Chemistry:Selenium disulfide

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Short description: Mixture of selenium sulfides
Selenium disulfide
Clinical data
Trade namesSelseb, Selsun Blue, others
Other namesSelenium sulfide
AHFS/Drugs.comMonograph
MedlinePlusa682258
Pregnancy
category
  • US: C (Risk not ruled out)[1]
Routes of
administration		Topical
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaS2Se
Molar mass143.09 g·mol−1
3D model (JSmol)
Density3 g/cm3
Melting point111 °C (232 °F)
Boiling point118 to 119 °C (244 to 246 °F) (decomposes)
Solubility in waternegligible mg/mL (20 °C)

Selenium disulfide, also known as selenium sulfide, is a chemical compound and medication used to treat seborrheic dermatitis, dandruff, and pityriasis versicolor.[2][3] It is applied to the affected area as a lotion or shampoo.[4] Symptoms frequently return if treatment is stopped.[5]

Side effects may include hair discoloration, skin irritation, and risk of systemic absorption and toxicity, among others.[2] Use is not recommended in children less than 2–5 years old.[2][5] Use in pregnancy or breastfeeding has not been studied.[1] It consists of a mixture of inorganic covalent compounds having an approximate empirical formulas of SeS2.[6] Selenium disulfide acts as a keratolytic and antifungal agent.[7][8][9]

Selenium disulfide was approved for medical use in the United States at least as early as 1951.[5] It is on the World Health Organization's List of Essential Medicines.[10] Selenium disulfide is available as a generic medication and over the counter.[4]

Medical uses

Selenium disulfide is sold as an antifungal agent in shampoos (such as Selsun Blue) for the treatment of dandruff and seborrheic dermatitis associated in the scalp with fungi of genus Malassezia.[11][12][13] It is also used on the body to treat tinea versicolor (pityriasis versicolor), a type of fungal skin infection caused by a different species of Malassezia.[3][14]

A 2015 systematic review of topical treatments for seborrheic dermatitis of the scalp identified only a single randomized controlled trial evaluating selenium disulfide for the condition.[15] It was a three-arm trial of 246 people with moderate to severe dandruff and compared treatment with 2% ketoconazole shampoo (n=97), 2.5% selenium disulfide shampoo (n=100), and placebo (shampoo base with no antiseborrheic agent) (n=49) for 29 days.[15][16] The study found a 73% reduction in dandruff score with ketoconazole, a 67% reduction with selenium disulfide, and a 45% reduction with placebo.[15][16] Based on the study, the systematic review concluded that selenium disulfide may be effective in the treatment of dandruff but that the available evidence is limited and overall evidence quality is low.[15] It also found that while selenium disulfide has infrequent side effects, it seems to have more side effects than ketoconazole shampoo.[15] Consequently, the review concluded that selenium disulfide should not be considered as a first-line therapy but instead should be used as an alternative treatment after other therapies like ketoconazole shampoo have proven not effective.[15]

A 2015 review recommended topical antifungal agents, topical corticosteroids, and topical calcineurin inhibitors like tacrolimus as the main treatments for seborrheic dermatitis based on good-quality evidence, rather than selenium disulfide for which evidence is much more limited.[17] However, the review did suggest use of over-the-counter selenium disulfide shampoos as an inexpensive option for managing mild symptoms of seborrheic dermatitis.[17]

Available forms

Selenium disulfide is available in the form of a prescription drug as a 2.25% medical shampoo.[18][19] In the United States , a 1% strength is available over-the-counter, and a 2.5% strength is also available with a prescription.[19] In Canada, the 2.5% strength is available over-the-counter.[19] Selsun Blue is an over-the-counter shampoo for dandruff with 1% selenium disulfide as its active ingredient.[20][19]

Side effects

Side effects of selenium disulfide shampoo for dandruff appear to be infrequent.[15][16] A randomized controlled trial of 100 people who received selenium disulfide reported side effects of itching or burning sensation of the scalp (3 people), eruption near the hairline (1 person), psoriasis (1 person), lightening or bleaching of hair color (2 people), orange staining of the scalp (1 person), and a chemical taste while shampooing (1 person).[15][16]

Selenium disulfide can cause discoloration of nails and light hair[7] and can alter the color of hair dyes. Several scattered case reports of orange to red–brown scalp discoloration with selenium sulfide shampoo exist.[7][21] The discoloration resolved shortly following discontinuation of selenium disulfide shampoo and its removal could be facilitated by lightly swabbing with isopropyl alcohol.[21] Selenium disulfide may also discolor metallic jewellery. Case reports of temporary diffuse hair loss with selenium disulfide shampoo exist as well.[22][23] Excessive environmental or occupational exposure to selenium has also been associated with hair loss and other adverse effects.[22] However, hair loss has not been reported with topical selenium disulfide in several large studies.[21]

Selenium disulfide should not be applied to damaged skin as there is a risk of systemic absorption and associated toxicity.[2] Systemic symptoms may include tremors, weakness, lethargy, lower abdominal pain, and occasional vomiting.[2] These symptoms usually resolve within 10 days following exposure.[2]

Pharmacology

Pharmacodynamics

Selenium disulfide acts as an antifungal and keratolytic agent to treat seborrheic dermatitis and dandruff.[7][8][9]

Pharmacokinetics

The systemic absorption and toxicity of orally administered selenium sulfide has been studied in animals.[24][7] Topical use of selenium sulfide in the form of a shampoo or lotion in humans does not appear to normally increase circulating or urinary selenium levels.[25][26][27][28][29] However, application of selenium disulfide to damaged skin can result in systemic absorption and has been associated with cases of toxicity.[2] Selenium disulfide appears to be much less toxic than other selenium salts, which may be attributed to its low aqueous solubility and very poor systemic absorption.[7]

Chemistry

Composition

Structure of 1,2,3-Se3S5, illustrative of selenium sulfide.

Selenium disulfide has a composition that approximates to SeS2 and is sometimes called selenium sulfide. However, as used in proprietary formulations, it is not a pure chemical compound but a mixture of eight-membered-ring compounds where the overall Se:S ratio is 1:2. The specific chemicals contain a variable number of S and Se atoms, SenS8−n.[30]

Many selenium sulfides are known, as indicated by 77Se-NMR spectroscopy.[31]

History

Selenium sulfide was introduced for medical use in the United States in 1951.[5][19]

Selenium monosulfide, along with elemental selenium and sulfur, has been used in medicinal preparations in the past,[32] causing confusion and contradiction[33] as to exactly what form selenium is in any given topical preparation.

Society and culture

Popular culture

In the film Evolution selenium was mentioned as an active ingredient of Head & Shoulders. A group of academics, therefore, tried to use this brand of shampoo to stop an alien invasion after discovering that the alien life form was sensitive to selenium.[34]

Research

Selenium disulfide has been suggested to be effective as a treatment for hyperkeratosis based on a small case series of three treated patients.[35] It has also been reported to be effective in the treatment of scalp psoriasis based on clinical observation of over 100 treated patients and two case reports of dramatic response.[36]

Selenium sulfide is under development for the treatment of meibomianitis (meibomian gland dysfunction) and dry eyes in topical and ophthalmic formulations.[37][38][19] As of March 2021, it is in phase 2/3 clinical trials for meibomianitis and phase 2 trials for dry eyes.[37] The developmental code name of selenium sulfide for these uses is AZR-MD-001 and it is being developed by Azura Ophthalmics.[37]

References

  1. ↑ 1.0 1.1 "Selenium sulfide topical Use During Pregnancy". https://www.drugs.com/pregnancy/selenium-sulfide-topical.html. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 WHO Model Formulary 2008. World Health Organization. 2009. p. 297. ISBN 9789241547659. 
  3. ↑ 3.0 3.1 "Management of seborrheic dermatitis and pityriasis versicolor". American Journal of Clinical Dermatology 1 (2): 75–80. 2000. doi:10.2165/00128071-200001020-00001. PMID 11702314. 
  4. ↑ 4.0 4.1 Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. 2015. p. 194. ISBN 9781284057560. 
  5. ↑ 5.0 5.1 5.2 5.3 "Selenium Sulfide". The American Society of Health-System Pharmacists. https://www.drugs.com/monograph/selenium-sulfide.html. 
  6. ↑ (in en) Biological Interactions Of Sulfur Compounds. CRC Press. 2003. p. 174. ISBN 9780203362525. https://books.google.com/books?id=bRw7mvUzq9MC&pg=PA174. 
  7. ↑ 7.0 7.1 7.2 7.3 7.4 7.5 "The Biological Activity of Selenium Sulfide". Sulfur Reports 13 (2): 279–289. August 1993. doi:10.1080/01961779308048957. ISSN 0196-1772. 
  8. ↑ 8.0 8.1 "Treatment of seborrheic dermatitis: a comprehensive review". The Journal of Dermatological Treatment 30 (2): 158–169. March 2019. doi:10.1080/09546634.2018.1473554. PMID 29737895. 
  9. ↑ 9.0 9.1 "Etiology and management of Seborrheic dermatitis". Dermatology 208 (2): 89–93. 2004. doi:10.1159/000076478. PMID 15056994. 
  10. ↑ World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 2019. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO. 
  11. ↑ "Selenium(IV) sulfide". Pharmacy Codes. http://pharmacycode.com/Selenium(IV)_sulfide.html. 
  12. ↑ "Chemicals of Selenium". selenium.se. http://www.selenium.se/selenium-disulfide.html. 
  13. ↑ "Selenium sulfide". DermNet NZ. New Zealand Dermatological Society Incorporated. http://dermnetnz.org/treatments/selenium.html. 
  14. ↑ "Diagnosis and treatment of tinea versicolor". The Journal of Family Practice 43 (2): 127–132. August 1996. PMID 8708621. 
  15. ↑ 15.0 15.1 15.2 15.3 15.4 15.5 15.6 15.7 "Seborrhoeic dermatitis of the scalp". BMJ Clinical Evidence 2015. May 2015. PMID 26016669. 
  16. ↑ 16.0 16.1 16.2 16.3 "A randomized, double-blind, placebo-controlled trial of ketoconazole 2% shampoo versus selenium sulfide 2.5% shampoo in the treatment of moderate to severe dandruff". Journal of the American Academy of Dermatology 29 (6): 1008–1012. December 1993. doi:10.1016/0190-9622(93)70282-x. PMID 8245236. 
  17. ↑ 17.0 17.1 "Diagnosis and treatment of seborrheic dermatitis". American Family Physician 91 (3): 185–190. February 2015. PMID 25822272. 
  18. ↑ "Selenium sulfide shampoo". Bi-Coastal Pharma International LLC. January 2022. https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=dacbcc5a-d37c-4ea3-8f47-35abb64c7519&type=display. 
  19. ↑ 19.0 19.1 19.2 19.3 19.4 19.5 "Meibomian Gland Dysfunction: A Dermatological Perspective on Pathogenesis and Treatment Outlook". Clinical Ophthalmology 15: 4399–4404. 2021. doi:10.2147/OPTH.S327407. PMID 34785886. 
  20. ↑ "A randomized, controlled clinical trial of four anti-dandruff shampoos". The Journal of International Medical Research 9 (2): 152–156. 1981. doi:10.1177/030006058100900213. PMID 7014286. 
  21. ↑ 21.0 21.1 21.2 "Scalp discoloration from selenium sulfide shampoo: a case series and review of the literature". Pediatric Dermatology 29 (1): 84–88. 2012. doi:10.1111/j.1525-1470.2011.01410.x. PMID 21453309. 
  22. ↑ 22.0 22.1 "Adverse health effects of selenium in humans". Reviews on Environmental Health 16 (4): 233–251. 2001. doi:10.1515/reveh.2001.16.4.233. PMID 12041880. 
  23. ↑ "Diffuse hair loss associated with selenium (selsun) sulfide shampoo". Journal of the American Medical Association 160 (16): 1397–1398. April 1956. doi:10.1001/jama.1956.02960510023006. PMID 13306564. 
  24. ↑ "[On the absorption and toxicity of selenium sulfide]" (in German). Archiv für Toxikologie 24 (4): 341–344. 1969. doi:10.1007/BF00577584. PMID 5795758. 
  25. ↑ "Disposition kinetics of selenium in healthy volunteers following therapeutic shampoo treatment". Environmental Toxicology and Pharmacology 29 (3): 252–259. May 2010. doi:10.1016/j.etap.2010.02.001. PMID 21787610. 
  26. ↑ "Lack of serum selenium rise after overnight application of selenium sulfide". Archives of Dermatology 129 (5): 646–648. May 1993. doi:10.1001/archderm.1993.01680260118023. PMID 8481030. 
  27. ↑ "Selenium sulfide in tinea versicolor: blood and urine levels". Journal of the American Academy of Dermatology 11 (2 Pt 1): 238–241. August 1984. doi:10.1016/s0190-9622(84)70156-3. PMID 6480923. 
  28. ↑ "Safety evaluation of selenium sulfide antidandruff shampoos". Toxicology and Applied Pharmacology 20 (1): 89–96. September 1971. doi:10.1016/0041-008x(71)90092-5. PMID 5110829. 
  29. ↑ "Treatment of seborrheic dermatitis with a shampoo containing selenium disulfide". A.M.A. Archives of Dermatology and Syphilology 64 (1): 41–48. July 1951. doi:10.1001/archderm.1951.01570070044007. PMID 14837491. 
  30. ↑ Cyclic selenium sulfides R. Steudel, R. Laitinen, Topics in Current Chemistry, (1982), 102, 177-197
  31. ↑ "Chalcogen ring interconversion pathways. 77Se NMR spectroscopic study of the decomposition of 1,2,3,4,5-Se5S2 to 1,2,3,4,5,6-Se6S2 and 1,2,3,4-Se4S2". Inorganic Chemistry 30 (19): 3679. 1991. doi:10.1021/ic00019a022. 
  32. ↑ "Definition: selenium sulfide". Online Medical Dictionary. http://cancerweb.ncl.ac.uk/cgi-bin/omd?selenium+sulfide. 
  33. ↑ "Selenium Sulfide". DrugBank. http://redpoll.pharmacy.ualberta.ca/drugbank/cgi-bin/getCard.cgi?CARD=APRD01323.txt. 
  34. ↑ "Evolution (2001)". https://www.imdb.com/title/tt0251075/trivia. 
  35. ↑ "Topical Selenium Sulfide for the Treatment of Hyperkeratosis". Dermatology and Therapy 8 (4): 639–646. December 2018. doi:10.1007/s13555-018-0259-9. PMID 30203232. 
  36. ↑ "Treatment of psoriasis with topical selenium sulphide". The British Journal of Dermatology 117 (5): 665–666. November 1987. doi:10.1111/j.1365-2133.1987.tb07503.x. PMID 3689688. 
  37. ↑ 37.0 37.1 37.2 "AZR MD 001". AdisInsight. Springer Nature Switzerland AG. https://adisinsight.springer.com/drugs/800050488. 
  38. ↑ "ARVO 2021: Investigational Agent Containing Selenium Sulfide Shows Promise for Meibomian Gland Dysfunction" (in en). https://www.practiceupdate.com/content/arvo-2021-investigational-agent-containing-selenium-sulfide-shows-promise-for-meibomian-gland-dysfunction/118093. 

Further reading

External links



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