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Chemistry

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Also known as: 5051-22-9, R-(+)-propranolol, (+)-propranolol, D-propranolol, Dextropropranolol, 2r-propranolol

Molecular Formula

C₁₆H₂₁NO₂

Molecular Weight

259.34 g/mol

InChI Key

AQHHHDLHHXJYJD-CQSZACIVSA-N

FDA UNII

PG6KY07UD7

A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.

1 2D Structure

Dexpropranolol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R)-1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol

2.1.2 InChI

InChI=1S/C16H21NO2/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16/h3-9,12,14,17-18H,10-11H2,1-2H3/t14-/m1/s1

2.1.3 InChI Key

AQHHHDLHHXJYJD-CQSZACIVSA-N

2.1.4 Canonical SMILES

CC(C)NCC(COC1=CC=CC2=CC=CC=C21)O

2.1.5 Isomeric SMILES

CC(C)NC[C@H](COC1=CC=CC2=CC=CC=C21)O

2.2 Other Identifiers

2.2.1 UNII

PG6KY07UD7

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Anaprilin

2. Anapriline

3. Avlocardyl

4. Ay 20694

5. Ay-20694

6. Ay20694

7. Betadren

8. Dociton

9. Hydrochloride, Propranolol

10. Inderal

11. Obsidan

12. Obzidan

13. Propanolol

14. Propranolol

15. Propranolol Hydrochloride

16. Rexigen

2.3.2 Depositor-Supplied Synonyms

1. 5051-22-9

2. R-(+)-propranolol

3. (+)-propranolol

4. D-propranolol

5. Dextropropranolol

6. 2r-propranolol

7. (r)-(+)-propranolol

8. (r)-propranolol

9. R (+)-propanolol

10. Dexpropranololum

11. (+)-1-isopropylamino-3-(1-naphthyloxy)-2-propanol

12. R(+)-propranolol

13. (2r)-1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol

14. Propranolol, (r)-

15. Pg6ky07ud7

16. Chebi:8736

17. 2-propanol, 1-(isopropylamino)-3-(1-naphthyloxy)-, (+)-

18. Ncgc00016429-05

19. 2-propanol, 1-((1-methylethyl)amino)-3-(1-naphthalenyloxy)-, (r)-

20. 2-propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-, (2r)-

21. 2-propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-, (r)-

22. Dsstox_cid_25304

23. Dsstox_rid_80790

24. Dsstox_gsid_45304

25. Despropranolo [dcit]

26. Despropranolo

27. (r)-1-(isopropylamino)-3-(naphthalen-1-yloxy)propan-2-ol

28. (2r)-1-(naphthalen-1-yloxy)-3-[(propan-2-yl)amino]propan-2-ol

29. (2r)-3-(naphthalen-1-yloxy)-1-(propan-2-ylamino)propan-2-ol

30. Mls001333595

31. Dexpropranolol [inn:ban]

32. Dexpropranololum [inn-latin]

33. Cas-5051-22-9

34. Smr000875288

35. Einecs 225-749-2

36. Unii-pg6ky07ud7

37. R-propanolol

38. Propranolol-(r)

39. Rnp

40. D-(+)-propranolol

41. (r)-(+)-propanolol Hydrochloride

42. (2r)-1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol;hydrochloride

43. Tocris-0624

44. Tocris-0835

45. (+)-(r)-propranolol

46. Prestwick0_001075

47. Prestwick1_001075

48. Prestwick2_001075

49. Lopac-p-0884

50. Lopac-p-8688

51. Cas-318-98-9

52. Dexpropranolol [inn]

53. Schembl25255

54. Cid_66366

55. Bidd:gt0130

56. Spbio_002995

57. Chembl275742

58. Gtpl7596

59. Dtxsid3045304

60. Bdbm60973

61. Zinc20240

62. Tox21_110435

63. Mfcd00066275

64. Pdsp1_000775

65. Pdsp1_001089

66. Pdsp2_000763

67. Pdsp2_001073

68. Akos025212355

69. Tox21_110435_1

70. Cas-839971

71. Db03322

72. Ncgc00015798-01

73. Ncgc00015798-02

74. Ncgc00015798-03

75. Ncgc00015798-11

76. Ncgc00016429-01

77. Ncgc00016429-02

78. Ncgc00016429-03

79. Ncgc00016429-04

80. Ncgc00016429-06

81. Ncgc00024690-01

82. Ncgc00024814-01

83. Ncgc00024814-02

84. Cas-13071-11-9

85. Ab00514691

86. Brd-k92830582-003-04-8

87. Q27088458

88. (+)-1-(isopropylamino)-3-(1-naphthyloxy)-2-propanol

89. (2r)-1-(isopropylamino)-3-(1-naphthyloxy)propan-2-ol

90. 1-(isopropylamino)-3-(1-naphthyloxy)-2-propanol, (r)-

91. (2r)-1-(isopropylamino)-3-(1-naphthoxy)propan-2-ol;hydrochloride

92. (2r)-1-(1-naphthalenyloxy)-3-(propan-2-ylamino)-2-propanol;hydrochloride

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₂₁NO₂
Molecular Weight	259.34 g/mol
XLogP3	3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	6
Exact Mass	259.157228913 g/mol
Monoisotopic Mass	259.157228913 g/mol
Topological Polar Surface Area	41.5 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	257
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 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.)

Anti-Arrhythmia Agents

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)

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.)

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

4.2 Metabolism/Metabolites

Dexpropranolol (propranolol) has known human metabolites that include 4-Hydroxypropranolol, 5-Hydroxypropranolol, and N-Desisopropylpropranolol.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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