Jump to content

Benzoyl peroxide

From Wikipedia, the free encyclopedia

Benzoyl peroxide
Skeletal formula (top) Ball-and-stick model (bottom)
Clinical data
Trade namesBenzac, Panoxyl, others
Other namesbenzoperoxide, dibenzoyl peroxide (DBPO), BPO
AHFS/DrugsProfessional Drug Facts
MedlinePlusa601026
License data
Routes of
administration		Topical
ATC code
Legal status
Legal status
Identifiers
  • benzoic peroxyanhydride[3]
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.002.116Edit this at Wikidata
Chemical and physical data
FormulaC14H10O4
Molar mass242.230g·mol−1
3D model (JSmol)
Density1.334 g/cm3
Melting point103 to 105 °C (217 to 221 °F) decomposes
Solubility in waterpoor mg/mL (20 °C)
  • c1ccc(cc1)C(=O)OOC(=O)c2ccccc2
  • 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
  • Key:OMPJBNCRMGITSC-UHFFFAOYSA-N
Data page
Benzoyl peroxide (data page)

Benzoyl peroxideis achemical compound(specifically, anorganic peroxide) withstructural formula(C6H5−C(=O)O−)2,often abbreviated as (BzO)2.In terms of its structure, the molecule can be described as twobenzoyl(C6H5−C(=O)−,Bz) groups connected by aperoxide(−O−O−). It is a white granular solid with a faint odour ofbenzaldehyde,poorly soluble in water but soluble inacetone,ethanol,and many other organic solvents. Benzoyl peroxide is anoxidizer,which is principally used in the production of polymers.[4]

Benzoyl peroxide is mainly used in production ofplastics[5]and for bleachingflour,hair,plasticsandtextiles.[6][7]

As ableach,it has been used as amedicationand awater disinfectant.[5][7]

As a medication, benzoyl peroxide is mostly used to treatacne,either alone or in combination with other treatments.[8]Some versions are sold mixed withantibioticssuch asclindamycin.[9][10]It is on theWorld Health Organization's List of Essential Medicines.[11]It is available as anover-the-counterandgeneric medication.[12][9]It is also used indentistryforteeth whitening.In 2021, it was the 284th most commonly prescribed medication in the United States, with more than 700,000 prescriptions.[13][14]

History

[edit]

Benzoyl peroxide was first prepared and described byJustus von Liebigin 1858.[15] Donald Holroyde HeyFRS[16](12 September 1904 – 21 January 1987) was aWelshorganic chemist who inferred that the decomposition ofbenzoyl peroxidegeneratedfree phenyl radicals.[17][18]

Structure and reactivity

[edit]
Structure of dibenzoyl peroxide fromX-ray crystallography.The O=C-O-O dihedral angle is 90°. The O-O distance is 1.434 Å.[19]

The original 1858 synthesis by Liebig reactedbenzoyl chloridewithbarium peroxide,[15]a reaction that probably follows this equation:

2 C6H5C(O)Cl + BaO2→ (C6H5CO)2O2+ BaCl2

Benzoyl peroxide is usually prepared bytreatinghydrogen peroxidewithbenzoyl chlorideunderalkaline conditions.

2 C6H5COCl + H2O2+ 2 NaOH → (C6H5CO)2O2+ 2 NaCl + 2 H2O

The oxygen–oxygen bond in peroxides is weak. Thus, benzoyl peroxide readily undergoeshomolysis(symmetrical fission), formingfree radicals:

(C6H5CO)2O2→ 2C
6H
5CO•
2

The symbol•indicates that the products are radicals; i.e., they contain at least one unpaired electron. Such species are highly reactive. The homolysis is usually induced by heating. Thehalf-lifeof benzoyl peroxide is one hour at 92 °C. At 131 °C, the half-life is one minute.[20]

In 1901, it was observed that the compound made the tincture ofguaiacum tinctureturn blue, a sign ofoxygenbeing released.[21]Around 1905, Loevenhart reported on the successful use of benzoyl peroxide to treat various skin conditions, includingburns,chronicvaricose leg tumors,andtinea sycosis.He also reported animal experiments that showed the relatively low toxicity of the compound.[22][6][23]

Treatment with benzoyl peroxide was proposed for wounds in 1929, and forsycosis vulgarisandacne varioliformisin 1934.[23]However, preparations were often of questionable quality.[6]It was officially approved for the treatment of acne in the US in 1960.[6]

Polymerization

[edit]

Benzoyl peroxide is mainly used as aradical initiatorto inducechain-growth polymerizationreactions,[4]such as forpolyesterandpoly(methyl methacrylate)(PMMA) resins anddental cementsandrestoratives.[24]It is the most important among the various organicperoxidesused for this purpose, a relatively safe alternative to the much more hazardousmethyl ethyl ketone peroxide.[25][26]It is also used in rubber curing and as a finishing agent for someacetate yarns.[24]

Other uses

[edit]
Tube of a water-based 5% benzoyl peroxide preparation for the treatment ofacne

Benzoyl peroxide is effective for treatingacne lesions.It does not induceantibiotic resistance.[27][28]It may be combined withsalicylic acid,sulfur,erythromycinorclindamycin(antibiotics), oradapalene(a syntheticretinoid). Two commoncombination drugsincludebenzoyl peroxide/clindamycinandadapalene/benzoyl peroxide,adapalenebeing a chemically stable retinoid that can be combined with benzoyl peroxide[29]unliketezaroteneandtretinoin.Combination products such as benzoyl peroxide/clindamycin and benzoyl peroxide/salicylic acidappear to be slightly more effective than benzoyl peroxide alone for the treatment of acne lesions.[28]The combinationtretinoin/benzoyl peroxidewas approved for medical use in the United States in 2021.

Benzoyl peroxide for acne treatment is typically applied to the affected areas in gel, cream, or liquid, in concentrations of 2.5% increasing through 5.0%, and up to 10%.[27]No strong evidence supports the idea that higher concentrations of benzoyl peroxide are more effective than lower concentrations.[27]

Mechanism of action

[edit]

Classically, benzoyl peroxide is thought to have a three-fold activity in treating acne. It is sebostatic, comedolytic, and inhibits growth ofCutibacterium acnes,the mainbacteriumassociated with acne.[27][30]In general, acne vulgaris is a hormone-mediated inflammation of sebaceous glands and hair follicles. Hormone changes cause an increase in keratin and sebum production, leading to blocked drainage.C. acneshas many lytic enzymes that break down the proteins and lipids in the sebum, leading to an inflammatory response. The free-radical reaction of benzoyl peroxide can break down the keratin, therefore unblocking the drainage of sebum (comedolytic). It can cause nonspecific peroxidation ofC. acnes,making it bactericidal,[6]and it was thought to decrease sebum production, but disagreement exists within the literature on this.[30][31]

Some evidence suggests that benzoyl peroxide has an anti-inflammatory effect as well. In micromolar concentrations it prevents neutrophils from releasing reactive oxygen species, part of the inflammatory response in acne.[31]

Side effects

[edit]
Skin irritation due to benzoyl peroxide

Application of benzoyl peroxide to the skin may result in redness, burning, and irritation. This side effect is dose-dependent.[8][12]

Because of these possible side effects, it is recommended to start with a low concentration and build up as appropriate, as the skin gradually developstoleranceto the medication. Skin sensitivity typically resolves after a few weeks of continuous use.[31][32]Irritation can also be reduced by avoiding harsh facial cleansers and wearingsunscreenprior to sun exposure.[32]

One in 500 people experiencehypersensitivityto benzoyl peroxide and are liable to experience burning,itching,crusting, and possiblyswelling.[33][34]About one-third of people experiencephototoxicityunder exposure toultraviolet(UVB) light.[35]

Dosage

[edit]

In the US, the typical concentration for benzoyl peroxide is 2.5% to 10% for bothprescriptionandover-the-counter drugpreparations that are used in treatment for acne.[36]

Other medical uses

[edit]

Benzoyl peroxide is used in dentistry as atooth whiteningproduct.

Safety

[edit]

Explosion hazard

[edit]

Benzoyl peroxide is potentiallyexplosive[37]like otherorganic peroxides,and can cause fireswithout external ignition.The hazard is acute for the pure material, so the compound is generally used as a solution or a paste. For example, cosmetics contain only a small percentage of benzoyl peroxide and pose no explosion risk.

Toxicity

[edit]

Benzoyl peroxide breaks down in contact with skin, producingbenzoic acidand oxygen, neither of which is very toxic.[38]

Thecarcinogenicpotential of benzoyl peroxide has been investigated. A 1981 study published in the journalSciencefound that although benzoyl peroxide is not a carcinogen, it does promote cell growth when applied to aninitiated tumor.The study concluded, "caution should be recommended in the use of this and other free radical-generating compounds".[39]

A 1999IARCreview of carcinogenicity studies found no convincing evidence linking benzoyl peroxide acne medication toskin cancersin humans. However, some animal studies found that the compound could act as a carcinogen and enhance the effect of known carcinogens.[24]

Benzoyl peroxide can break down into carcinogenbenzeneat temperatures above 50°C.[40][41]

Skin irritation

[edit]

In a 1977, study using a human maximization test, 76% of subjects acquired a contact sensitization to benzoyl peroxide. Formulations of 5% and 10% were used.[42]

The USNational Institute for Occupational Safety and Healthhas developed criteria for a recommended standard for occupational exposure to benzoyl peroxide.[43]

Cloth staining

[edit]
A bleached fabric stain caused by contact with benzoyl peroxide

Contact withfabricsorhair,such as from still-moist acne medication, can cause permanent color dampening almost immediately. Even secondary contact can cause bleaching, for example, contact with a towel that has been used to wash off benzoyl peroxide-containing hygiene products.[44]

See also

[edit]

References

[edit]
  1. ^"Epsolay- benzoyl peroxide cream".DailyMed.25 April 2022.Archivedfrom the original on 16 May 2022.Retrieved15 May2022.
  2. ^"Epsolay- benzoyl peroxide cream".DailyMed.5 May 2022.Archivedfrom the original on 20 June 2022.Retrieved19 June2022.
  3. ^IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-65.7.5". In Favre HA, Powell WH (eds.).Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013.IUPAC–RSC.ISBN978-0-85404-182-4.
  4. ^abHerbert K, Götz PH, Siegmeier R, Mayr W. "Peroxy Compounds, Organic".Ullmann's Encyclopedia of Industrial Chemistry.Weinheim: Wiley-VCH.doi:10.1002/14356007.a19_199.ISBN978-3527306732.
  5. ^abStellman JM (1998).Encyclopaedia of Occupational Health and Safety: Guides, indexes, directory.International Labour Organization. p. 104.ISBN978-92-2-109817-1.Archivedfrom the original on 18 September 2017.
  6. ^abcdePlewig G, Kligman AM (2012).ACNE and ROSACEA(3 ed.). Springer Science & Business Media. p. 613.ISBN978-3-642-59715-2.Archivedfrom the original on 18 September 2017.
  7. ^abPommerville JC (2012).Alcamo's Fundamentals of Microbiology: Body Systems.Jones & Bartlett Publishers. p. 214.ISBN978-1-4496-0595-7.Archivedfrom the original on 18 September 2017.
  8. ^abWorld Health Organization(2009). Stuart MC, Kouimtzi M, Hill SR (eds.).WHO Model Formulary 2008.World Health Organization. pp. 307–308.hdl:10665/44053.ISBN978-92-4-154765-9.
  9. ^abBritish national formulary: BNF 69(69 ed.). British Medical Association. 2015. p. 820.ISBN978-0-85711-156-2.
  10. ^Braun-Falco O, Plewig G, Wolff HH, Burgdorf W (2012).Dermatology(2 ed.). Springer Science & Business Media. p. 1039.ISBN978-3-642-97931-6.Archivedfrom the original on 18 September 2017.
  11. ^World Health Organization(2023).The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023).Geneva: World Health Organization.hdl:10665/371090.WHO/MHP/HPS/EML/2023.02.
  12. ^abHamilton R (2015).Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition.Jones & Bartlett Learning. p. 173.ISBN978-1-284-05756-0.
  13. ^"The Top 300 of 2021".ClinCalc.Archivedfrom the original on 15 January 2024.Retrieved14 January2024.
  14. ^"Benzoyl Peroxide - Drug Usage Statistics".ClinCalc.Retrieved14 January2024.
  15. ^abBrodie BC (1858)."Ueber die Bildung der Hyperoxyde organischer Säureradicale"[On the Formation of the Peroxides of Organic Acid Radicals].Justus Liebigs Ann. Chem.108:79–83.doi:10.1002/jlac.18581080117.Archivedfrom the original on 29 November 2020.Retrieved2 July2019.
  16. ^Cadogan JI,Davies DI (1988)."Donald Holroyde Hey. 12 September 1904-21 January 1987".Biographical Memoirs of Fellows of the Royal Society.34:294–320.doi:10.1098/rsbm.1988.0011.JSTOR770054.
  17. ^Hey DH(1934). "432. Amphoteric aromatic substitution. Part II. Reactions of benzoyl peroxide and phenylazotriphenylmethane".Journal of the Chemical Society (Resumed):1966.doi:10.1039/JR9340001966.
  18. ^Davies J,Jenkins N, Menna B, Lynch PI, eds. (2008).The Welsh Academy Encyclopaedia of Wales.Cardiff: University of Wales Press. pp. 367–368.ISBN978-0-7083-1953-6.
  19. ^McBride JM, Vary MW (1982). "Radical pair in crystalline dibenzoyl peroxide evidence for triplet ground states".Tetrahedron.38(6): 765–775.doi:10.1016/0040-4020(82)80157-9.
  20. ^Li III H (1998)."Chapter 2"(PDF).Synthesis, Characterization and Properties of Vinyl Ester Matrix Resins(Ph.D.). University of Vermont.hdl:10919/30521.Archived fromthe originalon 20 September 2006.Retrieved17 February2007.
  21. ^Kastle JH, Loevenhart AS (1901). "On the Nature of Certain Oxidizing Ferments".American Chemical Journal.2:539–566.
  22. ^Loevenhart AS (1905). "Benzoylsuperoxyds, ein neues therapeutisches Agens".Therap Monatscheftel(in German).12:426–428.
  23. ^abMerker PC (March 2002). "Benzoyl peroxide: a history of early research and researchers".International Journal of Dermatology.41(3): 185–8.doi:10.1046/j.1365-4362.2002.01371.x.PMID12010349.S2CID24091844.
  24. ^abcInternational Agency for Research on Cancer (1999): "Benzoyl peroxide". inRe-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen PeroxideArchived15 July 2020 at theWayback Machine.Monographs on the Evaluation of Carcinogenic Risks to Humans, number 71, pages 345–358.ISBN92-832-1271-1
  25. ^"Initiation By Diacyl Peroxides".Polymer Properties Database.Archivedfrom the original on 19 October 2018.Retrieved19 October2018.
  26. ^"Error - Evonik Industries AG"(PDF).Archivedfrom the original on 29 August 2021.Retrieved12 April2011.
  27. ^abcdSimonart T (December 2012). "Newer approaches to the treatment of acne vulgaris".American Journal of Clinical Dermatology.13(6): 357–64.doi:10.2165/11632500-000000000-00000.PMID22920095.S2CID12200694.
  28. ^abSeidler EM, Kimball AB (July 2010). "Meta-analysis comparing efficacy of benzoyl peroxide, clindamycin, benzoyl peroxide with salicylic acid, and combination benzoyl peroxide/clindamycin in acne".Journal of the American Academy of Dermatology.63(1): 52–62.doi:10.1016/j.jaad.2009.07.052.PMID20488582.
  29. ^Tolaymat L, Dearborn H, Zito PM (2022)."Adapalene".StatPearls.Treasure Island (FL): StatPearls Publishing.PMID29494115.Retrieved24 July2022.
  30. ^abCotterill JA (1 January 1980)."Benzoyl peroxide".Acta Dermato-Venereologica. Supplementum.89:57–63.doi:10.2340/00015555895763.PMID6162349.
  31. ^abcWorret WI, Fluhr JW (April 2006). "[Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid]" [Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid].Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology(in German).4(4): 293–300.doi:10.1111/j.1610-0387.2006.05931.x.PMID16638058.S2CID6924764.
  32. ^abAlldredge BK, Koda-Kimble MA, Young LY, eds. (2013).Applied Therapeutics: The Clinical Use of Drugs(10th ed.). Baltimore: Wolters Kluwer Health/Lippincott Williams & Wilkins. p. 949.ISBN978-1-60913-713-7.
  33. ^Cunliffe WJ, Burke B (1982)."Benzoyl peroxide: lack of sensitization".Acta Dermato-Venereologica.62(5): 458–9.doi:10.2340/0001555562458459.PMID6183909.
  34. ^"Benzoyl peroxide".Mayo Clinic. 1 January 2016.Archivedfrom the original on 18 July 2016.
  35. ^Jeanmougin M, Pedreiro J, Bouchet J, Civatte J (1 January 1983). "[Phototoxic activity of 5% benzoyl peroxide in man. Use of a new methodology]".Dermatologica.167(1): 19–23.doi:10.1159/000249739.PMID6628794.
  36. ^"Benzoyl Peroxide: Side Effects, Uses, Dosage, Interactions, Warnings".RxList.Retrieved11 August2024.
  37. ^Cartwright H (17 March 2005)."Chemical Safety Data: Benzoyl peroxide".Oxford University.Archivedfrom the original on 12 October 2010.Retrieved13 August2011.
  38. ^Benzoyl peroxide(PDF),SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, April 2004
  39. ^Slaga TJ, Klein-Szanto AJ, Triplett LL, Yotti LP, Trosko KE (August 1981). "Skin tumor-promoting activity of benzoyl peroxide, a widely used free radical-generating compound".Science.213(4511): 1023–5.Bibcode:1981Sci...213.1023S.doi:10.1126/science.6791284.PMID6791284.
  40. ^Kucera K, Zenzola N, Hudspeth A, Dubnicka M, Hinz W, Bunick CG, et al. (March 2024)."Benzoyl Peroxide Drug Products Form Benzene".Environmental Health Perspectives.132(3): 37702.doi:10.1289/EHP13984.PMC10939128.PMID38483533.
  41. ^"USP Statement on Third Party Laboratory Benzene Findings | USP".usp.org.Retrieved16 March2024.
  42. ^Leyden JJ, Kligman AM (October 1977). "Contact sensitization to benzoyl peroxide".Contact Dermatitis.3(5): 273–5.doi:10.1111/j.1600-0536.1977.tb03674.x.PMID145346.S2CID33553359.
  43. ^"Criteria for a Recommended Standard: Occupational Exposure to Benzoyl Peroxide (77-166)".CDC - NIOSH Publications and Products.6 June 2014.doi:10.26616/NIOSHPUB76128.Archivedfrom the original on 9 August 2016.Retrieved15 July2016.
  44. ^Bojar RA, Cunliffe WJ, Holland KT (February 1995). "The short-term treatment of acne vulgaris with benzoyl peroxide: effects on the surface and follicular cutaneous microflora".The British Journal of Dermatology.132(2): 204–8.doi:10.1111/j.1365-2133.1995.tb05014.x.PMID7888356.S2CID22468429.
[edit]
Retrieved from "https://en.wikipedia.org/w/index.php?title=Benzoyl_peroxide&oldid=1245971220"