Azelaic acid

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Azelaic acid
Skeletal formula of azelaic acid
Ball-and-stick model of the azelaic acid molecule
Preferred IUPAC name
Nonanedioic acid
3D model (JSmol)
ECHA InfoCard 100.004.246 Edit this at Wikidata
EC Number
  • 204-669-1
  • InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13) checkY
  • InChI=1/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
Molar mass 188.22 g/mol
Appearance white solid
Density 1.443 g/mL
Melting point 109 to 111 °C (228 to 232 °F; 382 to 384 K)[1]
Boiling point 286 °C (547 °F; 559 K) at 100 mmHg[1]
2.14 g/L[2]
Acidity (pKa) 4.550, 5.498[2]
D10AX03 (WHO)
Very low
12 h
Legal status
GHS pictograms GHS07: Harmful
GHS Signal word Warning
H315, H319
P264, P280, P302+352, P305+351+338, P321, P332+313, P337+313, P362
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Azelaic acid (AzA) is an organic compound with the formula HOOC(CH2)7COOH.[3] This saturated dicarboxylic acid exists as a white powder. It is found in wheat, rye, and barley. It is a precursor to diverse industrial products including polymers and plasticizers, as well as being a component of a number of hair and skin conditioners.[4] AzA inhibits tyrosinase.


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.[5]

Biological function[edit]

In plants, azelaic acid serves as a "distress flare" involved in defense responses after infection.[6] It serves as a signal that induces the accumulation of salicylic acid, an important component of a plant's defensive response.[7]


Azelaic acid cream labeled in Russian.

Polymers and related materials[edit]

Esters of this dicarboxylic acid find applications in lubrication and plasticizers. In lubricant industries it is used as a thickening agent in lithium complex grease. With hexamethylenediamine, azelaic acid forms Nylon-6,9, which finds specialized uses as a plastic.[4]


Azelaic acid is used to treat mild to moderate acne, both comedonal acne and inflammatory acne.[8][9] It belongs to a class of medication called dicarboxylic acids. It works by killing acne bacteria that infect skin pores. It also decreases the production of keratin, which is a natural substance that promotes the growth of acne bacteria.[10] Azelaic acid is also used as a topical gel treatment for rosacea, due to its ability to reduce inflammation.[9] It clears the bumps and swelling caused by rosacea. The mechanism of action is thought to be through the inhibition of hyperactive protease activity that converts cathelicidin into the antimicrobial skin peptide LL-37.[11]

Acne treatment[edit]

Azelaic acid is effective for mild to moderate acne when applied topically at a 15%-20% concentration.[12][13][14][15] In patients with moderate acne twice daily over 3 month topical 20% AzA significantly reduced numbers of comedones, papules and pustules;[16] at this strength it’s considered to be equally effective as benzoyl peroxide 5%, tretinoin 0.05%, erythromycin 2% and oral tetracycline 500mg-1000mg.[17][18] In a comparative review of effects of topical AzA, Salicylic acid, Nicotinamide, Sulfur, Zinc, and alpha-hydroxy acid AzA enjoyed more high-quality evidence of effectiveness than the rest.[19] Results can be expected after 4 weeks of twice-daily treatment. The effectiveness of long term use is unclear but it’s been recommended that AzA be used for at least 6 months continuously for maintenance.[17]

Whitening agent[edit]

Azelaic acid has been used for treatment of skin pigmentation including melasma and postinflammatory hyperpigmentation, particularly in those with darker skin types. It has been recommended as an alternative to hydroquinone.[20] As a tyrosinase inhibitor, azelaic acid reduces synthesis of melanin.[21] According to one report of 1988 azelaic acid (in combination with zinc sulfate) in vitro showed to be a potent (90% inhibition) 5α-Reductase inhibitor, similar to the hair loss drugs finasteride and dutasteride.[22][non-primary source needed] Middle 80s in vitro research evaluating acid's depigmenting (whitening) capability concluded it is effective (cytotoxic to melanocytes) only at high concentrations.[23]

More recent review claimed 20% AzA being more potent than 4% hydroquinon after period of application for three months without latter's adverse effects and even more effective if applied along with tretinoin for the same period of time.[24][16]

Azelaic Acid is tyrosinase inhibitor.[25]

Brand names[edit]

Brand names for azelaic acid include Dermaz 99,[26] Crema Pella Perfetta (micronized azelaic acid, kojic dipalmitate, and liquorice extract), Azepur99, Azetec99, Azaclear (azelaic acid and niacinamide), AzClear Action, Azelex, White Action cream, Finacea, Finevin, Melazepam, Skinoren, Ezanic, Azelac, Azaderm, (Acnegen, Eziderm, Acnicam, Azelexin in Pakistan)[27]


  1. ^ a b Sigma-Aldrich catalog Archived April 9, 2008, at the Wayback Machine
  2. ^ a b 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. ^ Del Rosso, James Q. (2006-02-01). "The use of topical azelaic acid for common skin disorders other than inflammatory rosacea". Cutis. 77 (2 Suppl): 22–24. ISSN 0011-4162. PMID 16566285.
  4. ^ a b Cornils, Boy; Lappe, Peter (2006). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523. ISBN 3527306730.
  5. ^ Integrative medicine. David Rakel (Fourth ed.). Philadelphia, PA. 2018. ISBN 978-0-323-35868-2. OCLC 982188831.CS1 maint: others (link)
  6. ^ Sarah Everts (January 31, 2011). "Vegetative Warfare". Chemical & Engineering News. 89 (5): 53–55. doi:10.1021/cen-v089n005.p053.
  7. ^ Jung, H. W.; Tschaplinski, T. J.; Wang, L.; Glazebrook, J.; Greenberg, J. T. (2009). "Priming in Systemic Plant Immunity". Science. 324 (5923): 89–91. Bibcode:2009Sci...324...89W. doi:10.1126/science.1170025. PMID 19342588.
  8. ^ "Azelaic Acid for Acne". WebMD.
  9. ^ a b "Azelaic acid topical".
  10. ^ 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". Arch. Dermatol. 142 (8): 1047–1052. doi:10.1001/archderm.142.8.1047. PMID 16924055.
  11. ^ Reinholz, M.; Ruzicka, T.; Schauber, J. (2012). "Cathelicidin LL-37: An Antimicrobial Peptide with a Role in Inflammatory Skin Disease". Annals of Dermatology. 24 (2): 126–135. doi:10.5021/ad.2012.24.2.126. PMC 3346901. PMID 22577261.
  12. ^ Sieber MA, Hegel JK (November 2013). "Azelaic acid: Properties and mode of action". Skin Pharmacology and Physiology (Review). 27 Suppl 1 (Supplement 1): 9–17. doi:10.1159/000354888. PMID 24280644. S2CID 8848543.
  13. ^ Pugashetti R, Shinkai K (July 2013). "Treatment of acne vulgaris in pregnant patients". Dermatologic Therapy (Review). 26 (4): 302–11. doi:10.1111/dth.12077. PMID 23914887. S2CID 5750718.
  14. ^ Gollnick, H. P.; Graupe, K.; Zaumseil, R. P. (2004). "15% Azelainsauregel in der Behandlung der Akne. Zwei doppelblinde klinische Vergleichsstudien" [Azelaic acid 15% gel in the treatment of acne vulgaris. Combined results of two double-blind clinical comparative studies]. Journal der Deutschen Dermatologischen Gesellschaft. 2 (10): 841–847. doi:10.1046/j.1439-0353.2004.04731.x. PMID 16281587. Retrieved 2021-05-14.
  15. ^ Thiboutot, Diane (January 2008). "Versatility of azelaic acid 15% gel in treatment of inflammatory acne vulgaris". Journal of Drugs in Dermatology. 7 (1): 13–16. ISSN 1545-9616. PMID 18246693.
  16. ^ a b Fitton, A.; Goa, K. L. (May 1991). "Azelaic acid. A review of its pharmacological properties and therapeutic efficacy in acne and hyperpigmentary skin disorders". Drugs. 41 (5): 780–798. doi:10.2165/00003495-199141050-00007. ISSN 0012-6667. PMID 1712709.
  17. ^ a b Morelli V, Calmet E, Jhingade V (June 2010). "Alternative therapies for common dermatologic disorders, part 2". Primary Care (Review). 37 (2): 285–96. doi:10.1016/j.pop.2010.02.005. PMID 20493337.
  18. ^ Woolery-Lloyd, Heather C.; Keri, Jonette; Doig, Stefan (2013-04-01). "Retinoids and azelaic acid to treat acne and hyperpigmentation in skin of color". Journal of Drugs in Dermatology. 12 (4): 434–437. ISSN 1545-9616. PMID 23652891.
  19. ^ Liu, Haibo; Yu, Haiyan; Xia, Jun; Liu, Ling; Liu, Guanjian; Sang, Hong; Peinemann, Frank (2020-11-01). "Evidence-based topical treatments (azelaic acid, salicylic acid, nicotinamide, sulfur, zinc, and fruit acid) for acne: an abridged version of a Cochrane systematic review". Journal of Evidence-Based Medicine. 13 (4): 275–283. doi:10.1111/jebm.12411. ISSN 1756-5391. PMID 33034949.
  20. ^ Draelos, Z. (Sep–Oct 2007). "Skin lightening preparations and the hydroquinone controversy". Dermatol. Ther. 20 (5): 308–313. doi:10.1111/j.1529-8019.2007.00144.x. PMID 18045355.
  21. ^ Grimes, Pearl E. (2007-07-01). Aesthetics and Cosmetic Surgery for Darker Skin Types. Lippincott Williams & Wilkins. pp. 74 ff. ISBN 978-0-7817-8403-0. Retrieved 9 August 2011.
  22. ^ Stamatiadis, D; Bulteau-Portois, Marie-Claire; Mowszowicz, Irene (1988). "Inhibition of 5α-reductase activity in human skin by zinc and azelaic acid". British Journal of Dermatology. 119 (5): 627–32. doi:10.1111/j.1365-2133.1988.tb03474.x. PMID 3207614.
  23. ^ Pathak, M. A.; Ciganek, E. R.; Wick, M.; Sober, A. J.; Farinelli, W. A.; Fitzpatrick, T. B. (September 1985). "An evaluation of the effectiveness of azelaic acid as a depigmenting and chemotherapeutic agent". The Journal of Investigative Dermatology. 85 (3): 222–228. doi:10.1111/1523-1747.ep12276684. ISSN 0022-202X. PMID 4031538.
  24. ^ Breathnach, A. S. (1996-01-01). "Melanin hyperpigmentation of skin: melasma, topical treatment with azelaic acid, and other therapies". Cutis. 57 (1 Suppl): 36–45. ISSN 0011-4162. PMID 8654129.
  25. ^ Pillaiyar, Thanigaimalai; Manickam, Manoj; Namasivayam, Vigneshwaran (2017-01-18). "Skin whitening agents: medicinal chemistry perspective of tyrosinase inhibitors". Journal of Enzyme Inhibition and Medicinal Chemistry. 32 (1): 403–425. doi:10.1080/14756366.2016.1256882. ISSN 1475-6366. PMC 6010116. PMID 28097901.
  26. ^[full citation needed][permanent dead link]
  27. ^ "Azelaic Acid brands in Pakistan". Retrieved 2021-04-17.

External links[edit]