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    Technical details about Prestwick2_000912, learn more about the structure, uses, toxicity, action, side effects and more

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    Prestwick2_000912

    APIs // Active Pharmaceutical Ingredients

    PRICE INFORMATION

    DOSSIERs // Finished Dosage Forms

    MARKET PLACE

    ANALYTICAL SOLUTION(s)

    PharmaCompass

    Minakem offers CDMO services for API & HPAPI, generics, regulatory expertise, track record performance & FDA & GMP certifications.

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    2D Structure
    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

    2D Structure

    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 Weight 200.23 g/mol
    Molecular Formula C13H12O2
    XLogP33.4
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count3
    Exact Mass200.083729621 g/mol
    Monoisotopic Mass200.083729621 g/mol
    Topological Polar Surface Area29.5 Ų
    Heavy Atom Count15
    Formal Charge0
    Complexity167
    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 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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