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Prostaglandin E1

Prostaglandin E1 (PGE1), also known as alprostadil, is a naturally occurring prostaglandin which is used as a medication.[1] 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.[2] By injection into the penis or placement in the urethra, it is used to treat erectile dysfunction.[3]

Prostaglandin E1
Clinical data
Trade namesCaverject, Muse, others
AHFS/Drugs.comMonograph
MedlinePlusa695022
License data
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
  • 745-65-3 Y
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
ECHA InfoCard100.010.925
Chemical and physical data
FormulaC20H34O5
Molar mass354.487 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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
 NY (what is this?)  (verify)

Common side effects when given to babies include decreased breathing, fever, and low blood pressure.[1] When used for erectile dysfunction side effects may include penile pain, bleeding at the site of injection, and prolonged erection (priapism).[1] Prostaglandin E1 is in the vasodilator family of medications.[1] It works by opening blood vessels and relaxing smooth muscle.[1]

Prostaglandin E1 was isolated in 1957 and approved for medical use in the United States in 1981.[1][4] It is on the World Health Organization's List of Essential Medicines.[5]

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., 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 Edit

Alprostadil is sold in the United States as urethral suppositories and in injectable form. The suppositories are sold under the brand name Muse.[6] The injectable forms are Edex[7] and Caverject.[8] 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.[9] 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 with diabetes or heart problems and those who have undergone a prostatectomy.[10] 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 Edit

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.[11]

Contrast-induced nephropathy Edit

Preventative administration of alprostadil may reduce the risk of kidney injury (specifically contrast-induced nephropathy) in persons having cardiac angiography or percutaneous coronary intervention.[12][13]

Adverse effects Edit

Biosynthesis Edit

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 Edit

Misoprostol is another synthetic prostaglandin E1 analog used to prevent gastric ulcers when taken on a continuous basis,[15] to treat missed miscarriage,[16] to induce labor,[17] and to induce abortion.[18]

References Edit

  1. ^ a b c d e f "Alprostadil". The American Society of Health-System Pharmacists. from the original on 16 January 2017. Retrieved 8 January 2017.
  2. ^ 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. from the original on 13 January 2017.
  3. ^ British National Formulary (BNF) (69th ed.). British Medical Association. 2015. p. 569. ISBN 9780857111562.
  4. ^ Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 185. ISBN 9780470015520. from the original on 13 January 2017.
  5. ^ 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.
  6. ^ "Muse Suppository - Facts and Comparisons". Drugs.com. from the original on 19 January 2013. Retrieved 4 January 2013.
  7. ^ . Drugs.com. Archived from the original on 26 October 2012.
  8. ^ . Drugs.com. Archived from the original on 26 October 2012.
  9. ^ . Medicines.org.uk. Archived from the original on 11 February 2015.
  10. ^ . Meds4All.co.uk. Archived from the original on 11 February 2015.
  11. ^ 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.
  12. ^ Ye Z, Lu H, Guo W, Dai W, Li H, Yang H, Li L (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.
  13. ^ 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.
  14. ^ 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. from the original on 10 August 2014.
  15. ^ 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.
  16. ^ 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.
  17. ^ 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.
  18. ^ "Medical abortion". Mayo Clinic. Retrieved 28 April 2022.

External links Edit

  • "Alprostadil". Drug Information Portal. U.S. National Library of Medicine.

prostaglandin, prostaglandin, pge1, also, known, alprostadil, naturally, occurring, prostaglandin, which, used, medication, infants, with, congenital, heart, defects, delivered, slow, injection, into, vein, open, ductus, arteriosus, until, surgery, carried, in. Prostaglandin E1 PGE1 also known as alprostadil is a naturally occurring prostaglandin which is used as a medication 1 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 2 By injection into the penis or placement in the urethra it is used to treat erectile dysfunction 3 Prostaglandin E1Clinical dataTrade namesCaverject Muse othersAHFS Drugs comMonographMedlinePlusa695022License dataUS DailyMed AlprostadilRoutes ofadministrationIVATC codeC01EA01 WHO G04BE01 WHO Legal statusLegal statusCA only UK POM Prescription only US onlyIdentifiersIUPAC name 7 1R 3R 3 hydroxy 2 1E 3S 3 hydroxyoct 1 en 1 yl 5 oxocyclopentyl heptanoic acidCAS Number745 65 3 YPubChem CID5280723IUPHAR BPS1882DrugBankDB00770 NChemSpider4444306 NUNIIF5TD010360KEGGC04741ChEBICHEBI 15544 NChEMBLChEMBL495 NCompTox Dashboard EPA DTXSID9022578ECHA InfoCard100 010 925Chemical and physical dataFormulaC 20H 34O 5Molar mass354 487 g mol 13D model JSmol Interactive imageSMILES CCCCC C H C C C H 1 C H CC O C H 1CCCCCCC O O O OInChI 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 NKey GMVPRGQOIOIIMI DWKJAMRDSA N N N Y what is this verify Common side effects when given to babies include decreased breathing fever and low blood pressure 1 When used for erectile dysfunction side effects may include penile pain bleeding at the site of injection and prolonged erection priapism 1 Prostaglandin E1 is in the vasodilator family of medications 1 It works by opening blood vessels and relaxing smooth muscle 1 Prostaglandin E1 was isolated in 1957 and approved for medical use in the United States in 1981 1 4 It is on the World Health Organization s List of Essential Medicines 5 Contents 1 Medical uses 1 1 Patent ductus arteriosus 1 2 Sexual dysfunction 1 3 Critical limb ischemia 1 4 Contrast induced nephropathy 1 5 Adverse effects 2 Biosynthesis 3 Other versions 4 References 5 External linksMedical uses EditPatent ductus arteriosus Edit This section does not cite any sources Please help improve this section by adding citations to reliable sources Unsourced material may be challenged and removed December 2019 Learn how and when to remove this template message 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 Edit Alprostadil is sold in the United States as urethral suppositories and in injectable form The suppositories are sold under the brand name Muse 6 The injectable forms are Edex 7 and Caverject 8 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 mg 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 This section contains content that is written like an advertisement Please help improve it by removing promotional content and inappropriate external links and by adding encyclopedic content written from a neutral point of view May 2021 Learn how and when to remove this template message Most recently the compound has been made easily accessible in an applicable topical cream form known as Vitaros 9 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 with diabetes or heart problems and those who have undergone a prostatectomy 10 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 Edit 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 11 Contrast induced nephropathy Edit Preventative administration of alprostadil may reduce the risk of kidney injury specifically contrast induced nephropathy in persons having cardiac angiography or percutaneous coronary intervention 12 13 Adverse effects Edit Accidental injury Muse only Apnea Bleeding Cerebral Urethral Bradycardia Cardiac arrest Congestive heart failure Cortical proliferation of long bones Diarrhea Disseminated intravascular coagulation Edema Fever Flushing Hyperemia Hypotension Injection site haematoma Injection site ecchymosis Caverject only Pain Back Pelvic Penile Testicular Muse only Urethral Prolonged erection Penile fibrosis Second degree heart block Seizures Sepsis Shock Spasm of right ventricle infundibulum Supraventricular tachycardia Tachycardia Ventricular fibrillation Urethral burning Uterine ruptureBiosynthesis EditProstaglandin E1 is biosynthesized on an as needed basis from dihomo g linolenic acid an omega 6 fatty acid in healthy humans without coronary artery disease 14 and or a genetic disorder Other versions EditMisoprostol is another synthetic prostaglandin E1 analog used to prevent gastric ulcers when taken on a continuous basis 15 to treat missed miscarriage 16 to induce labor 17 and to induce abortion 18 References Edit 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 Northern Neonatal Network 208 Neonatal Formulary Drug Use in Pregnancy and the First Year of Life 5 ed John Wiley amp Sons p 2010 ISBN 9780470750353 Archived from the original on 13 January 2017 British National Formulary BNF 69th ed British Medical Association 2015 p 569 ISBN 9780857111562 Sneader W 2005 Drug Discovery A History John Wiley amp Sons p 185 ISBN 9780470015520 Archived from the original on 13 January 2017 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 Muse Suppository Facts and Comparisons Drugs com Archived from the original on 19 January 2013 Retrieved 4 January 2013 Edex Facts and Comparisons Drugs com Archived from the original on 26 October 2012 Caverject Facts and Comparisons Drugs com Archived from the original on 26 October 2012 Vitaros 3 mg g cream Summary of Product Characteristics Medicines org uk Archived from the original on 11 February 2015 Vitaros New Erectile Dysfunction Topical Treatment Meds4All co uk Archived from the original on 11 February 2015 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 Ye Z Lu H Guo W Dai W Li H Yang H Li L 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 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 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 Archived from the original on 10 August 2014 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 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 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 Medical abortion Mayo Clinic Retrieved 28 April 2022 External links Edit Alprostadil Drug Information Portal U S National Library of Medicine Portal Medicine Retrieved from https en wikipedia org w index php title Prostaglandin E1 amp oldid 1170709238, wikipedia, wiki, book, books, library,

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