Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H31O5.Na |
Molecular Weight | 374.4469 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[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=LMHIPJMTZHDKEW-XQYLJSSYSA-M
InChI=1S/C20H32O5.Na/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);/q;+1/p-1/b11-10+,15-8-;/t14-,16+,17+,18+,19-;/m0./s1
Molecular Formula | C20H31O5 |
Molecular Weight | 351.4571 |
Charge | -1 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 2 |
Optical Activity | UNSPECIFIED |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
1398.0 nM [Ki] | |||
Target ID: Q9H244 Gene ID: 64805.0 Gene Symbol: P2RY12 Target Organism: Homo sapiens (Human) |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | FLOLAN Approved UseFLOLAN 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. Launch Date8.1155523E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
347 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22515646/ |
2 ng/kg/min other, intravenous dose: 2 ng/kg/min route of administration: Intravenous experiment type: OTHER co-administered: |
6-KETO-PROSTAGLANDIN F1ALPHA plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1972 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22515646/ |
2 ng/kg/min other, intravenous dose: 2 ng/kg/min route of administration: Intravenous experiment type: OTHER co-administered: |
6-KETO-PROSTAGLANDIN F1ALPHA plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.22 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22515646/ |
2 ng/kg/min other, intravenous dose: 2 ng/kg/min route of administration: Intravenous experiment type: OTHER co-administered: |
6-KETO-PROSTAGLANDIN F1ALPHA plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
8 ng/kg/min single, intravenous Highest studied dose Dose: 8 ng/kg/min Route: intravenous Route: single Dose: 8 ng/kg/min Sources: |
healthy, 33.7 years (range: 18–45 years) n = 20 Health Status: healthy Age Group: 33.7 years (range: 18–45 years) Sex: M Population Size: 20 Sources: |
Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea (1 patient) Sources: Vomiting (1 patient) |
110.5 ng/kg/min multiple, intravenous (max) Highest studied dose Dose: 110.5 ng/kg/min Route: intravenous Route: multiple Dose: 110.5 ng/kg/min Sources: |
unhealthy, 42 years n = 1 Health Status: unhealthy Condition: pulmonary hypertension Age Group: 42 years Sex: M Population Size: 1 Sources: |
|
0.05 ug/kg/min multiple, respiratory (complex) Dose: 0.05 ug/kg/min Route: respiratory Route: multiple Dose: 0.05 ug/kg/min Sources: |
unhealthy, 56.4 ± 15.3 years n = 52 Health Status: unhealthy Condition: refractory hypoxemia Age Group: 56.4 ± 15.3 years Sex: M+F Population Size: 52 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nausea | 1 patient Disc. AE |
8 ng/kg/min single, intravenous Highest studied dose Dose: 8 ng/kg/min Route: intravenous Route: single Dose: 8 ng/kg/min Sources: |
healthy, 33.7 years (range: 18–45 years) n = 20 Health Status: healthy Age Group: 33.7 years (range: 18–45 years) Sex: M Population Size: 20 Sources: |
Vomiting | 1 patient Disc. AE |
8 ng/kg/min single, intravenous Highest studied dose Dose: 8 ng/kg/min Route: intravenous Route: single Dose: 8 ng/kg/min Sources: |
healthy, 33.7 years (range: 18–45 years) n = 20 Health Status: healthy Age Group: 33.7 years (range: 18–45 years) Sex: M Population Size: 20 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Arterial walls are protected against deposition of platelet thrombi by a substance (prostaglandin X) which they make from prostaglandin endoperoxides. | 1976 Nov |
|
Some direct and reflex cardiovascular actions of prostacyclin (PGI2) and prostaglandin E2 in anaesthetized dogs. | 1980 Mar |
|
Preliminary investigation on the central action of prostacyclin (PGI2) in rats. | 1981 |
|
Effect of prostaglandins on morphine-induced catalepsy in mice. | 1983 Sep-Dec |
|
Acute effects of captopril on the baroreflex of normotensive and spontaneously hypertensive rats. | 1986 Jul |
|
Reduction by prostacyclin of acetaminophen-induced liver toxicity in the mouse. | 1988 Mar-Apr |
|
Further confirmation of the role of adenyl cyclase and of cAMP-dependent protein kinase in primary afferent hyperalgesia. | 1991 |
|
[Massive pulmonary embolism disclosing thrombocytopenia induced by low molecular weight heparin. Therapeutic success of prostacyclin]. | 1991 Dec |
|
Effects of tolazoline and prostacyclin on pulmonary hypertension in infants after cardiac surgery. | 1992 Sep |
|
Primary pulmonary hypertension and fenfluramine use. | 1993 Dec |
|
Paradoxical acute brain thromboembolism during prostacyclin (PGI2) acute challenge for primary pulmonary hypertension. | 1996 Jan |
|
Site-directed mutagenesis of human prostacyclin synthase: Alteration of Cys441 of the Cys-pocket, and Glu347 and Arg350 of the EXXR motif. | 1996 Jul 8 |
|
Cyclooxygenase-2 acts as an endogenous brake on endothelin-1 release by human pulmonary artery smooth muscle cells: implications for pulmonary hypertension. | 2002 Nov |
|
Prostacyclin production in rat aortic smooth muscle cells: role of protein kinase C, phospholipase D and cyclooxygenase-2 expression. | 2003 Nov 1 |
|
Cocaine affects prostaglandin production in human umbilical cord cell cultures. | 2003 Oct |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Bradykinin B2 receptor knockout mice are protected from thrombosis by increased nitric oxide and prostacyclin. | 2006 Jul 1 |
|
Effects of vascular endothelial growth factor receptor inhibitor SU5416 and prostacyclin on murine lung metastasis. | 2007 Mar |
|
Traditional nonsteroidal anti-inflammatory drugs and postmenopausal hormone therapy: a drug-drug interaction? | 2007 May |
|
Imbalanced synthesis of cyclooxygenase-derived thromboxane A2 and prostacyclin compromises vasomotor function of the thoracic aorta in Marfan syndrome. | 2007 Oct |
|
Treatment of pulmonary arterial hypertension in pregnancy. | 2007 Sep 15 |
|
Endometrial HSD11B1 and cortisol regeneration in the ovine uterus: effects of pregnancy, interferon tau, and prostaglandins. | 2012 Apr |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/epoprostenol.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24914192
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.
Substance Class |
Chemical
Created
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admin
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Edited
Fri Dec 15 15:23:47 UTC 2023
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Record UNII |
4K04IQ1OF4
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Record Status |
Validated (UNII)
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Record Version |
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C270
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C78568
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