Benzoyl peroxide
Clinical data | |
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Trade names | Benzac, Panoxyl, others |
Other names | benzoperoxide, dibenzoyl peroxide (DBPO), BPO |
AHFS/Drugs.com | Professional Drug Facts |
MedlinePlus | a601026 |
License data | |
Topical | |
ATC code | |
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Identifiers | |
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JSmol) | |
Density | 1.334 g/cm3 |
Melting point | 103 to 105 °C (217 to 221 °F) decomposes |
Solubility in water | poor mg/mL (20 °C) |
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Data page | |
Benzoyl peroxide (data page) |
Benzoyl peroxide is a
Benzoyl peroxide is mainly used in production of
As a
As a medication, benzoyl peroxide is mostly used to treat
History
Benzoyl peroxide was first prepared and described by Justus von Liebig in 1858.[15]
Structure and reactivity
The original 1858 synthesis by Liebig reacted benzoyl chloride with barium peroxide,[15] a reaction that probably follows this equation:
- 2 C6H5C(O)Cl + BaO2 → (C6H5CO)2O2 + BaCl2
Benzoyl peroxide is usually prepared by treating hydrogen peroxide with benzoyl chloride under alkaline conditions.
- 2 C6H5COCl + H2O2 + 2 NaOH → (C6H5CO)2O2 + 2 NaCl + 2 H2O
The oxygen–oxygen bond in peroxides is weak. Thus, benzoyl peroxide readily undergoes homolysis (symmetrical fission), forming free radicals:
- (C6H5CO)2O2 → 2 C
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. The half-life of benzoyl peroxide is one hour at 92 °C. At 131 °C, the half-life is one minute.[17]
In 1901, it was observed that the compound made the tincture of
Treatment with benzoyl peroxide was proposed for wounds in 1929, and for sycosis vulgaris and acne varioliformis in 1934.[20] However, preparations were often of questionable quality.[6] It was officially approved for the treatment of acne in the US in 1960.[6]
Polymerization
Benzoyl peroxide is mainly used as a radical initiator to induce chain-growth polymerization reactions,[4] such as for polyester and poly(methyl methacrylate) (PMMA) resins and dental cements and restoratives.[21] It is the most important among the various organic peroxides used for this purpose, a relatively safe alternative to the much more hazardous methyl ethyl ketone peroxide.[22][23] It is also used in rubber curing and as a finishing agent for some acetate yarns.[21]
Other uses
Benzoyl peroxide is effective for treating
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%.[24] No strong evidence supports the idea that higher concentrations of benzoyl peroxide are more effective than lower concentrations.[24]
Mechanism of action
Classically, benzoyl peroxide is thought to have a three-fold activity in treating acne. It is sebostatic, comedolytic, and inhibits growth of
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.[28]
Side effects
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 develops tolerance to the medication. Skin sensitivity typically resolves after a few weeks of continuous use.[28][29] Irritation can also be reduced by avoiding harsh facial cleansers and wearing sunscreen prior to sun exposure.[29]
One in 500 people experience
Dosage
In the US, the typical concentration for benzoyl peroxide is 2.5% to 10% for both prescription and over-the-counter drug preparations that are used in treatment for acne.
Other medical uses
Benzoyl peroxide is used in dentistry as a tooth whitening product.
Safety
Explosion hazard
Benzoyl peroxide is potentially
Toxicity
Benzoyl peroxide breaks down in contact with skin, producing benzoic acid and oxygen, neither of which is very toxic.[34]
The
A 1999 IARC review of carcinogenicity studies found no convincing evidence linking benzoyl peroxide acne medication to skin cancers in humans. However, some animal studies found that the compound could act as a carcinogen and enhance the effect of known carcinogens.[21]
Benzoyl peroxide can break down into carcinogen benzene at temperatures above 50°C.[36][37]
Skin irritation
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.[38]
The US National Institute for Occupational Safety and Health has developed criteria for a recommended standard for occupational exposure to benzoyl peroxide.[39]
Cloth staining
Contact with
References
- ^ "Epsolay- benzoyl peroxide cream". DailyMed. 25 April 2022. Archived from the original on 16 May 2022. Retrieved 15 May 2022.
- ^ "Epsolay- benzoyl peroxide cream". DailyMed. 5 May 2022. Archived from the original on 20 June 2022. Retrieved 19 June 2022.
- ISBN 978-0-85404-182-4.
- ^ ISBN 978-3527306732.
- ^ ISBN 978-92-2-109817-1. Archivedfrom the original on 18 September 2017.
- ^ ISBN 978-3-642-59715-2. Archivedfrom the original on 18 September 2017.
- ^ ISBN 978-1-4496-0595-7. Archivedfrom the original on 18 September 2017.
- ^ ISBN 978-92-4-154765-9.
- ^ ISBN 978-0-85711-156-2.
- ISBN 978-3-642-97931-6. Archivedfrom the original on 18 September 2017.
- hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
- ^ ISBN 978-1-284-05756-0.
- ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
- ^ "Benzoyl Peroxide - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
- ^ from the original on 29 November 2020. Retrieved 2 July 2019.
- .
- hdl:10919/30521. Archived from the originalon 20 September 2006. Retrieved 17 February 2007.
- ^ Kastle JH, Loevenhart AS (1901). "On the Nature of Certain Oxidizing Ferments". American Chemical Journal. 2: 539–566.
- ^ Loevenhart AS (1905). "Benzoylsuperoxyds, ein neues therapeutisches Agens". Therap Monatscheftel (in German). 12: 426–428.
- ^ S2CID 24091844.
- ^ ISBN 92-832-1271-1
- ^ "Initiation By Diacyl Peroxides". Polymer Properties Database. Archived from the original on 19 October 2018. Retrieved 19 October 2018.
- ^ "Error - Evonik Industries AG" (PDF). Archived from the original on 29 August 2021. Retrieved 12 April 2011.
- ^ S2CID 12200694.
- ^ PMID 20488582.
- PMID 29494115. Retrieved 24 July 2022.
- ^ PMID 6162349.
- ^ S2CID 6924764.
- ^ ISBN 978-1-60913-713-7.
- PMID 6183909.
- ^ "Benzoyl peroxide". Mayo Clinic. 1 January 2016. Archived from the original on 18 July 2016.
- PMID 6628794.
- ^ Cartwright H (17 March 2005). "Chemical Safety Data: Benzoyl peroxide". Oxford University. Archived from the original on 12 October 2010. Retrieved 13 August 2011.
- ^ Benzoyl peroxide (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, April 2004
- PMID 6791284.
- PMID 38483533.
- ^ "USP Statement on Third Party Laboratory Benzene Findings | USP". www.usp.org. Retrieved 16 March 2024.
- S2CID 33553359.
- from the original on 9 August 2016. Retrieved 15 July 2016.
- S2CID 22468429.
External links
- International Chemical Safety Card 0225
- NIOSH Pocket Guide to Chemical Hazards. "#0052". National Institute for Occupational Safety and Health (NIOSH).
- SIDS Initial Assessment Report from the Organisation for Economic Co-operation and Development(OECD)
- Organic Peroxide Producers Safety Division (OPPSD)