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385 Canada

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13 Evonik
18 Rochem International Inc
27 SPI Pharma
2 Seqens
42 DKSH
1 Jai Radhe Sales
1 PMC Isochem
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12 Faran Shimi Pharmaceutical
10 Boai NKY Pharmaceuticals Ltd
16 Gangwal Healthcare
1 ICE Pharma
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37 Nanjing Well Pharmaceutical
8 Pfanstiehl
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4 Alcedo Pharmachem
9 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd
63 BASF
1 Beijing Mesochem Technology
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3 BioSpectra
4 Clariant
29 Corel Pharma Chem
3 DFE Pharma
3 Doshion Polyscience
9 Finar
27 Gangwal Chemicals
4 Hayashibara
1 Huzhou Sunflower Pharmaceutical
12 Ideal Cures Pvt Ltd
4 Ingredion Pharma Solutions
22 Kerry
5 Kima Chemical
6 Lonza Capsugel
10 Lubrizol Life Science Health
34 Microlex e.U
4 Nanjing Bold Chemical
2 Nippon Fine Chemical
2 Nomisma Healthcare
5 Novo Excipients
4 Pharmatrans-Sanaq
14 Pluviaendo
3 Prachin Chemical
1 Qianhao Chemical (Hebei) Co., Ltd
2 Qualicaps
48 Roquette
35 Seppic
3 Shandong Focus Biotechnology Co., Ltd
2 Shanghai Hegeng Industrial Co. Ltd
8 Shanghai Shenmei Pharmaceutical Technology Co., Ltd
1 Shanghai Welltone Material Technology Co., Ltd
4 Shijiazhuang Huaxu Pharmaceutical
10 Sigachi Industries
4 The Dow Chemical Company
1 TopChem Pharmaceuticals
3 Ulanqab Kema New Material
4 Valens Pharmachem
4 Vasa Pharmachem
1 Vertellus
2 Zhejiang Huakang Pharmaceutical

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Synopsis

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FDA Orange Book

Europe

385

Canada

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Chemistry

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Also known as: 70356-09-1, Parsol 1789, Butyl methoxydibenzoylmethane, 1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione, Escalol 517, Eusolex 9020

Molecular Formula

C₂₀H₂₂O₃

Molecular Weight

310.4 g/mol

InChI Key

XNEFYCZVKIDDMS-UHFFFAOYSA-N

FDA UNII

G63QQF2NOX

Avobenzone is a sunscreen blocker. Avobenzone is a topical, broad range UV protector and blocks UVA I, UVA II, and UVB wavelengths, thereby limiting the impact of UV rays on skin. (NCI05)

1 2D Structure

Avobenzona

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione

2.1.2 InChI

InChI=1S/C20H22O3/c1-20(2,3)16-9-5-14(6-10-16)18(21)13-19(22)15-7-11-17(23-4)12-8-15/h5-12H,13H2,1-4H3

2.1.3 InChI Key

XNEFYCZVKIDDMS-UHFFFAOYSA-N

2.1.4 Canonical SMILES

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

2.2 Other Identifiers

2.2.1 UNII

G63QQF2NOX

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-tert-butyl-4'-methoxydibenzoylmethane

2. Bmdbm Cpd

3. Butyl-methoxydibenzoylmethane

4. Parsol 1789

5. Parsol-1789

2.3.2 Depositor-Supplied Synonyms

1. 70356-09-1

2. Parsol 1789

3. Butyl Methoxydibenzoylmethane

4. 1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione

5. Escalol 517

6. Eusolex 9020

7. 4-tert-butyl-4'-methoxy-dibenzoylmethane

8. Neoheliopan 357

9. 1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)-1,3-propanedione

10. 1-(4-(tert-butyl)phenyl)-3-(4-methoxyphenyl)propane-1,3-dione

11. 1,3-propanedione, 1-[4-(1,1-dimethylethyl)phenyl]-3-(4-methoxyphenyl)-

12. G63qqf2nox

13. Nsc-758680

14. 1-(p-tert-butylphenyl)-3-(p-methoxyphenyl)-1,3-propanedione

15. 1-(4-(1,1-dimethylethyl)phenyl)-3-(4-methoxyphenyl)-1,3-propanedione

16. Ncgc00095112-01

17. 1,3-propanedione, 1-(4-(1,1-dimethylethyl)phenyl)-3-(4-methoxyphenyl)-

18. Dsstox_cid_24829

19. Dsstox_rid_80510

20. Dsstox_gsid_44829

21. 87075-14-7

22. Avobenzona

23. Avobenzonum

24. Avobenzonum [inn-latin]

25. 1-[4-(1,1-dimethylethyl)phenyl]-3-(4-methoxyphenyl)-1,3-propanedione

26. Avobenzona [inn-spanish]

27. Parsol A

28. Smr001562107

29. Cas-70356-09-1

30. Hsdb 7423

31. Einecs 274-581-6

32. Unii-g63qqf2nox

33. 4-tert-butyl-4'-methoxydibenzoylmethane

34. Avobenzone [usan:usp:inn]

35. 4-methoxy-4'-tert-butyldibenzoylmethane

36. Spectrum_001715

37. Bf2avb

38. Avobenzone [mi]

39. Specplus_000764

40. Avobenzone (usp/inn)

41. Avobenzone [inn]

42. Spectrum2_001663

43. Spectrum3_000990

44. Spectrum4_001116

45. Spectrum5_001358

46. Avobenzone [hsdb]

47. Avobenzone [usan]

48. Avobenzone(parsol 1789)

49. Ec 274-581-6

50. Avobenzone [mart.]

51. Avobenzone [usp-rs]

52. Avobenzone [who-dd]

53. Avobenzone (parsol 1789)

54. Schembl15650

55. Bspbio_002659

56. Kbiogr_001592

57. Kbioss_002195

58. Zinc973

59. Mls002695918

60. Mls006010050

61. Bidd:er0196

62. Divk1c_006860

63. Spectrum1504190

64. Spbio_001845

65. Avobenzone, Analytical Standard

66. Avobenzone [orange Book]

67. Chembl1200522

68. Dtxsid9044829

69. Kbio1_001804

70. Kbio2_002195

71. Kbio2_004763

72. Kbio2_007331

73. Kbio3_001879

74. Avobenzone [usp Impurity]

75. Chebi:134751

76. Avobenzone [usp Monograph]

77. Hms1922f17

78. Hms2093c04

79. Hms3655c22

80. Hms3715f14

81. Pharmakon1600-01504190

82. Hy-b0316

83. Tox21_111427

84. Tox21_202796

85. Ccg-39080

86. Mfcd00210252

87. Nsc758680

88. S1904

89. 1-(4-(1,1-dimethylethyl)phenyl)-3-(4-methoxyphenyl)-1,3-propanedi- One

90. 1-(4-(1,1-dimethylethyl)phenyl)-3-(4-methoxyphenyl)propane-1,3-dione

91. Akos015838120

92. Tox21_111427_1

93. Ac-1682

94. Db09495

95. Nsc 758680

96. Anthelios Sx Component Avobenzone

97. Ncgc00095112-02

98. Ncgc00095112-03

99. Ncgc00095112-04

100. Ncgc00095112-05

101. Ncgc00260342-01

102. Rac-erythro Methylphenidate Hydrochloride

103. 23644-60-2

104. As-12797

105. Capital Soleil Component Avobenzone

106. Shade Uvaguard Component Avobenzone

107. Parsol 1789 100 Microg/ml In Methanol

108. Sbi-0052777.p002

109. Avobenzone Component Of Anthelios Sx

110. Butyl Methoxydibenzoylmethane [inci]

111. Avobenzone Component Of Capital Soleil

112. Avobenzone Component Of Shade Uvaguard

113. B3382

114. Ft-0623334

115. Sw219665-1

116. Parsol 1789 100 Microg/ml In Acetonitrile

117. D03015

118. Ab00053273_04

119. Ab00053273_05

120. A836855

121. Sr-05000001974

122. Q-200661

123. Q2775914

124. Sr-05000001974-1

125. 1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione

126. 1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)-propane-1,3-dione

127. 1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propan-1,3-dione

128. Avobenzone, United States Pharmacopeia (usp) Reference Standard

129. Avobenzone, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₂O₃
Molecular Weight	310.4 g/mol
XLogP3	4.8
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	6
Exact Mass	310.15689456 g/mol
Monoisotopic Mass	310.15689456 g/mol
Topological Polar Surface Area	43.4 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	405
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

Daily use of a sunscreen with a high SPF (greater than 15) on usually exposed skin is recommended for residents of areas of high ... /solar radiation/ who work outdoors or ... /enjoy/ regular outdoor recreation. Daily use of a sunscreen can reduce the cumulative ... /solar/ exposure that causes actinic keratoses and squamous-cell carcinoma.

IARC Working Group on the Evaluation of Cancer-Preventive Agents (2001) Sunscreens (IARC Handbooks of Cancer Prevention, Vol. 5), Lyon, IARC; Unit of Chemoprevention: Cancer-Preventive Effects of Sunscreens.

Sunscreen agents are indicated for the prevention of sunburn. In addition to limiting the skin's exposure to the sun, using sunscreen agents regularly when in the sun may help reduce long-term sun damage such as premature aging of the skin and skin cancer. /Sunscreen agents, topical; Included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

Sunscreen preparations should be applied uniformly and generously to all exposed skin surfaces, including lips, before exposure to UVB radiation. Two applications of the sunscreen may be needed for maximum protection. PABA-containing sunscreens are most effective when applied 1-2 hours before exposure to sunlight. Sunscreen products that are not water resistant should be reapplied after swimming, towel-drying, or profuse sweating and, because most sunscreens are easily removed from the skin, reapplication every 1-2 hours or according to the manufacturer's directions usually is required to provide adequate protection from UVB light. /Sunscreens/

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013

4.2 Drug Warning

The manufacturers of sunscreen preparations with propellants warn that concentrating and subsequently inhaling the fumes from these preparations may be harmful or fatal. /Propellants/

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013

Because the absorptive characteristics of skin of children younger than 6 months of age may differ from those of adults and because the immaturity of metabolic and excretory pathways of these children may limit their ability to eliminate any percutaneously absorbed sunscreen agent, sunscreen products should be used in children younger than 6 months of age only as directed by a clinician. It is possible that the characteristics of geriatric skin also differ from those of skin in younger adults, but these characteristics and the need for special considerations regarding use of sunscreen preparations in this age group are poorly understood. /Sunscreens/

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013

Little information is available regarding the safety of chronic sunscreen usage, but commercially available physical and chemical sunscreens appear to have a low incidence of adverse effects. Derivatives of PABA, benzophenone, cinnamic acid, and salicylate and 2-phenylbenzimidazole-5-sulfonic acid have caused skin irritation including burning, stinging, pruritus, and erythema on rare occasions. /Sunscreens/

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013

Sunscreens should not be used as a means of extending the duration of solar exposure, such as prolonging sunbathing, and should not be used as a substitute for clothing on usually unexposed sites, such as the trunk and buttocks. /Sunscreens/

For more Drug Warnings (Complete) data for AVOBENZONE (11 total), please visit the HSDB record page.

4.3 Drug Indication

Sun protection factor, added in the sunscreen products for its wide spectrum ultraviolet absorption properties.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Sunscreening Agents

Chemical or physical agents that protect the skin from sunburn and erythema by absorbing or blocking ultraviolet radiation. (See all compounds classified as Sunscreening Agents.)

5.2 Absorption, Distribution and Excretion

Solvents used in sunscreen products affect the stability and binding of the drug to the skin; in general, alcoholic solvents allow for the most rapid and deepest epidermal penetration of sunscreens. It appears that sunscreen agents are absorbed by the intact epidermis to varying degrees. /Sunscreens/

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013

5.3 Mechanism of Action

It blocks UVA I, UVA II, and UVB wavelengths, thereby limiting the impact of UV rays on skin. Diminish the penetration of ultraviolet (UV) light through the epidermis by absorbing UV radiation within a specific wavelength range. The amount and wavelength of UV radiation absorbed are affected by the molecular structure of the sunscreen agent.

Diminish the penetration of ultraviolet (UV) light through the epidermis by absorbing UV radiation within a specific wavelength range. The amount and wavelength of UV radiation absorbed are affected by the molecular structure of the sunscreen agent. /Sunscreen agents, topical/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

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