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    Chemistry

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    Also known as: 81846-19-7, Remodulin, Uniprost, Rumodolin, Orenitram, Tyvaso
    Molecular Formula
    C23H34O5
    Molecular Weight
    390.5  g/mol
    InChI Key
    PAJMKGZZBBTTOY-ZFORQUDYSA-N
    FDA UNII
    RUM6K67ESG
    Treprostinil Sodium
    Treprostinil is a synthetic analogue of prostacyclin, used to treat pulmonary hypertension.
    Treprostinil is a Prostacycline Vasodilator. The physiologic effect of treprostinil is by means of Vasodilation.
    1 2D Structure

    Treprostinil Sodium

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[[(1R,2R,3aS,9aS)-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[g]naphthalen-5-yl]oxy]acetic acid
    2.1.2 InChI
    InChI=1S/C23H34O5/c1-2-3-4-7-17(24)9-10-18-19-11-15-6-5-8-22(28-14-23(26)27)20(15)12-16(19)13-21(18)25/h5-6,8,16-19,21,24-25H,2-4,7,9-14H2,1H3,(H,26,27)/t16-,17-,18+,19-,21+/m0/s1
    2.1.3 InChI Key
    PAJMKGZZBBTTOY-ZFORQUDYSA-N
    2.1.4 Canonical SMILES
    CCCCCC(CCC1C(CC2C1CC3=C(C2)C(=CC=C3)OCC(=O)O)O)O
    2.1.5 Isomeric SMILES
    CCCCC[C@@H](CC[C@H]1[C@@H](C[C@H]2[C@@H]1CC3=C(C2)C(=CC=C3)OCC(=O)O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    RUM6K67ESG
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. ((1r,2r,3as,9as)-2-hydroxy-1-((3s)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1h-cylopent(b)naphthalen-5-yl)oxy)acetate

    2. Orenitram

    3. Remodulin

    4. Trepostinil Sodium

    5. Treprostinil Diethanolamine

    6. Treprostinil Diolamin

    7. Treprostinil Diolamine

    8. Treprostinil Sodium

    9. Ut-15

    10. Ut-15c

    2.3.2 Depositor-Supplied Synonyms

    1. 81846-19-7

    2. Remodulin

    3. Uniprost

    4. Rumodolin

    5. Orenitram

    6. Tyvaso

    7. Lrx-15

    8. Ut-15

    9. 15au81

    10. Treprostinil Free Acid

    11. Rum6k67esg

    12. 2-(((1r,2r,3as,9as)-2-hydroxy-1-((s)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1h-cyclopenta[b]naphthalen-5-yl)oxy)acetic Acid

    13. Chebi:50861

    14. 81846-19-7 (free Acid)

    15. ((1r,2r,3as,9as)-2-hydroxy-1-((3s)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1h-cylopent(b)naphthalen-5-yl)oxy)acetate

    16. 2-[[(1r,2r,3as,9as)-2-hydroxy-1-[(3s)-3-hydroxyoctyl]-2,3,3a,4,9,9a-hexahydro-1h-cyclopenta[g]naphthalen-5-yl]oxy]acetic Acid

    17. 289480-64-4

    18. 15-au-81

    19. L-606

    20. Treprostinilo

    21. Treprostinilum

    22. Lrx 15

    23. Treprostinil [usan:inn]

    24. Remodulin (tn)

    25. Unii-rum6k67esg

    26. U 62840

    27. Tresprostinil

    28. Trevyent

    29. U-62,840

    30. Treprostinil [mi]

    31. Treprostinil [inn]

    32. Treprostinil [jan]

    33. Treprostinil [usan]

    34. Treprostinil [vandf]

    35. Treprostinil Pound>>ut-15

    36. Treprostinil [mart.]

    37. Treprostinil [who-dd]

    38. 15au

    39. Gtpl5820

    40. Schembl4349618

    41. Treprostinil (jan/usan/inn)

    42. Chembl1237119

    43. Lrx -15

    44. Dtxsid901021654

    45. Hms3648g07

    46. Treprostinil [orange Book]

    47. Amy22230

    48. Bcp10253

    49. Ex-a1414

    50. Zinc3800475

    51. Mfcd00888847

    52. Akos027470173

    53. Cs-7872

    54. Db00374

    55. Ncgc00343944-03

    56. ({(1r,2r,3as,9as)-2-hydroxy-1-[(3s)-3-hydroxyoctyl]-2,3,3a,4,9,9a-hexahydro-1h-cyclopenta[b]naphthalen-5-yl}oxy)acetic Acid

    57. 2-[[(1r,2r,3as,9as)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-[(3s)-3-hydroxyoctyl]-1h-benz[f]inden-5-yl]oxy]acetic Acid

    58. Ac-30207

    59. As-56364

    60. L606

    61. Hy-100441

    62. D06213

    63. Sr-01000946210

    64. Q3495231

    65. Sr-01000946210-1

    66. Brd-k19706299-001-01-4

    67. [[(1r,2r,3as,9as)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-[(s)-3-hydroxyoctyl]-1h-benzo[f]indene-5-yl]oxy]acetic Acid

    68. [[(1r,2r,3as,9as)-2,3,4,9,9a-hexahydro-2-hydroxy-1-[(3s)-3-hydroxyoctyl]-1h-benz[f]inden-5-yl]oxy]acetic Acid

    69. 2-((1r,2r,3as,9as)-2-hydroxy-1-((s)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1h-cyclopenta[b]naphthalen-5-yloxy)acetic Acid

    70. 2-[[(1r,2r,3as,9as)-2,3,4,9,9a-hexahydro-2-hydroxy-1-[(3s)-3-hydroxyoctyl]-1h-benz[f]inden-5-yl]oxy]-acetic Acid

    71. 2-[[(2r,3r,3as,9as)-2-hydroxy-3-[(3s)-3-hydroxyoctyl]-2,3,3a,4,9,9a-hexahydro-1h-cyclopenta[g]naphthalen-8-yl]oxy]acetic Acid

    72. 2-{[(1r,2r,3as,9as)-2-hydroxy-1-[(3s)-3-hydroxyoctyl]-1h,2h,3h,3ah,4h,9h,9ah-cyclopenta[b]naphthalen-5-yl]oxy}acetic Acid

    73. Acetic Acid, (((1r,2r,3as,9as)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((3s)-3-hydroxyoctyl)-1h-benz(f)inden-5-yl)oxy)-

    74. Acetic Acid, ((2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-(3-hydroxyoctyl)-1h-benz(f)inden-5-yl)oxy)-, (1r-(1alpha(s*),2beta,3aalpha,9aalpha))-

    75. Acetic Acid,(((1r,2r,3as,9as)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((3s)-3-hydroxyoctyl)-1h-benz(f)inden-5-yl)oxy)-

    2.4 Create Date
    2006-07-28
    3 Chemical and Physical Properties
    Molecular Weight 390.5 g/mol
    Molecular Formula C23H34O5
    XLogP34.5
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count10
    Exact Mass390.24062418 g/mol
    Monoisotopic Mass390.24062418 g/mol
    Topological Polar Surface Area87 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity495
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameRemodulin
    PubMed HealthTreprostinil
    Drug ClassesAntihypertensive, Cardiovascular Agent, Platelet Aggregation Inhibitor, Vasodilator
    Drug LabelRemodulin (treprostinil) Injection is a sterile solution of treprostinil formulated for subcutaneous or intravenous administration. Remodulin is supplied in 20 mL multidose vials in four strengths, containing 20 mg, 50 mg, 100 mg, or 200 mg (1 mg/mL,...
    Active IngredientTreprostinil
    Dosage FormInjectable
    RouteIv (infusion), subcutaneous
    Strength1mg/ml; 2.5mg/ml; 10mg/ml; 5mg/ml
    Market StatusPrescription
    CompanyUnited Therap

    2 of 4  
    Drug NameTyvaso
    PubMed HealthTreprostinil (By breathing)
    Drug ClassesVasodilator
    Drug LabelTyvaso is a sterile formulation of treprostinil intended for administration by oral inhalation using the Tyvaso Inhalation System. Tyvaso is supplied in 2.9 mL low density polyethylene (LDPE) ampules, containing 1.74 mg treprostinil (0.6 mg/mL). Each...
    Active IngredientTreprostinil
    Dosage FormSolution
    RouteInhalation
    Strengtheq 0.6mg base/ml
    Market StatusPrescription
    CompanyUnited Therap

    3 of 4  
    Drug NameRemodulin
    PubMed HealthTreprostinil
    Drug ClassesAntihypertensive, Cardiovascular Agent, Platelet Aggregation Inhibitor, Vasodilator
    Drug LabelRemodulin (treprostinil) Injection is a sterile solution of treprostinil formulated for subcutaneous or intravenous administration. Remodulin is supplied in 20 mL multidose vials in four strengths, containing 20 mg, 50 mg, 100 mg, or 200 mg (1 mg/mL,...
    Active IngredientTreprostinil
    Dosage FormInjectable
    RouteIv (infusion), subcutaneous
    Strength1mg/ml; 2.5mg/ml; 10mg/ml; 5mg/ml
    Market StatusPrescription
    CompanyUnited Therap

    4 of 4  
    Drug NameTyvaso
    PubMed HealthTreprostinil (By breathing)
    Drug ClassesVasodilator
    Drug LabelTyvaso is a sterile formulation of treprostinil intended for administration by oral inhalation using the Tyvaso Inhalation System. Tyvaso is supplied in 2.9 mL low density polyethylene (LDPE) ampules, containing 1.74 mg treprostinil (0.6 mg/mL). Each...
    Active IngredientTreprostinil
    Dosage FormSolution
    RouteInhalation
    Strengtheq 0.6mg base/ml
    Market StatusPrescription
    CompanyUnited Therap

    4.2 Drug Indication

    For use as a continuous subcutaneous infusion or intravenous infusion (for those not able to tolerate a subcutaneous infusion) for the treatment of pulmonary arterial hypertension in patients with NYHA Class II-IV symptoms to diminish symptoms associated with exercise.

    FDA Label

    Treatment of adult patients with WHO Functional Class (FC) III or IV and:

    - inoperable chronic thromboembolic pulmonary hypertension (CTEPH), or

    - persistent or recurrent CTEPH after surgical treatment

    to improve exercise capacity.

    Treatment of pulmonary arterial hypertension

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Pulmonary arterial hypertension (PAH) is a disease in which blood pressure is abnormally high in the arteries between the heart and lungs. PAH is characterized by symptoms of shortness of breath during physical exertion. The condition can ultimately lead to heart failure. Treprostinil is a potent oral antiplatelet agent. The major pharmacologic actions of treprostinil are direct vasodilation of pulmonary and systemic arterial vascular beds and inhibition of platelet aggregation. In animals, the vasodilatory effects reduce right and left ventricular afterload and increase cardiac output and stroke volume. Other studies have shown that treprostinil causes a dose-related negative inotropic and lusitropic effect. No major effects on cardiac conduction have been observed.

    5.2 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.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    TREPROSTINIL
    5.3.2 FDA UNII
    RUM6K67ESG
    5.3.3 Pharmacological Classes
    Prostaglandins I [CS]; Vasodilation [PE]; Prostacycline Vasodilator [EPC]
    5.4 ATC Code

    B01AC21

    B - Blood and blood forming organs

    B01 - Antithrombotic agents

    B01A - Antithrombotic agents

    B01AC - Platelet aggregation inhibitors excl. heparin

    B01AC21 - Treprostinil

    5.5 Absorption, Distribution and Excretion

    Absorption

    Relatively rapid and complete after subcutaneous infusion, with an absolute bioavailability approximately 100%. In patients with mild (n=4) or moderate (n=5) hepatic insufficiency and portopulmonary hypertension following a subcutaneous dose of 10 ng per kg of body weight per min for 150 mins the AUC 0-∞ was increased 3-fold and 5-fold respectively.

    Volume of Distribution

    14 L/70 kg

    5.6 Metabolism/Metabolites

    Substantially metabolized by the liver, but the precise enzymes responsible are unknown. Five metabolites have been described (HU1 through HU5) however, the biological activity and metabolic fate of these are unknown. The chemical structure of HU1 is unknown. The metabolite HU5 is the glucuronide conjugate of treprostinil. The other metabolites are formed by oxidation of the 3-hydroxyoctyl side chain (HU2) and subsequent additional oxidation (HU3) or dehydration (HU4). Study results of in vitro human hepatic cytochrome P450 demonstrates that treprostinil does not inhibit CYP-1A2, 2C9, 2C19, 2D6, 2E1, or 3A. There have been no studies that evaluate the potential of treprostinil to induce these enzymes.

    5.7 Biological Half-Life

    Terminal elimination half-life is approximately 2 to 4 hours. Plasma half-life is 34 and 85 minutes for intravenous and subcutaneous infusion of the drug, respectively.

    5.8 Mechanism of Action

    The major pharmacological actions of treprostinil are direct vasodilation of pulmonary and systemic arterial vascular beds and inhibition of platelet aggregation. In addition to treprostinil's direct vasodilatory effects, it also inhibits inflammatory cytokine. As a synthetic analogue of prostacyclin, it binds to the prostacyclin receptor, which subsequently induces the aforementioned downstream effects.

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