3D model (Jmol)
|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).
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.
Mechanism of action
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.
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.
In a 2002 study for the treatment of warts, the responders consisted of 135 individuals (87.7%) that had complete clearance of warts. Reported adverse effects were local and included with pruritus (itching) (15.6%), with blistering (7.1%), and with eczematous reactions (eczema)(14.2%). 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.
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.
- 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.
- 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
- 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.
- 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.