO)
Legal status
Legal status
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNING[1]Rx-only
Identifiers
IUPAC name
  • 7-[(1R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
CAS Number
  • 745-65-3 checkY
PubChem CID
  • 5280723
IUPHAR/BPS
  • 1882
DrugBank
  • DB00770 ☒N
ChemSpider
  • 4444306 ☒N
UNII
  • F5TD010360
KEGG
  • C04741
ChEBI
  • CHEBI:15544 ☒N
ChEMBL
  • ChEMBL495 ☒N
CompTox Dashboard (EPA)
  • DTXSID9022578 Edit this at Wikidata
ECHA InfoCard100.010.925 Edit this at Wikidata
Chemical and physical data
FormulaC20H34O5
Molar mass354.487 g·mol−1
3D model (JSmol)
  • Interactive image
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
 ☒NcheckY (what is this?)  (verify)

Prostaglandin E1 (PGE1) is a naturally occurring prostaglandin and is also used as a medication (alprostadil).[2]

In infants with congenital heart defects, it is delivered by slow injection into a vein to open the ductus arteriosus until surgery can be carried out.[3] By injection into the penis or placement in the urethra, it is used to treat erectile dysfunction.[4]

Common side effects when given to babies include decreased breathing, fever, and low blood pressure.[2] When injected into the penis for erectile dysfunction; side effects may include penile pain, bleeding at the site of injection, and prolonged erection (priapism).[2] Prostaglandin E1 is in the vasodilator family of medications.[2] It works by opening blood vessels and relaxing smooth muscle.[2]

Prostaglandin E1 was isolated in 1957 and approved for medical use in the United States in 1981.[2][5] It is on the World Health Organization's List of Essential Medicines.[6]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  2. ^ a b c d e f "Alprostadil". The American Society of Health-System Pharmacists. Archived from the original on 16 January 2017. Retrieved 8 January 2017.
  3. ^ 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.
  4. ^ British National Formulary (BNF) (69th ed.). British Medical Association. 2015. p. 569. ISBN 9780857111562.
  5. ^ Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 185. ISBN 9780470015520. Archived from the original on 13 January 2017.
  6. ^ 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.

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especially similar to selective COX-2 inhibitors. Paracetamol inhibits prostaglandin synthesis by reducing the active form of COX-1 and COX-2 enzymes. This...

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cases, uterine rupture may occur. It is a prostaglandin analogue—specifically, a synthetic prostaglandin E1 (PGE1). Misoprostol was developed in 1973...

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administered intravenously to horses. A single dose has been shown to reduce prostaglandin E2 production and inflammatory exudate for up to 15 hours, although...

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swelling from inflammation. It works by inhibiting the production of prostaglandins, endogenous signaling molecules known to cause these symptoms. It does...

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period. Like other NSAIDs, it works by inhibiting the production of prostaglandins by decreasing the activity of the enzyme cyclooxygenase (COX). Ibuprofen...

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non-selectively to block the prostaglandin synthesis by inhibition of prostaglandin G/H synthesis 1 and 2. Prostaglandin functions in the body as a messenger...

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antipyretic effects. It acts by inhibiting the body's production of prostaglandin. It was patented in 1967 and approved for medical use in 1980. Ketoprofen...

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Prostaglandin H2 (PGH2), or prostaglandin H2 (PGH2), is a type of prostaglandin and a precursor for many other biologically significant molecules. It...

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Erectile dysfunction

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10–20 μg of prostaglandin E1, with evaluations of the arterial flow every five minutes for 25–30 min (see image). The use of prostaglandin E1 is contraindicated...

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Thromboxane

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enzyme found in platelets, converts the arachidonic acid derivative prostaglandin H2 to thromboxane. People with asthma tend to have increased thromboxane...

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Dexketoprofen

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involved in the production of chemicals in the body called prostaglandins. Prostaglandins are produced in response to injury or certain diseases and would...

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Lubiprostone

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citation needed] Lubiprostone is a bicyclic fatty acid derived from prostaglandin E1 that acts by specifically activating ClC-2 chloride channels on the...

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Prostaglandin EP3 receptor (EP3, 53kDa), is a prostaglandin receptor for prostaglandin E2 (PGE2) encoded by the human gene PTGER3; it is one of four identified...

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response. Prostanoids are a subclass of eicosanoids consisting of the prostaglandins (mediators of inflammatory and anaphylactic reactions), the thromboxanes...

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the eye, itchiness, and darkening of the iris. Latanoprost is in the prostaglandin analogue family of medications. It works by increasing the outflow of...

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in animal fats. It is a precursor in the formation of leukotrienes, prostaglandins, and thromboxanes. Together with omega-3 fatty acids and other omega-6...

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characterized by a fast onset of action. It works by blocking the production of prostaglandins (a chemical associated with pain), thereby relieving pain and inflammation...

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