Dibutyl squarate

Last updated
Dibutyl squarate
Dibutyl squarate.svg
Names
IUPAC name
3,4-Dibutoxy-3-cyclobutene-1,2-dione
Other names
Squaric acid dibutyl ester; SADBE
Identifiers
3D model (JSmol)
1968189
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.157.137 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 628-906-7
PubChem CID
UNII
  • InChI=1S/C12H18O4/c1-3-5-7-15-11-9(13)10(14)12(11)16-8-6-4-2/h3-8H2,1-2H3
    Key: XBRWELTXMQSEIN-UHFFFAOYSA-N
  • CCCCOC1=C(C(=O)C1=O)OCCCC
Properties
C12H18O4
Molar mass 226.272 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H317, H319, H335
P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P313, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dibutyl squarate (also known as squaric acid dibutyl ester or SADBE) is a chemical compound with the molecular formula C12H18O4. It is the dibutyl derivative of squaric acid.

Medically, it is used for the treatment of warts [1] and for treating alopecia areata or alopecia totalis (autoimmune hair loss) through topical immunotherapy involving the production of an allergic rash. [2] [3] Dibutyl squarate is currently undergoing trials for use in treating herpes labialis (cold sores). [4]

Related Research Articles

<span class="mw-page-title-main">Wart</span> Small, rough growth resembling a cauliflower or a solid blister

Warts are non-cancerous viral growths usually occurring on the hands and feet but can also affect other locations, such as the genitals or face. One or many warts may appear. They are distinguished from cancerous tumors as they are caused by a viral infection, such as a human papillomavirus, rather than a cancerous growth.

<span class="mw-page-title-main">Alopecia areata</span> Medical condition

Alopecia areata, also known as spot baldness, is a condition in which hair is lost from some or all areas of the body. It often results in a few bald spots on the scalp, each about the size of a coin. Psychological stress and illness are possible factors in bringing on alopecia areata in individuals at risk, but in most cases there is no obvious trigger. People are generally otherwise healthy. In a few cases, all the hair on the scalp is lost, or all body hair is lost. Hair loss can be permanent, or temporary.

<span class="mw-page-title-main">Plantar wart</span> Medical condition

A plantar wart, or verruca vulgaris, is a wart occurring on the bottom of the foot or toes. Its color is typically similar to that of the skin. Small black dots often occur on the surface. One or more may occur in an area. They may result in pain with pressure such that walking is difficult.

<span class="mw-page-title-main">Aciclovir</span> Antiviral medication used against herpes, chickenpox and shingles

Aciclovir (ACV), also known as acyclovir, is an antiviral medication. It is primarily used for the treatment of herpes simplex virus infections, chickenpox, and shingles. Other uses include prevention of cytomegalovirus infections following transplant and severe complications of Epstein–Barr virus infection. It can be taken by mouth, applied as a cream, or injected.

<span class="mw-page-title-main">Adapalene</span> Third-generation topical retinoid

Adapalene is a third-generation topical retinoid primarily used in the treatment of mild-moderate acne, and is also used off-label to treat keratosis pilaris as well as other skin conditions. Studies have found adapalene is as effective as other retinoids, while causing less irritation. It also has several advantages over other retinoids. The adapalene molecule is more stable compared to tretinoin and tazarotene, which leads to less concern for photodegradation. It is also chemically more stable compared to the other two retinoids, allowing it to be used in combination with benzoyl peroxide. Due to its effects on keratinocyte proliferation and differentiation, adapalene is superior to tretinoin for the treatment of comedonal acne and is often used as a first-line agent. The Swiss company Galderma sells adapalene under the brand-name product Differin.

<span class="mw-page-title-main">Clobetasol propionate</span> Clobetasol Propionate Cream usp 0.05

Clobetasol propionate is a corticosteroid used to treat skin conditions such as eczema, contact dermatitis, seborrheic dermatitis, and psoriasis. It is applied to the skin as a cream, ointment, or shampoo. Use should be short term and only if other weaker corticosteroids are not effective. Use is not recommended in rosacea or perioral dermatitis.

<span class="mw-page-title-main">Alopecia universalis</span> Medical condition

Alopecia universalis(AU), also known as alopecia areata universalis, is a medical condition involving the loss of all body hair, including eyebrows, eyelashes, chest hair, armpit hair, and pubic hair. It is the most severe form of alopecia areata. People with the disease are usually healthy and have no other symptoms and a normal life expectancy.

The management of hair loss, includes prevention and treatment of alopecia, baldness, and hair thinning, and regrowth of hair.

<span class="mw-page-title-main">Latanoprost</span> Chemical compound

Latanoprost, sold under the brand name Xalatan among others, is a medication used to treat increased pressure inside the eye. This includes ocular hypertension and open-angle glaucoma. Latanaprost is applied as eye drops to the eyes. Onset of effects is usually within four hours, and they last for up to a day.

Squaric acid, also called quadratic acid because its four carbon atoms approximately form a square, is a diprotic organic acid with the chemical formula C4O2(OH)2.

<span class="mw-page-title-main">Imiquimod</span> Chemical compound

Imiquimod, sold under the brand name Aldara among others, is a medication that acts as an immune response modifier that is used to treat genital warts, superficial basal cell carcinoma, and actinic keratosis. Scientists at 3M's pharmaceuticals division discovered the drug and 3M obtained the first FDA approval in 1997. As of 2015, imiquimod is generic and is available worldwide under many brands.

Hypnodermatology is an informal label for the use of hypnosis in treating the skin conditions that fall between conventional medical dermatology and the mental health disciplines.

1-Docosanol, also known as behenyl alcohol, is a saturated fatty alcohol containing 22 carbon atoms, used traditionally as an emollient, emulsifier, and thickener in cosmetics.

Madarosis is a condition that results in the loss of eyelashes, and sometimes eyebrows. The term "madarosis" is derived from the ancient Greek "madaros", meaning "bald". It originally was a disease of only losing eyelashes but it currently is the loss of both eyelashes and eyebrows. Eyebrows and eyelashes are both important in the prevention of bacteria and other foreign objects from entering the eye. A majority of patients with madarosis have leprosy, and it was reported that 76% of patients with varying types of leprosy had madarosis.

Non scarring hair loss, also known as noncicatricial alopecia is the loss of hair without any scarring being present. There is typically little inflammation and irritation, but hair loss is significant. This is in contrast to scarring hair loss during which hair follicles are replaced with scar tissue as a result of inflammation. Hair loss may be spread throughout the scalp (diffuse) or at certain spots (focal). The loss may be sudden or gradual with accompanying stress.

<span class="mw-page-title-main">Herpes</span> Viral disease caused by herpes simplex viruses

Herpes simplex, often known simply as herpes, is a viral infection caused by the herpes simplex virus. Herpes infections are categorized by the area of the body that is infected. The two major types of herpes are oral herpes and genital herpes, though other forms also exist.

<span class="mw-page-title-main">Cold sore</span> Herpes simplex virus infection of the lip

A cold sore is a type of herpes infection caused by the herpes simplex virus that affects primarily the lip. Symptoms typically include a burning pain followed by small blisters or sores. The first attack may also be accompanied by fever, sore throat, and enlarged lymph nodes. The rash usually heals within ten days, but the virus remains dormant in the trigeminal ganglion. The virus may periodically reactivate to create another outbreak of sores in the mouth or lip.

<span class="mw-page-title-main">Tofacitinib</span> Medication

Tofacitinib, sold under the brand Xeljanz among others, is a medication used to treat rheumatoid arthritis, psoriatic arthritis, ankylosing spondylitis, polyarticular course juvenile idiopathic arthritis, and ulcerative colitis. It is a janus kinase (JAK) inhibitor, discovered and developed by the National Institutes of Health and Pfizer.

<span class="mw-page-title-main">Diphenylcyclopropenone</span> Chemical compound

Diphenylcyclopropenone (diphencyprone) is a topically administered experimental drug intended for treating alopecia areata and alopecia totalis. Topical immunotherapy using diphenylcyclopropenone may also be an effective treatment option for recalcitrant warts. It is not approved by either the Food and Drug Administration or the European Medicines Agency.

<span class="mw-page-title-main">Baricitinib</span> Chemical compound

Baricitinib, sold under the brand name Olumiant among others, is an immunomodulatory medication used for the treatment of rheumatoid arthritis, alopecia areata, and COVID-19. It acts as an inhibitor of janus kinase (JAK), blocking the subtypes JAK1 and JAK2.

References

  1. Silverberg, Nanette B.; Lim, Joseph K.; Paller, Amy S.; Mancini, Anthony J. (2000). "Squaric acid immunotherapy for warts in children". Journal of the American Academy of Dermatology. 42 (5): 803–808. doi:10.1067/mjd.2000.103631. PMID   10775858.
  2. Yoshimasu, Takashi; Furukawa, Fukumi (2016). "Modified immunotherapy for alopecia areata". Autoimmunity Reviews. 15 (7): 664–667. doi:10.1016/j.autrev.2016.02.021. PMID   26932732.
  3. Holzer, A. M.; Kaplan, L. L.; Levis, W. R. (2006). "Haptens as drugs: contact allergens are powerful topical immunomodulators". J. Drugs Dermatol. 5 (5): 410–416. PMID   16703776.
  4. Kimball, Alexandra (2017-05-05). "A Clinical Trial to Test the Safety and Efficacy of Squaric Acid Dibutyl Ester for the Treatment of Herpes Labialis". Massachusetts General Hospital.{{cite journal}}: Cite journal requires |journal= (help)