Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H10O |
Molecular Weight | 206.2393 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1C(=C1C2=CC=CC=C2)C3=CC=CC=C3
InChI
InChIKey=HCIBTBXNLVOFER-UHFFFAOYSA-N
InChI=1S/C15H10O/c16-15-13(11-7-3-1-4-8-11)14(15)12-9-5-2-6-10-12/h1-10H
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/26551938Curator's Comment: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/26370645
Sources: http://www.ncbi.nlm.nih.gov/pubmed/26551938
Curator's Comment: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/26370645
Diphencyprone (DPCP) is a potent topical sensitizing agent that has been used since the late 1970s by physicians for the treatment of alopecia areata (AA), viral warts (human papillomavirus) and cutaneous metastases of melanoma. Although to date the compound is not approved as a drug by the FDA or EMA, physicians have continued to use DPCP because of its proven effects in these dermatological conditions. 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. The efficacy of DPCP has generally been ascribed to immunological reactions by the host. Inducing inflammation with a contact sensitizer is counterintuitive to treating AA, an autoimmune disorder. Studies using microarray and miRNA profiling may provide information about how DPCP induces inflammation in human skin at different times. Gene targets and microRNAs identified through these data may be modulated by an RNA interference approach to enhance DPCP efficacy and response rates
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0002376 Sources: http://www.ncbi.nlm.nih.gov/pubmed/26551938 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Ultraviolet radiation causes less immunosuppression in patients with polymorphic light eruption than in controls. | 2004 Feb |
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UV-induced tolerance to a contact allergen is impaired in polymorphic light eruption. | 2010 Nov |
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A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells. | 2010 Sep |
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Impaired hapten sensitization in patients with autoimmune disease. | 2011 Sep |
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High altitude impairs in vivo immunity in humans. | 2013 Jun |
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Systemic immunogenicity of para-Phenylenediamine and Diphenylcyclopropenone: two potent contact allergy-inducing haptens. | 2014 Jan |
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Human relevance of an in vitro gene signature in HaCaT for skin sensitization. | 2015 Feb |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.skintherapyletter.com/2000/5.5/2.html
sensitization with 2% diphencyprone (DPCP) followed by weekly application of a lower concentration that will be slowly increased each week until a mild eczema is elicited.
Route of Administration:
Topical
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/21139337
Curator's Comment: Was conformed, the expression in DPCP-treated cells of spliced XBP1, a known marker of ER stress
Diphencyprone (DPCP) induced an increase of cell-surface thiols not only in THP-1 cells, but also in primary monocytes. The intracellular reduced-form glutathione/oxidized-form glutathione ratio (GSH/GSSG ratio) was not affected by DPCP treatment
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NCI_THESAURUS |
C2139
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FDA ORPHAN DRUG |
164502
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FDA ORPHAN DRUG |
473615
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EU-Orphan Drug |
EU/3/06/380
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C029402
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ACTIVE MOIETY