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Synopsis

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Chemistry

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Also known as: Orciprenaline, 586-06-1, Alupent, Orciprenalinum, Orciprenalinum [inn-latin], Orciprenalina [inn-spanish]

Molecular Formula

C₁₁H₁₇NO₃

Molecular Weight

211.26 g/mol

InChI Key

LMOINURANNBYCM-UHFFFAOYSA-N

FDA UNII

53QOG569E0

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

Metaproterenol is a beta2-Adrenergic Agonist. The mechanism of action of metaproterenol is as an Adrenergic beta2-Agonist.

1 2D Structure

Metaproterenol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,3-diol

2.1.2 InChI

InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-9(13)5-10(14)4-8/h3-5,7,11-15H,6H2,1-2H3

2.1.3 InChI Key

LMOINURANNBYCM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)NCC(C1=CC(=CC(=C1)O)O)O

2.2 Other Identifiers

2.2.1 UNII

53QOG569E0

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Alotec

2. Alupent

3. Astmopent

4. Metaprel

5. Metaproterenol Polistirex

6. Metaproterenol Sulfate

7. Orciprenaline

8. Orciprenaline Sulfate

9. Polistirex, Metaproterenol

2.3.2 Depositor-Supplied Synonyms

1. Orciprenaline

2. 586-06-1

3. Alupent

4. Orciprenalinum

5. Orciprenalinum [inn-latin]

6. Orciprenalina [inn-spanish]

7. Orciprenaline [inn]

8. Prometa

9. 5-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,3-diol

10. Orciprenaline (inn)

11. (rs)-1-(3,5-dihydroxyphenyl)-2-isopropylaminoethanol

12. Chembl776

13. Chebi:6792

14. 5-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,3-diol

15. 1,3-benzenediol, 5-(1-hydroxy-2-((1-methylethyl)amino)ethyl)-

16. 53qog569e0

17. Nsc-757089

18. Orciprenalina

19. 1,3-benzenediol, 5-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]-

20. Ccris 9017

21. Th-152

22. Sr-01000075168

23. Einecs 209-569-1

24. Orciprenaline [inn:ban]

25. Brn 2807247

26. Orciprenalin

27. Unii-53qog569e0

28. 3,5-dihydroxy-alpha-((isopropylamino)methyl)benzyl Alcohol

29. Spectrum_000925

30. Prestwick0_000505

31. Prestwick1_000505

32. Prestwick2_000505

33. Prestwick3_000505

34. Spectrum2_000096

35. Spectrum3_000492

36. Spectrum4_000044

37. Spectrum5_000952

38. M-3070

39. Metaproterenol [mi]

40. Schembl4270

41. Lopac0_000734

42. Bspbio_000429

43. Bspbio_001983

44. Kbiogr_000507

45. Kbioss_001405

46. Divk1c_000645

47. Metaproterenol [vandf]

48. Spectrum1500390

49. Spbio_000052

50. Spbio_002350

51. Orciprenaline [who-dd]

52. Bpbio1_000473

53. Gtpl7250

54. Dtxsid8048529

55. Chebi:83329

56. Hms502a07

57. Hy-b1276a

58. Kbio1_000645

59. Kbio2_001405

60. Kbio2_003973

61. Kbio2_006541

62. Kbio3_001483

63. Ninds_000645

64. Hms1920l09

65. Hms2091d04

66. Hms3259j13

67. Pharmakon1600-01500390

68. Benzyl Alcohol, 3,5-dihydroxy-alpha-((isopropylamino)methyl)-

69. Bdbm50295572

70. Ccg-38914

71. Nsc757089

72. Db00816

73. Nc00651

74. Nsc 757089

75. Sdccgsbi-0050712.p005

76. Idi1_000645

77. Ncgc00015655-02

78. Ncgc00015655-03

79. Ncgc00015655-04

80. Ncgc00015655-05

81. Ncgc00015655-06

82. Ncgc00015655-14

83. Ncgc00094718-01

84. Ncgc00094718-02

85. Ncgc00094718-03

86. Sbi-0050712.p004

87. Ab00052037

88. Cs-0013668

89. C07144

90. D08300

91. 1-(3,5-dihydroxyphenyl)-2-isopropylaminoethanol

92. Ab00052037_09

93. Ab00052037_10

94. 586o061

95. L000678

96. Q416473

97. Sr-01000075168-1

98. Sr-01000075168-4

99. Brd-a07780951-001-06-3

100. 5-(1-hydroxy-2-(isopropylamino)ethyl)benzene-1,3-diol

101. 5-(1-hydroxy-2-isopropylamino-ethyl)-benzene-1,3-diol

102. 5-[1-hydroxy-2-(isopropanylamino)ethyl]benzene-1,3-diol

103. 5-[1-hydroxy-2-(isopropylamino)ethyl]-1,3-benzenediol #

104. [2-(3,5-dihydroxy-phenyl)-2-hydroxy-ethyl]-isopropyl-ammonium

105. 3,5-dihydroxy-.alpha.-((isopropylamino)methyl)benzyl Alcohol

106. 5-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,3-diol, 6

107. Benzyl Alcohol, 3,5-dihydroxy-.alpha.-((isopropylamino)methyl)-

108. [2-(3,5-dihydroxy-phenyl)-2-hydroxy-ethyl]-isopropyl-ammonium (orciprenaline)

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₇NO₃
Molecular Weight	211.26 g/mol
XLogP3	0.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	211.12084340 g/mol
Monoisotopic Mass	211.12084340 g/mol
Topological Polar Surface Area	72.7 Å²
Heavy Atom Count	15
Formal Charge	0
Complexity	177
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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

4.2 Drug Indication

For the treatment of bronchospasm, chronic bronchitis, asthma, and emphysema.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Orciprenaline (also known as metaproterenol), a synthetic amine, is structurally and pharmacologically similar to isoproterenol. Orciprenaline is used exclusively as a bronchodilator. The pharmacological effects of beta adrenergic agonist drugs, such as orciprenaline, are at least in part attributable to stimulation through beta adrenergic receptors of intracellular adenyl cyclase, the enzyme which catalyzes the conversion of adenosine triphosphate (ATP) to cyclic- 3',5'- adenosine monophosphate (c-AMP). Increased cAMP levels lead to relaxation of bronchial smooth muscles and inhibition of the release of inalammatory mediators from mast cells that are involved in promoting immediate hypersensitivity .

5.2 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.)

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.)

Adrenergic beta-2 Receptor Agonists

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

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

METAPROTERENOL

5.3.2 FDA UNII

53QOG569E0

5.3.3 Pharmacological Classes

Established Pharmacologic Class [EPC] - beta2-Adrenergic Agonist

5.4 ATC Code

R - Respiratory system

R03 - Drugs for obstructive airway diseases

R03A - Adrenergics, inhalants

R03AB - Non-selective beta-adrenoreceptor agonists

R03AB03 - Orciprenaline

R - Respiratory system

R03 - Drugs for obstructive airway diseases

R03C - Adrenergics for systemic use

R03CB - Non-selective beta-adrenoreceptor agonists

R03CB03 - Orciprenaline

5.5 Absorption, Distribution and Excretion

Absorption

3% (oral bioavailability of 40%)

5.6 Metabolism/Metabolites

Hepatic and gastric. The major metabolite, orciprenaline-3-0-sulfate, is produced in the gastrointestinal tract. Orciprenaline is not metabolized by catechol-0-methyltransferase nor have glucuronide conjugates been isolated to date.

5.7 Biological Half-Life

6 hours

5.8 Mechanism of Action

Orciprenaline stimulates the 2-adrenergic receptor expressed in the lungs, uterus, and vasculature supplying skeletal muscles by acting as a moderately selective agonist. It exerts minimal or no effect on alpha-adrenergic receptors. Intracellularly, the actions of orciprenaline are mediated by cAMP, the production of which is augmented by beta stimulation. The drug is believed to work by activating adenylate cyclase, the enzyme responsible for producing the cellular mediator cAMP.

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