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Also known as: Flolan, Epoprostenol, Prostacyclin sodium salt, 61849-14-7, Sodium prostacyclin, Prostaglandin i2
Molecular Formula
C20H31NaO5
Molecular Weight
374.4  g/mol
InChI Key
LMHIPJMTZHDKEW-XQYLJSSYSA-M
FDA UNII
4K04IQ1OF4

Epoprostenol Sodium
A prostaglandin that is a powerful vasodilator and inhibits platelet aggregation. It is biosynthesized enzymatically from PROSTAGLANDIN ENDOPEROXIDES in human vascular tissue. The sodium salt has been also used to treat primary pulmonary hypertension (HYPERTENSION, PULMONARY).
1 2D Structure

Epoprostenol Sodium

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;(5Z)-5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-ylidene]pentanoate
2.1.2 InChI
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
2.1.3 InChI Key
LMHIPJMTZHDKEW-XQYLJSSYSA-M
2.1.4 Canonical SMILES
CCCCCC(C=CC1C(CC2C1CC(=CCCCC(=O)[O-])O2)O)O.[Na+]
2.1.5 Isomeric SMILES
CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C/C(=C/CCCC(=O)[O-])/O2)O)O.[Na+]
2.2 Other Identifiers
2.2.1 UNII
4K04IQ1OF4
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Epoprostanol

2. Epoprostenol

3. Epoprostenol Sodium Salt, (5z,9alpha,11alpha,13e,15s)-isomer

4. Flolan

5. Prostacyclin

6. Prostaglandin I(2)

7. Prostaglandin I2

8. Veletri

2.3.2 Depositor-Supplied Synonyms

1. Flolan

2. Epoprostenol

3. Prostacyclin Sodium Salt

4. 61849-14-7

5. Sodium Prostacyclin

6. Prostaglandin I2

7. U-53217a

8. U-53,217a

9. 4k04iq1of4

10. Cyclo-prostin

11. 35121-78-9

12. Epoprostenol Sodium [usan:ban]

13. Ncgc00167427-01

14. Einecs 263-273-7

15. Unii-4k04iq1of4

16. Floran

17. U 53,217a

18. Epoprostenolsodium

19. Prostacyclin Sodium

20. Prostaglandin X Sodium

21. Prostaglandin I2 Na

22. Chembl962

23. Dsstox_cid_26617

24. Dsstox_rid_81769

25. Sodium (5z,13e,15s)-6,9alpha-epoxy-11alpha,15-dihydroxyprosta-5,13-dien-1-oate

26. Dsstox_gsid_46617

27. Schembl41344

28. 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

29. Bml1-f10

30. Dtxsid3046617

31. Epoprostenol Sodium [jan]

32. 4ua76

33. Epoprostenol Sodium [usan]

34. Hms1361k18

35. Hms3648l14

36. Epoprostenol Sodium [vandf]

37. Epoprostenol Sodium [mart.]

38. Tox21_112431

39. Epoprostenol Sodium [usp-rs]

40. Epoprostenol Sodium [who-dd]

41. Prostacyclin Sodium Salt [mi]

42. Akos024457370

43. Epoprostenol Sodium [orange Book]

44. Prosta-5,13-dien-1-oic Acid, 6,9-epoxy-11,15-dihydroxy-, Sodium Salt, (5z,9alpha,11alpha,13e,15s)-

45. Cas-61849-14-7

46. Q27259818

47. (5z,13e,8r,9s,11r,12r,15s)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oic Acid Sodium Salt

48. Prosta-5,13-dien-1-oic Acid, 6,9-epoxy-11,15-dihydroxy-, Sodium Salt, (5z,9.alpha.,11.alpha.,13e,15s)-

49. 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

50. Sodium (z)-5-((3ar,4r,5r,6as)-5-hydroxy-4-((s,e)-3-hydroxyoct-1-enyl)hexahydro-2h-cyclopenta[b]furan-2-ylidene)pentanoate

2.4 Create Date
2005-07-19
3 Chemical and Physical Properties
Molecular Weight 374.4 g/mol
Molecular Formula C20H31NaO5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count10
Exact Mass374.20691837 g/mol
Monoisotopic Mass374.20691837 g/mol
Topological Polar Surface Area89.8 Ų
Heavy Atom Count26
Formal Charge0
Complexity491
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameEpoprostenol sodium
PubMed HealthEpoprostenol (Injection)
Drug ClassesPeripheral Vasodilator, Platelet Aggregation Inhibitor
Drug LabelEpoprostenol sodium for injection is a sterile sodium salt formulated for intravenous (IV) administration. Each vial of epoprostenol sodium for injection contains epoprostenol sodium equivalent to either 0.5 mg (500,000 ng) or 1.5 mg (1,500,000 ng) e...
Active IngredientEpoprostenol sodium
Dosage FormInjectable
RouteInjection
Strengtheq 1.5mg base/vial; eq 0.5mg base/vial
Market StatusPrescription
CompanyTeva Pharms Usa

2 of 4  
Drug NameFlolan
Drug LabelFLOLAN (epoprostenol sodium) for Injection is a sterile sodium salt formulated for intravenous (IV) administration. Each vial of FLOLAN contains epoprostenol sodium equivalent to either 0.5mg (500,000ng) or 1.5mg (1,500,000ng) epoprostenol, 3...
Active IngredientEpoprostenol sodium
Dosage FormInjectable
RouteInjection
Strengtheq 1.5mg base/vial; eq 0.5mg base/vial
Market StatusPrescription
CompanyGlaxosmithkline

3 of 4  
Drug NameEpoprostenol sodium
PubMed HealthEpoprostenol (Injection)
Drug ClassesPeripheral Vasodilator, Platelet Aggregation Inhibitor
Drug LabelEpoprostenol sodium for injection is a sterile sodium salt formulated for intravenous (IV) administration. Each vial of epoprostenol sodium for injection contains epoprostenol sodium equivalent to either 0.5 mg (500,000 ng) or 1.5 mg (1,500,000 ng) e...
Active IngredientEpoprostenol sodium
Dosage FormInjectable
RouteInjection
Strengtheq 1.5mg base/vial; eq 0.5mg base/vial
Market StatusPrescription
CompanyTeva Pharms Usa

4 of 4  
Drug NameFlolan
Drug LabelFLOLAN (epoprostenol sodium) for Injection is a sterile sodium salt formulated for intravenous (IV) administration. Each vial of FLOLAN contains epoprostenol sodium equivalent to either 0.5mg (500,000ng) or 1.5mg (1,500,000ng) epoprostenol, 3...
Active IngredientEpoprostenol sodium
Dosage FormInjectable
RouteInjection
Strengtheq 1.5mg base/vial; eq 0.5mg base/vial
Market StatusPrescription
CompanyGlaxosmithkline

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)


Platelet Aggregation Inhibitors

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Prostaglandins I [CS]; Vasodilation [PE]; Prostacycline Vasodilator [EPC]
5.3 ATC Code

B - Blood and blood forming organs

B01 - Antithrombotic agents

B01A - Antithrombotic agents

B01AC - Platelet aggregation inhibitors excl. heparin

B01AC09 - Epoprostenol


API Reference Price

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30-Jan-2021
07-May-2024
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DOSAGE - INJECTABLE;INJECTION - EQ 0.5MG BASE...DOSAGE - INJECTABLE;INJECTION - EQ 0.5MG BASE/VIAL

USFDA APPLICATION NUMBER - 22260

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DOSAGE - INJECTABLE;INJECTION - EQ 1.5MG BASE...DOSAGE - INJECTABLE;INJECTION - EQ 1.5MG BASE/VIAL

USFDA APPLICATION NUMBER - 22260

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