Prostaglandin E1

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Prostaglandin E1
Alprostadil.svg
Prostaglandin-E1-from-xtal-3D-bs-17.png
Clinical data
Trade names Caverject, Muse, others
AHFS/Drugs.com Monograph
MedlinePlus a695022
License data
Routes of
administration 		Intravenous, intracavernous
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
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KEGG
ChEBI
ChEMBL
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ECHA InfoCard 100.010.925 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C20H34O5
Molar mass 354.487 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 X mark.svgN
  • Key:GMVPRGQOIOIIMI-DWKJAMRDSA-N X mark.svgN
 X mark.svgNYes check.svgY  (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. [2] [3] 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. [2] [4]

Contents

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. [4] By injection into the penis or placement in the urethra, alprostadil is used to treat erectile dysfunction. [5] 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 was isolated in 1957 and approved for medical use in the United States in 1981. [2] [6]

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. [7] It is on the World Health Organization's List of Essential Medicines for its obstetric uses. [8]

Lubiprostone is a PGE1 derivative used to treat chronic constipation. It is taken orally. [9] Common side effects include diarrhea, vomiting, and abdominal pain. [10]

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 [11] and/or a genetic disorder.

Medical uses

Alprostadil

Alprostadil is used for two main purposes: the treatment of newborns with congenital heart defects and in treatment of erectile dysfunction. [3]

Some babies are born with heart defects which compromise blood flow to the body. In some defects, including tetralogy of Fallot, aortic valvular atresia, and Eisenmenger pulmonary hypertension, alprostadil is given intravenously by a nurse until surgery can be performed to repair the defect. [7] The medication maintains a patent ductus arteriosus. The ductus arteriosus is a shortcut between the aorta and pulmonary artery, two large vessels branching off the heart. This shortcut allows the fetus to maintain blood flow before birth. However, it closes shortly after birth when the newborn can breathe oxygen. In babies with certain congenital defects, however, it's essential to keep the ductus arteriosus open to ensure at least some blood flow throughout the body. Side effects include decreased breathing or a lack of breathing at high doses. The medication can also cause hypotension, or low blood pressure. [4]

Alprostadil is also used for adults with erectile dysfunction. It is typically given when other medications are ineffective. The medication relaxes smooth muscle and allows the arteries in the corpus cavernosum of the penis to dilate. Blood then flows to the penis. This blood flow compresses the veins which drain blood from the penis, trapping the blood in the corpus cavernosum. This process leads to erection. [12] When injected into the base of the penis, alprostadil may cause penile pain, dizziness, headache, high blood pressure, Peyronie disease, and burning at the injection site. When inserted into the urethra, alprostadil may cause urethral burning, penile pain, dizziness, headache, and urethral bleeding. When someone engages in vaginal sex after using an alprostadil urethral suppository, their partner may experience vaginal itching. [3]

Clinical trials for the treatment showed positive results in around 3,000 men that it was tested on; it is said to be usable by men with diabetes or heart problems and those who have undergone a prostatectomy. [13]

Misoprostol

Misoprostol has a variety of uses in obstetrics and gynecology. It is also used to relieve pain from duodenal ulcers when other treatments have been ineffective. [14]

Misoprostol can be used to induce labor in patients at the end of pregnancy. It causes cervical ripening, or the thinning and shortening of the cervix in preparation for birth. It also causes uterine contractions, allowing the body to expel the baby. For this purpose, it is placed inside the vagina. [8] [15]

Misoprostol is also used to prevent and treat postpartum hemorrhage (PPH), or uncontrolled bleeding following childbirth. The World Health Organization estimates that PPH causes 70,000 maternal deaths each year. [16] Misoprostol induces uterine contractions, encouraging the uterus to shrink after childbirth. This shrinking puts pressure on blood vessels on the uterus, forcing them to close rather than continue to bleed. To prevent PPH, misoprostol is given orally or dissolved under the tongue immediately after delivery. To treat PPH, it is given orally, dissolved under the tongue, or placed in the rectum. [17]

For the management of miscarriage in the first trimester of pregnancy, misoprostol is used to completely empty the uterus. This is important because the patient may develop an infection if they retain the products of conception. Misoprostol causes uterine contractions, forcing the body to expel the pregnancy. It can be used alone, but it is more effective in conjunction with mifepristone. Misoprostol is swallowed, placed inside the vagina, or dissolved in the mouth for this purpose. [18]

Misoprostol can also be used to induce abortion. It can be used on its own or following administration of mifepristone. Misoprostol may be used up to and after 28 weeks gestational age to terminate a pregnancy; [17] however, it is typically only used in the first trimester. Later abortions are less common and are usually performed surgically, at least in the United States. [19] For first-trimester abortion, it is dissolved in the cheek or under the tongue; for later abortions, it can also be given as a vaginal suppository. Misoprostol may also be used to ripen the cervix in preparation for surgical abortion. [20]

Misoprostol is given orally for the treatment of ulcers. It interacts with prostaglandin receptors in the stomach to reduce secretion of stomach acids. It increases the production of gastric mucus, which forms a protective coating against stomach acid. Finally, misoprostol encourages the production of bicarbonate, which is a base that counteracts stomach acid. [7] The medication can also protect against stomach ulcers in people who take NSAIDs such as ibuprofen on a daily basis. [21]

Misoprostol can cause nausea, nausea, stomach pain, and stomach cramps. [22] In rare cases, it may lead to uterine rupture, which requires immediate emergency surgery. [17]

Other uses

Prostanoids, including alprostadil, do not reduce the risk of limb amputation but may offer a slight improvement in rest-pain and leg ulcer healing in persons with critical limb ischemia. [23]

Preventative administration of alprostadil may reduce the risk of kidney injury (specifically contrast-induced nephropathy) in persons having cardiac angiography or percutaneous coronary intervention. [24] [25]

Lubiprostone is a PGE1 derivative used to treat chronic constipation. It is taken orally. [9] Common side effects include diarrhea, vomiting, and abdominal pain. [26]

Related Research Articles

Erectile dysfunction (ED), also referred to as impotence, is a form of sexual dysfunction in males characterized by the persistent or recurring inability to achieve or maintain a penile erection with sufficient rigidity and duration for satisfactory sexual activity. It is the most common sexual problem in males and can cause psychological distress due to its impact on self-image and sexual relationships.

<span class="mw-page-title-main">Nonsteroidal anti-inflammatory drug</span> Class of therapeutic drug for relieving pain and inflammation

Non-steroidal anti-inflammatory drugs (NSAID) are members of a therapeutic drug class which reduces pain, decreases inflammation, decreases fever, and prevents blood clots. Side effects depend on the specific drug, its dose and duration of use, but largely include an increased risk of gastrointestinal ulcers and bleeds, heart attack, and kidney disease.

<span class="mw-page-title-main">Priapism</span> Medical condition where an erection lasts excessively long

Priapism is a condition in which a penis remains erect for hours in the absence of stimulation or after stimulation has ended. There are three types: ischemic (low-flow), nonischemic (high-flow), and recurrent ischemic (intermittent). Most cases are ischemic. Ischemic priapism is generally painful while nonischemic priapism is not. In ischemic priapism, most of the penis is hard; however, the glans penis is not. In nonischemic priapism, the entire penis is only somewhat hard. Very rarely, clitoral priapism occurs in women.

<span class="mw-page-title-main">Prostaglandin</span> Group of physiologically active lipid compounds

Prostaglandins (PG) are a group of physiologically active lipid compounds called eicosanoids that have diverse hormone-like effects in animals. Prostaglandins have been found in almost every tissue in humans and other animals. They are derived enzymatically from the fatty acid arachidonic acid. Every prostaglandin contains 20 carbon atoms, including a 5-carbon ring. They are a subclass of eicosanoids and of the prostanoid class of fatty acid derivatives.

<span class="mw-page-title-main">Mifepristone</span> Antiprogestogen and antiglucocorticoid drug

Mifepristone, and also known by its developmental code name RU-486, is a drug typically used in combination with misoprostol to bring about a medical abortion during pregnancy. This combination is 97% effective during the first 63 days of pregnancy, yet effective in the second trimester as well. It is also used on its own to treat Cushing's Syndrome or for use as a low-dose emergency contraceptive.

<span class="mw-page-title-main">Misoprostol</span> Medication to induce abortion and treat ulcers

Misoprostol is a synthetic prostaglandin medication used to prevent and treat stomach and duodenal ulcers, induce labor, cause an abortion, and treat postpartum bleeding due to poor contraction of the uterus. It is taken by mouth when used to prevent gastric ulcers in people taking nonsteroidal anti-inflammatory drugs (NSAID). For abortions it is used by itself or in conjunction with mifepristone or methotrexate. By itself, effectiveness for abortion is between 66% and 90%. For labor induction or abortion, it is taken by mouth, dissolved in the mouth, or placed in the vagina. For postpartum bleeding it may also be used rectally.

<span class="mw-page-title-main">Ductus arteriosus</span> Fetal blood vessel bypassing the lungs

The ductus arteriosus, also called the ductus Botalli, named after the Italian physiologist Leonardo Botallo, is a blood vessel in the developing fetus connecting the trunk of the pulmonary artery to the proximal descending aorta. It allows most of the blood from the right ventricle to bypass the fetus's fluid-filled non-functioning lungs. Upon closure at birth, it becomes the ligamentum arteriosum.

<span class="mw-page-title-main">Indometacin</span> Anti-inflammatory drug

Indometacin, also known as indomethacin, is a nonsteroidal anti-inflammatory drug (NSAID) commonly used as a prescription medication to reduce fever, pain, stiffness, and swelling from inflammation. It works by inhibiting the production of prostaglandins, endogenous signaling molecules known to cause these symptoms. It does this by inhibiting cyclooxygenase, an enzyme that catalyzes the production of prostaglandins.

Cervical dilation is the opening of the cervix, the entrance to the uterus, during childbirth, miscarriage, induced abortion, or gynecological surgery. Cervical dilation may occur naturally, or may be induced surgically or medically.

<span class="mw-page-title-main">Ketorolac</span> Nonsteroidal anti-inflammatory drug (NSAID; analgesic)

Ketorolac, sold under the brand name Toradol, Acular and Sprix, among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain. Specifically it is recommended for moderate to severe pain. Recommended duration of treatment is less than six days, and in Switzerland not more than seven days. It is used by mouth, by nose, by injection into a vein or muscle, and as eye drops. Effects begin within an hour and last for up to eight hours. Ketorolac also has antipyretic (fever-reducing) properties.

<span class="mw-page-title-main">Self-induced abortion</span> Abortion performed by a pregnant person themselves outside the recognized medical system

A self-induced abortion is an abortion performed by the pregnant woman herself, or with the help of other, non-medical assistance. Although the term includes abortions induced outside of a clinical setting with legal, sometimes over-the-counter medication, it also refers to efforts to terminate a pregnancy through alternative, potentially more dangerous methods. Such practices may present a threat to the health of women.

Prostaglandin E<sub>2</sub> Chemical compound

Prostaglandin E2 (PGE2), also known as dinoprostone, is a naturally occurring prostaglandin with oxytocic properties that is used as a medication. Dinoprostone is used in labor induction, bleeding after delivery, termination of pregnancy, and in newborn babies to keep the ductus arteriosus open. In babies it is used in those with congenital heart defects until surgery can be carried out. It is also used to manage gestational trophoblastic disease. It may be used within the vagina or by injection into a vein.

<span class="mw-page-title-main">Uterine atony</span> Loss of tone in the uterine musculature

Uterine atony is the failure of the uterus to contract adequately following delivery. Contraction of the uterine muscles during labor compresses the blood vessels and slows flow, which helps prevent hemorrhage and facilitates coagulation. Therefore, a lack of uterine muscle contraction can lead to an acute hemorrhage, as the vasculature is not being sufficiently compressed. Uterine atony is the most common cause of postpartum hemorrhage, which is an emergency and potential cause of fatality. Across the globe, postpartum hemorrhage is among the top five causes of maternal death. Recognition of the warning signs of uterine atony in the setting of extensive postpartum bleeding should initiate interventions aimed at regaining stable uterine contraction.

<span class="mw-page-title-main">Postpartum bleeding</span> Loss of blood following childbirth

Postpartum bleeding or postpartum hemorrhage (PPH) is often defined as the loss of more than 500 ml or 1,000 ml of blood following childbirth. Some have added the requirement that there also be signs or symptoms of low blood volume for the condition to exist. Signs and symptoms may initially include: an increased heart rate, feeling faint upon standing, and an increased breathing rate. As more blood is lost, the patient may feel cold, blood pressure may drop, and they may become restless or unconscious. In severe cases circulatory collapse, disseminated intravascular coagulation and death can occur. The condition can occur up to twelve weeks following delivery in the secondary form. The most common cause is poor contraction of the uterus following childbirth. Not all of the placenta being delivered, a tear of the uterus, or poor blood clotting are other possible causes. It occurs more commonly in those who already have a low amount of red blood, are Asian, have a larger fetus or more than one fetus, are obese or are older than 40 years of age. It also occurs more commonly following caesarean sections, those in whom medications are used to start labor, those requiring the use of a vacuum or forceps, and those who have an episiotomy.

<span class="mw-page-title-main">Gemeprost</span> Chemical compound

Gemeprost (16, 16-dimethyl-trans-delta2 PGE1 methyl ester) is an analogue of prostaglandin E1.

Prostaglandin EP<sub>4</sub> receptor Protein-coding gene in the species Homo sapiens

Prostaglandin E2 receptor 4 (EP4) is a prostaglandin receptor for prostaglandin E2 (PGE2) encoded by the PTGER4 gene in humans. It is one of four identified EP receptors, the others being EP1, EP2, and EP3, all of which bind with and mediate cellular responses to PGE2 and also, but generally with lesser affinity and responsiveness, certain other prostanoids (see Prostaglandin receptors). EP4 has been implicated in various physiological and pathological responses in animal models and humans.

Trimix is a prescription combination drug containing alprostadil, papaverine, and phentolamine. It is used to treat erectile dysfunction.

<span class="mw-page-title-main">Sulprostone</span> Chemical compound

Sulprostone is an analogue of prostaglandin E2 (PGE2) that has oxytocic activity in assays of rat kidney cells and tissues. There are four known receptors which mediate various but often different cellular and tissue responses to PGE2: prostaglandin EP1 receptor, prostaglandin EP2 receptor, prostaglandin EP3 receptor, and prostaglandin EP4 receptor. Sulprosotone binds to and activates the prostaglandin EP3 receptor with far greater efficacy than the other PGE2 receptors and also has the advantage of being relatively resistant, compared with PGE2, to becoming metabolically degraded. It is listed as a comparatively weak receptor agonist of the prostaglandin EP1 receptor. In all events, this as well as other potent synthetic EP3 receptor antagonists have the realized or potential ability to promote the beneficial effects of prostaglandin EP3 receptor activation.

A uterotonic, also known as an oxytocic or ecbolic, is a type of medication used to induce contraction or greater tonicity of the uterus. Uterotonics are used both to induce labor and to reduce postpartum hemorrhage.

A medical abortion, also known as medication abortion or non-surgical abortion, occurs when drugs (medication) are used to bring about an abortion. Medical abortions are an alternative to surgical abortions such as vacuum aspiration or dilation and curettage. Medical abortions are more common than surgical abortions in most places around the world.

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 October 2023.
  2. 1 2 3 4 5 "Alprostadil". The American Society of Health-System Pharmacists. Archived from the original on 16 January 2017. Retrieved 8 January 2017.
  3. 1 2 3 Hew MR, Gerriets V (3 April 2023). "Prostaglandin E1". StatPearls. PMID   31536236 – via National Library of Medicine.
  4. 1 2 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.
  5. ↑ British National Formulary (BNF) (69th ed.). British Medical Association. 2015. p. 569. ISBN   9780857111562.
  6. ↑ Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 185. ISBN   9780470015520. Archived from the original on 13 January 2017.
  7. 1 2 3 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.
  8. 1 2 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.
  9. 1 2 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.
  10. ↑ "Lubiprostone: Drug Information". UpToDate Lexidrug. Wolters Kluwer. 2025.
  11. ↑ Meller SM, Stilp E, Walker CN, Mena-Hurtado C (June 2013). "The link between vasculogenic erectile dysfunction, coronary artery disease, and peripheral artery disease: role of metabolic factors and endovascular therapy". The Journal of Invasive Cardiology. 25 (6): 313–319. PMID   23735361.
  12. ↑ Vogel Anderson K, Atkinson K (2023). "Drugs for Urologic Disorders". In Whalen K, Lerchenfeldt S, Giordano C (eds.). Pharmacology (8th ed.). Wolters Kluwer. pp. 670–679. ISBN   9781975170554.
  13. ↑ "Vitaros- New Erectile Dysfunction Topical Treatment". Meds4All.co.uk. Archived from the original on 11 February 2015.
  14. ↑ Krugh M, Patel P, Maani CV (11 December 2024). "Misoprostol". StatPearls. PMID   30969695 – via National Library of Medicine.
  15. ↑ Goldberg AB, Greenberg MB, Darney PD (January 2001). "Misoprostol and pregnancy". The New England Journal of Medicine. 344 (1): 38–47. doi:10.1056/NEJM200101043440107. PMID   11136959.
  16. ↑ "WHO postpartum haemorrhage (PPH) summit". World Health Organization . 29 September 2022.
  17. 1 2 3 "Misoprostol: Drug information". UpToDate Lexidrug. Wolters Kluwer. 2025.
  18. ↑ Hamel CC, Snijders MP, Coppus SF, Vandenbussche FP, Braat DD, Adang EM (2022). "Economic evaluation of a randomized controlled trial comparing mifepristone and misoprostol with misoprostol alone in the treatment of early pregnancy loss". PLOS ONE. 17 (2): e0262894. Bibcode:2022PLoSO..1762894H. doi: 10.1371/journal.pone.0262894 . PMC   8827447 . PMID   35139105.
  19. ↑ Diamant J, Mohamed B, Leppert R (25 March 2024). "What the data says about abortion in the U.S." Pew Research Center .
  20. ↑ Morris JL, Winikoff B, Dabash R, Weeks A, Faundes A, Gemzell-Danielsson K, et al. (September 2017). "FIGO's updated recommendations for misoprostol used alone in gynecology and obstetrics". International Journal of Gynaecology and Obstetrics. 138 (3): 363–366. doi:10.1002/ijgo.12181. PMID   28643396.
  21. ↑ Watkinson G, Hopkins A, Akbar FA (1988). "The therapeutic efficacy of misoprostol in peptic ulcer disease". Postgraduate Medical Journal. 64 (Suppl 1): 60–77. PMID   3138682.
  22. ↑ "Misoprostol (Cytotec)". Cleveland Clinic Health Library. Cleveland Clinic.
  23. ↑ Vietto V, Franco JV, Saenz V, Cytryn D, Chas J, Ciapponi A (January 2018). "Prostanoids for critical limb ischaemia". The Cochrane Database of Systematic Reviews. 1 (1): CD006544. doi:10.1002/14651858.CD006544.pub3. PMC   6491321 . PMID   29318581.
  24. ↑ Ye Z, Lu H, Guo W, Dai W, Li H, Yang H, et al. (November 2016). "The effect of alprostadil on preventing contrast-induced nephropathy for percutaneous coronary intervention in diabetic patients: A systematic review and meta-analysis". Medicine. 95 (46): e5306. doi:10.1097/MD.0000000000005306. PMC   5120914 . PMID   27861357.
  25. ↑ Xie J, Jiang M, Lin Y, Deng H, Li L (August 2019). "Effect of Alprostadil on the Prevention of Contrast-Induced Nephropathy: A Meta-Analysis of 36 Randomized Controlled Trials". Angiology. 70 (7): 594–612. doi:10.1177/0003319719825597. PMID   30669852. S2CID   58950588.
  26. ↑ "Lubiprostone: Drug Information". UpToDate Lexidrug. Wolters Kluwer. 2025.
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