Epoprostenol

Drugbox

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IUPAC_name = (5"Z")-5- [(3a"R",4"R",5"R",6a"S")-5-hydroxy-4-
[("E",3"S")-3-hydroxyoct-1-enyl] -3,3a,4,5,6,6a-
hexahydrocyclopenta ["d"] furan-2-ylidene] pentanoic acid
CAS_number = 35121-78-9
ATC_prefix = B01
ATC_suffix = AC09
ATC_supplemental =
PubChem = 114805
DrugBank = APRD00949
C=20 | H=32 | O=5
molecular_weight = 352.465 g/mol
smiles = OC(=O)CCCC=C1C [C@@H] 2 [C@@H] (/C=C/ [C@@H] (O)CCCCC) [C@H] (O)C [C@@H] 2O1
bioavailability= Not applicable (IV only)
metabolism = To 6-keto-PGF_1α and 6,15-diketo-13,14-dihydro-PGF_1α
elimination_half-life= 6 minutes ("in vitro")
licence_US = EPOPROSTENOL_SODIUM
pregnancy_US = B
routes_of_administration=Intravenous
excretion = Renal
legal_status = Rx-only

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.