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Monobenzone

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Also known as: 4-benzyloxyphenol, 103-16-2, 4-(benzyloxy)phenol, Hydroquinone monobenzyl ether, Benoquin, Benzoquin

Molecular Formula

C₁₃H₁₂O₂

Molecular Weight

200.23 g/mol

InChI Key

VYQNWZOUAUKGHI-UHFFFAOYSA-N

FDA UNII

9L2KA76MG5

Monobenzone is a monobenzyl ether of hydroquinone with topical depigmentation activity. Although the exact mechanism of action of depigmentation is unknown, the metabolites of monobenzone appear to have a cytotoxic effect on melanocytes. Furthermore, the depigmentation effect might be mediated through the inhibition of tyrosinase, which is essential in the synthesis of melanin pigments, thereby causing permanent depigmentation of the skin.

Monobenzone is a Depigmenting Agent. The mechanism of action of monobenzone is as a Melanin Synthesis Inhibitor. The physiologic effect of monobenzone is by means of Depigmenting Activity.

1 2D Structure

Monobenzone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-phenylmethoxyphenol

2.1.2 InChI

InChI=1S/C13H12O2/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-9,14H,10H2

2.1.3 InChI Key

VYQNWZOUAUKGHI-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C(C=C1)COC2=CC=C(C=C2)O

2.2 Other Identifiers

2.2.1 UNII

9L2KA76MG5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Agerite Alba

2. Benoquin

3. Hydroquinone Monobenzyl Ether

4. Monobenzyl Ether Hydroquinone

5. Novo-depigman

6. P-(benzyloxy)phenol

2.3.2 Depositor-Supplied Synonyms

1. 4-benzyloxyphenol

2. 103-16-2

3. 4-(benzyloxy)phenol

4. Hydroquinone Monobenzyl Ether

5. Benoquin

6. Benzoquin

7. P-(benzyloxy)phenol

8. Monobenzyl Hydroquinone

9. Leucodinine

10. Monobenzon

11. Superlite

12. Agerite Alba

13. Hydroquinone Benzyl Ether

14. Dermochinona

15. Carmifal

16. Depigman

17. 4-(phenylmethoxy)phenol

18. Pigmex

19. P-hydroxyphenyl Benzyl Ether

20. Alba-dome

21. Benzyl P-hydroxyphenyl Ether

22. Monobenzyl Ether Hydroquinone

23. 4-(benzyloxyl)phenol

24. Agerite

25. Benzyl Hydroquinone

26. Phenol, 4-(phenylmethoxy)-

27. Monobenzone [inn]

28. 4-phenylmethoxyphenol

29. Monobenzonum

30. Monobenzona

31. Monobenzonum [inn-latin]

32. Monobenzona [inn-spanish]

33. Superlite (antioxidant)

34. Alba

35. Hydrochinon Monobenzylether [czech]

36. P-benzyloxyphenol

37. Phenol, P-(benzyloxy)-

38. Hydrochinon Monobenzylether

39. Monobenzyl Ether Of Hydroquinone

40. 4-phenylmethoxy-phenol

41. Nsc 2132

42. Mfcd00002333

43. 4-benzyloxy-phenol

44. Monobenzone (benoquin)

45. Nsc-2132

46. 4-benzyloxy Phenol

47. 9l2ka76mg5

48. Pbp

49. Chebi:34380

50. Ncgc00016360-01

51. Cas-103-16-2

52. Dsstox_cid_717

53. Hydroquinone Monobenzylether

54. Wln: Qr Do1r

55. Dsstox_rid_75755

56. Dsstox_gsid_20717

57. Benoquin (tn)

58. Hsdb 4019

59. Sr-05000001819

60. Monobenzone (usp/inn)

61. Monobenzone [usp:inn]

62. Einecs 203-083-3

63. Brn 1958305

64. Unii-9l2ka76mg5

65. 4-benzoxyphenol

66. Ai3-14325

67. 4-benzyloxylphenol

68. P-benzyloxy Phenol

69. P-benzyloxy-phenol

70. Monobenzone, Usp

71. 4(benzyloxy)phenol

72. (p)-benzyloxyphenol

73. 4-(benzyloxy)-phenol

74. Para-(benzyloxy)phenol

75. Monobenzone [mi]

76. Prestwick0_000912

77. Prestwick1_000912

78. Prestwick2_000912

79. Prestwick3_000912

80. Monobenzone [hsdb]

81. Monobenzone [vandf]

82. Chembl1388

83. Monobenzone [mart.]

84. Oprea1_698781

85. Schembl35631

86. Bspbio_000784

87. Monobenzone [usp-rs]

88. Monobenzone [who-dd]

89. 4-(benzyloxy)phenol, 98%

90. 4-06-00-05728 (beilstein Handbook Reference)

91. Bidd:er0003

92. Spbio_002973

93. Bpbio1_000864

94. Gtpl6830

95. Zinc1748

96. Dtxsid2020717

97. 4-(benzyloxy)phenol, >=99%

98. Monobenzone [orange Book]

99. Nsc2132

100. Hms1570h06

101. Hms1580p12

102. Hms2097h06

103. Hms3655k15

104. Hms3714h06

105. Pharmakon1600-01503031

106. Monobenzone [usp Monograph]

107. Act04723

108. Bcp09974

109. Cs-b0870

110. Nsc33918

111. Tox21_110396

112. Tox21_201147

113. Bdbm50410520

114. Nsc-33918

115. Nsc758211

116. S1652

117. Stl283939

118. Akos000119555

119. Tox21_110396_1

120. Ac-2492

121. Ccg-213094

122. Db00600

123. Nsc-758211

124. Ps-8213

125. Ncgc00016360-02

126. Ncgc00016360-03

127. Ncgc00016360-05

128. Ncgc00016360-06

129. Ncgc00258699-01

130. Hy-30272

131. Sy001650

132. Ab00513959

133. Am20020110

134. Ft-0616695

135. Sw197310-3

136. D05072

137. F11201

138. Ab00513959-03

139. Ab00513959_04

140. Ab00513959_05

141. 103h162

142. A800687

143. Q-200440

144. Q2768526

145. Sr-05000001819-1

146. Sr-05000001819-2

147. Sr-05000001819-3

148. Brd-k54262262-001-01-7

149. Brd-k54262262-001-06-6

150. F0777-0782

151. Z199511588

152. Monobenzone, United States Pharmacopeia (usp) Reference Standard

153. 4-(benzyloxy)phenol ; Hydroquinone Monobenzyl Ether ; Pbp ; Monobenzone

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₁₂O₂
Molecular Weight	200.23 g/mol
XLogP3	3.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
Exact Mass	200.083729621 g/mol
Monoisotopic Mass	200.083729621 g/mol
Topological Polar Surface Area	29.5 Å²
Heavy Atom Count	15
Formal Charge	0
Complexity	167
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	1

4 Drug and Medication Information

4.1 Therapeutic Uses

MONOBENZONE, MONOBENZYL ETHER OF HYDROQUINONE, IS AMELANOTIC AGENT USED IN SEVERE FRECKLING & OTHER CONDITIONS CHARACTERIZED BY HYPERPIGMENTATION OF SKIN.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 954

IT IS APPLIED TO HYPERPIGMENTED AREAS 2 OR 3 TIMES DAILY FOR UP TO 4 MO, OR UNTIL DEPIGMENTATION HAS OCCURRED, & THEN TWICE WEEKLY TO MAINTAIN EFFECT. ... IF SATISFACTORY RESPONSE IS NOT OBSERVED WITHIN 4 MO, TREATMENT SHOULD BE DISCONTINUED.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 955

...POSSIBLY EFFECTIVE FOR TREATMENT OF HYPERPIGMENTATION CAUSED BY EXCESSIVE FORMATION OF MELANIN, SUCH AS OCCURS IN GENERALIZED LENTIGO...MELASMA OF PREGNANCY, & HYPERPIGMENTATION FOLLOWING INFLAMMATION OF SKIN.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 955

VITILIGO PATIENTS USED 20% MONOBENZONE 2 TIMES/DAY UNTIL DEPIGMENTATION; THOSE ACHIEVING COMPLETE DEPIGMENTATION WERE TREATED FOR 10 MO OR MORE. DEPIGMENTATION INDUCED BY MONOBENZONE IS GENERALLY IRREVERSIBLE.

MOSHER ET AL; BR J DERMATOL 97 669-679 (DEC 1977)

For more Therapeutic Uses (Complete) data for P-(BENZYLOXY)PHENOL (6 total), please visit the HSDB record page.

4.2 Drug Warning

TREATED AREAS SHOULD NOT BE EXPOSED TO SUNLIGHT; ULTRAVIOLET LIGHT NEUTRALIZES DEPIGMENTING EFFECT.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 955

MONOBENZONE THERAPY IS OFTEN DIFFICULT TO MANAGE & REQUIRES CAREFUL PT FOLLOW-UP; IT CAN PRODUCE BIZARRE PATTERNS, WITH HYPOPIGMENTATION @ SITES DISTANT FROM AREA OF APPLICATION.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 911

...SHOULD ONLY BE USED TO PERMANENTLY REMOVE REMAINING AREAS OF NORMAL PIGMENTATION IN PT WITH DISSEMINATED VITILIGO. ...NOT RECOMMENDED IN TREATMENT OF MELASMA OR POSTINFLAMMATORY & OTHER TYPES OF HYPERPIGMENTATION. ...MAY CAUSE HYPERSENSITIVITY REACTIONS.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 911

SINCE DRUG DOES NOT DESTROY MELANOCYTES OR FACILITATE LOSS OF PREVIOUSLY SYNTHESIZED MELANIN, RESPONSE TO THERAPY IS USUALLY NOT APPARENT UNTIL 1-4 MO. ... UNLESS CAREFULLY APPLIED, UNSIGHTLY DEPIGMENT PATCHES MAY RESULT FROM ITS USE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 955

4.3 Drug Indication

Used topically to treat the loss of skin color (vitiligo).

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Monobenzone is the monobenzyl ether of hydroquinone. Monobenzone, applied topically to the skin, is used as a depigmenting agent inhibitting melanin produced by polymerization of oxidation products of tyrosine and dihydroxyphenyl compounds. Monobenzone works by permanently removing color from normal skin located around skin with vitiligo.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

MONOBENZONE

5.2.2 FDA UNII

9L2KA76MG5

5.2.3 Pharmacological Classes

Mechanisms of Action [MoA] - Melanin Synthesis Inhibitors

5.3 ATC Code

D - Dermatologicals

D11 - Other dermatological preparations

D11A - Other dermatological preparations

D11AX - Other dermatologicals

D11AX13 - Monobenzone

5.4 Metabolism/Metabolites

... Predicted by its low chronic toxicity ... hydroquinone monobenzyl ether may readily be metabolized in the same manner as phenol.

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 2532

5.5 Mechanism of Action

Monobenzone is a depigmenting agent whose mechanism of action is not fully understood. It is proposed that it increases the excretion of melanin from the melanocytes. This effect is erratic and may take one to four months to occur while existing melanin is lost with normal sloughing of the stratum corneum. Hyperpigmented skin appears to fade more rapidly than does normal skin, and exposure to sunlight reduces the depigmenting effect of the drug. Following skin depigmentation after topical application of monobenzone, the histological studies indicate similar results as that seen in vitiligo, where the epidermis is intact but with the absence of identifiable melanocytes.

...INTERFERES WITH BIOSYNTHESIS OF MELANIN. IT INHIBITS ENZYME TYROSINASE & THEREBY PREVENTS CONVERSION OF TYROSINE TO DIHYDROXYPHENYLALANINE, PRECURSOR OF MELANIN.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 955

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