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
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
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 |
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| Patients with epidermodysplasia verruciformis show no response to contact immunotherapy. | 2001 |
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| Current and potential agents for the treatment of alopecia areata. | 2001 Feb |
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| Squaric acid dibutylester: indications for use and efficacy in alopecia areata. | 2001 Jul |
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| [Treatment of alopecia areata with diphencyprone]. | 2001 Oct-Dec |
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| An answer to some questions raised by skin reactions observed during squaric acid dibutylester contact sensitization. | 2001 Sep |
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| The therapeutic use of topical contact sensitizers in benign dermatoses. | 2001 Sep |
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| Adult and paediatric contact immunotherapy with squaric acid dibutylester (SADBE) for recurrent, multiple, resistant, mucocutaneous anogenital warts. | 2002 Aug |
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| Insights into the quantitative relationship between sensitization and challenge for allergic contact dermatitis reactions. | 2002 Aug 15 |
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| A clinical study of childhood alopecia areata in Singapore. | 2002 Jul-Aug |
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| Topical immunotherapy with squaric acid dibutylester: unusual hair pigmentary changes in two cases of alopecia areata. | 2002 Mar |
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| The pattern and profile of alopecia areata in Singapore--a study of 219 Asians. | 2002 Nov |
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| Topical immunotherapy with contact sensitizers: a model to study the natural history of delayed hypersensitivity. | 2002 Oct |
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| Seventeen cases of alopecia areata: combination of SADBE topical immunotherapy with other therapies. | 2002 Oct |
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| Lentiginous eruption due to topical immunotherapy. | 2003 Apr |
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| Alopecia areata: treatment of today and tomorrow. | 2003 Jun |
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| Topical sensitizers in alopecia areata. | 2004 Aug |
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| Chronic delayed-type hypersensitivity reaction as a means to treat alopecia areata. | 2004 Mar |
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| 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 |
|
| Topical immunotherapy of severe alopecia areata with diphenylcyclopropenone (DPCP): experience in an Iranian population. | 2005 May 26 |
|
| Prolonged dermatitis distant to the site of squaric acid dibutyl ester applications and recovery of alopecia areata. | 2005 Sep |
|
| Determination of the sildenafil effect on alopecia areata in childhood: An open-pilot comparison study. | 2006 |
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| A chronic contact eczema impedes migration of antigen-presenting cells in alopecia areata. | 2006 Jul |
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| Efficacy and safety of the topical sensitizer squaric acid dibutyl ester in Alopecia areata and factors influencing the outcome. | 2006 Mar |
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| Haptens as drugs: contact allergens are powerful topical immunomodulators. | 2006 May |
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| Biphenyls as potent vitronectin receptor antagonists. Part 3: Squaric acid amides. | 2007 Nov 15 |
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| The importance of myeloid-derived suppressor cells in the regulation of autoimmune effector cells by a chronic contact eczema. | 2007 Oct 15 |
|
| 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 |
|
| Determination of in vivo dose response and allergen-specific T cells in subjects contact-sensitized to squaric acid dibutyl ester. | 2008 Mar-Apr |
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| Usefulness of topical immunotherapy with squaric acid dibutylester for refractory common warts on the face and neck. | 2009 Dec |
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| Treatment of alopecia areata in children. | 2009 Jul |
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| Immunotherapy for childhood warts. | 2009 Jul |
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| Fexofenadine hydrochloride enhances the efficacy of contact immunotherapy for extensive alopecia areata: Retrospective analysis of 121 cases. | 2009 Jun |
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| Long-pulsed Nd:YAG laser treatment of warts: report on a series of 369 cases. | 2009 Oct |
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| Vitiligo after diphencyprone for alopecia areata. | 2010 |
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| Renbok phenomenon and contact sensitization in a patient with alopecia universalis. | 2010 Apr |
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| Topical immunotherapy in alopecia areata. | 2010 Jan |
|
| Contact immunotherapy-induced Renbök phenomenon in a patient with alopecia areata and psoriasis vulgaris. | 2010 Jan-Feb |
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| Management of alopecia areata. | 2010 Jul 23 |
|
| Squaric acid/4-aminoquinoline conjugates: novel potent antiplasmodial agents. | 2013 Nov |
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C020637
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ACTIVE MOIETY
