Ammonium bituminosulfonate

Ammonium bituminosulfonate or ammonium bituminosulphonate (synonyms of ichthammol, CAS#8029-68-3 brand name: Ichthyol) is a product of natural origin obtained in the first step by dry distillation of sulfur-rich oil shale (bituminous schists). By sulfonation of the resulting oil (or purified fractions thereof), and subsequent neutralization with ammonia, Ichthammol results as a viscous, water-soluble substance with a characteristic bitumen-like odor. It is used in medicine (sometimes in combination with zinc oxide) as a treatment for different skin diseases, including eczema and psoriasis (see below). Ointments containing 10% or 20% Ichthammol are most common. They are sometimes called "black ointments" or "drawing salves". Ichthammol's dermatological action was promoted by German physician Paul Gerson Unna.[1]

"Black ointment" redirects here. It is not to be confused with black salve.
A tube of medicinal ammonium bituminosulfonate (ichthyol)

Composition

From elemental analysis, the composition of Ichthammol was calculated to be C28H36S5O6(NH4)2.[2] However, as a product of natural origin, it is a mixture of many different compounds.[3]

Chemically, it is a sulfonated shale oil that 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.

Differentiation from Chinese Materials

Materials made in China (Pinyin transcription: yushizhi and yushizhi ruangao) and offered outside China as Ichthammol or Ammonium Bituminosulfonate do not meet the requirements for this substance in the United States Pharmacopoeia (USP) or European Pharmacopoeia (Ph.Eur). Also, there is no conformity with the definition as connected to CAS# 8029-68-3. The Chinese material is derived from vegetable oils (e.g., soybean oil) instead of bituminous schists as required (Chinese definition according to ChP 10: "Ichthammol is a mixture obtained by sulfuration of vegetable oils (soybean oil, tung oil, corn oil, etc.), sulfonation, and neutralization with ammonia").[4] As a result, its chemical basis is totally different from the one of Ichthammol USP/Ph.Eur./CAS# 8029-68-3. The characteristic bitumen-like odor (originating from the bituminous source material) is missing with Chinese material and, thereby, the original qualities according to common standards cannot be identified without doubt. Noncomparable."[5]

Usage

Human

Bituminosulfonates are classified as local therapeutic agents with very good tolerability.[6] Pharmacologically, Ichthammol has anti-inflammatory, bactericidal, and fungicidal properties.[7] It is used to treat a variety of skin disorders as e.g. eczema, psoriasis, Acne rosacea and acne,[8][9][10] and it decreases microorganisms in the area surrounding a skin condition. It is commonly used in 10% or 20% concentrate ointment, applied topically.

In otology, a mixture of glycerol and ichthammol (G & I) is used for the topical treatment of ear infections.[11] It is effective against Gram-positive organisms. The anti-inflammatory action is explained by its influence on the formation, secretion, and effect of inflammation mediators.[12][13]

Ichthammol is available in pharmacies for compounding medications. Different sources of information exist for exemplary formulations (creams, shake lotions, suppositories, etc.).[14][15][16]

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.[17] 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.[18] 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).[19]

Veterinary

The European Medicines Agency published a summary report on ichthyol-substances (synonym: bituminosulfonates) during the course of the European Maximum Residue Limits (MRL) procedure[20] 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.

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See also

References
  1. Paul Gerson Unna: About Ichthyol. In: Monatshefte für praktische Dermatologie, Band XXV, 1897 (in German).
  2. E. Baumann, C. Schotten: Über das Ichthyol. In: Monatshefte für praktische Dermatologie, Band II, S. 257, 1883 (in German).
  3. Scheibler H (1915). "Über die chemischen Bestandteile der schwefelreichen, bituminösen Teeröle (Ichthyolöle)". Berichte der Deutschen Chemischen Gesellschaft. 48 (2): 1815–26. doi:10.1002/cber.19150480276.
  4. People's Republic of China Pharmacopoeia, 2010 edition.
  5. Bracher, F. et al. (ed.), Kommentar zum Europäischen Arzneibuch (Commentary to the European Pharmacopoeia), Wissenschaftliche Erläuterungen zum Arzneibuch, Volume 4, Ammoniumbituminosulfonat, Wissenschaftliche Verlagsgesellschaft Stuttgart, 2014
  6. Schmid-Wendtner MH. Bituminosulfonate. In: Korting HC, Sterry W: Therapeutische Verfahren in der Dermatologie - Dermatika und Kosmetika. Berlin, Wien: Blackwell Wissenschafts-Verlag, 2001: p. 165-71
  7. Gayko G, Cholcha W, Kietzmann M (October 2000). "Anti-inflammatory, antibacterial and antimycotic effects of dark sulfonated shale oil (ichthammol)". Berl. Munch. Tierarztl. Wochenschr. 113 (10): 368–73. PMID 11084753.
  8. Boyd, Alan S. (July 2010). "Ichthammol revisited". International Journal of Dermatology. 49 (7): 757–60. doi:10.1111/j.1365-4632.2010.04551.x. PMID 20618493.
  9. Warnecke J, Wendt A (February 1998). "Anti-inflammatory action of pale sulfonated shale oil (ICHTHYOL pale) in UVB erythema test". Inflamm. Res. 47 (2): 75–8. doi:10.1007/s000110050282. PMID 9535545.
  10. Fisher S, Ziv M (July 2020). "Efficacy of topical ichthammol 10% for hidradenitis suppurativa: Case series and systematic review of its use in dermatology". Dermatologic Therapy. 33 (4). doi:10.1111/dth.13868.
  11. Masood A, Moumoulidis I, Ray S, Chawla O, Panesar J (August 2008). "A randomised controlled trial comparing Triadcortyl with 10% glycerine-ichthammol in the initial treatment of severe acute otitis externa". Eur. Arch. Otorhinolaryngol. 265 (8): 881–5. doi:10.1007/s00405-007-0463-1. PMID 17922130.
  12. Czarnetzki, BM (December 1986). "Inhibitory effects of shale oils (Ichthyols) on the secretion of chemotactic leukotrienes from human leukocytes and on leukocyte migration". J. Invest. Derm. 87 (6): 694–7. doi:10.1111/1523-1747.ep12456630. PMID 2878051.
  13. Schewe C, Schewe T, Rohde E, Diezel W, Czarnetzki BM (1994). "Inhibitory effects of sulfonated shale oils (ammonium bituminosulphonates, Ichthyols) on enzymes of polyenoic fatty acid metabolism". Arch. Dermatol. Res. 286 (3–4): 137–41. doi:10.1007/bf00374208. PMID 7911653.
  14. Altmeyer P., Therapielexikon Dermatologie und Allerlogie, Springer, Berlin, 2nd edition, 2005, p. 1024; p. 1040; p. 1051
  15. Langley, C.A. and Belcher, D., Pharmaceutical Compounding and Dispensing, Pharmaceutical Press, London, UK, 2nd edition, 2012, p. 143
  16. Staubach P; Metz, M (October 2013). "Magistral formulations and pruritus therapy – What is established, what is confirmed, what is new?". Journal of the German Society of Dermatology (JDDG). 11 (8): 1049–55. doi:10.1111/ddg.12230. PMID 24119119.
  17. 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)
  18. Werfel T, et al. (January 2016). "Leitlinie Neurodermitis [atopisches Ekzem; atopische Dermatitis]". Journal of the German Society of Dermatology (JDDG). 14 (1): e1–e75. doi:10.1111/ddg.12884. PMID 26713660.
  19. Wollenberg A, et al. (May 2018). "Consensus-based European guidelines for treatment of atopic eczema (atopic dermatitis) in adults and children: part I". J Eur Acad Dermatol Venereol. 32 (5): 657–682. doi:10.1111/jdv.14891.
  20. "Veterinary MRL: Report on ICHTHYOL-substances" (PDF). European Medicines Agency. September 2004. Archived from the original (PDF) on 2006-07-18.

External sources
  • Cholcha W, Leuschner J, Leuschner F (July 1994). "[The adverse effects of dark sulfonated shale oil following local and systemic administration]". Arzneimittelforschung (in German). 44 (7): 844–9. PMID 7945520.
  • Diezel W, Schewe T, Rohde E, Rosenbach T, Czarnetzki BM (December 1992). "[Ammonium bituminosulfonate (Ichthyol). Anti-inflammatory effect and inhibition of the 5-lipoxygenase enzyme]". Hautarzt (in German). 43 (12): 772–4. PMID 1361926.
  • Nilssen E, Wormald PJ, Oliver S (April 1996). "Glycerol and Ichthammol: medicinal solution or mythical potion?". J. Laryngol. Otol. 110 (4): 319–21. doi:10.1017/s0022215100133547. PMID 8733451.
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