List of Drug Master Files (DMF) of Tox21_202425 Active Pharmaceutical Ingredient listed on PharmaCompass.com

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Chemistry

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Also known as: 119-61-9, Diphenylmethanone, Diphenyl ketone, Benzoylbenzene, Methanone, diphenyl-, Phenyl ketone
Molecular Formula
C13H10O
Molecular Weight
182.22  g/mol
InChI Key
RWCCWEUUXYIKHB-UHFFFAOYSA-N
FDA UNII
701M4TTV9O

Benzophenone
Diphenylketone is a metabolite found in or produced by Saccharomyces cerevisiae.
1 2D Structure

Benzophenone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
diphenylmethanone
2.1.2 InChI
InChI=1S/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H
2.1.3 InChI Key
RWCCWEUUXYIKHB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)C(=O)C2=CC=CC=C2
2.2 Other Identifiers
2.2.1 UNII
701M4TTV9O
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 119-61-9

2. Diphenylmethanone

3. Diphenyl Ketone

4. Benzoylbenzene

5. Methanone, Diphenyl-

6. Phenyl Ketone

7. Ketone, Diphenyl

8. Alpha-oxoditane

9. Benzene, Benzoyl-

10. Alpha-oxodiphenylmethane

11. Diphenylketone

12. Diphenyl-methanone

13. Kayacure Bp

14. .alpha.-oxoditane

15. Adjutan 6016

16. Fema No. 2134

17. .alpha.-oxodiphenylmethane

18. Diphenyl-methanon

19. 1dzp

20. Nsc 8077

21. Mfcd00003076

22. Chembl90039

23. 701m4ttv9o

24. Dtxsid0021961

25. Chebi:41308

26. Nsc-8077

27. Ncgc00090787-05

28. Dsstox_cid_1961

29. Dsstox_rid_76429

30. Dsstox_gsid_21961

31. Diphenylmethanone (benzophenone)

32. Caswell No. 081g

33. Cas-119-61-9

34. Ccris 629

35. Hsdb 6809

36. Wln: Rvr

37. Einecs 204-337-6

38. Epa Pesticide Chemical Code 000315

39. Benzophenone (8ci)

40. Phenylketone

41. Unii-701m4ttv9o

42. Benzopheneone

43. Benzophenon

44. Benzophenone-

45. Benzoyl-benzene

46. A-oxoditane

47. Ai3-00754

48. Meta-benzophenone

49. Alpha -oxoditane

50. Fema 2134

51. Benzophenone Flakes

52. Di(phenyl)methanone

53. A-oxodiphenylmethane

54. Methanone, Diphenyl- (9ci)

55. Ph2co

56. Speedcure Bp

57. Darocur Bp

58. Diphenylmethanone, 9ci

59. Alpha -oxodiphenylmethane

60. Dimenhydrinate Impurity J

61. Benzophenone [mi]

62. Benzophenone [fcc]

63. Upcmld-dp071

64. Benzophenone [fhfi]

65. Benzophenone [hsdb]

66. Benzophenone [iarc]

67. Benzophenone [inci]

68. Ec 204-337-6

69. Bidd:pxr0008

70. Schembl17745

71. Mls001055400

72. Adk Stab 1413

73. Benzophenone [usp-rs]

74. Benzophenone [who-dd]

75. Bidd:er0022

76. Benzophenone (diphenyl-ketone)

77. Benzophenone (diphenylmethanone)

78. Upcmld-dp071:001

79. Bdbm22726

80. Benzophenone, Analytical Standard

81. Diphenhydramine Impurity E

82. Amy7704

83. Nsc8077

84. Hms2268a24

85. Zinc968233

86. Benzophenone [usp Impurity]

87. Benzophenone, >=99%, Fcc, Fg

88. Hy-y0546

89. Tox21_113465

90. Tox21_202425

91. Tox21_300058

92. Benzophenone, Reagentplus(r), 99%

93. S4438

94. Stl363250

95. Benzophenone, For Synthesis, 98.0%

96. Akos000119029

97. Tox21_113465_1

98. Benzophenone (diphenyl-ketone)

99. Db01878

100. Benzophenone 100 Microg/ml In Methanol

101. Benzophenone, Purum, >=99.0% (gc)

102. Benzophenone, Reagentplus(r), >=99%

103. Ncgc00090787-01

104. Ncgc00090787-03

105. Ncgc00090787-04

106. Ncgc00090787-06

107. Ncgc00090787-07

108. Ncgc00090787-08

109. Ncgc00254183-01

110. Ncgc00259974-01

111. Bp-21212

112. Smr000112143

113. Phenytoin Impurity A [ep Impurity]

114. Benzophenone, Saj First Grade, >=99.0%

115. Db-061602

116. B0083

117. Cs-0015323

118. Ft-0622720

119. Ft-0693251

120. Benzophenone, Purified By Sublimation, >=99%

121. Benzophenone, Vetec(tm) Reagent Grade, 98%

122. C06354

123. D72506

124. Dimenhydrinate Impurity J [ep Impurity]

125. Phenytoin Sodium Impurity A [ep Impurity]

126. Q409482

127. Melting Point Standard 47-49c, Analytical Standard

128. Q-200691

129. Phenytoin Impurity Benzophenone [usp Impurity]

130. F0001-0309

131. Z1245792986

132. Benzophenone, European Pharmacopoeia (ep) Reference Standard

133. Diphenhydramine Hydrochloride Impurity E [ep Impurity]

134. Mettler-toledo Calibration Substance Me 18870, Benzophenone

135. Phenytoin Sodium Impurity Benzophenone [usp Impurity]

136. Benzophenone, United States Pharmacopeia (usp) Reference Standard

137. Hydrocodone Hydrogen Tartrate 2.5-hydrate Impurity H [ep Impurity]

138. Benzophenone, Pharmaceutical Secondary Standard; Certified Reference Material

139. Mettler-toledo Calibration Substance Me 18870, Benzophenone, For The Calibration Of The Thermosystem 900, Traceable To Primary Standards (lgc)

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 182.22 g/mol
Molecular Formula C13H10O
XLogP33.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count2
Exact Mass182.073164938 g/mol
Monoisotopic Mass182.073164938 g/mol
Topological Polar Surface Area17.1 Ų
Heavy Atom Count14
Formal Charge0
Complexity165
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Photosensitizing Agents

Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms. (See all compounds classified as Photosensitizing Agents.)


4.2 Absorption, Distribution and Excretion

The percutaneous absorption of benzophenone was determined in vivo in monkeys. Absorption through occluded skin was approximately 70% of the applied dose in 24 hr. Under unoccluded conditions skin penetration was reduced to 44%, presumably because of evaporation from the site of application.

European Commission/European Chemical Substances Information System; IUCLID Dataset, Benzophenone (CAS No. 119-61-9) (2000). Available from, as of March 18, 2015: https://esis.jrc.ec.europa.eu/


/The authors/ gave /benzophenone/ orally ... (100 or 400 mg/kg) ... once per day for 3 days, to ovariectomized Sprague-Dawley (SD) rats, and all rats were killed 24 h after being given the last dose. ... At 24 hr after the last dose, the mean serum concentrations of benzophenone, benzhydrol and p-hydroxybenzophenone in the high-dosed rats were 10.4+/-1.0, 1.5+/-0.3, and 0.7+/-0.2 (mean +/- SE) umol/L, respectively, whereas in the serum of low-dosed rats these compounds were not detected. When a single oral administration of benzophenone (100 or 400 mg/kg) was given to intact female rats, serum concentrations of benzophenone, benzhydrol and p-hydroxybenzophenone increased in a dose-dependent manner 6 hr later. ...

PMID:1245144 Nakagawa Y, Tayama K; Arch Toxicol 76 (12): 727-31 (2002)


... The percutaneous absorption of the fragrances benzyl acetate and five other benzyl derivatives (benzyl alcohol, benzyl benzoate, benzamide, benzoin and benzophenone) was determined in vivo in monkeys. Absorption through occluded skin was high for all cmpd (approx 70% of the applied dose in 24 hr) and no significant differences between the values for the different cmpd were observed. No correlations were seen between skin penetration of these cmpd and their octanol-water partition coefficients. Under unoccluded conditions skin penetration of the fragrances was reduced and there was great variability between cmpd, presumably because of variations in the rates of evaporation from the site of application.

PMID:2379896 Bronaugh RL et al; Food Chem Toxicol 28 (5): 369-73 (1990)


4.3 Metabolism/Metabolites

In male Sprague-Dawley rats that received benzophenone by gavage, 1% of the administered dose was detected as p-hydroxybenzophenone in enzymetreated urine samples, but not in unhydrolyzed urine (Stocklinski et al., 1979). No p-hydroxybenzophenone was detected in the feces.

DHHS/NTP; Toxicology and Carcinogenesis Studies of Benzophenone (CAS No. 119-61-9) Toxicity Report Series No. 61 NIH Pub No. 00-3943. Available from, as of March 18, 2015: https://ntp-server.niehs.nih.gov


The results from recent studies show that some benzophenones (BPs) and their hydroxylated metabolites can function as weak estrogens (E2) in the environment. However, little is known about the structure-activity relationship of these molecules. We have examined the effects of exposure to ten different BPs on the proliferation of estrogen receptor (ER)-positive breast cancer cells and on the transcriptional activity of E2-target genes. We analyzed two genes that are tightly linked with estrogen-mediated proliferation, the CXCL12 and amphiregulin genes and two classical estrogen-responsive genes, the pS2 and progesterone receptor. Significant differences in the BPs efficiency to induce cell proliferation and endogenous E2-target gene expressions were observed. Using ERE-, Sp1-, AP1- and C3-reporter genes that contain different ER-binding sites in their promoter, we also showed significant differences in the BPs efficiency in activation of the ER transactivation. Together, our analyzes showed that the most active molecule is 4-hydroxy-BP. Docking analysis of the interaction of BPs in the ligand-binding pocket of ERa suggests that the minimum structural requirement for the estrogenic activity of BPs is a hydroxyl (OH) group in the phenyl A-ring that allows interaction with Glu-353, Arg-394 or Phe-404, which enhances the stability between BPs and ERa. Our modeling also indicates a loss of interaction between the OH groups of the phenyl B-ring and His-524. In addition, the presence of some OH groups in the phenyl B-ring can create repulsion forces, which may constrain helix 12 in an unfavorable position, explaining the differential estrogenic effects of BPs. These results, together with our analysis of BPs for their potency in activation of cell proliferation and ER-mediated transcription, report an improved understanding of the mechanism and structure-activity relationship of BPs. /benzophenones/

Kerdivel G et al; PLoS One. 8(4):e60567 (2013)


Benzophenone's main metabolic pathway in the rabbit is by reduction to benzhydrol, which is excreted in urine conjugated with glucoronic acid. Small amount (1%) is converted to p-hydroxybenzophenone following oral administration to rats. No p-hydroxybenzohydrol was detected in urine or feces.

European Commission/European Chemical Substances Information System; IUCLID Dataset, Benzophenone (CAS No. 119-61-9) (2000). Available from, as of March 18, 2015: https://esis.jrc.ec.europa.eu/


Benzophenone is a known human metabolite of cinnarizine.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


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02-Jan-2021
31-Aug-2024
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