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Alupent

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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

A beta-2 adrenergic agonist used in the treatment of ASTHMA and BRONCHIAL SPASM.

1 2D Structure

Alupent

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 Formula	C₂₂H₃₆N₂O₁₀S
Molecular Weight	520.6 g/mol
Hydrogen Bond Donor Count	10
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	8
Exact Mass	520.20906652 g/mol
Monoisotopic Mass	520.20906652 g/mol
Topological Polar Surface Area	228 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	258
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Metaproterenol sulfate
Drug Label	Metaproterenol 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 Ingredient	Metaproterenol sulfate
Dosage Form	Tablet; Syrup; Solution
Route	Oral; Inhalation
Strength	10mg/5ml; 0.4%; 0.6%; 10mg; 20mg
Market Status	Prescription
Company	Wockhardt; Silarx; Mylan Speclt; Par Pharm

2 of 2
Drug Name	Metaproterenol sulfate
Drug Label	Metaproterenol 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 Ingredient	Metaproterenol sulfate
Dosage Form	Tablet; Syrup; Solution
Route	Oral; Inhalation
Strength	10mg/5ml; 0.4%; 0.6%; 10mg; 20mg
Market Status	Prescription
Company	Wockhardt; 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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