|style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers|
|SMILES||Script error: No such module "collapsible list".|
|InChI||Script error: No such module "collapsible list".|
|style="background: #F8EABA; text-align: center;" colspan="2" | Properties|
|Molar mass||188.22 g mol−1|
286 °C at 100 mmHg
|Solubility in water||2.14 g/L|
|Acidity (pKa)||4.550, 5.598|
|style="background: #F8EABA; text-align: center;" colspan="2" | Pharmacology|
| Routes of
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is a natural substance that is produced by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. It is industrially produced by the ozonolysis of oleic acid. It is effective against a number of skin conditions, such as mild to moderate acne, when applied topically in a cream formulation of 20%. Azelaic acid may be useful as a hair growth stimulant, although at present there are no clinical studies to confirm its efficacy.
Brand names: Acnederm (20% lotion, Ego Pharmaceuticals), Azelex (20% cream, Allergan), Finacea (15% gel, Intendis/Berlex Laboratories, subsidiaries of Bayer AG), Finevin (20% cream, Intendis/Berlex Laboratories), Skinoren (20% cream or 15% gel, Intendis).
- Antibacterial: it reduces the growth of bacteria in the follicle (Propionibacterium acnes and Staphylococcus epidermidis).
- Keratolytic & comedolytic: it returns to normal the disordered growth of the skin cells, lining the follicle.
- Scavenger of free radicals and reduces inflammation.
- Reduces pigmentation: it is particularly useful for darker-skinned patients, who have melasma, or whose acne spots leave persistent brown marks known as actinic lentigines. (per the product insert: "There have been reports of hypopigmentation after use of azelaic acid. Since azelaic acid has not been well studied in patients with dark complexions, these patients should be monitored for early signs of hypopigmentation.")
- Non-toxic, and is well tolerated by most patients.
Azelaic acid does not result in bacterial resistance to antibiotics, reduction in sebum production, photosensitivity (easy sunburn), staining of skin or clothing, or bleaching of normal skin or clothing.
Uses of azelaic acid
Azelaic acid is used to treat mild to moderate acne; i.e. both comedonal acne and inflammatory acne. It works in part by stopping the growth of skin bacteria that cause acne, and by keeping skin pores clear.
Azelaic acid is also used as a topical gel treatment for rosacea, due to its ability to reduce inflammation. In some cases, females have reported hair growth on face and neck.
Azelaic acid may be useful as a hair growth stimulant. A research report by Stamatiadis in 1988 suggested that azelaic acid (and combinations of it, with zinc ion and vitamin B6) was a strong type I 5-alpha reductase (5-AR) inhibitor. The enzyme, 5-AR (both Types I and II) convert testosterone to dihydrotestosterone (DHT). DHT has been shown to contribute to prostate enlargement (benign prostatic hyperplasia, BPH) and to damage hair follicles. However, no clinical studies have confirmed its efficacy in helping with hair loss.
Notes and references
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- Sigma-Aldrich catalog
- Bretti, C.; Crea, F.; Foti, C.; Sammartano, S. (2006). "Solubility and Activity Coefficients of Acidic and Basic Nonelectrolytes in Aqueous Salt Solutions. 2. Solubility and Activity Coefficients of Suberic, Azelaic, and Sebacic Acids in NaCl(aq), (CH3)4NCl(aq), and (C2H5)4NI(aq) at Different Ionic Strengths and at t = 25 C". J. Chem. Eng. Data. 51 (5): 1660–1667. doi:10.1021/je060132t.
- Liu R. H., Smith M. K., Basta S. A., Farmer E. R. ( (2006). "Azelaic acid in the treatment of papulopustular rosacea - A systematic review of randomized controlled trials". Archive of Dermatology. 142 (8): 1047–1052. doi:10.1001/archderm.142.8.1047. PMID 16924055.
- Stamatiadis D, Bulteau-Portois MC, Mowszowicz I (Nov. 1988). "Inhibition of 5 alpha-reductase activity in human skin by zinc and azelaic acid". Br J Dermatol. 119 (5): 627–632. doi:10.1111/j.1365-2133.1988.tb03474.x. PMID 3207614. Check date values in: