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2D Structure
Also known as: 94-36-0, Peroxide, dibenzoyl, Dibenzoyl peroxide, Benzoyl superoxide, Benzoperoxide, Acetoxyl
Molecular Formula
C14H10O4
Molecular Weight
242.23  g/mol
InChI Key
OMPJBNCRMGITSC-UHFFFAOYSA-N
FDA UNII
W9WZN9A0GM

A peroxide derivative that has been used topically for BURNS and as a dermatologic agent in the treatment of ACNE and POISON IVY DERMATITIS. It is used also as a bleach in the food industry.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
benzoyl benzenecarboperoxoate
2.1.2 InChI
InChI=1S/C14H10O4/c15-13(11-7-3-1-4-8-11)17-18-14(16)12-9-5-2-6-10-12/h1-10H
2.1.3 InChI Key
OMPJBNCRMGITSC-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)C(=O)OOC(=O)C2=CC=CC=C2
2.2 Other Identifiers
2.2.1 UNII
W9WZN9A0GM
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Benzoyl Superoxide

2. Dibenzoyl Peroxide

3. Diphenylglyoxal Superoxide

4. Panoxyl

5. Peroxide, Benzoyl

6. Peroxide, Dibenzoyl

7. Superoxide, Benzoyl

8. Superoxide, Diphenylglyoxal

2.3.2 Depositor-Supplied Synonyms

1. 94-36-0

2. Peroxide, Dibenzoyl

3. Dibenzoyl Peroxide

4. Benzoyl Superoxide

5. Benzoperoxide

6. Acetoxyl

7. Benoxyl

8. Lucidol

9. Panoxyl

10. Benzol Peroxide

11. Dibenzoylperoxid

12. Benzoylperoxid

13. Asidopan

14. Persadox

15. Benzac

16. Eloxyl

17. Mytolac

18. Oxylite

19. Diphenylglyoxal Peroxide

20. Resdan Akne

21. Epi-clear

22. Persa-gel

23. Akneroxid 5

24. Dry And Clear

25. Duresthin 5

26. Benzoyl Benzenecarboperoxoate

27. Luperco Ast

28. Nayper Bo

29. Benzoylperoxyde

30. Loroxide

31. Theraderm

32. Dibenzoylperoxyde

33. Peroxyde De Benzoyle

34. Lucidol B 50

35. Lucidol G 20

36. Perossido Di Benzoile

37. Benzoylperoxide

38. Benzoic Acid, Peroxide

39. Acnegel

40. Benzaknen

41. Brevoxyl

42. Debroxide

43. Desanden

44. Incidol

45. Novadelox

46. Vanoxide

47. Garox

48. Topex

49. Xerac

50. Luperox Fl

51. Akneroxide L

52. Cadox Bs

53. Quinolor Compound

54. Desquam E

55. Benzac W

56. Clear By Design

57. Luperco Aa

58. Cadox B

59. Nayper B And Bo

60. Aztec Bpo

61. Benzagel 10

62. Lucidol (peroxide)

63. Benzagel

64. Benzashave

65. Cadox 40e

66. Norox Bzp-250

67. Norox Bzp-c-35

68. Desquam X

69. Desquam-x

70. Acne-aid Cream

71. Benbel C

72. Cadat Bpo

73. Lucidol-70

74. Aksil 5

75. Lucidol 50p

76. Lucidol Kl 50

77. Oxy-10 Cover

78. Superox 744

79. Chaloxyd Bp 50ft

80. Abcat 40

81. Benox 50

82. Diphenylperoxyanhydride

83. Benzoic Peroxyanhydride

84. Cadox B 40e

85. Cadox B 50p

86. Cadox B 70w

87. Oxy 5

88. Oxy-5

89. Cadox B-ch 50

90. Fostex Bpo

91. Phisoac Bp

92. Xerac Bp

93. Benzoyl Peroxide [usan]

94. Benoxyl (5&10) Lotion

95. Epi Clear Antiseptic Lotion

96. Stri-dex B.p.

97. Peroxyderm

98. Benzaknew

99. Benzoyl

100. Bzf-60

101. Dermoxyl

102. Luzidol

103. Nericur

104. Oxy-10

105. Peroxydex

106. Preoxydex

107. Sanoxit

108. Superox

109. Benzoylperoxid [german]

110. Cadet

111. Benzoyl-peroxide

112. Dibenzoylperoxide

113. Benzoyl Peroxyde

114. Akneroxid L

115. Dibenzoylperoxid [german]

116. Clearasil Antibacterial Acne Lotion

117. Lucidol 75fp

118. Oxy-l

119. Component Of Oxy-5

120. Component Of Vanoxide

121. Xerac Bp 5

122. Bpo

123. Oxy Wash

124. Xerac Bp 10

125. Nsc-671

126. Nsc-675

127. Ins No.928

128. Abcure S-40-25

129. Anhydrous Benzoyl Peroxide

130. Benzoyl Peroxide Anhydrous

131. W9wzn9a0gm

132. Clearasil Bp Acne Treatment

133. Ins-928

134. Nsc671

135. Chebi:82405

136. Clearasil Benzoyl Peroxide Lotion

137. Nsc 675

138. Ncgc00159380-02

139. Ncgc00159380-05

140. Benzoylperoxid (german)

141. Wln: Rvoovr

142. Benzoyl Peroxide (usan)

143. Dibenzoylperoxid (german)

144. E-928

145. Dsstox_cid_1072

146. Novadelox (18% Benzoyl Peroxide, 78% Calcium Sulphate, 4% Magnesium Carbonate)

147. Dsstox_rid_77460

148. Dsstox_gsid_24591

149. Benprox

150. Benzefoam

151. Lavoclen

152. Benzoylperoxyde [dutch]

153. Pacnex

154. Neobenz Micro

155. Dibenzoylperoxyde [dutch]

156. Peroxide, Benzoyl

157. Cas-94-36-0

158. Ccris 630

159. Stri-dex B.p

160. Superoxide, Benzoyl

161. Benzoyl Peroxide Gel

162. Peroxyde De Benzoyle [french]

163. Hsdb 372

164. Perossido Di Benzoile [italian]

165. Nsc 671

166. B 75w

167. Clearasil Bp Acne Treatment Cream

168. Diphenylglyoxal Superoxide

169. Einecs 202-327-6

170. Unii-w9wzn9a0gm

171. Superoxide, Diphenylglyoxal

172. Thermaderm

173. G 20

174. Lucilite

175. Lucipal

176. Novadeiox

177. Periygel

178. Peroxyl

179. Presadox

180. Bezoyl Peroxide

181. Florox

182. Benzoyl Peroide

183. Bepio

184. Silica Hydrogel

185. Triaz

186. Benzoyl Peroxide [usan:usp]

187. Luperco A

188. Di-benzoylperoxide

189. Dibenzoy Lperoxide

190. Dibenzoyl Peroxyde

191. Dibenzoyl-peroxide

192. Lucidol Gs

193. Lucidol Rm

194. Luperco Ac

195. Luperco Afr

196. Bzoobz

197. Nyper B

198. Bis Benzoylperoxide

199. Bisbenzoyl Peroxide

200. Cadox Bta

201. Nyper Bmt

202. Di-benzoyl Peroxide

203. Perkadox 20s

204. Cuticura Acne Cream

205. Lucidol 70

206. Lucidol 78

207. Lucidol-78

208. Luperox A98

209. Mfcd00003071

210. Bbpo

211. Epsolay

212. Bepio (tn)

213. Benzagel (salt/mix)

214. Benzoyl Dioxide

215. Luperco Afr-250

216. Sulfoxyl (salt/mix)

217. Cadet Bpo 78w

218. Cadet Bpo-70w

219. Cadox Bpo-w40

220. Cadox Btw-50

221. Benzoyl Peroxide(usan)

222. Benzoyl Peroxide [1]

223. Benzoyl Peroxide [2]

224. Benzoyl Peroxide [3]

225. Benzoyl Peroxide [4]

226. Benzoyl Peroxide [5]

227. Benzoyl Peroxide [6]

228. Benzoyl Peroxide [7]

229. Benzoyl Peroxide [8]

230. Benzoyl Peroxide [9]

231. Hydrous Benzoyl Peroxide

232. Benzoyl Peroxide, Usan

233. Xerac Bp (salt/mix)

234. Acetoxyl 2.5 And 5

235. Benzoyl Peroxide (usp)

236. Diphenylperoxyanhydride #

237. Schembl63

238. Triaz;dibenzoyl Peroxide

239. Fostex Bpo (salt/mix)

240. Aztec Benzoyl Peroxide-dry

241. Ec 202-327-6

242. Benzoylis Peroxidum Cum Aqua

243. Benzoyl Peroxide (jan/usp)

244. Mls000028899

245. Benzoyl Peroxide [mi]

246. Bidd:gt0840

247. Benzoyl Peroxide (wet)

248. Benzoyl Peroxide [fcc]

249. Benzoyl Peroxide [jan]

250. Aztec Benzoyl Peroxide-70-77

251. Nsc675

252. Zinc1016

253. Benzoyl Peroxide [hsdb]

254. Benzoyl Peroxide [iarc]

255. Benzoyl Peroxide [inci]

256. Benzoyl Peroxide [vandf]

257. Chembl1200370

258. Dtxsid6024591

259. Benzoyl Peroxide [mart.]

260. Benzoyl Peroxide, Remainder Water

261. Fostex Bpo Bar, Gel, And Wash

262. Benzoyl Peroxide [who-dd]

263. Component Of Vanoxide (salt/mix)

264. Hms2092f22

265. Pharmakon1600-01503004

266. Phenylcarbonyl Benzenecarboperoxoate

267. Na 2085 (dot)

268. Un 2085 (dot)

269. Idp-126 Component Benzoyl Peroxide

270. Tox21_111619

271. Benzoyl Peroxide (luperox(r) A75)

272. Benzoyl Peroxide (luperox(r) A98)

273. Br1012

274. Nsc758205

275. Benzoyl Peroxide (luperox(r) A70s)

276. Akos000120600

277. Benzenecarboperoxoic Acid Benzoyl Ester

278. Benzoyl Peroxide [orange Book]

279. Duac Component Benzoyl Peroxide

280. Tox21_111619_1

281. Benzoyl Peroxide (luperox(r) A75fp)

282. Benzoyl Peroxide [usp Impurity]

283. Ccg-213090

284. Db09096

285. Nsc-758205

286. Sc10147

287. Un 2086

288. Un 2088

289. Acanya Component Benzoyl Peroxide

290. Epiduo Component Benzoyl Peroxide

291. Twyneo Component Benzoyl Peroxide

292. Ncgc00159380-03

293. Ncgc00159380-04

294. 2685-64-5

295. Benzoyl Peroxide Component Of Duac

296. Bp-21236

297. E928

298. Hydrous Benzoyl Peroxide [who-ip]

299. Smr000058568

300. W 75

301. Benzaclin Component Benzoyl Peroxide

302. Sbi-0206719.p001

303. Benzamycin Component Benzoyl Peroxide

304. Benzoyl Peroxide Component Of Acanya

305. Benzoyl Peroxide Component Of Epiduo

306. Benzoyl Peroxide Component Of Twyneo

307. Db-022598

308. B3152

309. Benzoyl Peroxide, Blend In Dibutyl Phthalate

310. Benzoyl Peroxide Component Of Benzaclin

311. Benzoyl Peroxide, Blend In Tricresyl Phosphate

312. Benzoyl Peroxide Component Of Benzamycin

313. C19346

314. D03093

315. Ab01562988_01

316. Benzoyl Peroxide, For Synthesis, 72.0-80.0%

317. Hydrous Benzoyl Peroxide [usp Monograph]

318. Mixture Of Dibenzoyl Peroxide And Calcium Sulfate

319. A844933

320. Mixture Of Dibenzoyl Peroxide And Calcium Sulphate

321. Q411424

322. Sr-05000001817

323. Benzoylis Peroxidum Cum Aqua [who-ip Latin]

324. Sr-05000001817-1

325. Brd-k59986511-001-02-3

326. Benzoyl Peroxide, 97% (dry Wt.), Wet With 25% Water

327. Benzoyl Peroxide, Saj First Grade, >=98.0% Dry Basis

328. F0001-2260

329. Luperox(r) A75, Benzoyl Peroxide 75%, Remainder Water

330. Luperox(r) A70s, Benzoyl Peroxide, 70%, Remainder Water

331. Luperox(r) A75, Benzoyl Peroxide, 75%, Remainder Water

332. Luperox(r) A98, Benzoyl Peroxide, Reagent Grade, >=98%

333. Benzoyl Peroxide Blend With Dicyclohexyl Phthalate, Technical, ~50% (t)

334. Luperox(r) Atc50, Benzoyl Peroxide, ~50 Wt. % In Tricresyl Phosphate

335. Luperox(r) Afr40, Benzoyl Peroxide Solution, 40 Wt. % In Dibutyl Phthalate

336. Benzoyl Peroxide Blend With Dicyclohexyl Phthalate, Suitable For Use As A Catalyst For Electron Microscopy. Modified To Render It Safe In Transit.

337. Luperox(r) A75fp, Benzoyl Peroxide, 75% Remainder Water, Contains 25 Wt. % Water As Stabilizer, 75%

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 242.23 g/mol
Molecular Formula C14H10O4
XLogP33.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Exact Mass242.05790880 g/mol
Monoisotopic Mass242.05790880 g/mol
Topological Polar Surface Area52.6 Ų
Heavy Atom Count18
Formal Charge0
Complexity258
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

MEDICATION (VET): Keratolytic.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 197


Its principal use is in the treatment of mild acne vulgaris (in which it is comedolytic) and acne rosacea, but it also is used in the treatment of decubital and stasis ulcers.

Troy, D.B. (Ed); Remmington The Science and Practice of Pharmacy. 21 st Edition. Lippincott Williams & Williams, Philadelphia, PA 2005, p. 1288


Three multicenter, randomized, double blind, parallel-group, placebo controlled studies involving 3,855 subjects established the safety and efficacy of an adapalene benzoyl peroxide topical gel in the treatment of acne for all skin types. The data from these 3 studies were pooled and the subgroup of self-identified black subjects was analyzed separately. Significantly more black subjects had IGA success with adapalene-BPO than with vehicle at week 12. Significantly more black subjects also had decreased total, inflammatory, and noninflammatory lesion counts with adapalene-BPO that were seen as early as week 1. Adapalene-BPO was well tolerated in the black subjects included in this analysis and no cases of treatment-related PIH were observed. Similar results were obtained for this subgroup as the overall population from the 3 studies. Based on the results from this analysis, adapalene-BPO is a safe and effective treatment for acne in black skin. /Adapalene-BPO/

PMID:24509968 Alexis AF et al; J Drugs Dermatol 13 (2): 170-4 (2014)


/The study objective was to/ compare the safety and efficacy of 1% and 5% silica encapsulated benzoyl peroxide (E-BPO) in patients with papulopustular rosacea. /This was a/ multi-centered randomized, double blind, vehicle controlled parallel group, 12 week treatment in 92 patients with papulopustular rosacea. Primary endpoints were dichotomized IGA with success defined as clear/near clear and reduction in inflammatory lesions. /The study included/ 92 patients: 74% graded as moderate IGA, 14% severe and 12% mild. The mean inflammatory lesion count was 24. /The intervention was/ once daily treatment for 12 weeks with vehicle, 1% or 5% E-BPO. 1% and 5% E-BPO were superior to vehicle in reducing papulopustular lesions P =0.01 and P =0.02. 5% E-BPO was superior to vehicle for IGA P =0.0013.

PMID:24918558 Leyden JJ; J Drugs Dermatol 13 (6): 685-8 (2014)


For more Therapeutic Uses (Complete) data for Dibenzoyl peroxide (11 total), please visit the HSDB record page.


4.2 Drug Warning

Benzoyl peroxide should not be applied under an occlusive dressing, because it is a potent experimental contact sensitizer (delayed hypersensitivity). ... When hypersensitivity is suspected, patch tests may be performed with a freshly prepared 5% concentration in petrolatum or diluted commercial product.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 1201


Contact hypersensitivity is observed in 1% to 3% of patients under conditions of recommended use.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 1201


4.3 Minimum/Potential Fatal Human Dose

3. 3= Moderately toxic: Probable oral lethal dose (human) 0.5-5 g/kg, between 1 oz and 1 pint (or 1 lb) for 70 kg person (150 lb).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-75


4.4 Drug Indication

Benzoyl peroxide is formulated with antibiotics such as [erythromycin] and [clindamycin] for the treatment of acne vulgaris. Benzoyl peroxide is formulated as a number of topical products for the treatment of acne. Benzoyl peroxide is also indicated in combination with [tretinoin] for the treatment of acne vulgaris in patients aged nine years and older.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Benzoyl peroxide is a topical treatment for acne that generates free radicals to break down comedones and increase the rate of epithelial cell turnover. It has a short duration of action as its active free radical metabolites quickly react to form inactive metabolites. The therapeutic index is wide, as overdoses are rare, however patients may still experience skin peeling. Patients should be counselled regarding increased risks of skin irritation, dryness, and sunburn.


5.2 MeSH Pharmacological Classification

Dermatologic Agents

Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic Agents.)


5.3 ATC Code

D10AE01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


D - Dermatologicals

D10 - Anti-acne preparations

D10A - Anti-acne preparations for topical use

D10AE - Peroxides

D10AE01 - Benzoyl peroxide


5.4 Absorption, Distribution and Excretion

Absorption

In a sample of excised skin, 1.9% of a radiolabelled topical dose fully penetrates the skin, and 2.6% remains in the skin. The radiolabelled dose that fully penetrates the skin is recovered as benzoic acid, while the dose in the skin is approximately half benzoic acid and half benzoyl peroxide. 95.5% of a radiolabelled dose is not absorbed or metabolized after 8 hours.


Route of Elimination

Benzoyl peroxide's metabolite benzoic acid, is eliminated in the urine. Data regarding fecal elimination is not readily available.


Approximately one-half of a dose of benzoyl peroxide is absorbed to some extent after topical application to the forearm of primates ... .

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 1201


Skin absorption of benzoyl peroxide from a topical lotion containing freely dispersed drug was compared with that from the same lotion in which the drug was entrapped in a controlled-release styrene-divinylbenzene polymer system. In an in vitro diffusion system, statistically significant (p = 0.01) differences were found in the content of benzoyl peroxide in excised human skin and in percutaneous absorption. In vivo, significantly (p = 0.002) less benzoyl peroxide was absorbed through rhesus monkey skin from the polymeric system. This controlled release of benzoyl peroxide to skin can alter the dose relation that exists between efficacy and skin irritation. Corresponding studies showed reduced skin irritation in cumulative irritancy studies in rabbits and human beings, whereas in vivo human antimicrobial efficacy studies showed that application of the formulations containing entrapped benzoyl peroxide significantly reduced counts of Propionibacterium acnes (p less than 0.001) and aerobic bacteria (p less than 0.001) and the free fatty acid/triglyceride ratio in skin lipids. These findings support the hypothesis that, at least for this drug, controlled topical delivery can enhance safety without sacrificing efficacy.

PMID:1869643 Wester RC et al; J Am Acad Dermatol 24 (5 Pt 1): 720-6 (1991)


The transepidermal penetration and metabolic disposition of (14)C-benzoyl peroxide were assessed in vitro (excised human skin) and in vivo (rhesus monkey). In vitro, the benzoyl peroxide penetrated into the skin, through the stratum corneum or the follicular openings, or both, and was recovered on the dermal side as benzoic acid. In vivo, benzoic acid was recovered from urine in amounts equivalent to 45% and 98% of the radiolabel following, respectively, topical and intramuscular administration of small amounts of (14)C-benzoyl peroxide. We conclude that benzoyl peroxide penetrates as such into the skin layers and is converted therein to benzoic acid, which, in turn is absorbed into the systemic circulation. Renal clearance of the metabolite is sufficiently rapid as to preclude its hepatic conjugation with glycine, since following topical administration to rhesus monkeys, no hippuric acid was found in the urine, as could have been expected had a significant amount of benzoic acid passed through the liver.

PMID:7204686 Nacht S et al; J Am Acad Dermatol 4 (1): 31-7 (1981)


The percutaneous penetration and the metabolism of benzoyl peroxide (BPO) were assessed in vitro on human skin and in vivo on 5 patients with leg ulcers. The BPO in vitro absorbed by the skin was converted to benzoic acid preferably in the dermis. The portion penetrated through the skin was benzoic acid only. Also in patients treated with BPO, no BPO could be detected in the serum. These findings show that BPO as such is absorbed by the skin, but is systemically absorbed only after the metabolization to benzoic acid. Therefore a systemic-toxic effect in local therapy with BPO can be excluded.

PMID:7200789 Morsches B, Holzmann H; Arzneimittelforsch 32 (3): 298-300 (1982)


For more Absorption, Distribution and Excretion (Complete) data for Dibenzoyl peroxide (7 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

The peroxide bond of benzoyl peroxide is cleaved to form 2 benzoyloxy radicals. The benzyoyloxy radicals may interact with other molecules, forming benzoic acid; alternatively, benzoyloxy radicals can break down further to release carbon dioxide and a phenyl radical.


Benzoic acid is a major metabolite.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 1201


The transepidermal penetration and metabolic disposition of (14)C-benzoyl peroxide were assessed in vitro (excised human skin) and in vivo (rhesus monkey). In vitro, the benzoyl peroxide penetrated into the skin, through the stratum corneum or the follicular openings, or both, and was recovered on the dermal side as benzoic acid. In vivo, benzoic acid was recovered from urine in amounts equivalent to 45% and 98% of the radiolabel following, respectively, topical and intramuscular administration of small amounts of (14)C-benzoyl peroxide. We conclude that benzoyl peroxide penetrates as such into the skin layers and is converted therein to benzoic acid, which, in turn is absorbed into the systemic circulation. Renal clearance of the metabolite is sufficiently rapid as to preclude its hepatic conjugation with glycine, since following topical administration to rhesus monkeys, no hippuric acid was found in the urine, as could have been expected had a significant amount of benzoic acid passed through the liver.

PMID:7204686 Nacht S et al; J Am Acad Dermatol 4 (1): 31-7 (1981)


Benzoyl peroxide (BzPO) is both a tumor promoter and progressor in mouse skin; however, BzPO is neither an initiator nor a complete carcinogen in this tissue. Although not mutagenic, BzPO has been observed to produce strand breaks in DNA of exposed cells. These actions are presumed to be mediated by free-radical derivatives of BzPO. Previous studies suggested that the metabolism of BzPO in keratinocytes proceeds via the initial cleavage of the peroxide bond, yielding benzoyloxy radicals which, in turn, can either fragment to form phenyl radicals and carbon dioxide or abstract H atoms from biomolecules to yield benzoic acid. Benzoic acid is the major stable metabolite of BzPO produced by keratinocytes. In the present study we have investigated the role of BzPO and its metabolites in the generation of strand scissions in a cell-free system using phi X-174 plasmid DNA. In this system BzPO produced DNA damage that was dose-dependent over a concentration range of 0.1-1 mM and required the presence of copper but not other transition metals. By contrast, benoic acid did not produce DNA damage in this system, either in the presence or in the absence of copper. The inclusion of spin trapping agents, such as N-tert-butyl-alpha-phenylnitrone (PBN), 3,5-dibromo-4-nitrosobenzenesulfonate, and nitrosobenzene, in incubations was found to significantly reduce the extent of DNA damage generated via the copper-mediated activation of BzPO. Electron paramagnetic resonance spectroscopy studies suggested that the primary radical trapped by PBN following copper-mediated decomposition of BzPO was the benzoyloxy radical.

PMID:1782351 Swauger JE et al; Chem Res Toxicol 4 (2): 223-8 (1991)


5.6 Biological Half-Life

No reports found; [TDR, p. 174]

TDR - Ryan RP, Terry CE, Leffingwell SS (eds). Toxicology Desk Reference: The Toxic Exposure and Medical Monitoring Index, 5th Ed. Washington DC: Taylor & Francis, 1999., p. 174


5.7 Mechanism of Action

Acne vulgaris is caused by inflammation in the pilosebaceous gland. Acne is generally caused by increased excretion of sebum from pilosebaceous glands, endocrine factors such as androgenic hormones, keratin developing around follicles, bacterial growth, and inflammation. These factors contribute to the formation of comedones (whiteheads and blackheads). The peroxide bond of benzoyl peroxide is cleaved to form 2 benzoyloxy radicals. These radicals interact nonspecifically with bacterial proteins, interfering with their function, and survival of the bacteria. Over time, free radical interactions with bacterial proteins lead to decreased keratin and sebum around follicles. Benzoyl peroxide can also increase the turnover rate of epithelial cells, leading to skin peeling, and breaking down comedones.