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Labetalol Hydrochloride
Also known as: 32780-64-6, Labetalol hcl, Amipress, Presdate, Normodyne, Trandate
Molecular Formula
C19H25ClN2O3
Molecular Weight
364.9  g/mol
InChI Key
WQVZLXWQESQGIF-UHFFFAOYSA-N
FDA UNII
1GEV3BAW9J

A salicylamide derivative that is a non-cardioselective blocker of BETA-ADRENERGIC RECEPTORS and ALPHA-1 ADRENERGIC RECEPTORS.
1 2D Structure

Labetalol Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-hydroxy-5-[1-hydroxy-2-(4-phenylbutan-2-ylamino)ethyl]benzamide;hydrochloride
2.1.2 InChI
InChI=1S/C19H24N2O3.ClH/c1-13(7-8-14-5-3-2-4-6-14)21-12-18(23)15-9-10-17(22)16(11-15)19(20)24;/h2-6,9-11,13,18,21-23H,7-8,12H2,1H3,(H2,20,24);1H
2.1.3 InChI Key
WQVZLXWQESQGIF-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(CCC1=CC=CC=C1)NCC(C2=CC(=C(C=C2)O)C(=O)N)O.Cl
2.2 Other Identifiers
2.2.1 UNII
1GEV3BAW9J
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ah 5158

2. Ah-5158

3. Ah5158

4. Albetol

5. Apo Labetalol

6. Apo-labetalol

7. Apolabetalol

8. Dilevalol

9. Hydrochloride, Labetalol

10. Labetalol

11. Labetalol, (r,r)-isomer

12. Labetolol

13. Normodyne

14. Presolol

15. R,r Labetalol

16. R,r-labetalol

17. Sch 19927

18. Sch-19927

19. Sch19927

20. Trandate

2.3.2 Depositor-Supplied Synonyms

1. 32780-64-6

2. Labetalol Hcl

3. Amipress

4. Presdate

5. Normodyne

6. Trandate

7. Labetalol (hydrochloride)

8. Sch 15719w

9. Ah 5158a

10. Sch-15719w

11. 2-hydroxy-5-(1-hydroxy-2-((4-phenylbutan-2-yl)amino)ethyl)benzamide Hydrochloride

12. Ibidomide Hydrochloride

13. Labetalol Hydrochloride

14. Ah-5158a

15. 1gev3baw9j

16. Nsc-290312

17. 32780-64-6 (hcl)

18. Mls000069666

19. Ah-5158a Hydrochloride

20. Sch-15719w Hydrochloride

21. 2-hydroxy-5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]benzamide Hydrochloride

22. 5-(1-hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)salicylamide Monohydrochloride

23. Ah-5158 Hydrochloride;sch-15719w

24. Labetalol Hcl (mixture Of Diastereomers)

25. Labrocol

26. Pressalolo

27. Smr000058463

28. Ipolab

29. 2-hydroxy-5-(1-hydroxy-2-(4-phenylbutan-2-ylamino)ethyl)benzamide Hcl

30. 2-hydroxy-5-[1-hydroxy-2-(4-phenylbutan-2-ylamino)ethyl]benzamide Hydrochloride

31. 2-hydroxy-5-[1-hydroxy-2-(4-phenylbutan-2-ylamino)ethyl]benzamide;hydrochloride

32. 5-(1-hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)salicylamide Hydrochloride

33. 5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]salicylamide Hydrochloride

34. 5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]salicylamide Monohydrochloride

35. Benzamide, 2-hydroxy-5-(1-hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)-, Monohydrochloride

36. Dsstox_cid_24654

37. Dsstox_rid_80378

38. Dsstox_gsid_44654

39. Ccris 1086

40. Sr-01000000209

41. Einecs 251-211-1

42. Unii-1gev3baw9j

43. Nsc 290312

44. 2-hydroxy-5-(1-hydroxy-2-(4-phenylbutan-2-ylamino)ethyl)benzamide Hydrochloride

45. 2-hydroxy-5-(1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl)benzamide Hydrochloride

46. Normodyne (tn)

47. Trandate (tn)

48. Prestwick_290

49. Einecs 276-694-6

50. Mfcd00057663

51. Labetalolhydrochloride

52. Labetalol Hydrochloride [usan:usp:jan]

53. Ah-5158 Hydrochloride

54. La.beta.lol Hydrochloride

55. Opera_id_1625

56. Benzamide,monohydrochloride

57. Ncgc00016810-01

58. Salicylamide, Hydrochloride

59. Cas-32780-64-6

60. Salicylamide, 5-(1-hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)-, Hydrochloride

61. Schembl41230

62. 72487-34-4

63. Mls001148626

64. Mls002222197

65. Spectrum1503243

66. Chebi:6344

67. Chembl1200323

68. Dtxsid0044654

69. Amy8842

70. Hms1568h16

71. Hms1922m13

72. Pharmakon1600-01503243

73. 72487-35-5

74. Bcp13886

75. Ex-a4940

76. Hy-b1108

77. Labetalol Hydrochloride [mi]

78. Tox21_110623

79. Tox21_302725

80. Tox21_500687

81. Ccg-40314

82. Labetalol Hydrochloride (jp17/usp)

83. Labetalol Hydrochloride [jan]

84. Nsc290312

85. Nsc758438

86. S4291

87. Labetalol Hydrochloride [usan]

88. Akos015895575

89. Ac-1389

90. Ah-5158

91. Cs-4706

92. Labetalol Hydrochloride [mart.]

93. Labetalol Hydrochloride [vandf]

94. Lp00687

95. Nc00571

96. Nsc-758438

97. Ss-4219

98. Labetalol Hydrochloride [usp-rs]

99. Labetalol Hydrochloride [who-dd]

100. Ncgc00094044-01

101. Ncgc00094044-02

102. Ncgc00094044-03

103. Ncgc00094044-04

104. Ncgc00094044-05

105. Ncgc00256847-01

106. Ncgc00261372-01

107. (r*,r*)-(1)-5-(1-hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)salicylamide Monohydrochloride

108. Benzamide,2-hydroxy-5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]-, Hydrochloride(1:1)

109. Db-048265

110. Eu-0100687

111. Ft-0630564

112. Ft-0773231

113. Labetalol Hydrochloride [orange Book]

114. Sw196595-3

115. Labetalol Hydrochloride [ep Monograph]

116. D00600

117. Labetalol Hydrochloride [usp Monograph]

118. Labetalol Hydrochloride, >98% (tlc), Powder

119. 780l646

120. Normozide Component Labetalol Hydrochloride

121. Sr-01000000209-2

122. Sr-01000000209-7

123. Labetalol Hydrochloride Component Of Normozide

124. Q27252396

125. 2-hydroxy-5-(1-hydroxy-2-((4-phenylbutan-2-yl)amino)ethyl)benzamide Hcl

126. Labetalol Hydrochloride, European Pharmacopoeia (ep) Reference Standard

127. Labetalol Hydrochloride, United States Pharmacopeia (usp) Reference Standard

128. Labetalol Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

129. Benzamide, 2-hydroxy-5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]-, Hydrochloride (1:1)

130. Benzamide,2-hydroxy-5-[(1s)-1-hydroxy-2-[[(1r)-1-methyl-3-phenylpropyl]amino]ethyl]-,hydrochloride (1:1), Rel-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 364.9 g/mol
Molecular Formula C19H25ClN2O3
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count4
Rotatable Bond Count8
Exact Mass364.1553704 g/mol
Monoisotopic Mass364.1553704 g/mol
Topological Polar Surface Area95.6 Ų
Heavy Atom Count25
Formal Charge0
Complexity385
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count2
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 NameLabetalol hydrochloride
Drug LabelLabetalol HCl USP tablets are adrenergic receptor blocking agents that have both selective alpha1-adrenergic and non-selective beta-adrenergic receptor blocking actions in a single substance.Labetalol HCl USP is a racemate, chemically designated as 5...
Active IngredientLabetalol hydrochloride
Dosage FormTablet; Injectable
RouteInjection; Oral
Strength200mg; 300mg; 5mg/ml; 100mg
Market StatusPrescription
CompanyHospira; Gland Pharma; Sandoz; Watson Labs; Ivax Sub Teva Pharms; Eurohlth Intl; Par Form; Akorn

2 of 2  
Drug NameLabetalol hydrochloride
Drug LabelLabetalol HCl USP tablets are adrenergic receptor blocking agents that have both selective alpha1-adrenergic and non-selective beta-adrenergic receptor blocking actions in a single substance.Labetalol HCl USP is a racemate, chemically designated as 5...
Active IngredientLabetalol hydrochloride
Dosage FormTablet; Injectable
RouteInjection; Oral
Strength200mg; 300mg; 5mg/ml; 100mg
Market StatusPrescription
CompanyHospira; Gland Pharma; Sandoz; Watson Labs; Ivax Sub Teva Pharms; Eurohlth Intl; Par Form; Akorn

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Adrenergic beta-Antagonists

Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety. (See all compounds classified as Adrenergic beta-Antagonists.)


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 alpha-1 Receptor Antagonists

Drugs that bind to and block the activation of ADRENERGIC ALPHA-1 RECEPTORS. (See all compounds classified as Adrenergic alpha-1 Receptor Antagonists.)


Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
beta-Adrenergic Blocker [EPC]; Adrenergic beta-Antagonists [MoA]
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  • TABLET;ORAL - 100MG
  • TABLET;ORAL - 200MG
  • TABLET;ORAL - 300MG
  • TABLET;ORAL - 400MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
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