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Chemistry

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Also known as: 550-99-2, Naphazoline hcl, Albalon, Rhinantin, Vasocon, Opcon
Molecular Formula
C14H15ClN2
Molecular Weight
246.73  g/mol
InChI Key
DJDFFEBSKJCGHC-UHFFFAOYSA-N
FDA UNII
MZ1131787D

Naphazoline Hydrochloride
An adrenergic vasoconstrictor agent used as a decongestant.
1 2D Structure

Naphazoline Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole;hydrochloride
2.1.2 InChI
InChI=1S/C14H14N2.ClH/c1-2-7-13-11(4-1)5-3-6-12(13)10-14-15-8-9-16-14;/h1-7H,8-10H2,(H,15,16);1H
2.1.3 InChI Key
DJDFFEBSKJCGHC-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CN=C(N1)CC2=CC=CC3=CC=CC=C32.Cl
2.2 Other Identifiers
2.2.1 UNII
MZ1131787D
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Afazol Grin

2. Ak Con

3. Ak-con

4. Albalon

5. All Clear

6. Clear Eyes

7. Colirio Alfa

8. Hydrochloride, Naphazoline

9. Idril

10. Miraclar

11. Monohydrochloride, Naphazoline

12. Nafazair

13. Naphazoline

14. Naphazoline Monohydrochloride

15. Naphazoline Nitrate

16. Naphcon

17. Naphcon Forte

18. Nitrate, Naphazoline

19. Optazine

20. Pensa, Vasoconstrictor

21. Privin

22. Privine

23. Proculin

24. Siozwo

25. Tele Stulln

26. Tele-stulln

27. Vasoclear

28. Vasocon

29. Vasocon Regular

30. Vasoconstrictor Pensa

31. Vasonit

2.3.2 Depositor-Supplied Synonyms

1. 550-99-2

2. Naphazoline Hcl

3. Albalon

4. Rhinantin

5. Vasocon

6. Opcon

7. Albalon Liquifilm

8. Rhinoperd

9. Stricylon

10. Naphcon

11. Niazol

12. Rinofug

13. Naphcon Forte

14. 2-(1-naphthylmethyl)-2-imidazoline Hydrochloride

15. Clera Hydrochloride

16. Naphazoline Chloride

17. Privine Hydrochloride

18. Prizole Hydrochloride

19. Nafazair

20. Sanorin

21. 2-(1-naphthylmethyl)imidazoline Hydrochloride

22. Naphazoline (hydrochloride)

23. Nsc-35711

24. 2-(naphthalen-1-ylmethyl)-4,5-dihydro-1h-imidazole Hydrochloride

25. 2-(1-naphthylmethyl)-2-imidazoline Monohydrochloride

26. 1h-imidazole, 4,5-dihydro-2-(1-naphthalenylmethyl)-, Monohydrochloride

27. Mls000028434

28. Chebi:7470

29. Naphazoline Hydrochloride (naphcon)

30. Mz1131787d

31. Smr000058292

32. Vasoclear

33. Coldan

34. 2-(naphthalen-1-ylmethyl)-4,5-dihydro-1h-imidazole;hydrochloride

35. Comfort Eye Drops

36. Degest-2

37. Naphazoliniumchlorid

38. Naphazolini Chloridum

39. Naphthasolium Chloride

40. Chembl1706

41. Clear Eyes

42. Naphazoline Hydrochloride [jan]

43. Hsdb 2174

44. Naphthylmethylimidazolinhydrochlorid

45. Einecs 208-989-2

46. Mfcd00012554

47. Nsc 35711

48. Albacon

49. 2-(1-naphthylmethyl)-4,5-dihydro-1h-imidazole

50. Sr-01000000067

51. Unii-mz1131787d

52. Prestwick_507

53. Albalon (tn)

54. Vasocon (tn)

55. Component Of Nasocon

56. Naphazoline Hydrochloride [usp:jan]

57. 2-imidazoline, 2-(1-naphthylmethyl)-, Monohydrochloride

58. Opera_id_230

59. Ac1lcwb1

60. Surecn1649580

61. Schembl24153

62. Mls001148448

63. Mls002222217

64. Naphazolinehydrochloride

65. Naphazoline Hydrochloride,(s)

66. Spectrum1500424

67. 2-(1-naphthylmethyl)-2-imidazoline Hydro- Chloride

68. Naphazoline Hcl [inci]

69. 2-imidazoline, Monohydrochloride

70. Dtxsid7045788

71. Molport-000-703-064

72. Hms1568i13

73. Hms1920p11

74. Pharmakon1600-01500424

75. Amy23173

76. Ex-a4103

77. Hy-b0446

78. Nsc35711

79. Ccg-40122

80. Nsc757110

81. S2519

82. Naphazoline Hydrochloride [mi]

83. Akos015908797

84. Naphazoline Hydrochloride (jp17/usp)

85. Nc00523

86. Nsc-757110

87. Naphazoline Hydrochloride [hsdb]

88. Naphazoline Hydrochloride [mart.]

89. Naphazoline Hydrochloride [vandf]

90. Ncgc00094732-01

91. Ncgc00094732-02

92. Ncgc00094732-03

93. Ncgc00094732-04

94. As-16861

95. Naphazoline Hydrochloride [usp-rs]

96. Naphazoline Hydrochloride [who-dd]

97. 2-(naphthalen-1-ylmethyl)-4,5-dihydro-

98. Wln: L66j B1- Bt5m Cn Butj &gh

99. Ft-0603466

100. Lt00114215

101. Lt00233108

102. N0542

103. Sw196701-3

104. C07898

105. D00743

106. H12006

107. Naphazoline Hydrochloride [ep Impurity]

108. Naphazoline Hydrochloride [ep Monograph]

109. Naphazoline Hydrochloride [orange Book]

110. Naphazoline Hydrochloride [usp Monograph]

111. A830484

112. Opcon-a Component Naphazoline Hydrochloride

113. Visine-a Component Naphazoline Hydrochloride

114. Naphcon-a Component Naphazoline Hydrochloride

115. Sr-01000000067-3

116. Vasocon-a Component Naphazoline Hydrochloride

117. W-105587

118. Naphazoline Hydrochloride Component Of Opcon-a

119. Naphazoline Hydrochloride Component Of Visine-a

120. Q27887678

121. Naphazoline Hydrochloride Component Of Naphcon-a

122. Naphazoline Hydrochloride Component Of Vasocon-a

123. 4,5-dihydro-2-(1-naphthylmethyl)-1h-imidazole Hydrochloride

124. 1h-imidazole,5-dihydro-2-(1-naphthalenylmethyl)-, Monohydrochloride

125. Hydron;2-(naphthalen-1-ylmethyl)-4,5-dihydro-1h-imidazole;chloride

126. 1h-imidazole, 4,5-dihydro-2-(1-naphthalenylmethyl)-, Hydrochloride (1:1)

127. Naphazoline Hydrochloride, European Pharmacopoeia (ep) Reference Standard

128. Naphazoline Hydrochloride, United States Pharmacopeia (usp) Reference Standard

2.3.3 Other Synonyms

1. Naphazoline

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 246.73 g/mol
Molecular Formula C14H15ClN2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count1
Rotatable Bond Count2
Exact Mass246.0923762 g/mol
Monoisotopic Mass246.0923762 g/mol
Topological Polar Surface Area24.4 Ų
Heavy Atom Count17
Formal Charge0
Complexity272
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
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 NameNaphazoline hydrochloride
Drug LabelNaphazoline Hydrochloride, an ocular vasoconstrictor, is an imidazoline derivative sympathomimetic amine. It occurs as a white, odorless crystalline powder having a bitter taste and is freely soluble in water and in alcohol. The active ingredient is...
Active IngredientNaphazoline hydrochloride
Dosage FormSolution/drops
RouteOphthalmic
Strength0.1%
Market StatusPrescription
CompanyAkorn

2 of 2  
Drug NameNaphazoline hydrochloride
Drug LabelNaphazoline Hydrochloride, an ocular vasoconstrictor, is an imidazoline derivative sympathomimetic amine. It occurs as a white, odorless crystalline powder having a bitter taste and is freely soluble in water and in alcohol. The active ingredient is...
Active IngredientNaphazoline hydrochloride
Dosage FormSolution/drops
RouteOphthalmic
Strength0.1%
Market StatusPrescription
CompanyAkorn

4.2 Therapeutic Uses

Adrenergic alpha-Agonists; Nasal Decongestants

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Naphazoline is applied topically to the conjunctiva to temporarily relieve congestion, itching, and minor irritation. Ocular decongestants are ineffective in the treatment of delayed hypersensitivity reactions such as contact dermatoconjunctivitis. The vasoconstrictor effects of naphazoline may be used during some ocular diagnostic procedures, but some clinicians prefer phenylephrine to naphazoline for this use.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 2823


Ophthalmic solutions containing naphazoline in combination with antihistamines such as antazoline phosphate or pheniramine maleate and/or astringents such as zinc sulfate are commercially available. In the concentrations usually employed, zinc sulfate is a relatively ineffective antiseptic and may promote vasodilation.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 2824


Adrenergic (vasoconstrictor); decongestant.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1142


Naphazoline hydrochloride (0.1%), an imidazole derivative with preferential alpha-2 activity, /was instilled/ in 17 eyes of 12 patients with myopathic ptosis due to involvement of the levator palpebrae superioris, in the attempt to selectively stimulate Muller's smooth muscle. Naphazoline significantly widened the palpebral fissure with little change in pupillary diameter and no significant change in ocular pressure, visual acuity and near point determination. However, a reduction of the effect, probably due to tachyphylaxis, was noticed when using naphazoline regularly several times a day for few weeks. In conclusion naphazoline has powerful cosmetical and functional effects in mild to moderate myopathic ptosis above all if taken occasionally.

PMID:8503264 Uncini A et al; Acta Neurol Scand 87 (4): 322-4 (1993)


4.3 Drug Warning

Ophthalmic use of naphazoline may occasionally cause systemic sympathomimetic effects such as headache, hypertension, cardiac irregularities, nervousness, nausea, dizziness, weakness, and sweating.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 2824


Use of naphazoline in the eye may cause blurred vision, mild transient stinging and/or irritation, mydriasis, and increased or decreased intraocular pressure. Conjunctival application of naphazoline, especially when high concentrations are used in geriatric patients, may liberate pigment granules, presumably from the iris. Rebound congestion, characterized by reactive hyperemia frequently occurs with prolonged use and may result in overuse of the drug. Prolonged use of the drug should be avoided for these reasons.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 2824


The incidence of serious adverse effects is low in patients receiving therapeutic dosages of ophthalmic solutions of naphazoline hydrochloride. When naphazoline hydrochloride is used in combination preparations, the cautions applicable to each ingredient in the formulation must be observed. Excessive dosage and/or prolonged or too frequent use may irritate the conjunctiva and, especially in children, cause adverse systemic effects.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 2824


Naphazoline hydrochloride ophthalmic solution should be used with caution in patients with hypertension, cardiovascular abnormalities, diabetes mellitus, hyperthyroidism, infection, or injury.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 2824


For more Drug Warnings (Complete) data for NAPHAZOLINE HYDROCHLORIDE (14 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Adrenergic alpha-Agonists

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


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.)


5.2 Absorption, Distribution and Excretion

Following topical application of naphazoline hydrochloride solutions to the conjunctiva, local vasoconstriction usually occurs within 10 minutes and may persist for 2-6 hours. Occasionally, enough naphazoline may be absorbed to produce systemic effects. Information on the distribution and elimination of the drug in humans is not available

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 2824


5.3 Mechanism of Action

Naphazoline constricts the vascular system of the conjunctiva. It is presumed that this effect is due to direct stimulation action of the drug upon the alpha-adrenergic receptors in the arterioles of the conjunctiva, resulting in decreased conjunctival congestion.

Physician's Desk Reference for Ophthalmic Medicines. 35rd Edition.Thomson PDR. Montvale, NJ. p. 219 (2006)


The mechanism of action of naphazoline has not been conclusively determined. Most pharmacologists believe that the drug directly stimulates alpha-adrenergic receptors of the sympathetic nervous system and exerts little or no effect on beta-adrenergic receptors. Following topical application of naphazoline to the conjunctiva, small arterioles are constricted and conjunctival congestion is temporarily relieved, but reactive hyperemia may occur. The drug also may produce mydriasis when applied to the conjunctiva, but this effect is usually minimal with the concentrations used as ocular decongestants.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 2824


API Reference Price

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29-Jan-2021
31-Oct-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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DOSAGE - SOLUTION/DROPS;OPHTHALMIC - 0.02675%...DOSAGE - SOLUTION/DROPS;OPHTHALMIC - 0.02675%;0.315%

USFDA APPLICATION NUMBER - 20065

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DOSAGE - SOLUTION/DROPS;OPHTHALMIC - 0.025%;0...DOSAGE - SOLUTION/DROPS;OPHTHALMIC - 0.025%;0.3%

USFDA APPLICATION NUMBER - 20485

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