Ammonium bituminosulfonate

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Ichthammol
Ichthyol-Salbe.jpg
A tube of medicinal ammonium bituminosulfonate (ichthyol)
Clinical data
Trade names Ichthyol
Other namesammonium bituminosulfonate; ammonium bituminosulphonate; bituminosulfonates
Identifiers
CAS Number
DrugBank
UNII
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Ichthammol or ammonium bituminosulfonate (brand name Ichthyol), also known as black ointment, 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.

Contents

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 names Ichthyol-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
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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

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References

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  2. Paul Gerson Unna: About Ichthyol. In: Monatshefte für praktische Dermatologie, Band XXV, 1897 (in German).
  3. "Unna, Paul Gerson - Deutsche Biographie". Deutsche Biographie (in German). Retrieved 2021-07-19.
  4. "110 Jahre Ichthyol-Schieferöl: Klassiker mit breitem Spektrum an Indikationen". Deutsches Ärzteblatt (in German). Deutscher Ärzteverlag GmbH, Redaktion Deutsches. 1995-03-10. Retrieved 2021-07-19.
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  11. 1 2 "Veterinary MRL: Report on ICHTHYOL-substances" (PDF). European Medicines Agency. September 2004. Archived from the original (PDF) on 2006-07-18.
  12. People's Republic of China Pharmacopoeia, 2010 edition. (Chinese text for 2020 edition)
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  21. 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". Archives of Dermatological Research. 286 (3–4): 137–141. doi:10.1007/bf00374208. PMID   7911653. S2CID   12647893.
  22. Altmeyer P (2005). Therapielexikon Dermatologie und Allerlogie (2nd ed.). Berlin: Springer. pp. 1024, 1040, 1051.
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  24. Staubach P, Metz M (November 2013). "Magistral formulations and pruritus therapy - What is established, what is confirmed, what is new?". Journal der Deutschen Dermatologischen Gesellschaft. 11 (11): 1049–1055. doi: 10.1111/ddg.12230 . PMID   24119119.
  25. Gayko G, Cholcha W, Kietzmann M (October 2000). "[Anti-inflammatory, antibacterial and antimycotic effects of dark sulfonated shale oil (ichthammol)]". Berliner und Munchener Tierarztliche Wochenschrift. 113 (10): 368–373. PMID   11084753.

Further reading