Prostaglandin E1

Prostaglandin E1
Clinical data
Trade names	Caverject, Muse, others
AHFS/Drugs.com	Monograph
MedlinePlus	a695022
License data	US DailyMed: Alprostadil;
Routes of; administration	Intravenous, intracavernous
ATC code	C01EA01 (WHO) G04BE01 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); 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 ;
PubChem CID	5280723;
IUPHAR/BPS	1882;
DrugBank	DB00770 ;
ChemSpider	4444306 ;
UNII	F5TD010360;
KEGG	C04741;
ChEBI	CHEBI:15544 ;
ChEMBL	ChEMBL495 ;
CompTox Dashboard (EPA)	DTXSID9022578 ;
ECHA InfoCard	100.010.925
Chemical and physical data
Formula	C20H34O5
Molar mass	354.487 g·mol−1
3D model (JSmol)	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 ; Key:GMVPRGQOIOIIMI-DWKJAMRDSA-N ;
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Prostaglandin E₁ (PGE₁) is a naturally occurring prostaglandin with various medical uses. Alprostadil and misoprostol are synthetic forms of prostaglandin E1 used as medications. Lubiprostone, a derivative of prostaglandin E1, is also used as a medication. Prostaglandin E₁ is a vasodilator. It has various effects in the body that include opening blood vessels, relaxing smooth muscle, inhibiting clotting, and causing uterine contractions.

In infants with certain congenital heart defects, alprostadil is delivered by slow injection into a vein to maintain a patent ductus arteriosus until surgery can be carried out. By injection into the penis or placement in the urethra, alprostadil is used to treat erectile dysfunction. Common side effects when given to babies include decreased breathing, fever, and low blood pressure. When injected into the penis for erectile dysfunction; side effects may include penile pain, bleeding at the site of injection, and prolonged erection (priapism). Prostaglandin E₁ was isolated in 1957 and approved for medical use in the United States in 1981.

Misoprostol has various obstetric uses. It is used to induce abortion, to completely empty the uterus after a miscarriage, to induce labor, and to prevent and treat postpartum hemorrhage. The medication is available through many routes. It can be swallowed, dissolved in the mouth, placed in the vagina, or placed in the rectum. Misoprostol can also be used to manage duodenal ulcers and peptic ulcer disease when other medications are not effective. It is on the World Health Organization's List of Essential Medicines for its obstetric uses.

Lubiprostone is a PGE₁ derivative used to treat chronic constipation. It is taken orally. Common side effects include diarrhea, vomiting, and abdominal pain.