Details
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 |
|
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.
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 |
---|---|---|
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 |
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Effects of prostacyclin on cardiovascular reflexes from the ventricular epicardium of the dog: comparison with the effects of prostaglandin E2. | 1981 Jun |
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Studies on the behavioral and hypotensive effects of intraventricular prostacyclin (PGI2) in rats. | 1981 Nov |
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Side effects occurring during administration of epoprostenol (prostacyclin, PGI2), in man. | 1982 Aug |
|
Effect of prostaglandins on morphine-induced catalepsy in mice. | 1983 Sep-Dec |
|
Hypotension induced by prostacyclin treatment during cardiopulmonary bypass does not increase the risk of cerebral complications. | 1984 Nov |
|
Proarrhythmic and antiarrhythmic effects of intravenous prostacyclin in man. | 1985 Jul |
|
Myocardial ischemia induced by prostacyclin and iloprost. | 1985 Jul |
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Stimulation of prostacyclin production in isolated rat adipocytes by angiotensin II, vasopressin, and bradykinin: evidence for two separate mechanisms of prostaglandin synthesis. | 1985 Jun |
|
Depression and prostacyclin infusion. | 1986 Aug 30 |
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Prostaglandin I2 and the nitric oxide donor molsidomine have synergistic effects on thromboresistance in man. | 1992 Mar |
|
[Cardioprotective effects by ramipril after ischemia and reperfusion in animal experiment studies]. | 1994 |
|
The effects of prostacyclin on gastric intramucosal pH in patients with septic shock. | 1995 May |
|
Systemic and pulmonary hypertension after abrupt cessation of prostacyclin: role of thromboxane A2. | 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 |
|
[Aerosolized prostacyclin for preoperative evaluation and post-cardiosurgical treatment of patients with pulmonary hypertension]. | 1997 Feb |
|
Primary pulmonary hypertension associated with the use of fenfluramine derivatives. | 1998 Sep |
|
Trophic effects of the cyclooxygenase-2 product prostaglandin E(2) in cardiac myocytes. | 2002 Feb |
|
Soluble CD40 ligand in pulmonary arterial hypertension: possible pathogenic role of the interaction between platelets and endothelial cells. | 2004 Aug 24 |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Celecoxib induces hepatic stellate cell apoptosis through inhibition of Akt activation and suppresses hepatic fibrosis in rats. | 2009 Nov |
|
Effects of PCB126 and 17β-oestradiol on endothelium-derived vasoactive factors in human endothelial cells. | 2011 Jul 11 |
|
A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis. | 2012 |
|
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
by
admin
on
Edited
Sat Dec 16 16:05:27 UTC 2023
by
admin
on
Sat Dec 16 16:05:27 UTC 2023
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Record UNII |
DCR9Z582X0
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000175416
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FDA ORPHAN DRUG |
8785
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LIVERTOX |
359
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NDF-RT |
N0000011280
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FDA ORPHAN DRUG |
2884
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FDA ORPHAN DRUG |
783
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NDF-RT |
N0000011280
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NCI_THESAURUS |
C78568
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FDA ORPHAN DRUG |
705119
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WHO-ATC |
B01AC09
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FDA ORPHAN DRUG |
121698
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WHO-VATC |
QB01AC09
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NDF-RT |
N0000009909
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NCI_THESAURUS |
C270
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NDF-RT |
N0000011280
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8814
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PROSTACYCLIN
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m9256
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5282411
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D011464
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DB01240
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SALT/SOLVATE -> PARENT |
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METABOLITE LESS ACTIVE -> PARENT |
MAJOR
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METABOLITE LESS ACTIVE -> PARENT |
Formed by spontaneous degradation; Pharmacological activity orders of magnitude less than epoprostenol in animal test systems
MAJOR
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ACTIVE MOIETY |