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
| Molecular Formula | C12H18O4 |
| Molecular Weight | 226.2689 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Squaric acid/4-aminoquinoline conjugates: novel potent antiplasmodial agents. | 2013-11 |
|
| Management of alopecia areata. | 2010-07-23 |
|
| Renbok phenomenon and contact sensitization in a patient with alopecia universalis. | 2010-04 |
|
| Topical immunotherapy in alopecia areata. | 2010-01 |
|
| Vitiligo after diphencyprone for alopecia areata. | 2010 |
|
| Usefulness of topical immunotherapy with squaric acid dibutylester for refractory common warts on the face and neck. | 2009-12 |
|
| Contact immunotherapy-induced Renbök phenomenon in a patient with alopecia areata and psoriasis vulgaris. | 2009-10-14 |
|
| Long-pulsed Nd:YAG laser treatment of warts: report on a series of 369 cases. | 2009-10 |
|
| Treatment of alopecia areata in children. | 2009-07 |
|
| Immunotherapy for childhood warts. | 2009-07 |
|
| Fexofenadine hydrochloride enhances the efficacy of contact immunotherapy for extensive alopecia areata: Retrospective analysis of 121 cases. | 2009-06 |
|
| Determination of in vivo dose response and allergen-specific T cells in subjects contact-sensitized to squaric acid dibutyl ester. | 2008-04-17 |
|
| Discoid lupus erythematosus exacerbated by contact dermatitis caused by use of squaric acid dibutylester for topical immunotherapy in a patient with alopecia areata. | 2008-03 |
|
| Biphenyls as potent vitronectin receptor antagonists. Part 3: Squaric acid amides. | 2007-11-15 |
|
| The importance of myeloid-derived suppressor cells in the regulation of autoimmune effector cells by a chronic contact eczema. | 2007-10-15 |
|
| A chronic contact eczema impedes migration of antigen-presenting cells in alopecia areata. | 2006-07 |
|
| Haptens as drugs: contact allergens are powerful topical immunomodulators. | 2006-05 |
|
| Efficacy and safety of the topical sensitizer squaric acid dibutyl ester in Alopecia areata and factors influencing the outcome. | 2006-03 |
|
| Determination of the sildenafil effect on alopecia areata in childhood: An open-pilot comparison study. | 2006 |
|
| Prolonged dermatitis distant to the site of squaric acid dibutyl ester applications and recovery of alopecia areata. | 2005-09 |
|
| Topical immunotherapy of severe alopecia areata with diphenylcyclopropenone (DPCP): experience in an Iranian population. | 2005-05-26 |
|
| 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. | 2005-02 |
|
| Topical sensitizers in alopecia areata. | 2004-08 |
|
| Chronic delayed-type hypersensitivity reaction as a means to treat alopecia areata. | 2004-03 |
|
| Alopecia areata: treatment of today and tomorrow. | 2003-06 |
|
| Lentiginous eruption due to topical immunotherapy. | 2003-04 |
|
| The pattern and profile of alopecia areata in Singapore--a study of 219 Asians. | 2002-11 |
|
| Topical immunotherapy with contact sensitizers: a model to study the natural history of delayed hypersensitivity. | 2002-10 |
|
| Seventeen cases of alopecia areata: combination of SADBE topical immunotherapy with other therapies. | 2002-10 |
|
| A clinical study of childhood alopecia areata in Singapore. | 2002-09-11 |
|
| Insights into the quantitative relationship between sensitization and challenge for allergic contact dermatitis reactions. | 2002-08-15 |
|
| Adult and paediatric contact immunotherapy with squaric acid dibutylester (SADBE) for recurrent, multiple, resistant, mucocutaneous anogenital warts. | 2002-08 |
|
| [Treatment of alopecia areata with diphencyprone]. | 2002-07-03 |
|
| Topical immunotherapy with squaric acid dibutylester: unusual hair pigmentary changes in two cases of alopecia areata. | 2002-03 |
|
| An answer to some questions raised by skin reactions observed during squaric acid dibutylester contact sensitization. | 2001-09 |
|
| The therapeutic use of topical contact sensitizers in benign dermatoses. | 2001-09 |
|
| Squaric acid dibutylester: indications for use and efficacy in alopecia areata. | 2001-07 |
|
| Current and potential agents for the treatment of alopecia areata. | 2001-02 |
|
| Patients with epidermodysplasia verruciformis show no response to contact immunotherapy. | 2001 |
|
| The loss of contact sensitization in man. | 1991-03 |
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 18:59:49 GMT 2025
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Mon Mar 31 18:59:49 GMT 2025
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| Record UNII |
4RTO57VG65
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| Record Status |
Validated (UNII)
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