Diphenylcyclopropenone

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Diphenylcyclopropenone
Diphenylcyclopropenone.svg
Names
IUPAC name
2,3-Diphenylcycloprop-2-en-1-one
Other names
Diphencyprone; DPCP
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.011.772
UNII
Properties
C15H10O
Molar mass 206.24 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Diphenylcyclopropenone (diphencyprone) is a topically administered drug intended for treating alopecia areata and alopecia totalis. Topical immunotherapy using diphenylcyclopropenone may also be an effective treatment option for recalcitrant warts.[1]

Mechanism of action[edit]

Diphenylcyclopropenone acts as a local irritant, triggering a local sensitization. It triggers an immune response that opposes the action of the autoreactive cells that otherwise cause hair loss.[2]

Studies[edit]

A study of 41 alopecia areata patients showed significant hair regrowth in 40% at 6 months, being sustained in two thirds of these after a 12-month-follow up-period.[3]

In a 2002 study for the treatment of warts, the responders consisted of 135 individuals (87.7%) that had complete clearance of warts.[1] Reported adverse effects were local and included with pruritus (itching) (15.6%), with blistering (7.1%), and with eczematous reactions (eczema)(14.2%).[1] The majority of the patients tolerated the treatment very well. One patient developed local impetigo (minor infection). Patients had an average of 5 treatments over a 6-month period.

Chemical properties[edit]

The chemical properties of diphenylcyclopropenone are dominated by the strong polarization of the carbonyl group, which gives a partial positive charge with aromatic stabilization on the cyclopropene ring and a partial negative charge on oxygen. Furthermore, the phenyl groups stabilize the partial positive charge in the ring through resonance.

Diphenylcyclopropenone reacts with oxalyl chloride to give 1,1-dichloro-2,3-diphenylcyclopropene, which is a reagent for the activation of carboxylic acids:[4]

acidchloridecyclopro

See also[edit]

References[edit]

  1. ^ a b c Upitis, JA; Krol, A (2002). "The use of diphenylcyclopropenone in the treatment of recalcitrant warts". Journal of cutaneous medicine and surgery. 6 (3): 214–7. doi:10.1007/s10227-001-0050-9. PMID 11951129. 
  2. ^ Public summary of positive opinion for orphan designation of diphenylcyclopropenone for the treatment of alopecia totalis, European Medicines Agency. Document Date: London, 23 April 2009. Doc.Ref.:EMEA/COMP/428277/2006
  3. ^ Sotiriadis, D.; Patsatsi, A.; Lazaridou, E.; Kastanis, A.; Vakirlis, E.; Chrysomallis, F. (2006). "Topical immunotherapy with diphenylcyclopropenone in the treatment of chronic extensive alopecia areata". Clinical and Experimental Dermatology. 32 (1): 48–51. doi:10.1111/j.1365-2230.2006.02256.x. PMID 17004987. 
  4. ^ Hardee, David J.; Kovalchuke, Lyudmila; Lambert, Tristan H. (2010). "Nucleophilic Acyl Substitution via Aromatic Cation Activation of Carboxylic Acids: Rapid Generation of Acid Chlorides under Mild Conditions". Journal of the American Chemical Society. 132 (14): 5002–5003. doi:10.1021/ja101292a.