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Oxymetazoline

Oxymetazoline

Synopsis, Chemistry

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Also known as: 2315-02-8, Oxymetazoline hcl, Ocuclear, Afrazine, Afrin hydrochloride, Sch 9384

Molecular Formula

C₁₆H₂₅ClN₂O

Molecular Weight

296.83 g/mol

InChI Key

BEEDODBODQVSIM-UHFFFAOYSA-N

FDA UNII

K89MJ0S5VY

A direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1251)

1 2D Structure

Oxymetazoline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol;hydrochloride

2.1.2 InChI

InChI=1S/C16H24N2O.ClH/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14;/h8,19H,6-7,9H2,1-5H3,(H,17,18);1H

2.1.3 InChI Key

BEEDODBODQVSIM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC(=C(C(=C1CC2=NCCN2)C)O)C(C)(C)C.Cl

2.2 Other Identifiers

2.2.1 UNII

K89MJ0S5VY

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Hydrochloride, Oxymetazoline

2. Oxymetazoline

2.3.2 Depositor-Supplied Synonyms

1. 2315-02-8

2. Oxymetazoline Hcl

3. Ocuclear

4. Afrazine

5. Afrin Hydrochloride

6. Sch 9384

7. Rhofade

8. Oxymetazoline (hydrochloride)

9. Visine L.r.

10. Vicks Sinex

11. Nsc-757254

12. K89mj0s5vy

13. 6-tert-butyl-3-(4,5-dihydro-1h-imidazol-2-ylmethyl)-2,4-dimethylphenol;hydrochloride

14. Mls000038040

15. Chebi:7863

16. Agn-199201

17. Sch-9384

18. Smr000059324

19. 2-(4-t-butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazolinium Chloride

20. 2,6-dimethyl-2-(4-tertiarybutyl-3-hydroxyphenyl)methylimidazoline Hydrochloride

21. 6-tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol Monohydrochloride

22. 6-tert-butyl-3-(4,5-dihydro-1h-imidazol-2-ylmethyl)-2,4-dimethylphenol Hydrochloride

23. Phenol, 3-((4,5-dihydro-1h-imidazol-2-yl)methyl)-6-(1,1-dimethylethyl)-2,4-dimethyl-, Monohydrochloride

24. 2-(3-hydroxy-2,6-dimethyl-4-tert-butylbenzyl)-2-imidazoline

25. Lliadine

26. Nasivin

27. Nasivine

28. Neonabel

29. Nostrilla

30. Nafrine Hydrochloride

31. 4-way Nasal Spray

32. Duration Nasal Spray

33. Oxymetazoline Chloride

34. Lliadin Mini Paediatric

35. Sr-01000002705

36. Neo-synephrine 12 Hour

37. Neo-synephrine 12 Hour Ntz

38. Sinex

39. Anefrin Nasal

40. Duration 12 Hour Nasal Spray

41. Benzedrex Nasal Spray 12 Hour

42. Dristan Long Lasting Nasal Mist

43. Sudafed Om

44. Ocuclear (tn)

45. Prestwick_373

46. Einecs 219-015-0

47. St. Joseph Nasal Spray For Children

48. Mfcd00058147

49. Rhfade (tn)

50. Upneeq

51. Opera_id_32

52. 2-(3-hydroxy-2,6-dimethyl-4-t-butylbenzyl)-2-imidazoline Hydrochloride

53. Unii-k89mj0s5vy

54. 3-[(4,5-dihydro-

55. Schembl41247

56. Mls002222207

57. Spectrum1500453

58. Oxymetazoline Hydrochloride,(s)

59. Chembl1200791

60. Hy-b0427a

61. Dtxsid80177729

62. Oximetazoline Hydrochloride

63. Hms1568n09

64. Hms1920d18

65. Pharmakon1600-01500453

66. Tox21_500903

67. Ccg-40216

68. Nsc757254

69. 6-t-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol Hydrochloride

70. Akos000280887

71. Oxymetazoline Hydrochloride (jan/usp)

72. Phenol, 6-t-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethyl-, Hydrochloride

73. Ks-5222

74. Lp00903

75. Nsc 757254

76. Oxymetazoline Hydrochloride [mi]

77. Ncgc00094218-01

78. Ncgc00094218-02

79. Ncgc00094218-03

80. Ncgc00094218-04

81. Ncgc00094218-05

82. Ncgc00261588-01

83. Oxymetazoline Hydrochloride [jan]

84. 2315-02-8 (hcl)

85. Oxymetazoline Hydrochloride [usan]

86. Oxymetazoline Hydrochloride [mart.]

87. Oxymetazoline Hydrochloride [vandf]

88. 4-(2-boc-amino-pyridin-4-yl)-benzoicacid

89. Oxymetazoline Hydrochloride [who-dd]

90. Oxymetazoline Hydrochloride, >=99%, Solid

91. Eu-0100903

92. Ft-0673462

93. O0520

94. Oxymetazoline Hydrochloride [usan:usp:jan]

95. Sw196632-3

96. D01022

97. D91882

98. O 2378

99. Oxymetazoline Hydrochloride, Analytical Standard

100. Oxymetazoline Hydrochloride [orange Book]

101. 315o028

102. A910982

103. Oxymetazoline Hydrochloride [ep Monograph]

104. Oxymetazoline Hydrochloride [usp Impurity]

105. Oxymetazoline Hydrochloride [usp Monograph]

106. Kovanaze Component Oxymetazoline Hydrochloride

107. Sr-01000002705-2

108. Sr-01000002705-4

109. Sr-01000002705-7

110. W-107424

111. Q27107602

112. Oxymetazoline Hydrochloride Component Of Kovanaze

113. Sinex Vapospray Moisturizing 12-hour Decongestant Ultrafine Mist

114. 2,6-dimethyl-4-tertiarybutyl-3-hydroxyphenyl)methylimidazoline Hydrochloride

115. 2-(4-tert-butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazolinium Chloride

116. 6-tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol Hydrochloride

117. Oxymetazoline Hydrochloride, European Pharmacopoeia (ep) Reference Standard

118. 1h-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethylphenol Hydrochloride

119. 2-(3-hydroxy-2,6-dimethyl-4-tert-butylbenzyl)-2-imidazoline Hydrochloride

120. 2-(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-4,5-dihydro-1h-imidazol-1-ium Chloride

121. 6-(tert-butyl)-3-((4,5-dihydro-1h-imidazol-2-yl)methyl)-2,4-dimethylphenol Hydrochloride

122. 6-tert-butyl-3-((4,5-dihydro-1h-imidazol-2-yl)methyl)-2,4-dimethylphenol Hydrochloride

123. Oxymetazoline Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

124. Oxymetazoline Hydrochloride, United States Pharmacopeia (usp) Reference Standard

125. 3-[(4,5-dihydro-1h-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethyl-phenol Hydrochloride

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₂₅ClN₂O
Molecular Weight	296.83 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
Exact Mass	296.1655411 g/mol
Monoisotopic Mass	296.1655411 g/mol
Topological Polar Surface Area	44.6 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	345
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Nasal Decongestants

Drugs designed to treat inflammation of the nasal passages, generally the result of an infection (more often than not the common cold) or an allergy related condition, e.g., hay fever. The inflammation involves swelling of the mucous membrane that lines the nasal passages and results in inordinate mucus production. The primary class of nasal decongestants are vasoconstrictor agents. (From PharmAssist, The Family Guide to Health and Medicine, 1993) (See all compounds classified as Nasal Decongestants.)

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-Agonists

Drugs that selectively bind to and activate alpha adrenergic receptors. (See all compounds classified as Adrenergic alpha-Agonists.)

4.2 FDA Pharmacological Classification

4.2.1 Pharmacological Classes

Increased Sympathetic Activity [PE]; Vasoconstriction [PE]; Vasoconstrictor [EPC]; Imidazolines [CS]