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    Also known as: Orciprenaline sulfate, 5874-97-5, Metaproterenol hemisulfate, Metaproterenol hemisulfate salt, Metaproterenol sulphate, Orciprenaline sulphate
    Molecular Formula
    C22H36N2O10S
    Molecular Weight
    520.6  g/mol
    InChI Key
    MKFFGUZYVNDHIH-UHFFFAOYSA-N
    FDA UNII
    GJ20H50YF0
    Metaproterenol Hemisulfate
    A beta-2 adrenergic agonist used in the treatment of ASTHMA and BRONCHIAL SPASM.
    1 2D Structure

    Metaproterenol Hemisulfate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,3-diol;sulfuric acid
    2.1.2 InChI
    InChI=1S/2C11H17NO3.H2O4S/c2*1-7(2)12-6-11(15)8-3-9(13)5-10(14)4-8;1-5(2,3)4/h2*3-5,7,11-15H,6H2,1-2H3;(H2,1,2,3,4)
    2.1.3 InChI Key
    MKFFGUZYVNDHIH-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C)NCC(C1=CC(=CC(=C1)O)O)O.CC(C)NCC(C1=CC(=CC(=C1)O)O)O.OS(=O)(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    GJ20H50YF0
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Alotec

    2. Alupent

    3. Astmopent

    4. Metaprel

    5. Metaproterenol

    6. Metaproterenol Polistirex

    7. Orciprenaline

    8. Orciprenaline Sulfate

    9. Polistirex, Metaproterenol

    2.3.2 Depositor-Supplied Synonyms

    1. Orciprenaline Sulfate

    2. 5874-97-5

    3. Metaproterenol Hemisulfate

    4. Metaproterenol Hemisulfate Salt

    5. Metaproterenol Sulphate

    6. Orciprenaline Sulphate

    7. Alupent

    8. Prometa

    9. Orciprenaline (hemisulfate)

    10. Metaproterenol (hemisulfate)

    11. Th-152

    12. Metaproterenol Sulfate, Orciprenaline Sulfate

    13. 5-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,3-diol;sulfuric Acid

    14. Dsstox_cid_25391

    15. Dsstox_rid_80848

    16. Dsstox_gsid_45391

    17. Gj20h50yf0

    18. Metaproterenol Sulfate [usan]

    19. Prestwick_845

    20. Alupent (tn)

    21. Ncgc00016662-01

    22. Cas-5874-97-5

    23. Schembl41815

    24. Metaproterenol Sulfate (usp)

    25. Orciprenaline Sulfate (jp17)

    26. Chembl1568057

    27. Dtxsid4045391

    28. Hms1569f11

    29. Hms2096f11

    30. Hms3262c10

    31. Hms3713f11

    32. Metaproterenol Sulfate [mi]

    33. Orciprenaline Sulfate [jan]

    34. Bcp13601

    35. Orciprenaline For System Suitability

    36. Tox21_110551

    37. Tox21_500734

    38. Metaproterenol Sulfate [vandf]

    39. Orciprenaline Sulfate [mart.]

    40. Akos015994757

    41. Orciprenaline Sulfate [who-dd]

    42. Tox21_110551_1

    43. Ccg-220505

    44. Ccg-222038

    45. Lp00734

    46. Metaproterenol Sulfate [usp-rs]

    47. Ss-4263

    48. Ncgc00015655-09

    49. Ncgc00094078-01

    50. Ncgc00261419-01

    51. Db-053257

    52. Metaproterenol Sulfate [orange Book]

    53. Orciprenaline Sulfate [ep Monograph]

    54. Eu-0100734

    55. Ft-0628263

    56. Sw198971-2

    57. En300-50867

    58. Metaproterenol Sulfate [usp Monograph]

    59. D00685

    60. M 2398

    61. 874m975

    62. Metaproterenol Sulfate;th-152; Th 152; Th152

    63. Sr-01000872665

    64. Sr-01000872665-1

    65. Metaproterenol Hemisulfate 100 Microg/ml In Methanol

    66. Q27279120

    67. Z955123630

    68. 5-(1-hydroxy-2-(isopropylamino)ethyl)benzene-1,3-diol Hemisulfate

    69. Bis(5-(1-hydroxy-2-(isopropylamino)ethyl)benzene-1,3-diol) Sulfate

    70. Metaproterenol Sulfate, United States Pharmacopeia (usp) Reference Standard

    71. Orciprenaline Sulfate, European Pharmacopoeia (ep) Reference Standard

    72. (+/-)-3,5-dihydroxy-.alpha.-((isopropylamino)methyl)benzyl Alcohol Sulfate (2:1)

    73. (+/-)-3,5-dihydroxy-.alpha.-((isopropylamino)methyl)benzyl Alcohol Sulphate (2:1)

    74. Bis(5-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,3-diol); Sulfuric Acid

    75. Orciprenaline For System Suitability, European Pharmacopoeia (ep) Reference Standard

    76. 1,3-benzenediol, 5-(1-hydroxy-2-(1-methylethyl)amino)ethyl-, (+/-)-, Sulfate (2:1) (salt)

    77. 1,3-benzenediol, 5-(1-hydroxy-2-(1-methylethyl)amino)ethyl-, (+/-)-, Sulphate (2:1) (salt)

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 520.6 g/mol
    Molecular Formula C22H36N2O10S
    Hydrogen Bond Donor Count10
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count8
    Exact Mass520.20906652 g/mol
    Monoisotopic Mass520.20906652 g/mol
    Topological Polar Surface Area228 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity258
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count2
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count3
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameMetaproterenol sulfate
    Drug LabelMetaproterenol sulfate syrup is an oral bronchodilator. Each teaspoonful (5 mL), for oral administration, contains metaproterenol sulfate 10 mg. In addition, each teaspoonful (5 mL) contains the following inactive ingredients:citric acid, edetate dis...
    Active IngredientMetaproterenol sulfate
    Dosage FormTablet; Syrup; Solution
    RouteOral; Inhalation
    Strength10mg/5ml; 0.4%; 0.6%; 10mg; 20mg
    Market StatusPrescription
    CompanyWockhardt; Silarx; Mylan Speclt; Par Pharm

    2 of 2  
    Drug NameMetaproterenol sulfate
    Drug LabelMetaproterenol sulfate syrup is an oral bronchodilator. Each teaspoonful (5 mL), for oral administration, contains metaproterenol sulfate 10 mg. In addition, each teaspoonful (5 mL) contains the following inactive ingredients:citric acid, edetate dis...
    Active IngredientMetaproterenol sulfate
    Dosage FormTablet; Syrup; Solution
    RouteOral; Inhalation
    Strength10mg/5ml; 0.4%; 0.6%; 10mg; 20mg
    Market StatusPrescription
    CompanyWockhardt; Silarx; Mylan Speclt; Par Pharm

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Tocolytic Agents

    Drugs that prevent preterm labor and immature birth by suppressing uterine contractions (TOCOLYSIS). Agents used to delay premature uterine activity include magnesium sulfate, beta-mimetics, oxytocin antagonists, calcium channel inhibitors, and adrenergic beta-receptor agonists. The use of intravenous alcohol as a tocolytic is now obsolete. (See all compounds classified as Tocolytic Agents.)

    Bronchodilator Agents

    Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)

    Adrenergic beta-2 Receptor Agonists

    Compounds bind to and activate ADRENERGIC BETA-2 RECEPTORS. (See all compounds classified as Adrenergic beta-2 Receptor Agonists.)

    Sympathomimetics

    Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. (See all compounds classified as Sympathomimetics.)

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