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    Ensulizole

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    MARKET PLACE

    REF. STANDARDS & IMPURITIES

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    $ API Ref.Price (USD/KG) : 17Xls

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    2D Structure
    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

    2D Structure

    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 Weight 274.30 g/mol
    Molecular Formula C13H10N2O3S
    XLogP32
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count2
    Exact Mass274.04121336 g/mol
    Monoisotopic Mass274.04121336 g/mol
    Topological Polar Surface Area91.4 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity414
    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 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.