Azelaic Acid

Indications

Azelaic acid (Azelex) is a naturally occurring dicarboxylic acid produced by the yeast Malassezia furfur. Azelaic acid inhibits tyrosinase, a rate-limiting enzyme in the synthesis of the pigment melanin. This may explain why diminution of melanin pigmentation occurs in the skin of some patients with pityriasis versicolor, a disease caused by M. furfur. Azelaic acid is bacteriostatic against a number of species thought to participate in the pathogenesis of acne, including Propionibacterium acnes. The drug may also reduce microcomedo formation by promoting normalization of epidermal keratinocytes.

Production Methods

Azelaic acid is industrially produced by the ozonolysis of oleic acid. The side product is nonanoic acid. It is produced naturally by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. The bacterial degradation of nonanoic acid gives azelaic acid.

Preparation

Azelaic acid is made by the ozonolysis of oleic acid:

Therapeutic Function

Antiacne, Depigmentor

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 4846, 1955 DOI: 10.1021/ja01623a048Organic Syntheses, Coll. Vol. 2, p. 53, 1943

Biochem/physiol Actions

Azelaic acid is a potent inhibitor of 5α-reductase activity. It is a reversible competitive inhibitor of thioredoxin reductase in human melanoma cells.

Safety Profile

Low toxicity by ingestion. A skinand eye irritant. Closely related to glutaric acid and adipicacid. Combustible when exposed to heat or flame; canreact with oxidizing materials.

Application

Azelaic acid, also known as azalea acid, is a white to slightly yellow powder. Azelaic acid is a medium-long chain dibasic acid[1]. In recent years, with the rapid development of the organic synthetic chemical industry, the demand for medium and long chain dibasic acids is increasing. The medium and long chain dibasic acids and their derivatives have a wide range of industrial applications and a broad product market.

Brand name

Azelex (Allergan); Finacea (Intendis);Skinoren.

Biotechnological Applications

In plants, azelaic acid serves as a "distress flare" involved in defense responses after infection. It serves as a signal that induces the accumulation of salicylic acid, an important component of a plant's defensive response.