prostaglandin e1 prostaglandin e1 prostaglandin e1 (pge1), also known as alprostadil, is a naturally occurring prostaglandin which is used as a medication. 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. by injection into the penis or placement in the urethra, it is used to treat erectile dysfunction. prostaglandin e1clinical datatrade namescaverject, muse, othersahfs/drugs.commonographmedlineplusa695022license data us dailymed: alprostadil routes ofadministrationivatc codec01ea01 (who) g04be01 (who)legal statuslegal status ca: ℞-only uk: pom (prescription only) us: ℞-only identifiers iupac name 7--5-oxocyclopentyl]heptanoic acid cas number745-65-3 ypubchem cid5280723iuphar/bps1882drugbankdb00770 nchemspider4444306 nuniif5td010360keggc04741chebichebi:15544 nchemblchembl495 ncomptox dashboard (epa)dtxsid9022578 echa infocard100.010.925 chemical and physical dataformulac20h34o5molar mass354.487 g·mol−13d model (jsmol)interactive image smiles ccccc(/c=c/1(cc(=o)1ccccccc(=o)o)o)o inchi 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 ny (what is this?) (verify) common side effects when given to babies include decreased breathing, fever, and low blood pressure. when used for erectile dysfunction side effects may include penile pain, bleeding at the site of injection, and prolonged erection (priapism). prostaglandin e1 is in the vasodilator family of medications. it works by opening blood vessels and relaxing smooth muscle. prostaglandin e1 was isolated in 1957 and approved for medical use in the united states in 1981. it is on the world health organization's list of essential medicines. 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. the injectable forms are edex and caverject. 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. 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. 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 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. 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. adverse effects 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 rupture 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 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.