Prostaglandin E1

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Prostaglandin E1
Alprostadil.svg
Alprostadil-BallStick.png
Systematic (IUPAC) name
7-[(1R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
Clinical data
MedlinePlusa695022
Pregnancy cat.C (US)
Legal statusRx only Canada
Identifiers
CAS number745-65-3 YesY
ATC codeC01EA01 G04BE01
PubChemCID 149351
IUPHAR ligand1882
DrugBankDB00770
ChEBICHEBI:15544 N
ChEMBLCHEMBL495 N
Chemical data
FormulaC20H34O5 
Mol. mass354.481 g/mol
 N (what is this?)  (verify)
 
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Prostaglandin E1
Alprostadil.svg
Alprostadil-BallStick.png
Systematic (IUPAC) name
7-[(1R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
Clinical data
MedlinePlusa695022
Pregnancy cat.C (US)
Legal statusRx only Canada
Identifiers
CAS number745-65-3 YesY
ATC codeC01EA01 G04BE01
PubChemCID 149351
IUPHAR ligand1882
DrugBankDB00770
ChEBICHEBI:15544 N
ChEMBLCHEMBL495 N
Chemical data
FormulaC20H34O5 
Mol. mass354.481 g/mol
 N (what is this?)  (verify)

Prostaglandin E1 (PGE1) is a prostaglandin.

The synthetic variant is known pharmaceutically as alprostadil.[1] It is a drug used in the continuous treatment of erectile dysfunction.[2] and has vasodilatory properties. 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.

Medical uses[edit]

Patent ductus arteriosus[edit]

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., pulmonary atresia/stenosis, tricuspid atresia/stenosis, transposition of the great arteries) and acyanotic lesions (e.g., coarctation of the aorta, hypoplastic left heart syndrome, critical aortic stenosis, and interrupted aortic arch).

Sexual dysfunction[edit]

Alprostadil is sold in the United States as urethral suppositories and in injectable form. The suppositories are sold under the brand name Muse.[3] The injectable forms are Edex[4] and Caverject.[5] 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.

Critical limb ischemia[edit]

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[edit]

Biosynthesis

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

References[edit]

  1. ^ Cawello W, Leonhardt A, Schweer H, Seyberth HW, Bonn R, Lomeli AL (September 1995). "Dose proportional pharmacokinetics of alprostadil (prostaglandin E1) in healthy volunteers following intravenous infusion". British Journal of Clinical Pharmacology 40 (3): 273–6. doi:10.1111/j.1365-2125.1995.tb05784.x. PMC 1365109. PMID 8527291. 
  2. ^ Harding LM, Adeniyi A, Everson R, Barker S, Ralph DJ, Baranowski AP (December 2002). "Comparison of a needle-free high-pressure injection system with needle-tipped injection of intracavernosal alprostadil for erectile dysfunction". International Journal of Impotence Research 14 (6): 498–501. doi:10.1038/sj.ijir.3900916. PMID 12494285. 
  3. ^ "Muse Suppository - Facts and Comparisons". Drugs.com. Retrieved 4 January 2013. 
  4. ^ Edex - Facts and Comparisons Drugs.com
  5. ^ Caverject - Facts and Comparisons Drugs.com
  6. ^ 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.