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Systematic (IUPAC) name
7-[(1R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
Clinical data
MedlinePlus a695022
Pregnancy cat.
US:*C
Legal status
Rx only Canada
Identifiers
CAS number 745-65-3*
ATC code C01EA01 G04BE01
PubChem CID 149351
IUPHAR ligand 1882
DrugBank DB00770
ChEBI CHEBI:15544*
ChEMBL CHEMBL495*
Chemical data
Formula C20H34O5*
Mol. mass 354.481 g/mol
The synthetic variant is known pharmaceutically as alprostadil.[1] It is a drug used in the continuous treatment of erectile dysfunction.[2] and has vasodilatory properties. 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.
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., 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, 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.[3] The injectable forms are Edex[4] and Caverject.[5] 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.
Critical limb ischemia
Alprostadil is also used for critical limb ischemia. It increases blood flow by peripheral vasodilation within five 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.
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 from dihomo-γ-linolenic acid (an omega-6 fatty acid) in healthy humans without coronary artery disease[6] and/or a genetic disorder.
7-[(1R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
Clinical data
MedlinePlus a695022
Pregnancy cat.
US:*C
Legal status
Rx only Canada
Identifiers
CAS number 745-65-3*
ATC code C01EA01 G04BE01
PubChem CID 149351
IUPHAR ligand 1882
DrugBank DB00770
ChEBI CHEBI:15544*
ChEMBL CHEMBL495*
Chemical data
Formula C20H34O5*
Mol. mass 354.481 g/mol
The synthetic variant is known pharmaceutically as alprostadil.[1] It is a drug used in the continuous treatment of erectile dysfunction.[2] and has vasodilatory properties. 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.
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., 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, 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.[3] The injectable forms are Edex[4] and Caverject.[5] 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.
Critical limb ischemia
Alprostadil is also used for critical limb ischemia. It increases blood flow by peripheral vasodilation within five 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.
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 from dihomo-γ-linolenic acid (an omega-6 fatty acid) in healthy humans without coronary artery disease[6] and/or a genetic disorder.
