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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

Metaproterenol
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 Weight 211.26 g/mol
Molecular Formula C11H17NO3
XLogP30.7
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Exact Mass211.12084340 g/mol
Monoisotopic Mass211.12084340 g/mol
Topological Polar Surface Area72.7 Ų
Heavy Atom Count15
Formal Charge0
Complexity177
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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

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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API | Excipient name

Metaproterenol

Synonyms

Orciprenaline, 586-06-1, Alupent, Orciprenalinum, Orciprenalinum [inn-latin], Orciprenalina [inn-spanish]

Cas Number

586-06-1

Unique Ingredient Identifier (UNII)

53QOG569E0

About Metaproterenol

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

Metaproterenol Manufacturers

A Metaproterenol manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Metaproterenol, including repackagers and relabelers. The FDA regulates Metaproterenol manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Metaproterenol API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Metaproterenol Suppliers

A Metaproterenol supplier is an individual or a company that provides Metaproterenol active pharmaceutical ingredient (API) or Metaproterenol finished formulations upon request. The Metaproterenol suppliers may include Metaproterenol API manufacturers, exporters, distributors and traders.

Metaproterenol GMP

Metaproterenol Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Metaproterenol GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Metaproterenol GMP manufacturer or Metaproterenol GMP API supplier for your needs.

Metaproterenol CoA

A Metaproterenol CoA (Certificate of Analysis) is a formal document that attests to Metaproterenol's compliance with Metaproterenol specifications and serves as a tool for batch-level quality control.

Metaproterenol CoA mostly includes findings from lab analyses of a specific batch. For each Metaproterenol CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Metaproterenol may be tested according to a variety of international standards, such as European Pharmacopoeia (Metaproterenol EP), Metaproterenol JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Metaproterenol USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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