Prostaglandin E1

Prostaglandin E1

Clinical data
Trade names	Caverject, Muse, others
AHFS/Drugs.com	Monograph
MedlinePlus	a695022
Pregnancy category	US: X (Contraindicated)
Routes of administration	IV
ATC code	C01EA01 (WHO) G04BE01 (WHO)
Legal status
Legal status	CA: ℞-only UK: POM (Prescription only) US: ℞-only
Identifiers
IUPAC name 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
ChEBI	CHEBI:15544 N
ChEMBL	CHEMBL495 N
ECHA InfoCard	100.010.925
Chemical and physical data
Formula	C20H34O5
Molar mass	354.481 g/mol
3D model (Jmol)	Interactive image
SMILES CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]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 N Key:GMVPRGQOIOIIMI-DWKJAMRDSA-N N
NY (what is this?)

Prostaglandin E1 (PGE1), also known as alprostadil, is a naturally occurring prostaglandin which is used as a medication. In babies with congenital heart defects it is used 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.

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. Prostaglandin E1 is in the vasodilator family of medications. It works by opening blood vessels by 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, the most effective and safe medicines needed in a health system. In the United Kingdom a dose costs the NHS about 75 pounds. In the United States it costs 100 to 200 USD per dose.Prostaglandin E2 works as well as prostaglandin E1 in babies; however, is much less expensive.

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).