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
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
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
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 and is also used as a medication (alprostadil). [2]

Contents

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]

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 [7] and/or a genetic disorder.

Medical uses

Patent ductus arteriosus

Alprostadil is also used in maintaining a patent ductus arteriosus in newborns, primarily for an infant with ductal-dependent congenital heart disease, including cyanotic lesions and acyanotic lesions.

Sexual dysfunction

Alprostadil is sold in the United States as urethral suppositories (brand name Muse [8] ) and in injectable form (brand names: Edex [9] and Caverject [10] ). As a penile suppository, the medication is inserted into the urethra at least ten minutes before the erection is needed. Other forms similarly fast-acting, but instead are injected by the syringe directly into the corpus cavernosum of the penis.

Alprostadil is also available as a generic. It must be mixed by a compounding pharmacy. 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.

The compound has been made into an applicable topical cream form known as Vitaros, [11] made by Takeda UK Ltd., it contains either 200 or 300 μg of alprostadil in 100mg of cream. The tip of the device is placed in the urethral meatus, and the cream is delivered into the urethra.

Off-brand Uses, Interactions

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. [12] It has no known interactions with food, alcohol or other medications.

Misoprostol is another synthetic prostaglandin E1 analog used to prevent gastric ulcers when taken on a continuous basis [13] , to treat missed miscarriage [14] , to induce labor [15] , and to induce abortion [16] .

Critical limb ischemia

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. [17]

Contrast-induced nephropathy

Preventative administration of alprostadil may reduce the risk of kidney injury (specifically contrast-induced nephropathy) in persons having cardiac angiography or percutaneous coronary intervention. [18] [19]

Adverse effects

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">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">Penis enlargement</span> Technique aimed to increase the size of a human penis

Penis enlargement, or male enhancement, is any technique aimed to increase the size of a human penis. Some methods aim to increase total length, others the shaft's girth, and yet others the glans size. Techniques include surgery, supplements, ointments, patches, and physical methods like pumping, jelqing, and traction.

<span class="mw-page-title-main">Penile fracture</span> Medical condition

Penile fracture is rupture of one or both of the tunica albuginea, the fibrous coverings that envelop the penis's corpora cavernosa. It is caused by rapid blunt force to an erect penis, usually during vaginal intercourse, or aggressive masturbation. It sometimes also involves partial or complete rupture of the urethra or injury to the dorsal nerves, veins and arteries.

<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.

A suppository is a dosage form used to deliver medications by insertion into a body orifice, where it dissolves or melts to exert local or systemic effects. There are three types of suppositories, each to insert into a different sections: rectal suppositories into the rectum, vaginal suppositories into the vagina, and urethral suppositories into the urethra of a male.

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

Papaverine is an opium alkaloid antispasmodic drug, used primarily in the treatment of visceral spasms and vasospasms, occasionally in the treatment of erectile dysfunction and acute mesenteric ischemia. While it is found in the opium poppy, papaverine differs in both structure and pharmacological action from the analgesic morphine and its derivatives.

Venous leak, also called venogenic erectile dysfunction and penile venous insufficiency, is one category of vasculogenic impotence — a cause of erectile dysfunction in males. It affects all ages, being particularly awkward in young men. Much about venous leaks has not reached a consensus among the medical community, and many aspects of the condition, particularly its treatment strategies, are controversial. The prevalence of the condition is still unknown, although some sources claim it to be a common cause of erectile dysfunction.

<span class="mw-page-title-main">Penile implant</span> Medical device

A penile implant is an implanted device intended for the treatment of erectile dysfunction, Peyronie's disease, ischemic priapism, deformity and any traumatic injury of the penis, and for phalloplasty or metoidioplasty, including in gender-affirming surgery. Men also opt for penile implants for aesthetic purposes. Men's satisfaction and sexual function is influenced by discomfort over genital size which leads to seek surgical and non-surgical solutions for penis alteration. Although there are many distinct types of implants, most fall into one of two categories: malleable and inflatable transplants.

<span class="mw-page-title-main">Human penis</span> Human male external reproductive organ

In human anatomy, the penis is an external male sex organ that additionally serves as the urinary duct. The main parts are the root, body, the epithelium of the penis including the shaft skin, and the foreskin covering the glans. The body of the penis is made up of three columns of tissue: two corpora cavernosa on the dorsal side and corpus spongiosum between them on the ventral side. The urethra passes through the prostate gland, where it is joined by the ejaculatory duct, and then through the penis. The urethra goes across the corpus spongiosum and ends at the tip of the glans as the opening, the urinary meatus. It is a passage both for excretion of urine and the ejaculation of semen.

Urethroplasty is the surgical repair of an injury or defect within the walls of the urethra. Trauma, iatrogenic injury and infections are the most common causes of urethral injury/defect requiring repair. Urethroplasty is regarded as the gold standard treatment for urethral strictures and offers better outcomes in terms of recurrence rates than dilatations and urethrotomies. It is probably the only useful modality of treatment for long and complex strictures though recurrence rates are higher for this difficult treatment group.

Prostaglandin EP<sub>3</sub> receptor Protein-coding gene in the species Homo sapiens

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 EP receptors, the others being EP1, EP2, and EP4, 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). EP has been implicated in various physiological and pathological responses.

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

<span class="mw-page-title-main">Erection</span> Physiological phenomenon involving the hardening and enlargement of the penis

An erection is a physiological phenomenon in which the penis becomes firm, engorged, and enlarged. Penile erection is the result of a complex interaction of psychological, neural, vascular, and endocrine factors, and is often associated with sexual arousal, sexual attraction or libido, although erections can also be spontaneous. The shape, angle, and direction of an erection vary considerably between humans.

An intracavernousinjection is an injection into the base of the penis. This injection site is often used to administer medications to check for or treat erectile dysfunction in adult men. The more common medications administered in this manner include Caverject, Trimix, Bimix, and Quadmix. These medications are all types of vasodilators and cause tumescence within 15 minutes. Common side effects include priapism, bruising, fibrosis, Peyronie's disease, and pain.

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.

<span class="mw-page-title-main">Clitoral erection</span> Physiological phenomenon involving the engorgement of the clitoris

Clitoral erection is a physiological phenomenon where the clitoris becomes enlarged and firm.

<span class="mw-page-title-main">Ronald Virag</span> French cardiovascular surgeon

Ronald Virag is a French cardiovascular surgeon who specialises in andrology, the study of the male reproductive system. After training in general and cardiovascular surgery at Paris University, he shifted his focus to the study of erectile dysfunction, which has been his primary area of study since 1978. In 1981, he founded a private institute in France dedicated to the clinical study of erectile dysfunction and developed early programs using intracavernosal drugs to treat the condition.

A penile injury is a medical emergency that afflicts the penis. Common injuries include fracture, avulsion injury, strangulation, entrapment, and amputation.

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 6 "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.
  7. Meller SM, Stilp E, Walker CN, Mena-Hurtado C (2013). "The link between vasculogenic erectile dysfunction, coronary artery disease, and peripheral artery disease: role of metabolic factors and endovascular therapy". J Invasive Cardiol. 25 (6): 313–9. PMID   23735361.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  8. "Muse Suppository - Facts and Comparisons". Drugs.com. Archived from the original on 19 January 2013. Retrieved 4 January 2013.
  9. "Edex - Facts and Comparisons". Drugs.com. Archived from the original on 26 October 2012.
  10. "Caverject - Facts and Comparisons". Drugs.com. Archived from the original on 26 October 2012.
  11. "Vitaros 3 mg/g cream - Summary of Product Characteristics". Medicines.org.uk. Archived from the original on 11 February 2015.
  12. "Vitaros- New Erectile Dysfunction Topical Treatment". Meds4All.co.uk. Archived from the original on 11 February 2015.
  13. Walt RP (November 1992). "Misoprostol for the treatment of peptic ulcer and antiinflammatory-drug-induced gastroduodenal ulceration". The New England Journal of Medicine. 327 (22): 1575–1580. doi:10.1056/NEJM199211263272207. PMID   1435885.
  14. Wu HL, Marwah S, Wang P, Wang QM, Chen XW (May 2017). "Misoprostol for medical treatment of missed abortion: a systematic review and network meta-analysis". Scientific Reports. 7 (1): 1664. Bibcode:2017NatSR...7.1664W. doi:10.1038/s41598-017-01892-0. PMC   5431938 . PMID   28490770.
  15. Chatsis V, Frey N (2018). Misoprostol for Cervical Ripening and Induction of Labour: A Review of Clinical Effectiveness, Cost-Effectiveness and Guidelines. CADTH Rapid Response Reports. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health. PMID   30907996.
  16. "Medical abortion". Mayo Clinic. Retrieved 28 April 2022.
  17. 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.
  18. 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.
  19. 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.