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Ensulizole

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Also known as: 27503-81-7, 2-phenylbenzimidazole-5-sulfonic acid, Phenylbenzimidazole sulfonic acid, 2-phenyl-1h-benzo[d]imidazole-5-sulfonic acid, 2-phenyl-5-benzimidazolesulfonic acid, 1h-benzimidazole-5-sulfonic acid, 2-phenyl-

Molecular Formula

C₁₃H₁₀N₂O₃S

Molecular Weight

274.30 g/mol

InChI Key

UVCJGUGAGLDPAA-UHFFFAOYSA-N

FDA UNII

9YQ9DI1W42

Ensulizole, also known as 2-phenylbenzimidazole-5-sulfonic acid, is a water-soluble sunscreen agent that absorbs strongly at UV-B wavelengths. It is commonly found in cosmetic products and sunscreen formulas in combination with other UV filter compounds due to its minimal protection against UV-A wavelengths. Due to its water solubility, ensulizole is commonly used in products formulated to feel light and less oily. It was demonstrated by studies that ensulizole treatment provided protection against cyclobutane pyrimidine dimers and photosensitized the formation of oxidized guanine bases after UV-A or UV-B exposure. According to the FDA, the maximal approved concentration of ensulizole is 148 mM although concentrations ranging between 74 and 148mM can be found in commercial sunscreen products.

1 2D Structure

Ensulizole

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-phenyl-3H-benzimidazole-5-sulfonic acid

2.1.2 InChI

InChI=1S/C13H10N2O3S/c16-19(17,18)10-6-7-11-12(8-10)15-13(14-11)9-4-2-1-3-5-9/h1-8H,(H,14,15)(H,16,17,18)

2.1.3 InChI Key

UVCJGUGAGLDPAA-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C(C=C1)C2=NC3=C(N2)C=C(C=C3)S(=O)(=O)O

2.2 Other Identifiers

2.2.1 UNII

9YQ9DI1W42

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-phenylbenzimidazole-5-sulfonic Acid

2. 2-phenylbenzimidazole-5-sulfonic Acid, Monosodium Salt

3. Eusolex 232

4. Novantisol

5. Phenylbenzimidazole Sulfonic Acid

6. Phenylbenzimidazole Sulphonic Acid

2.3.2 Depositor-Supplied Synonyms

1. 27503-81-7

2. 2-phenylbenzimidazole-5-sulfonic Acid

3. Phenylbenzimidazole Sulfonic Acid

4. 2-phenyl-1h-benzo[d]imidazole-5-sulfonic Acid

5. 2-phenyl-5-benzimidazolesulfonic Acid

6. 1h-benzimidazole-5-sulfonic Acid, 2-phenyl-

7. 2-phenyl-1h-benzo[d]imidazole-6-sulfonic Acid

8. 2-phenyl-1h-benzimidazole-5-sulfonic Acid

9. 2-phenyl-3h-benzimidazole-5-sulfonic Acid

10. Parsol Hs

11. 2-phenyl-1h-benzimidazole-5-sulphonic Acid

12. 9yq9di1w42

13. 1h-benzimidazole-6-sulfonic Acid, 2-phenyl-

14. Ncgc00166262-01

15. 1h-benzimidazole-5-sulfonic Acid-2-phenyl-

16. Dsstox_cid_18852

17. Dsstox_rid_79408

18. Dsstox_gsid_38852

19. Ensulizole [inn]

20. Cas-27503-81-7

21. Ultraviolet Absorbent Uv-t

22. Unii-9yq9di1w42

23. Ensulizole [usan:usp:inn]

24. Einecs 248-502-0

25. 2-phenylbenzimidazole-5-sulfonicacid

26. Mfcd00053007

27. Pbsa

28. Ensulizole [mi]

29. Ensulizole (usp/inn)

30. Ensulizole [usan]

31. Ec 248-502-0

32. Ensulizole [mart.]

33. Ensulizole [usp-rs]

34. Ensulizole [who-dd]

35. Schembl16277

36. Phenylbenzimidazole-sulfonic-acid

37. Chembl1987518

38. Dtxsid3038852

39. Chebi:135132

40. Bdbm181124

41. Ensulizole [usp Monograph]

42. Bcp17614

43. Zinc6467621

44. Tox21_112381

45. Tox21_200995

46. Bbl028055

47. S4419

48. Stk034479

49. 2-phenylbenzimidazole-5-sulphonic Acid

50. Akos005381771

51. Akos006029164

52. Parsol Hs 100 Microg/ml In Methanol

53. Tox21_112381_1

54. Us9138393, 2-phenyl Benzimidazole

55. Us9144538, 2-phenyl Benzimidazole

56. Ccg-245160

57. Db11115

58. 2-phenylbenz-imidazole-5-sulphonic Acid

59. Ncgc00166262-02

60. Ncgc00166262-03

61. Ncgc00258548-01

62. Ac-11988

63. As-12559

64. 2-phenylbenzo[d]imidazole-5-sulfonic Acid

65. Db-021496

66. Hy-109654

67. 2-phenyl-3h-benzimidazol-1-ium-5-sulfonate

68. 2-phenyl-5-benzimidazolesulfonic Acid, 96%

69. Cs-0033783

70. Ft-0613323

71. P1670

72. 2-phenyl-1h-1,3-benzodiazole-6-sulfonic Acid

73. D10005

74. H11816

75. Phenylbenzimidazole Sulfonic Acid [inci]

76. Ab00090049-01

77. 503p817

78. A819096

79. Sr-01000883690

80. Q-200317

81. Q7181424

82. Sr-01000883690-1

83. 2-phenylbenzimidazole-5-sulfonic Acid [vandf]

84. Us9138393, 2-phenyl-5- Benzimidazole Sulfonic Acid

85. Z275232302

86. Ensulizole, United States Pharmacopeia (usp) Reference Standard

87. 2-phenyl-5-benzimidazolesulfonic Acid, Analytical Reference Material

88. 2-phenyl-7ah-benzimidazole-5-sulfonic Acid;2-phenylbenzimidazole-5-sulfonic Acid

89. Ensulizole(2-phenylbenzimidazole 5-sulfonic Acid), Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2005-07-12

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₁₀N₂O₃S
Molecular Weight	274.30 g/mol
XLogP3	2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	274.04121336 g/mol
Monoisotopic Mass	274.04121336 g/mol
Topological Polar Surface Area	91.4 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	414
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 Drug Indication

Indicated to be used as an UV-B-absorbing molecule in sunscreen formulations.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Ensulizole is a selective UV-B filter with little activity against UV-A wavelengths. _In vitro_, ensulizole oxidizes guanine bases upon photoexcitation by UV-B and may cause photodamage on DNA, proteins and lipids in the cellular context.

5.2 Mechanism of Action

Ensulizole strongly absorbs UV-B wavelengths. It offers protection against UV-B-induced cyclobutane pyrimidine dimers. Based on the findings in vitro and in cellulo, ensulizole induces damage on the DNA, causes DNA strand breaks and photosensitizes the formation of oxidized guanines via type I and II photosensitization mechanisms following UV-A or UV-B irradiation. Ensulizole is capable of generating reactive oxygen species, including singlet oxygen upon photoexcitation.