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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
Structure of DIPHENCYPRONE

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

HIDE SMILES / InChI

Molecular Formula C15H10O
Molecular Weight 206.2393
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
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
Substance Class Chemical
Record UNII
I7G14NW5EC
Record Status Validated (UNII)
Record Version