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    Chemistry

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    Also known as: 200815-49-2, Brovana, (r,r)-arformoterol tartrate, Arformoterol tartrate [usan], 5p8vj2i235, Arformoterol tartrate (usan)
    Molecular Formula
    C23H30N2O10
    Molecular Weight
    494.5  g/mol
    InChI Key
    FCSXYHUNDAXDRH-OKMNHOJOSA-N
    FDA UNII
    5P8VJ2I235
    Arformoterol Tartrate
    Arformoterol Tartrate is the tartrate salt of arformoterol, the (R,R)-enantiomer of formoterol and a long-acting beta-2 adrenergic agonist with bronchodilator activity. Arformoterol selectively binds to and activates beta-2 adrenergic receptors in bronchiolar smooth muscle, thereby causing stimulation of adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic-3',5'-adenosine monophosphate (cAMP). Increased intracellular cAMP levels cause relaxation of bronchial smooth muscle and lead to an inhibition of release of inflammatory mediators from mast cells. This may eventually lead to an improvement of airway function.
    1 2D Structure

    Arformoterol Tartrate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R,3R)-2,3-dihydroxybutanedioic acid;N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]phenyl]formamide
    2.1.2 InChI
    InChI=1S/C19H24N2O4.C4H6O6/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22;5-1(3(7)8)2(6)4(9)10/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22);1-2,5-6H,(H,7,8)(H,9,10)/t13-,19+;1-,2-/m11/s1
    2.1.3 InChI Key
    FCSXYHUNDAXDRH-OKMNHOJOSA-N
    2.1.4 Canonical SMILES
    CC(CC1=CC=C(C=C1)OC)NCC(C2=CC(=C(C=C2)O)NC=O)O.C(C(C(=O)O)O)(C(=O)O)O
    2.1.5 Isomeric SMILES
    C[C@H](CC1=CC=C(C=C1)OC)NC[C@@H](C2=CC(=C(C=C2)O)NC=O)O.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    5P8VJ2I235
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 200815-49-2

    2. Brovana

    3. (r,r)-arformoterol Tartrate

    4. Arformoterol Tartrate [usan]

    5. 5p8vj2i235

    6. Arformoterol Tartrate (usan)

    7. Formamide, N-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[(1r)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-, (2r,3r)-2,3-dihydroxybutanedioate (1:1)

    8. (r,r)-formoterol Tartrate

    9. (-)-n-(2-hydroxy-5-((1r)-1-hydroxy-2-(((1r)-2-(4-methoxyphenyl)-1-methylethyl)amino)ethyl)phenyl)formamide Hydrogen (2r,3r)-2,3-dihydroxybutanedioate (salt)

    10. Formamide, N-(2-hydroxy-5-((1r)-1-hydroxy-2-(((1r)-2-(4-methoxyphenyl)-1-methylethyl)amino)ethyl)phenyl)-, (2r,3r)-2,3-dihydroxybutanedioate (1:1) (salt)

    11. N-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[(1r)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-formamide (2r,3r)-2,3-dihydroxybutanedioate (1:1) (salt)

    12. Brovana Inhalation Solution

    13. Unii-5p8vj2i235

    14. Brovana (tn)

    15. Arformotero Ltartrate

    16. Dtxsid80173903

    17. Arformoterol Tartrate [vandf]

    18. S5217

    19. Arformoterol Tartrate [mart.]

    20. Akos005145740

    21. Arformoterol Tartrate [who-dd]

    22. Ccg-269651

    23. Arformoterol Tartrate, >=98% (hplc)

    24. Ba171831

    25. Bs-42158

    26. Arformoterol Tartrate [orange Book]

    27. Formoterol R,r-form L-tartrate [mi]

    28. D02981

    29. 815f492

    30. Q-101035

    31. Q27262686

    32. (2r,3r)-2,3-dihydroxybutanedioic Acid;n-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]phenyl]formamide

    33. (r,r)-formoterol Tartrate; N-(2-hydroxy-5-((1r)-1-hydroxy-2-(((1r)-2-(4-methoxyphenyl)-1-methylethyl)amino)ethyl)phenyl)formamide (2r,3r)-2,3-dihydroxybutanedioate (1:1)

    34. [(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]-[(2r)-1-(4-methoxyphenyl)propan-2-yl]azanium;(2r,3r)-2,3,4-trihydroxy-4-oxobutanoate

    35. N-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[(1r)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide (2r,3r)-2,3-dihydroxybutane Dioate

    36. N-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[(1r)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide (2r,3r)-2,3-dihydroxybutanedioate

    37. N-[2-hydroxy-5-[(1r)-1-hydroxy-2-[[(1r)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide L-tartrate

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 494.5 g/mol
    Molecular Formula C23H30N2O10
    Hydrogen Bond Donor Count8
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count11
    Exact Mass494.19004516 g/mol
    Monoisotopic Mass494.19004516 g/mol
    Topological Polar Surface Area206 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity521
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameBrovana
    PubMed HealthArformoterol (By breathing)
    Drug ClassesBronchodilator
    Active IngredientArformoterol tartrate
    Dosage FormSolution
    RouteInhalation
    Strengtheq 0.015mg base/2ml
    Market StatusPrescription
    CompanySunovion

    2 of 2  
    Drug NameBrovana
    PubMed HealthArformoterol (By breathing)
    Drug ClassesBronchodilator
    Active IngredientArformoterol tartrate
    Dosage FormSolution
    RouteInhalation
    Strengtheq 0.015mg base/2ml
    Market StatusPrescription
    CompanySunovion

    5 Pharmacology and Biochemistry
    5.1 FDA Pharmacological Classification
    5.1.1 Pharmacological Classes
    beta2-Adrenergic Agonist [EPC]; Adrenergic beta2-Agonists [MoA]

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