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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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Ultraviolet radiation causes less immunosuppression in patients with polymorphic light eruption than in controls.
2004 Feb
UV-induced tolerance to a contact allergen is impaired in polymorphic light eruption.
2010 Nov
A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells.
2010 Sep
Impaired hapten sensitization in patients with autoimmune disease.
2011 Sep
High altitude impairs in vivo immunity in humans.
2013 Jun
Systemic immunogenicity of para-Phenylenediamine and Diphenylcyclopropenone: two potent contact allergy-inducing haptens.
2014 Jan
Human relevance of an in vitro gene signature in HaCaT for skin sensitization.
2015 Feb
Patents

Patents

Sample Use Guides

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
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:26:30 GMT 2023
Edited
by admin
on Fri Dec 15 15:26:30 GMT 2023
Record UNII
I7G14NW5EC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIPHENCYPRONE
MART.   MI   WHO-DD  
Common Name English
DIPHENCYPRONE [MI]
Common Name English
DIPHENYLCYCLOPENONE
Common Name English
Diphencyprone [WHO-DD]
Common Name English
2,3-DIPHENYL-2-CYCLOPROPEN-1-ONE
Systematic Name English
DIPHENCYPRONE [MART.]
Common Name English
DIPHENYLCYCLOPROPENONE
Systematic Name English
NSC-57541
Code English
Classification Tree Code System Code
NCI_THESAURUS C2139
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
FDA ORPHAN DRUG 164502
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
FDA ORPHAN DRUG 473615
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
EU-Orphan Drug EU/3/06/380
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
Code System Code Type Description
CAS
886-38-4
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
PRIMARY
EVMPD
SUB13621MIG
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
PRIMARY
FDA UNII
I7G14NW5EC
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
PRIMARY
WIKIPEDIA
DIPHENYLCYCLOPROPENONE
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
PRIMARY
PUBCHEM
65057
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
PRIMARY
NCI_THESAURUS
C28994
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
PRIMARY
ECHA (EC/EINECS)
212-948-4
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
PRIMARY
NSC
57541
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
PRIMARY
MERCK INDEX
m4608
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB12173
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
PRIMARY
CHEBI
53074
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
PRIMARY
MESH
C029402
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
PRIMARY
SMS_ID
100000088826
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID2046545
Created by admin on Fri Dec 15 15:26:30 GMT 2023 , Edited by admin on Fri Dec 15 15:26:30 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY