Systematic (IUPAC) name | |
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7-[(1R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid | |
Clinical data | |
MedlinePlus | a695022 |
Pregnancy cat. | ? |
Legal status | ? |
Identifiers | |
CAS number | 745-65-3 |
ATC code | C01EA01 G04BE01 |
PubChem | CID 149351 |
DrugBank | APRD00785 |
ChEMBL | CHEMBL495 |
Chemical data | |
Formula | C20H34O5 |
Mol. mass | 354.481 g/mol |
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(what is this?)
Prostaglandin E1 (PGE1), known pharmaceutically as alprostadil,[1] is a prostaglandin. It is a drug used in the treatment of erectile dysfunction[2] and has vasodilatory properties.
Alprostadil is sold in the United States as urethral suppositories and in injectable form. The suppositories are sold under the brand name MUSE [3] (Medicated Urethral Suppository for Erection). 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 will be needed. Caverject and Edex are similarly fast-acting, but instead are injected by syringe directly into the corpus cavernosum of the penis.
Apricus Biosciences is developing proprietary drugs; Vitaros for men with erectile dysfunction, Femprox for female sexual arousal disorder and RayVa for Raynaud’s phenomenon. Two Phase III studies have been completed for Vitaros, and approval has been granted in Canada. Apricus Biosciences is seeking regulatory approval in Europe, South America, and other territories. Apricus Biosciences sold the rights for Vitaros in the US to Warner Chilcott. [4]
Alprostadil is also available as a generic. The major cost is that it must be mixed by a compounding pharmacy and supplies of alprostadil may be difficult to obtain. There are different formulations, including Bimix and Trimix, which may include papaverine and/or phentolamine. A typical mix might be 30 mg of papaverine, 2 mg of phentolamine, and 20 mcg alprostadil. As a generic, it is much less expensive than the pre-packaged injectables. It is premixed and must be kept refrigerated and the user must load a syringe with the quantity needed. Alprostadil is also used for critical limb ischemia. It increases blood flow by peripheral vasodilation within 5 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.
Alprostadil is also used in maintaining a patent ductus arteriosus in newborns. This is primarily useful when there is threat of premature closure of the ductus arteriosus 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, interrupted aortic arch). For gastrointestinal applications, see misoprostol.
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