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
ATC code	C01EA01 (WHO) G04BE01 (WHO);
Legal status
Legal status	CA: ℞-only; UK: POM (Prescription only); US: WARNINGRx-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 ;
	(what is this?) (verify)

Prostaglandin E₁ (PGE₁) is a naturally occurring prostaglandin and is also used as a medication (alprostadil).^[2]

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.^[3] By injection into the penis or placement in the urethra, it is used to treat erectile dysfunction.^[4]

Common side effects when given to babies include decreased breathing, fever, and low blood pressure.^[2] When injected into the penis for erectile dysfunction; side effects may include penile pain, bleeding at the site of injection, and prolonged erection (priapism).^[2] Prostaglandin E₁ is in the vasodilator family of medications.^[2] It works by opening blood vessels and relaxing smooth muscle.^[2]

Prostaglandin E₁ was isolated in 1957 and approved for medical use in the United States in 1981.^[2]^[5] It is on the World Health Organization's List of Essential Medicines.^[6]

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ ^a ^b ^c ^d ^e ^f "Alprostadil". The American Society of Health-System Pharmacists. Archived from the original on 16 January 2017. Retrieved 8 January 2017.
^ Northern Neonatal Network (208). Neonatal Formulary: Drug Use in Pregnancy and the First Year of Life (5 ed.). John Wiley & Sons. p. 2010. ISBN 9780470750353. Archived from the original on 13 January 2017.
^ British National Formulary (BNF) (69th ed.). British Medical Association. 2015. p. 569. ISBN 9780857111562.
^ Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 185. ISBN 9780470015520. Archived from the original on 13 January 2017.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[AHFS2017-2] ^ ^a ^b ^c ^d ^e ^f "Alprostadil". The American Society of Health-System Pharmacists. Archived from the original on 16 January 2017. Retrieved 8 January 2017.

[No2010-3] Northern Neonatal Network (208). Neonatal Formulary: Drug Use in Pregnancy and the First Year of Life (5 ed.). John Wiley & Sons. p. 2010. ISBN 9780470750353. Archived from the original on 13 January 2017.

[BNF69-4] British National Formulary (BNF) (69th ed.). British Medical Association. 2015. p. 569. ISBN 9780857111562.

[5] Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 185. ISBN 9780470015520. Archived from the original on 13 January 2017.

[WHO21st-6] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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