Benzoyl peroxide

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Benzoyl peroxide
Skeletal formula (top) Ball-and-stick model (bottom)
Clinical data
Trade namesBenzac, Panoxyl, others
Other namesbenzoperoxide, dibenzoyl peroxide (DBPO), BPO
AHFS/Drugs.comProfessional Drug Facts
MedlinePlusa601026
License data
Topical
ATC code
Legal status
Legal status
Identifiers
  • benzoic peroxyanhydride[3]
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 peroxide is a

oxidizer, which is principally used as in the production of polymers.[4]

Benzoyl peroxide is mainly used in production of

plastics and textiles.[6][7]

As a

water disinfectant.[5][7]

As a medication, benzoyl peroxide is mostly used to treat

teeth whitening. In 2021, it was the 284th most commonly prescribed medication in the United States, with more than 700,000 prescriptions.[13][14]

History

Benzoyl peroxide was first prepared and described by Justus von Liebig in 1858.[15]

Structure and reactivity

Structure of dibenzoyl peroxide from X-ray crystallography. The O=C-O-O dihedral angle is 90°. The O-O distance is 1.434 Å.[16]

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

tinea sycosis. He also reported animal experiments that showed the relatively low toxicity of the compound.[19][6][20]

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

acne

Benzoyl peroxide is effective for treating

benzoyl peroxide/clindamycin and adapalene/benzoyl peroxide, adapalene being a chemically stable retinoid that can be combined with benzoyl peroxide[26] unlike tezarotene and tretinoin. Combination products such as benzoyl peroxide/clindamycin and benzoyl peroxide/salicylic acid appear to be slightly more effective than benzoyl peroxide alone for the treatment of acne lesions.[25] The combination tretinoin/benzoyl peroxide
was 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%.[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

bacterium associated with acne.[24][27] 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. acnes has 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 of C. acnes, making it bactericidal,[6] and it was thought to decrease sebum production, but disagreement exists within the literature on this.[27][28]

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

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 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

swelling.[30][31] About one-third of people experience phototoxicity under exposure to ultraviolet (UVB) light.[32]

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

organic peroxides, and can cause fires without 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

Benzoyl peroxide breaks down in contact with skin, producing benzoic acid and oxygen, neither of which is very toxic.[34]

The

carcinogenic potential of benzoyl peroxide has been investigated. A 1981 study published in the journal Science found that although benzoyl peroxide is not a carcinogen, it does promote cell growth when applied to an initiated tumor. The study concluded, "caution should be recommended in the use of this and other free radical-generating compounds".[35]

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

A bleached fabric stain caused by contact with benzoyl peroxide

Contact with

fabrics or hair, 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.[40]

References

  1. ^ "Epsolay- benzoyl peroxide cream". DailyMed. 25 April 2022. Archived from the original on 16 May 2022. Retrieved 15 May 2022.
  2. ^ "Epsolay- benzoyl peroxide cream". DailyMed. 5 May 2022. Archived from the original on 20 June 2022. Retrieved 19 June 2022.
  3. ISBN 978-0-85404-182-4
    .
  4. ^
    ISBN 978-3527306732
    .
  5. ^
    ISBN 978-92-2-109817-1. Archived
    from the original on 18 September 2017.
  6. ^
    ISBN 978-3-642-59715-2. Archived
    from the original on 18 September 2017.
  7. ^
    ISBN 978-1-4496-0595-7. Archived
    from the original on 18 September 2017.
  8. ^
    ISBN 978-92-4-154765-9
    .
  9. ^
    ISBN 978-0-85711-156-2
    .
  10. ISBN 978-3-642-97931-6. Archived
    from the original on 18 September 2017.
  11. hdl:10665/371090
    . WHO/MHP/HPS/EML/2023.02.
  12. ^
    ISBN 978-1-284-05756-0
    .
  13. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  14. ^ "Benzoyl Peroxide - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  15. ^
    doi:10.1002/jlac.18581080117. Archived
    from the original on 29 November 2020. Retrieved 2 July 2019.
  16. doi:10.1016/0040-4020(82)80157-9
    .
  17. hdl:10919/30521. Archived from the original
    on 20 September 2006. Retrieved 17 February 2007.
  18. ^ Kastle JH, Loevenhart AS (1901). "On the Nature of Certain Oxidizing Ferments". American Chemical Journal. 2: 539–566.
  19. ^ Loevenhart AS (1905). "Benzoylsuperoxyds, ein neues therapeutisches Agens". Therap Monatscheftel (in German). 12: 426–428.
  20. ^
    S2CID 24091844
    .
  21. ^
    ISBN 92-832-1271-1
  22. ^ "Initiation By Diacyl Peroxides". Polymer Properties Database. Archived from the original on 19 October 2018. Retrieved 19 October 2018.
  23. ^ "Error - Evonik Industries AG" (PDF). Archived from the original on 29 August 2021. Retrieved 12 April 2011.
  24. ^
    S2CID 12200694
    .
  25. ^
    PMID 20488582
    .
  26. PMID 29494115
    . Retrieved 24 July 2022.
  27. ^
    PMID 6162349
    .
  28. ^
    S2CID 6924764
    .
  29. ^
    ISBN 978-1-60913-713-7
    .
  30. PMID 6183909
    .
  31. ^ "Benzoyl peroxide". Mayo Clinic. 1 January 2016. Archived from the original on 18 July 2016.
  32. PMID 6628794
    .
  33. ^ Cartwright H (17 March 2005). "Chemical Safety Data: Benzoyl peroxide". Oxford University. Archived from the original on 12 October 2010. Retrieved 13 August 2011.
  34. ^ Benzoyl peroxide (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, April 2004
  35. PMID 6791284
    .
  36. PMID 38483533
    .
  37. ^ "USP Statement on Third Party Laboratory Benzene Findings | USP". www.usp.org. Retrieved 16 March 2024.
  38. S2CID 33553359
    .
  39. doi:10.26616/NIOSHPUB76128. Archived
    from the original on 9 August 2016. Retrieved 15 July 2016.
  40. S2CID 22468429
    .

External links
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