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Prostaglandin E1

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Prostaglandin E1
Clinical data
Trade namesCaverject, Muse, others
AHFS/Drugs.comMonograph
MedlinePlusa695022
Routes of
administration		IV
ATC code
Legal status
Legal status
Identifiers
  • 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
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.010.925 Edit this at Wikidata
Chemical and physical data
FormulaC20H34O5
Molar mass354.481 g/mol g·mol−1
3D model (JSmol)
  • CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)O)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)/b13-12+/t15-,16+,17+,19+/m0/s1 ☒N
  • Key:GMVPRGQOIOIIMI-DWKJAMRDSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Prostaglandin E1 (PGE1), also known as alprostadil, is a naturally occurring prostaglandin which is used as a medication.[2] In babies with congenital heart defects, it is used 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 used for erectile dysfunction side effects may include penile pain, bleeding at the site of injection, and prolonged erection.[2] Prostaglandin E1 is in the vasodilator family of medications.[2] It works by opening blood vessels by 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, the most effective and safe medicines needed in a health system.[6] In the United Kingdom a dose costs the NHS about 75 pounds.[7] In the United States it costs 100 to 200 USD per dose.[8] In babies, however, Prostaglandin E2 works as well as prostaglandin E1, and is much less expensive.[3]

Medical uses

Patent ductus arteriosus

Alprostadil is also used in maintaining a patent ductus arteriosus in newborns. This is primarily useful when the threat of premature closure of the ductus arteriosus exists in an infant with ductal-dependent congenital heart disease, including cyanotic lesions (e.g., hypoplastic left heart syndrome, pulmonary atresia/stenosis, tricuspid atresia/stenosis, transposition of the great arteries) and acyanotic lesions (e.g., coarctation of the aorta, critical aortic stenosis, and interrupted aortic arch).

Sexual dysfunction

Alprostadil is sold in the United States as urethral suppositories and in injectable form. The suppositories are sold under the brand name Muse.[9] The injectable forms are Edex[10] and Caverject.[11] Muse delivers alprostadil as a penile suppository, inserted into the urethra, at least ten minutes before the erection is needed. Caverject and Edex are similarly fast-acting, but instead are injected by syringe directly into the corpus cavernosum of the penis.

Alprostadil is also available as a generic. The major cost is that it must be mixed by a compounding pharmacy and supplies may be difficult to obtain. The different formulations, including bimix and trimix, may include papaverine and/or phentolamine. A typical mix might be 30 mg of papaverine, 2 mg of phentolamine, and 20 μg alprostadil. As a generic, it is much less expensive than the packaged injectables. It is premixed and must be kept refrigerated and the user must load a syringe with the quantity needed.

Most recently, the compound has been made easily accessible in an applicable topical cream form known as Vitaros.[12] Made by Takeda UK Ltd, it is now available in Europe and contains either 200 or 300 micrograms of alprostadil in 100 mg of cream which is directly administered as a topical cream applied to the urethra in a preloaded delivery device. The tip of the device is placed in the urethral meatus and the cream delivered into the urethra. Clinical trials for the treatment showed positive results in over 3000 men that it was tested on, and unlike other sexual dysfunction medication, it is said to be usable by men suffering from diabetes or heart problems and those who have undergone a prostatectomy.[13] It has no known interactions with food, alcohol or other medications making it safer than other treatments containing alprostadil. Similarly to the Bimix and Trimix injections though, it must be kept under cool temperatures.

Critical limb ischemia

Alprostadil is also used for critical limb ischemia. It increases blood flow by peripheral vasodilation within five minutes and induces angiogenesis. It is most effective when the ankle pressure is at least 30 mmHg and at least one tibial artery is patent.

Adverse effects

Biosynthesis

Prostaglandin E1 is biosynthesized on an as-needed basis from dihomo-γ-linolenic acid (an omega-6 fatty acid) in healthy humans without coronary artery disease[14] and/or a genetic disorder.

Other versions

Misoprostol is another synthetic prostaglandin E1 analog used to prevent gastric ulcers when taken on a continuous basis, to treat missed miscarriage, to induce labor, and to induce abortion.

References

  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 Oct 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. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  3. ^ 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 2017-01-13. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  4. ^ British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 569. ISBN 9780857111562.
  5. ^ Sneader, Walter (2005). Drug Discovery: A History. John Wiley & Sons. p. 185. ISBN 9780470015520. Archived from the original on 2017-01-13. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  6. ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived from the original (PDF) on 13 December 2016. Retrieved 8 December 2016. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  7. ^ Ainsworth, Sean B. (2014). Neonatal Formulary: Drug Use in Pregnancy and the First Year of Life. John Wiley & Sons. p. 436. ISBN 9781118819593. Archived from the original on 2017-01-13. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  8. ^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 477. ISBN 9781284057560.
  9. ^ "Muse Suppository - Facts and Comparisons". Drugs.com. Archived from the original on 19 January 2013. Retrieved 4 January 2013. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  10. ^ Edex - Facts and Comparisons Archived 2012-10-26 at the Wayback Machine Drugs.com
  11. ^ Caverject - Facts and Comparisons Archived 2012-10-26 at the Wayback Machine Drugs.com
  12. ^ Vitaros 3 mg/g cream - Summary of Product Characteristics Archived 2015-02-11 at the Wayback Machine Medicines.org.uk
  13. ^ Vitaros- New Erectile Dysfunction Topical Treatment Archived 2015-02-11 at the Wayback Machine Meds4All.co.uk
  14. ^ Stephanie M. Meller, BA, Erik Stilp, MD, Charles N. Walker, MD, Carlos Mena-Hurtado, MD (June 2013). "The Link Between Vasculogenic Erectile Dysfunction, Coronary Artery Disease, and Peripheral Artery Disease: Role of Metabolic Factors and Endovascular Therapy". Journal of Invasive Cardiology. 25 (6): 313–319. Archived from the original on 2014-08-10. {{cite journal}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)CS1 maint: multiple names: authors list (link)
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