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
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H]2O\C(C[C@H]12)=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 Date1995 |
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) Health Status: healthy Age Group: 33.7 years (range: 18–45 years) Sex: M 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 Highest studied dose Dose: 110.5 ng/kg/min Route: intravenous Route: multiple Dose: 110.5 ng/kg/min Sources: |
unhealthy, 42 years |
|
0.05 ug/kg/min multiple, respiratory Dose: 0.05 ug/kg/min Route: respiratory Route: multiple Dose: 0.05 ug/kg/min Sources: |
unhealthy, 56.4 ± 15.3 years Health Status: unhealthy Age Group: 56.4 ± 15.3 years Sex: M+F 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) Health Status: healthy Age Group: 33.7 years (range: 18–45 years) Sex: M 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) Health Status: healthy Age Group: 33.7 years (range: 18–45 years) Sex: M Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Endometrial HSD11B1 and cortisol regeneration in the ovine uterus: effects of pregnancy, interferon tau, and prostaglandins. | 2012-04 |
|
| A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis. | 2012 |
|
| Effects of PCB126 and 17β-oestradiol on endothelium-derived vasoactive factors in human endothelial cells. | 2011-07-11 |
|
| The successful management of severe protamine-induced pulmonary hypertension using inhaled prostacyclin. | 2010-02-01 |
|
| Celecoxib induces hepatic stellate cell apoptosis through inhibition of Akt activation and suppresses hepatic fibrosis in rats. | 2009-11 |
|
| Prothrombotic effects of diclofenac on arteriolar platelet activation and thrombosis in vivo. | 2009-10 |
|
| Prostacyclin treatment normalises the MCA flow velocity in nimodipine-resistant cerebral vasospasm after aneurysmal subarachnoid haemorrhage: a pilot study. | 2009-06 |
|
| Addition of sildenafil to long-term intravenous epoprostenol therapy in patients with pulmonary arterial hypertension: a randomized trial. | 2008-10-21 |
|
| Prostacyclin (epoprostenol) induces headache in healthy subjects. | 2008-09-30 |
|
| Estrogen protects the heart from ischemia-reperfusion injury via COX-2-derived PGI2. | 2008-09 |
|
| Imbalanced synthesis of cyclooxygenase-derived thromboxane A2 and prostacyclin compromises vasomotor function of the thoracic aorta in Marfan syndrome. | 2007-10 |
|
| Treatment of pulmonary arterial hypertension in pregnancy. | 2007-09-15 |
|
| Traditional nonsteroidal anti-inflammatory drugs and postmenopausal hormone therapy: a drug-drug interaction? | 2007-05 |
|
| Primary pulmonary hypertension associated with the use of fenfluramine derivatives. | 1998-09 |
|
| [Aerosolized prostacyclin for preoperative evaluation and post-cardiosurgical treatment of patients with pulmonary hypertension]. | 1997-02 |
|
| Site-directed mutagenesis of human prostacyclin synthase: Alteration of Cys441 of the Cys-pocket, and Glu347 and Arg350 of the EXXR motif. | 1996-07-08 |
|
| Systemic and pulmonary hypertension after abrupt cessation of prostacyclin: role of thromboxane A2. | 1996-01 |
|
| Paradoxical acute brain thromboembolism during prostacyclin (PGI2) acute challenge for primary pulmonary hypertension. | 1996-01 |
|
| The effects of prostacyclin on gastric intramucosal pH in patients with septic shock. | 1995-05 |
|
| [Cardioprotective effects by ramipril after ischemia and reperfusion in animal experiment studies]. | 1994 |
|
| Primary pulmonary hypertension and fenfluramine use. | 1993-12 |
|
| Chronic nicotine treatment enhances the depressor responses to arachidonic acid in the rat. | 1991 |
|
| [Responses of plasma eicosanoids and hemodynamics to myocardial ischemia and the salutary effect of calcium entry blocker]. | 1990-02 |
|
| Characterization of distinct phospholipases mediating bradykinin and noradrenaline hyperalgesia. | 1990 |
|
| Prostacyclin I2 (PGI2) increases left ventricular ejection fraction (LVEF). | 1989-06 |
|
| Coronary artery calibre after direct intra-arterial infusion of epoprostenol (prostacyclin). | 1988-11 |
|
| Characterization of the arachidonic acid metabolites mediating bradykinin and noradrenaline hyperalgesia. | 1988-08-23 |
|
| Reduction by prostacyclin of acetaminophen-induced liver toxicity in the mouse. | 1988-03-01 |
|
| Treatment of primary pulmonary hypertension intravenous epoprostenol (prostacyclin). | 1987-03 |
|
| Myocardial ischemia during intravenous prostacyclin administration: hemodynamic findings and precautionary measures. | 1987-02 |
|
| Epoprostenol sodium (prostacyclin) infusion in acute myocardial infarction. | 1986-11 |
|
| Depression and prostacyclin infusion. | 1986-08-30 |
|
| Acute effects of captopril on the baroreflex of normotensive and spontaneously hypertensive rats. | 1986-07 |
|
| A comparison of the acute hemodynamic effects of prostacyclin and hydralazine in primary pulmonary hypertension. | 1985-12 |
|
| Proarrhythmic and antiarrhythmic effects of intravenous prostacyclin in man. | 1985-07 |
|
| Myocardial ischemia induced by prostacyclin and iloprost. | 1985-07 |
|
| Stimulation of prostacyclin production in isolated rat adipocytes by angiotensin II, vasopressin, and bradykinin: evidence for two separate mechanisms of prostaglandin synthesis. | 1985-06 |
|
| Severe hypotension due to epoprostenol. | 1984-12-15 |
|
| Hypotension induced by prostacyclin treatment during cardiopulmonary bypass does not increase the risk of cerebral complications. | 1984-11 |
|
| Hemodynamic effects of iloprost, a prostacyclin analog. | 1984-10 |
|
| Plasma concentrations, renal excretion, and tissue release of prostaglandins in the rat with dexamethasone-induced hypertension. | 1984-03 |
|
| Inhibition of epinephrine-exacerbated coronary thrombus formation by prostacyclin in the dog. | 1984-02 |
|
| Effect of prostaglandins on morphine-induced catalepsy in mice. | 1983-09-01 |
|
| Side effects occurring during administration of epoprostenol (prostacyclin, PGI2), in man. | 1982-08 |
|
| Studies on the behavioral and hypotensive effects of intraventricular prostacyclin (PGI2) in rats. | 1981-11 |
|
| Effects of prostacyclin on cardiovascular reflexes from the ventricular epicardium of the dog: comparison with the effects of prostaglandin E2. | 1981-06 |
|
| Preliminary investigation on the central action of prostacyclin (PGI2) in rats. | 1981 |
|
| Some direct and reflex cardiovascular actions of prostacyclin (PGI2) and prostaglandin E2 in anaesthetized dogs. | 1980-03 |
|
| II - Prostaglandin hyperalgesia: the peripheral analgesic activity of morphine, enkephalins and opioid antagonists. | 1979-08 |
|
| Arterial walls are protected against deposition of platelet thrombi by a substance (prostaglandin X) which they make from prostaglandin endoperoxides. | 1976-11 |
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
Wed Apr 02 07:07:38 GMT 2025
by
admin
on
Wed Apr 02 07:07:38 GMT 2025
|
| Record UNII |
DCR9Z582X0
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NDF-RT |
N0000175416
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
||
|
FDA ORPHAN DRUG |
8785
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
||
|
LIVERTOX |
359
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
||
|
NDF-RT |
N0000011280
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
||
|
FDA ORPHAN DRUG |
2884
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
||
|
FDA ORPHAN DRUG |
783
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
||
|
NDF-RT |
N0000011280
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
||
|
NCI_THESAURUS |
C78568
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
||
|
FDA ORPHAN DRUG |
705119
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
||
|
WHO-ATC |
B01AC09
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
||
|
FDA ORPHAN DRUG |
121698
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
||
|
WHO-VATC |
QB01AC09
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
||
|
NDF-RT |
N0000009909
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
||
|
NCI_THESAURUS |
C270
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
||
|
NDF-RT |
N0000011280
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
SUB06581MIG
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | |||
|
35121-78-9
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | |||
|
DTXSID5022988
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | |||
|
C61748
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | |||
|
DCR9Z582X0
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | |||
|
8814
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | RxNorm | ||
|
PROSTACYCLIN
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | |||
|
DCR9Z582X0
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | |||
|
m9256
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | Merck Index | ||
|
5282411
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | |||
|
D011464
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | |||
|
4725
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | |||
|
1034
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | |||
|
1915
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | |||
|
CHEMBL1139
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | |||
|
15552
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | |||
|
100000084532
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY | |||
|
DB01240
Created by
admin on Wed Apr 02 07:07:38 GMT 2025 , Edited by admin on Wed Apr 02 07:07:38 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
SALT/SOLVATE -> PARENT |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
METABOLITE LESS ACTIVE -> PARENT |
MAJOR
|
||
|
METABOLITE LESS ACTIVE -> PARENT |
Formed by spontaneous degradation; Pharmacological activity orders of magnitude less than epoprostenol in animal test systems
MAJOR
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |