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Prestwick3_000223
Also known as: 526-36-3, Xylomethazoline, Otrivine, Otrivin, Otriven, Otrix
Molecular Formula
C16H24N2
Molecular Weight
244.37  g/mol
InChI Key
HUCJFAOMUPXHDK-UHFFFAOYSA-N
FDA UNII
WPY40FTH8K

Xylometazoline is an imidazoline derivative with sympathomimetic and nasal decongestant activity. Xylometazoline works by binding to alpha ()-adrenergic receptors to cause vasoconstriction of nasal blood vessels. Xylometazoline is available in over-the-counter (OTC) nasal sprays or drops to temporarily relieve nasal congestion due to cold, hay fever or other respiratory allergies. In some countries, it is available as combination products with [ipratropium], [domiphen], or [dexpanthenol].
1 2D Structure

Prestwick3_000223

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1H-imidazole
2.1.2 InChI
InChI=1S/C16H24N2/c1-11-8-13(16(3,4)5)9-12(2)14(11)10-15-17-6-7-18-15/h8-9H,6-7,10H2,1-5H3,(H,17,18)
2.1.3 InChI Key
HUCJFAOMUPXHDK-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC(=CC(=C1CC2=NCCN2)C)C(C)(C)C
2.2 Other Identifiers
2.2.1 UNII
WPY40FTH8K
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-(4'-tert-butyl-2',6'-dimethylphenylmethyl)imidazoline

2. Amidrin

3. Balkis

4. Chlorohist-la

5. Decongest

6. Espa-rhin

7. Gelonasal

8. Idasal

9. Idril N

10. Imidin

11. Nasan

12. Nasengel Al

13. Nasengel Ratiopharm

14. Nasenspray Al

15. Nasenspray Ratiopharm

16. Nasentropfen Al

17. Nasentropfen Ratiopharm

18. Novorin

19. Otradrops

20. Otraspray

21. Otriven

22. Otrivin

23. Otrivin Mentol

24. Rapako

25. Schnupfen Endrine

26. Snup

27. Stas

28. Xylometazoline Hydrochloride

29. Xylometazoline Monohydrochloride

2.3.2 Depositor-Supplied Synonyms

1. 526-36-3

2. Xylomethazoline

3. Otrivine

4. Otrivin

5. Otriven

6. Otrix

7. 2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1h-imidazole

8. Balminil

9. 2-(4-(tert-butyl)-2,6-dimethylbenzyl)-4,5-dihydro-1h-imidazole

10. 2-(4-tert-butyl-2,6-dimethyl-benzyl)-4,5-dihydro-1h-imidazole

11. Ba-11391

12. 2-(4-tert-butyl-2,6-dimethylbenzyl)-2-imidazoline

13. Wpy40fth8k

14. Chembl312448

15. 2-imidazoline, 2-(4-tert-butyl-2,6-dimethylbenzyl)-

16. Ba 11391; Otriven; Otrivin

17. Chebi:10082

18. 1h-imidazole, 2-((4-(1,1-dimethylethyl)-2,6-dimethylphenyl)methyl)-4,5-dihydro-

19. Xylometazoline (inn)

20. Xilometazolina

21. 2-(4-tert-butyl-2,6-dimethylbenzyl)-4,5-dihydro-1h-imidazole

22. 1h-imidazole, 2-[[4-(1,1-dimethylethyl)-2,6-dimethylphenyl]methyl]-4,5-dihydro-

23. Xylometazoline [inn]

24. Xylometazolinum

25. Xylometazoline [inn:ban]

26. Xylometazolinum [inn-latin]

27. Xilometazolina [inn-spanish]

28. Ncgc00016101-02

29. Einecs 208-390-6

30. Unii-wpy40fth8k

31. Ba 11391

32. Cas-1218-35-5

33. Brn 0180524

34. Balminil (tn)

35. Spectrum_000382

36. 2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1h-imidazole;hydrochloride

37. Prestwick0_000223

38. Prestwick1_000223

39. Prestwick2_000223

40. Prestwick3_000223

41. Spectrum2_000945

42. Spectrum3_000586

43. Spectrum4_000382

44. Spectrum5_001469

45. Lopac-x-6000

46. Xylometazoline [mi]

47. Lopac0_001269

48. Schembl34087

49. Bspbio_000265

50. Bspbio_002032

51. Gtpl517

52. Kbiogr_000903

53. Kbioss_000862

54. 5-23-07-00109 (beilstein Handbook Reference)

55. Divk1c_000158

56. Xylometazoline [vandf]

57. Spbio_000910

58. Spbio_002186

59. Bpbio1_000293

60. Xylometazoline [who-dd]

61. Dtxsid8046957

62. Bdbm30703

63. Cid_5282386

64. Kbio1_000158

65. Kbio2_000862

66. Kbio2_003430

67. Kbio2_005998

68. Kbio3_001532

69. Zinc57534

70. Ninds_000158

71. 2-{[4-(tert-butyl)-2,6-dimethylphenyl]methyl}-2-imidazoline

72. Hms3604m22

73. S5854

74. Stk558658

75. Akos000115430

76. Ccg-205342

77. Db06694

78. Ks-5071

79. Sdccgsbi-0051235.p004

80. 2-[[4-(1,1-dimethylethyl)-2,6-dimethylphenyl]methyl]-4,5-dihydro-1h-imidazole

81. Idi1_000158

82. Ncgc00016101-01

83. Ncgc00016101-03

84. Ncgc00016101-04

85. Ncgc00016101-05

86. Ncgc00016101-06

87. Ncgc00016101-07

88. Ncgc00016101-09

89. Ncgc00016101-18

90. Ncgc00024281-03

91. Sbi-0051235.p003

92. Db-052151

93. Ft-0603452

94. En300-02385

95. Vu0239751-6

96. C07913

97. D08684

98. Q31030

99. Ab00053567_11

100. Ab00053567_12

101. 526b363

102. L001171

103. Brd-k08356259-003-05-6

104. Brd-k08356259-003-15-5

105. F1371-0282

106. 2-(4-tert-butyl-2,6-dimethyl-benzyl)-2-imidazoline;hydrochloride

107. 2-(4-tert-butyl-2,6-dimethylbenzyl)-4,5-dihydro-1h-imidazole #

108. 2-[(2,6-dimethyl-4-tert-butyl-phenyl)methyl]-4,5-dihydroimidazole

109. 2-[(4-t-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1h-imidazole

110. 2-[(4-t-butyl-2,6-dimethylphenyl)methyl]4,5dihydro-1h-imidazole

111. 2-[(4-tert-butyl-2,6-dimethyl-phenyl)methyl]-4,5-dihydro-1h-imidazole;hydrochloride

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 244.37 g/mol
Molecular Formula C16H24N2
XLogP33.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count3
Exact Mass244.193948774 g/mol
Monoisotopic Mass244.193948774 g/mol
Topological Polar Surface Area24.4 Ų
Heavy Atom Count18
Formal Charge0
Complexity302
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Xylometazoline is indicated for the temporary relief of nasal congestion due to cold, hay fever or other respiratory allergies.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Xylometazoline is a sympathomimetic agent that causes vasoconstriction of the nasal mucosa. In one study comprising subjects with nasal congestion associated with the common cold, the median time of onset of subjective relief of nasal congestion was about 1.7 minutes and the time of subjective peak relief of nasal congestion was 30 minutes. Previous studies reported rebound swelling, rebound nasal congestion, rhinitis medicamentosa, and shorter duration of decongestant effect from the long-term use of xylometazoline in healthy volunteers, suggesting that the drug is most effective if used temporarily. An early _in vitro_ study demonstrated xylometazoline to exert anti-oxidant actions, where it inhibited microsomal lipid peroxidation and mediated hydroxyl radical scavenging activity. This suggests that xylometazoline has a beneficial effect against oxidants, which play a role in tissue damage in inflammation.


5.2 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.)


5.3 ATC Code

R01AA07

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


R - Respiratory system

R01 - Nasal preparations

R01A - Decongestants and other nasal preparations for topical use

R01AA - Sympathomimetics, plain

R01AA07 - Xylometazoline


R - Respiratory system

R01 - Nasal preparations

R01A - Decongestants and other nasal preparations for topical use

R01AB - Sympathomimetics, combinations excl. corticosteroids

R01AB06 - Xylometazoline


S - Sensory organs

S01 - Ophthalmologicals

S01G - Decongestants and antiallergics

S01GA - Sympathomimetics used as decongestants

S01GA03 - Xylometazoline


5.4 Absorption, Distribution and Excretion

Absorption

No information is available on xylometazoline pharmacokinetics.


Route of Elimination

No information is available on xylometazoline pharmacokinetics.


Volume of Distribution

No information is available on xylometazoline pharmacokinetics.


Clearance

No information is available on xylometazoline pharmacokinetics.


5.5 Metabolism/Metabolites

No information is available on xylometazoline pharmacokinetics.


5.6 Biological Half-Life

No information is available on xylometazoline pharmacokinetics.


5.7 Mechanism of Action

Nasal congestion is caused by various etiologies, such as rhinosinusitis and allergic or non-allergic rhinitis, leading to congestion of the venous sinusoids lining the nasal mucosa. Activation of -adrenergic receptors leads to vasoconstriction of the blood vessels of the nasal mucosa and resumption of nasal airflow. As the most abundantly expressed in the human nasal mucosa, 1A- and 2B-adrenoceptors may play the most important role in vasoconstriction of the human nasal mucosa. Xylometazoline is a more selective agonist at 2B-adrenoceptors, with affinity at 1A-, 2A-, 2C-, 1B-, and 1D-adrenoceptors. Xylometazoline decreases nasal resistance during inspiration and expiration and increases the volume of nasal airflow. Compared to [oxymetazoline], another imidazoline nasal decongestant, xylometazoline had a slightly faster onset of action although they had a similar duration of action. In one study, subjects with nasal congestion reported relief of earache and sore throat in addition to nasal decongestion: it is speculated that oxymetazoline mediates this effect by causing vasoconstriction of the nasal mucosa that contains the venous sinuses and nasal decongestion allows breathing through the nose, providing relief from sore throat caused by mouth breathing that dries and irritates the throat.


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