Chemistry:Ammonium bituminosulfonate

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Short description: Chemical compound
Ichthammol
Ichthyol-Salbe.jpg
A tube of medicinal ammonium bituminosulfonate (ichthyol)
Clinical data
Trade namesIchthyol
Other namesammonium bituminosulfonate; ammonium bituminosulphonate; bituminosulfonates
Identifiers
CAS Number
DrugBank
UNII

Ichthammol or ammonium bituminosulfonate (brand name Ichthyol) is a medication derived from sulfur-rich oil shale (bituminous schists). It is used (sometimes in combination with zinc oxide) as a treatment for different skin diseases, including eczema and psoriasis (see below). It is applied on the skin as an ointments, most commonly containing 10% or 20% ichthammol.

Bituminosulfonates are considered topical therapeutic agents with very good tolerability.[1]

The use of ichthammol in dermatology was promoted by German physician Paul Gerson Unna.[2][3][4]

Ichthammol ointments, commonly known as black ointment or drawing salve, should not be confused with black salve, an escharotic (corrosive) paste intended to destroy skin tissue.[5] In contrast, ichthammol does not have any corrosive properties on the skin.

Production

Ichthammol is obtained through three steps from bituminous schists: dry distillation, sulfonation of the resulting oil (or purified fractions thereof), and finally neutralization with ammonia.[6]

Properties

Ichthammol is a viscous, water-soluble substance with a characteristic bitumen-like odor.[6] It is incompatible with acids, alkali carbonates or hydrates and alkaloidal salts. It is a thick reddish brown liquid, possessing a bituminous odor and taste. It is soluble in water and miscible with glycerin, but is nearly insoluble in strong alcohol or concentrated ether. It contains a large percentage of organically combined sulfur.

Chemically speaking ichthammol is a sulfonated shale oil. From elemental analysis, the composition of ichthammol was calculated to be C28H36S5O6(NH4)2.[7] However, as a product of natural origin, it is a mixture of many different compounds.[8]

Similar materials

Similar substances can be made by altering the starting material. An "ammonium sufobitol" (Tumenol-Ammonium), made from light shale oil of the Messel pit, was sold until 2000 in Germany.[9] The Chinese material labelled as "ichthammol" are actually an ersatz product made from vegetable oil.

Ichtasol

Ichtasol
Clinical data
Trade namesIchthyol-Pale
Other namessodium shale oil sulfonate (former INCI); Ichthyolic Acid, Sodium Salt; sodium salt of light bitumenosulfonate
ATC code
Identifiers
CAS Number
DrugBank
UNII
KEGG

Ichtasol (USAN: Ictasol) is produced from the light (as opposed to heavy) fraction of distilled shale oil. It has a pale appearance.[10] There appears to be an oral preparation made from this mixture.[11]

Chinese vegetable oil product

"Ichthammol" (鱼石脂 Yushizhi) made in China does not meet standards for ichthammol as specified in United States Pharmacopoeia (USP), European Pharmacopoeia (Ph.Eur), or for the CAS number. Instead of requiring bituminous schists like these definitions, the Chinese Pharmacopoeia definition for "ichthammol" uses ordinary vegetable oil:

Ichthammol is a mixture obtained by sulfurization of vegetable oils (soybean oil, tung oil, corn oil, etc.), sulfonation, and neutralization with ammonia. Organic sulfur content ≥ 5.5%, ammonium content ≥ 2.5%. — Chinese definition according to ChP 10[12]

As a result, Chinese "ichthammol" is very different from standard ichthammol. The characteristic bitumen-like odor (originating from the bituminous source material) is missing with Chinese material.[13]

Medical use

Skin disorders

It is used to treat a variety of skin disorders as e.g. eczema, psoriasis, Acne rosacea and acne.[6][14][15]

According to the "list of preferred Specials" by the British Association of Dermatologists (BAD) ichthammol can be used in dermatology prescribing to treat acutely inflamed atopic eczema, among others.[16] A corresponding recommendation exists for bituminosulfonates in Germany. According to “guideline atopic eczema” bituminosulfonates can be considered for treatment of atopic eczema based on general clinic experience.[17] In the European Dermatology Forum (EDF) guidelines for treatment of atopic eczema ichthammol is recommended as a useful addition to the basic treatment regimen, especially in mild disease or if TCS treatment is not possible from a patient’s perspective, e.g. corticophobia (steroid phobia).[18]

Ear infections

In otology, a mixture of glycerol and ichthammol (G & I) is used for the topical treatment of ear infections.[19] It is effective against Gram-positive bacteria. The anti-inflammatory action is explained by its influence on the formation, secretion, and effect of inflammation mediators.[20][21]

Availability

Ichthammol is available in pharmacies for compounding medications. Different sources of information exist for exemplary formulations (creams, shake lotions, suppositories, etc.).[22][23][24]

Pharmacology

Ichthammol has anti-inflammatory, bactericidal, and fungicidal properties.[25]

Veterinary use

The European Medicines Agency published a summary report on ichthyol-substances (synonym: bituminosulfonates) during the course of the European Maximum Residue Limits (MRL) procedure[11] in veterinary medicine. The Committee for Medicinal Products for Veterinary Use (CVMP) decided that due to good tolerance and safety, there is no need to establish an MRL for ichthyol-substances. As a result, ichthyol-substances can be applied topically in all mammalian food-producing species without restriction.

See also

References

  1. ↑ "Bituminosulfonate.". Therapeutische Verfahren in der Dermatologie–Dermatika und Kosmetika. Berlin, Wien: Blackwell Wissenschafts-Verlag. 2001. pp. 165–171. 
  2. ↑ Paul Gerson Unna: About Ichthyol. In: Monatshefte für praktische Dermatologie, Band XXV, 1897 (in German).
  3. ↑ "Unna, Paul Gerson - Deutsche Biographie" (in de). Deutsche Biographie. https://www.deutsche-biographie.de/sfz107295.html. 
  4. ↑ "110 Jahre Ichthyol-Schieferöl: Klassiker mit breitem Spektrum an Indikationen" (in de). Deutsches Ärzteblatt. Deutscher Ärzteverlag GmbH, Redaktion Deutsches. 1995-03-10. https://www.aerzteblatt.de/archiv/82498/110-Jahre-Ichthyol-Schieferoel-Klassiker-mit-breitem-Spektrum-an-Indikationen. 
  5. ↑ "Facial eschar following a single application of black salve". Clinical Toxicology 55 (7): 676–677. August 2017. doi:10.1080/15563650.2017.1312428. PMID 28426257. 
  6. ↑ 6.0 6.1 6.2 "Ichthammol revisited". International Journal of Dermatology 49 (7): 757–760. July 2010. doi:10.1111/j.1365-4632.2010.04551.x. PMID 20618493. 
  7. ↑ "Über das "Ichthyol".". Monatshefte für praktische Dermatologie. 2: 257. 1883. 
  8. ↑ "Über die chemischen Bestandteile der schwefelreichen, bituminösen Teeröle (Ichthyolöle)". Berichte der Deutschen Chemischen Gesellschaft 48 (2): 1815–26. 1915. doi:10.1002/cber.19150480276. https://zenodo.org/record/1426593. 
  9. ↑ "Ammoniumbituminosulfonat statt Ammoniumsulfobitol". Pharmazeutische Zeitung. 28 February 2000. https://www.pharmazeutische-zeitung.de/pharm1-09-2000/. 
  10. ↑ "Ichthyol® Pale - Ichthyol". Ichthyol-Gesellschaft. 1 April 2022. https://www.ichthyol.de/en/raw-materials-for-corporate-customers/ichthyol-pale/. 
  11. ↑ 11.0 11.1 "Veterinary MRL: Report on ICHTHYOL-substances". European Medicines Agency. September 2004. http://www.emea.europa.eu/pdfs/vet/mrls/091004en.pdf. 
  12. ↑ People's Republic of China Pharmacopoeia, 2010 edition. (Chinese text for 2020 edition)
  13. ↑ "Ammoniumbituminosulfonat" (in de). Kommentar zum Europäischen Arzneibuch, Wissenschaftliche Erläuterungen zum Arzneibuch (Stuttgart: Wissenschaftliche Verlagsgesellschaft) 4. 2014. 
  14. ↑ "Anti-inflammatory action of pale sulfonated shale oil (ICHTHYOL pale) in UVB erythema test". Inflammation Research 47 (2): 75–78. February 1998. doi:10.1007/s000110050282. PMID 9535545. 
  15. ↑ "Efficacy of topical ichthammol 10% for hidradenitis suppurativa: Case series and systematic review of its use in dermatology". Dermatologic Therapy 33 (6): e13868. November 2020. doi:10.1111/dth.13868. PMID 32558051. 
  16. ↑ Buckley DA, Root T and Bath S, Specials Recommended by the British Association of Dermatologists for Skin Disease, Clinical Standards Unit of the British Association of Dermatologists, London, UK, 2014, p. 9 (www.bad.org.uk/specials accessed October 2nd, 2015)
  17. ↑ "[Not Available]". Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology 14 (1): e1-75. January 2016. doi:10.1111/ddg.12884. PMID 26713660. 
  18. ↑ "Consensus-based European guidelines for treatment of atopic eczema (atopic dermatitis) in adults and children: part I". Journal of the European Academy of Dermatology and Venereology 32 (5): 657–682. May 2018. doi:10.1111/jdv.14891. PMID 29676534. 
  19. ↑ "A randomised controlled trial comparing Triadcortyl with 10% glycerine-ichthammol in the initial treatment of severe acute otitis externa". European Archives of Oto-Rhino-Laryngology 265 (8): 881–885. August 2008. doi:10.1007/s00405-007-0463-1. PMID 17922130. 
  20. ↑ "Inhibitory effects of shale oils (Ichthyols) on the secretion of chemotactic leukotrienes from human leukocytes and on leukocyte migration". The Journal of Investigative Dermatology 87 (6): 694–697. December 1986. doi:10.1111/1523-1747.ep12456630. PMID 2878051. 
  21. ↑ "Inhibitory effects of sulfonated shale oils (ammonium bituminosulphonates, Ichthyols) on enzymes of polyenoic fatty acid metabolism". Archives of Dermatological Research 286 (3–4): 137–141. 1994. doi:10.1007/bf00374208. PMID 7911653. 
  22. ↑ Therapielexikon Dermatologie und Allerlogie (2nd ed.). Berlin: Springer. 2005. pp. 1024, 1040, 1051. 
  23. ↑ "Suppositories and pessaries". Pharmaceutical Compounding and Dispensing (2nd ed.). London, UK: Pharmaceutical Press. 2012. p. 143. ISBN 978-0-85711-055-8. 
  24. ↑ "Magistral formulations and pruritus therapy - What is established, what is confirmed, what is new?". Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology 11 (11): 1049–1055. November 2013. doi:10.1111/ddg.12230. PMID 24119119. 
  25. ↑ "[Anti-inflammatory, antibacterial and antimycotic effects of dark sulfonated shale oil (ichthammol)]". Berliner und Munchener Tierarztliche Wochenschrift 113 (10): 368–373. October 2000. PMID 11084753. 

Further reading

  • "[The adverse effects of dark sulfonated shale oil following local and systemic administration]" (in German). Arzneimittel-Forschung 44 (7): 844–849. July 1994. PMID 7945520. 
  • "[Ammonium bituminosulfonate (Ichthyol). Anti-inflammatory effect and inhibition of the 5-lipoxygenase enzyme]" (in German). Der Hautarzt; Zeitschrift Fur Dermatologie, Venerologie, und Verwandte Gebiete 43 (12): 772–774. December 1992. PMID 1361926. 
  • "Glycerol and ichthammol: medicinal solution or mythical potion?". The Journal of Laryngology and Otology 110 (4): 319–321. April 1996. doi:10.1017/s0022215100133547. PMID 8733451. 



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