Stereochemistry | ABSOLUTE |
Molecular Formula | C20H32O5 |
Molecular Weight | 352.4651 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@]1([H])C\C(O2)=C\CCCC(O)=O
InChI
InChIKey=KAQKFAOMNZTLHT-OZUDYXHBSA-N
InChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8-/t14-,16+,17+,18+,19-/m0/s1
Molecular Formula | C20H32O5 |
Molecular Weight | 352.4651 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 2 |
Optical Activity | UNSPECIFIED |
Epoprostenol (marketed as FLOLAN, VELETRI) is a prostaglandin that is a powerful vasodilator and inhibits platelet aggregation. Epoprostenol (PGI2, PGX, prostacyclin), a metabolite of arachidonic acid, is a naturally occurring prostaglandin with potent vasodilatory activity and inhibitory activity of platelet
aggregation. FLOLAN (epoprostenol sodium) for Injection is a sterile sodium salt formulated for intravenous (IV) administration. Epoprostenol has two major pharmacological actions: (1) direct vasodilation of pulmonary and systemic arterial vascular beds, and (2) inhibition of platelet aggregation. In animals, the vasodilatory effects reduce right and left ventricular afterload and increase cardiac output and stroke volume. The effect of epoprostenol on heart rate in animals varies with dose. At low doses, there is vagally mediated brudycardia, but at higher doses, epoprostenol causes reflex tachycardia in response to direct vasodilation and hypotension. No major effects on cardiac conduction have been observed. Additional pharmacologic effects of epoprostenol in animals include bronchodilation, inhibition of gastric acid secretion, and decreased gastric emptying. No available chemical assay is sufficiently sensitive and specific to assess the in vivo human pharmacokinetics of epoprostenol. FLOLAN is indicated for the long-term intravenous treatment of primary pulmonary hypertension and pulmonary hypertension associated with the scleroderma spectrum of disease in NYHA Class III and Class IV patients who do not respond adequately to conventional therapy.
Originator
Approval Year
Doses
AEs
Sourcing
Sample Use Guides
Usual Adult Dose for Pulmonary Hypertension
Acute Dose Ranging: 2 ng/kg/min and increased in increments of 2 ng/kg/min every 15 minutes or longer until dose-limiting pharmacologic effects are elicited.
The mean maximum dose which did not elicit dose-limiting pharmacologic effects was 8.6 ng/kg/min.
Continuous Chronic Infusion: 4 ng/kg/min less than the maximum tolerated infusion rate determined during acute dose ranging.
If the maximum tolerated infusion rate is less than 5 ng/kg/min, the chronic infusion should be started at one-half the maximum tolerated infusion rate. During clinical trials, the mean initial chronic infusion rate was 5 ng/kg/min.
Route of Administration:
Intravenous
Addition of prostacyclin (Epoprostenol) (10(–8)–10(–5) mol/L) to KCl-stimulated human
intrarenal arteries yielded concentration-dependent relaxations
≤10(–6) mol/L (EC50: −log 7.7 mol/L). At concentrations
of prostacyclin >10(–6) mol/L, the relaxation reversed
to a significant increase in tension.