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    Chemistry

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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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    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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