DIBUTYL SQUARATE

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H18O4
Molecular Weight	226.2689
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCOC1=C(OCCCC)C(=O)C1=O

InChI

InChIKey=XBRWELTXMQSEIN-UHFFFAOYSA-N

InChI=1S/C12H18O4/c1-3-5-7-15-11-9(13)10(14)12(11)16-8-6-4-2/h3-8H2,1-2H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25889130 | https://www.ncbi.nlm.nih.gov/pubmed/31237076 | https://www.ncbi.nlm.nih.gov/pubmed/18413111

Squaric acid dibutyl ester is a cyclic ketone and diether that is used as a topical sensitizing agent for the treatment of alopecia areata. The mechanism of action is not fully understood, but is believed to redirect the inflammatory response by invoking allergic contact dermatitis. In clinical trials Squaric acid dibutyl ester had a total response rate (defined as moderate to good regrowth or at least 30% improvement) from 29% to 87%. The most common adverse effects associated with Squaric acid dibutyl ester include eczema, auto-eczematization, blistering, and swelling of regional lymph nodes.

Approval Year

PubMed

Title	Date	PubMed
The loss of contact sensitization in man.	1991 Mar	1868701
Current and potential agents for the treatment of alopecia areata.	2001 Feb	11311114
Squaric acid dibutylester: indications for use and efficacy in alopecia areata.	2001 Jul	11453831
[Treatment of alopecia areata with diphencyprone].	2001 Oct-Dec	12092234
An answer to some questions raised by skin reactions observed during squaric acid dibutylester contact sensitization.	2001 Sep	11553162
The therapeutic use of topical contact sensitizers in benign dermatoses.	2001 Sep	11531828
Topical sensitizers in alopecia areata.	2004 Aug	15471045
Topical immunomodulator therapy with squaric acid dibutylester (SADBE) is effective treatment for severe alopecia areata (AA): results of an open-label, paired-comparison, clinical trial.	2005 Feb	15897160
Topical immunotherapy of severe alopecia areata with diphenylcyclopropenone (DPCP): experience in an Iranian population.	2005 May 26	15918897
Prolonged dermatitis distant to the site of squaric acid dibutyl ester applications and recovery of alopecia areata.	2005 Sep	16045698
Efficacy and safety of the topical sensitizer squaric acid dibutyl ester in Alopecia areata and factors influencing the outcome.	2006 Mar	16573260
Haptens as drugs: contact allergens are powerful topical immunomodulators.	2006 May	16703776
Biphenyls as potent vitronectin receptor antagonists. Part 3: Squaric acid amides.	2007 Nov 15	17910915
The importance of myeloid-derived suppressor cells in the regulation of autoimmune effector cells by a chronic contact eczema.	2007 Oct 15	17911592
Discoid lupus erythematosus exacerbated by contact dermatitis caused by use of squaric acid dibutylester for topical immunotherapy in a patient with alopecia areata.	2008 Mar	18346258
Treatment of alopecia areata in children.	2009 Jul	19685659
Fexofenadine hydrochloride enhances the efficacy of contact immunotherapy for extensive alopecia areata: Retrospective analysis of 121 cases.	2009 Jun	19500180
Vitiligo after diphencyprone for alopecia areata.	2010	20585597
Topical immunotherapy in alopecia areata.	2010 Jan	21188022
Management of alopecia areata.	2010 Jul 23	20656774
Squaric acid/4-aminoquinoline conjugates: novel potent antiplasmodial agents.	2013 Nov	24077527

Patents

Sample Use Guides

In Vivo Use Guide

2% solution applied for sensitization to the inner arm.

Route of Administration: Topical

Name

Type

Language

DIBUTYL SQUARATE

Common Name

English

SQUARIC ACID DIBUTYL ESTER

Preferred Name

English

SQUARIC ACID DIBUTYLESTER

Common Name

English

SQX-770

Common Name

English

Squaric acid dibutylester [WHO-DD]

Common Name

English

3,4-DIBUTOXY-3-CYCLOBUTENE-1,2-DIONE

Systematic Name

English

SQUARIC ACID DIBUTYLESTER [MI]

Common Name

English

SQX770

Code

English

NSC-113489

Code

English

Code System Code Type Description

SMS_ID

100000077827