Ammonium bituminosulfonate

Last updated
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
CompTox Dashboard (EPA)
ECHA InfoCard 100.029.485 OOjs UI icon edit-ltr-progressive.svg

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.

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
ECHA InfoCard 100.029.485 OOjs UI icon edit-ltr-progressive.svg

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

Related Research Articles

<span class="mw-page-title-main">Dermatitis</span> Inflammatory disease of the skin

Dermatitis is inflammation of the skin, typically characterized by itchiness, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become thickened. The area of skin involved can vary from small to covering the entire body. Dermatitis is often called eczema, and the difference between those terms is not standardized.

<span class="mw-page-title-main">Irritant diaper dermatitis</span> Medical condition

Irritant diaper dermatitis is a generic term applied to skin rash in the diaper area that are caused by various skin disorders and/or irritants.

<span class="mw-page-title-main">Seborrhoeic dermatitis</span> Skin disease

Seborrhoeic dermatitis is a long-term skin disorder. Symptoms include flaky, scaly, greasy, and occasionally itchy and inflamed skin. Areas of the skin rich in oil-producing glands are often affected including the scalp, face, and chest. It can result in social or self-esteem problems. In babies, when the scalp is primarily involved, it is called cradle cap. Seborrhoeic dermatitis of the scalp may be described in lay terms as dandruff due to the dry, flaky character of the skin. However, as dandruff may refer to any dryness or scaling of the scalp, not all dandruff is seborrhoeic dermatitis. Seborrhoeic dermatitis is sometimes inaccurately referred to as seborrhoea.

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

Pimecrolimus is an immunomodulating agent of the calcineurin inhibitor class used in the treatment of atopic dermatitis (eczema). It is available as a topical cream, once marketed by Novartis under the trade name Elidel.

Antipruritics, abirritants, or anti-itch drugs, are medications that inhibit the itching often associated with sunburns, allergic reactions, eczema, psoriasis, chickenpox, fungal infections, insect bites and stings like those from mosquitoes, fleas, and mites, and contact dermatitis and urticaria caused by plants such as poison ivy or stinging nettle. It can also be caused by chronic kidney disease and related conditions.

<span class="mw-page-title-main">Nummular dermatitis</span> Medical condition

Nummular dermatitis is one of the many forms of dermatitis. It is characterized by round or oval-shaped itchy lesions. The name comes from the Latin word "nummus," which means "coin."

<span class="mw-page-title-main">Coal oil</span> Oil derived from coal

Coal oil is a shale oil obtained from the destructive distillation of cannel coal, mineral wax, or bituminous shale, once used widely for illumination.

<span class="mw-page-title-main">Atopy</span> Predisposition towards allergy

Atopy is the tendency to produce an exaggerated immunoglobulin E (IgE) immune response to otherwise harmless substances in the environment. Allergic diseases are clinical manifestations of such inappropriate, atopic responses.

<span class="mw-page-title-main">Atopic dermatitis</span> Long-term form of skin inflammation

Atopic dermatitis (AD), also known as atopic eczema, is a long-term type of inflammation of the skin (dermatitis). It results in itchy, red, swollen, and cracked skin. Clear fluid may come from the affected areas, which can thicken over time. AD may also simply be called eczema, a term that generally refers to a larger group of skin conditions.

Natural skin care uses topical creams and lotions made of ingredients available in nature. Much of the recent literature reviews plant-derived ingredients, which may include herbs, roots, flowers and essential oils, but natural substances in skin care products include animal-derived products such as beeswax, and minerals. These substances may be combined with various carrier agents, preservatives, surfactants, humectants and emulsifiers.

Araroba powder, also known as Bahia powder and Goa powder, is a drug occurring in the form of a yellowish-brown powder, varying considerably in tint, from the Portuguese colony of Goa, where it appears to have been introduced about the year 1852.

<span class="mw-page-title-main">Vaseline</span> Brand of petroleum jelly-based products

Vaseline is an American brand of petroleum jelly-based products owned by transnational company Unilever. Products include plain petroleum jelly and a selection of skin creams, soaps, lotions, cleansers, and deodorants.

<span class="mw-page-title-main">Cutis verticis gyrata</span> Medical condition

Cutis verticis gyrata is a medical condition usually associated with thickening of the scalp. The condition is identified by excessive thickening of the soft tissues of the scalp and characterized by ridges and furrows, which give the scalp a cerebriform appearance. Clinically, the ridges are hard and cannot be flattened on applying pressure. Patients show visible folds, ridges or creases on the surface of the top of the scalp. The number of folds can vary from two to roughly ten and they are typically soft and spongy. The condition typically affects the central and rear regions of the scalp, but sometimes can involve the entire scalp.

Ablukast (INN) is an experimental drug that is a leukotriene antagonist. It was investigated for potential applications in the treatment of inflammatory conditions, including asthma, skin disorders, and inflammatory bowel disease. It reached Phase III clinical trials, but development was discontinued in 1996.

Topical steroids are the topical forms of corticosteroids. Topical steroids are the most commonly prescribed topical medications for the treatment of rash and eczema. Topical steroids have anti-inflammatory properties and are classified based on their skin vasoconstrictive abilities. There are numerous topical steroid products. All the preparations in each class have the same anti-inflammatory properties but essentially differ in base and price.

<span class="mw-page-title-main">Hand eczema</span> Skin condition

Hand eczema presents on the palms and soles, and may sometimes be difficult or impossible to differentiate from atopic dermatitis, allergic contact dermatitis, and psoriasis, which also commonly involve the hands. Even a biopsy of all these conditions may not result in a definitive diagnosis, as all three conditions may demonstrate spongiosis and crusting on the hands.

Postinflammatory hypopigmentation is a cutaneous condition characterized by decreased pigment in the skin following inflammation of the skin.

Sodium hypochlorite washes are skin cleansers formulated with sodium hypochlorite (NaOCl) and surfactants. These cleansing liquids or gels are lathered onto wet skin and rinsed off. They are recommended for inflammatory skin conditions, microbial driven skin disorders and body odor.

<span class="mw-page-title-main">Topical glucocorticoids</span>

Topical glucocorticoids are the topical forms of glucocorticoids. Topical glucocorticoids are used in the treatment of many skin conditions. They provide anti-inflammatory, antimitotic, and immune-system suppressing actions through various mechanisms.

Bernadette Eberlein is a dermatologist, allergologist, academic, and researcher. She is the Senior Physician of the private outpatient clinic, the Photodermatology unit, the unit for Soft X-Ray Therapy at Technical University of Munich.

References

  1. Schmid-Wendtner MH, Korting HC, Sterry W (2001). "Bituminosulfonate.". Therapeutische Verfahren in der Dermatologie–Dermatika und Kosmetika. Berlin, Wien: Blackwell Wissenschafts-Verlag. 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". 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.
  5. Laskey D, Tran M (August 2017). "Facial eschar following a single application of black salve". Clinical Toxicology. 55 (7): 676–677. doi:10.1080/15563650.2017.1312428. PMID   28426257. S2CID   29076775.
  6. 1 2 3 Boyd AS (July 2010). "Ichthammol revisited". International Journal of Dermatology. 49 (7): 757–760. doi:10.1111/j.1365-4632.2010.04551.x. PMID   20618493. S2CID   7367995.
  7. Baumann E, Schotten C (1883). "Über das "Ichthyol"". Monatshefte für praktische Dermatologie. 2: 257.
  8. 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.
  9. "Ammoniumbituminosulfonat statt Ammoniumsulfobitol". Pharmazeutische Zeitung . 28 February 2000.
  10. "Ichthyol® Pale - Ichthyol". Ichthyol-Gesellschaft. 1 April 2022.
  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)
  13. Bracher F, Heisig P, Langguth P, Mutschler E, Rücker G, Scriba G, Stahl-Biskup E, Troschütz R, eds. (2014). "Ammoniumbituminosulfonat". Kommentar zum Europäischen Arzneibuch, Wissenschaftliche Erläuterungen zum Arzneibuch[Commentary to the Pharmacopoeia Europaea, Scientific explanations of the Pharmacopoeia] (in German). Stuttgart: Wissenschaftliche Verlagsgesellschaft. 4.
  14. Warnecke J, Wendt A (February 1998). "Anti-inflammatory action of pale sulfonated shale oil (ICHTHYOL pale) in UVB erythema test". Inflammation Research. 47 (2): 75–78. doi:10.1007/s000110050282. PMID   9535545. S2CID   9014012.
  15. Fisher S, Ziv M (November 2020). "Efficacy of topical ichthammol 10% for hidradenitis suppurativa: Case series and systematic review of its use in dermatology". Dermatologic Therapy. 33 (6): e13868. doi: 10.1111/dth.13868 . PMID   32558051. S2CID   219907385.
  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. Werfel T, Aberer W, Ahrens F, Augustin M, Biedermann T, Diepgen T, et al. (January 2016). "[Not Available]". Journal der Deutschen Dermatologischen Gesellschaft. 14 (1): e1-75. doi:10.1111/ddg.12884. PMID   26713660. S2CID   203739944.
  18. Wollenberg A, Barbarot S, Bieber T, Christen-Zaech S, Deleuran M, Fink-Wagner A, et al. (May 2018). "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. doi: 10.1111/jdv.14891 . PMID   29676534.
  19. 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". European Archives of Oto-Rhino-Laryngology. 265 (8): 881–885. doi:10.1007/s00405-007-0463-1. PMID   17922130. S2CID   26976193.
  20. Czarnetzki BM (December 1986). "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. doi: 10.1111/1523-1747.ep12456630 . PMID   2878051.
  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.
  23. Langley CA, Belcher D (2012). "Suppositories and pessaries". Pharmaceutical Compounding and Dispensing (2nd ed.). London, UK: Pharmaceutical Press. p. 143. ISBN   978-0-85711-055-8.
  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