Salicylic acid

Salicylic acid
ATC Code D01AE12, D02AF01, D10AX11, D11AF01, S01BC08
Formula C7H6O3
Molar Mass (g·mol−1) 138,12
Physical State solid
Density (g·cm−3) 1,44
Melting Point (°C) 159
Boiling Point (°C) 211
PKS Value 2,75
CAS Number 69-72-7
PUB Number 338
Drugbank ID DB00936
Solubility schlecht löslich in Wasser

Basics

Salicylic acid is an acid that is nowadays used for external treatment to remove the outer layer of the skin. Therefore, salicylic acid is good for treating acne, psoriasis, calluses, corns, keratosis pilaris and warts. The compound can be obtained from the bark of white willow and the leaves of wintergreen, but, due to its relatively simple structure, is now mainly produced synthetically. It has bacteriostatic, fungicidal and keratolytic effects, and when taken orally, analgesic and antipyretic.

Willow has been used for medicinal purposes for a very long time. There are records of its use as far back as 1500 B.C. Its use for fever and pain can be observed over time and many different cultures. An extract of willow bark, called salicin after the Latin name of the white willow (Salix alba), was isolated and named by the German chemist Johann Andreas Buchner in 1828. The German chemist Hermann Kolbe succeeded in producing the substance fully synthetically for the first time in the 1850s. The bitter taste of the substance and side effects such as stomach complaints, prompted many scientists to search for alternatives. At the turn of the century, the acetylated form, acetylsalicylic acid, was introduced to the market. Due to its significantly improved side effect profile, acetylsalicylic acid largely replaced salicylic acid for the treatment of fever and pain.

Pharmacology

Pharmacodynamics

Salicylic acid as an orally ingested arngeic agent irreversibly inhibits both enzyme COX-1 and COX-2. In dissociated form as salicylate, it can competitively inhibit prostaglandin formation. This inhibits the development of fever and the transmission of pain. Additionally

External application of salicylic acid causes the cells of the epidermis to exfoliate more easily, preventing pores from clogging and making room for new cell growth. Salicylic acid inhibits the oxidation of uridine-5-diphosphoglucose (UDPG) competitively with nicotinamide adenine dinucleotide and non-competitively with UDPG.

The wound-healing retardant effect of salicylates is probably mainly due to their inhibitory effect on mucopolysaccharide synthesis.

Pharmacokinetics

Because salicylic acid in its pure form is now no longer used orally, there are few available data on pharmacokinetic parameters.

Salicylic acid is approximately 90% bound to plasma proteins. Salicylic acid is largely metabolized in the liver. Approximately 10% is excreted unchanged in the urine.

Toxicity

Side effects

Side effects are mainly allergic reactions, bleeding tendency, bronchoconstriction (bronchial asthma), gastric mucosal damage with bleeding, in isolated cases also liver damage.

Editorial principles

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Markus Falkenstätter

Markus Falkenstätter
Author

Markus Falkenstätter is a writer on pharmaceutical topics in Medikamio's medical editorial team. He is in the last semester of his pharmacy studies at the University of Vienna and loves scientific work in the field of natural sciences.

Mag. pharm Stefanie Lehenauer

Mag. pharm Stefanie Lehenauer
Lector

Stefanie Lehenauer has been a freelance writer for Medikamio since 2020 and studied pharmacy at the University of Vienna. She works as a pharmacist in Vienna and her passion is herbal medicines and their effects.

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