Epoprostenol detailed information

Epoprostenol detailed information

Clinical data
[[Regulation of therapeutic goods |Template:Engvar data]]	US FDA: EPOPROSTENOL_SODIUM
Pregnancy category	US: B (No risk in non-human studies)
Routes of administration	Intravenous
ATC code	B01AC09 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Not applicable (IV only)
Metabolism	To 6-keto-PGF1α and 6,15-diketo-13,14-dihydro-PGF1α
Elimination half-life	6 minutes (in vitro)
Excretion	Renal
Identifiers
IUPAC name (5Z)-5-[(3aR,4R,5R,6aS)-5-hydroxy-4- [(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a- hexahydrocyclopenta[d]furan-2-ylidene]pentanoic acid
CAS Number	35121-78-9
PubChem CID	114805
DrugBank	APRD00949
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C20H32O5
Molar mass	352.465 g/mol
3D model (JSmol)	Interactive image
SMILES OC(=O)CCC\C=C1\C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]2O1

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Epoprostenol is a synthetic form of prostacyclin, and is used to treat pulmonary hypertension. It is sold under the trade name Flolan.

Clinical pharmacology

As an analogue of prostacyclin PGI₂, epoprostenol effects vasodilation, which in turn lowers the blood pressure. Epoprotstenol also inhibits platelet aggregation, though the role this phenomenon may play in relation to pulmonary hypertension has yet to be determined.

Administration

Epoprostenol is given via continuous infusion that requires a semi-permanent central venous catheter. This means that the patient must be attached to an infusion pump at all times. This delivery system can cause sepsis and thrombosis. Because epoprostenol is unstable, it must be kept cold, even during administration. Since it has a half-life of 3 to 5 minutes, the infusion has to be continuous (24/7), and an interruption can lead to a potentially fatal rebound of symptoms.

History

Epoprostenol was developed by GlaxoSmithKline and approved in the USA as a medicine in 1995.

Marketing

It was licensed to Myogen, which was subsequently acquired by Gilead Sciences. Flolan is marketed in the United States by Gilead Sciences and elsewhere by GlaxoSmithKline.