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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
Structure of EPOPROSTENOL SODIUM

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

HIDE SMILES / InChI

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FLOLAN

Approved Use

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.

Launch Date

8.1155523E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
347 pg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
1972 pg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
0.22 h
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

Doses

DosePopulationAdverse 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)
Vomiting (1 patient)
Sources:
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

AEs

AESignificanceDosePopulation
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:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Patents

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:23:47 UTC 2023
Edited
by admin
on Fri Dec 15 15:23:47 UTC 2023
Record UNII
4K04IQ1OF4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPOPROSTENOL SODIUM
JAN   MART.   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
EPOPROSTENOL SODIUM [MART.]
Common Name English
FLOLAN
Brand Name English
SODIUM PROSTACYCLIN
Common Name English
PROSTA-5,13-DIEN-1-OIC ACID, 6,9-EPOXY-11,15-DIHYDROXY-, SODIUM SALT, (5Z,9.ALPHA.,11.ALPHA.,13E,15S)-
Common Name English
EPOPROSTENOL SODIUM [USP-RS]
Common Name English
EPOPROSTENOL SODIUM [USAN]
Common Name English
PROSTACYCLIN SODIUM SALT
MI  
Common Name English
EPOPROSTENOL SODIUM [VANDF]
Common Name English
EPOPROSTENOL SODIUM [ORANGE BOOK]
Common Name English
Epoprostenol sodium [WHO-DD]
Common Name English
SODIUM (Z)-(3AR,4R,5R,6AS)-HEXAHYDRO-5-HYDROXY-4-((E)-(3S)-3-HYDROXY-1-OCTENYL)-2H-CYCLOPENTA(B)FURAN-.DELTA.(SUP 2,.DELTA.)-VALERATE
Common Name English
U-53,217A
Code English
EPOPROSTENOL SODIUM [JAN]
Common Name English
PROSTACYCLIN SODIUM SALT [MI]
Common Name English
U-53217A
Code English
Classification Tree Code System Code
NCI_THESAURUS C270
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
NCI_THESAURUS C78568
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
Code System Code Type Description
CHEBI
15552
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
PRIMARY
PUBCHEM
6364626
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
PRIMARY
DAILYMED
4K04IQ1OF4
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
PRIMARY
EVMPD
SUB01918MIG
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
PRIMARY
FDA UNII
4K04IQ1OF4
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
PRIMARY
CAS
61849-14-7
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
PRIMARY
DRUG BANK
DBSALT001218
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
PRIMARY
RXCUI
104463
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1139
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
PRIMARY
EPA CompTox
DTXSID3046617
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
PRIMARY
MERCK INDEX
m9256
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
PRIMARY Merck Index
RS_ITEM_NUM
1237600
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
PRIMARY
ECHA (EC/EINECS)
263-273-7
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
PRIMARY
NCI_THESAURUS
C47514
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
PRIMARY
SMS_ID
100000091340
Created by admin on Fri Dec 15 15:23:47 UTC 2023 , Edited by admin on Fri Dec 15 15:23:47 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY