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Epoprostenol Sodium

Epoprostenol Sodium

Synopsis, Chemistry

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INJECTABLE;INJECTION - EQ 0.5MG BASE/VIAL, INJECTABLE;INJECTION - EQ 1.5MG BASE/VIAL

INJECTABLE;INJECTION - EQ 0.5MG BASE/VIAL
INJECTABLE;INJECTION - EQ 1.5MG BASE/VIAL

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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

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 Formula	C₂₀H₃₁NaO₅
Molecular Weight	374.4 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	10
Exact Mass	374.20691837 g/mol
Monoisotopic Mass	374.20691837 g/mol
Topological Polar Surface Area	89.8 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	491
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Epoprostenol sodium
PubMed Health	Epoprostenol (Injection)
Drug Classes	Peripheral Vasodilator, Platelet Aggregation Inhibitor
Drug Label	Epoprostenol 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 Ingredient	Epoprostenol sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 1.5mg base/vial; eq 0.5mg base/vial
Market Status	Prescription
Company	Teva Pharms Usa

2 of 4
Drug Name	Flolan
Drug Label	FLOLAN (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 Ingredient	Epoprostenol sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 1.5mg base/vial; eq 0.5mg base/vial
Market Status	Prescription
Company	Glaxosmithkline

3 of 4
Drug Name	Epoprostenol sodium
PubMed Health	Epoprostenol (Injection)
Drug Classes	Peripheral Vasodilator, Platelet Aggregation Inhibitor
Drug Label	Epoprostenol 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 Ingredient	Epoprostenol sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 1.5mg base/vial; eq 0.5mg base/vial
Market Status	Prescription
Company	Teva Pharms Usa

4 of 4
Drug Name	Flolan
Drug Label	FLOLAN (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 Ingredient	Epoprostenol sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 1.5mg base/vial; eq 0.5mg base/vial
Market Status	Prescription
Company	Glaxosmithkline

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