Azelaic acid

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Azelaic acid
File:Azelaic acid.png
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 123-99-9 YesY
PubChem 2266
ChemSpider 2179
DrugBank APRD00812
ATC code D10AX03
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InChI Script error: No such module "collapsible list".
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula C9H16O4
Molar mass 188.22 g mol−1
Melting point

109-111 °C[1]

Boiling point

286 °C at 100 mmHg[1]

Solubility in water 2.14 g/L[2]
Acidity (pKa) 4.550, 5.598[2]
style="background: #F8EABA; text-align: center;" colspan="2" | Pharmacology
Bioavailability Very low
Routes of
12 hours
Legal status


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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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).


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.

Because 20% azelaic acid can be a skin irritant, it should be used only when prescribed by a physician.

Uses of azelaic acid

Acne treatment

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.[3]

Rosacea treatment

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.

Hair loss

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.[4] 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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External links


fr:Acide azélaïque it:Acido azelaico lv:Azelaīnskābe nl:Azelaïnezuur pl:Kwas azelainowy pt:Ácido azelaico ru:Азелаиновая кислота

  1. 1.0 1.1 Sigma-Aldrich catalog
  2. 2.0 2.1 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. 
  3. 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. 
  4. 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: |date= (help)