Azelaic acid

Last updated

Azelaic acid
Azelaic acid.png
Azelaic acid 3D ball.png
Names
Preferred IUPAC name
Nonanedioic acid
Other names
Azelate
Identifiers
3D model (JSmol)
1101094
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.246 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-669-1
261342
KEGG
PubChem CID
UNII
  • InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13) Yes check.svgY
    Key: BDJRBEYXGGNYIS-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
    Key: BDJRBEYXGGNYIS-UHFFFAOYAK
  • O=C(O)CCCCCCCC(=O)O
Properties
C9H16O4
Molar mass 188.223 g·mol−1
Appearancewhite 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]
Pharmacology
D10AX03 ( WHO )
Topical
Pharmacokinetics:
Very low
12 h
Legal status
  • AU: S5 (Caution)/ Schedule 4,Schedule 2 Appendix E, clause 3 Appendix F, clause 4 [3]
  • US: ℞-only [4]
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)
Azelaic acid
Clinical data
MedlinePlus a603020
Identifiers
CompTox Dashboard (EPA)
ECHA InfoCard 100.004.246 OOjs UI icon edit-ltr-progressive.svg

Azelaic acid (AzA), or nonanedioic acid, is an organic compound with the formula HOOC(CH2)7 COOH. [5] 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 several hair and skin conditioners. [6] In medicine, topical formulations of AzA are used in the treatment of acne vulgaris, where they exert antimicrobial and keratolytic effects that reduce clogged hair follicles and inflammation. [7] In plants, AzA functions as a mobile signaling molecule that primes systemic acquired resistance against pathogens by inducing the accumulation of salicylic acid. [8] AzA also inhibits tyrosinase. [9]

Contents

Production

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. [10]

Biological function

Plants biology

In plants, azelaic acid (AzA) functions as an endogenous signaling molecule that plays a central role in systemic defense responses after infection. It acts as a "distress flare," produced primarily in response to biotic stress such as pathogen attack, and is transported from infected tissues to distant parts of the plant. [11] There, it primes systemic acquired resistance (SAR) against a broad spectrum of pathogens by inducing the accumulation of salicylic acid, a key component of the plant's immune response. [12] Mechanistically, AzA works in concert with other mobile signals, including glycerol-3-phosphate and specific lipid transfer proteins, to orchestrate a systemic defense network that enhances disease resistance and enables rapid defensive responses to subsequent infections. [13]

Human biology

Azelaic acid treats acne through a multifaceted mechanism that includes antibacterial, anti-keratinizing, and anti-inflammatory activities, as well as direct effects on skin microflora. It exerts bacteriostatic action against Propionibacterium acnes and Staphylococcus epidermidis by disrupting microbial cellular metabolism and membrane pH balance, resulting in reduced bacterial proliferation without promoting resistance. In keratinocytes, azelaic acid inhibits DNA, RNA, and protein synthesis, thus normalizing follicular keratinization, which helps prevent the formation of comedones—clogged hair follicles that can develop into acne lesions and are considered a hallmark of the disease. Additionally, its anti-inflammatory properties decrease the production of reactive oxygen species and pro-inflammatory cytokines, collectively reducing both visible inflammation and the severity of acne lesions. [7] [14]

Applications

Azelaic acid cream labeled in Russian 30g azelaic acid cream tube.png
Azelaic acid cream labeled in Russian

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. [6]

Medical

In 2023, it was the 309th most commonly prescribed medication in the United States, with more than 200,000 prescriptions. [15]

Azelaic acid is used to treat mild to moderate acne, both comedonal acne and inflammatory acne. [16] [17] It belongs to a class of chemicals 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[ clarification needed ] of acne bacteria. [18] Azelaic acid is also used as a topical gel treatment for rosacea, due to its ability to reduce inflammation. [17] It clears the bumps and swelling caused by rosacea.

In topical pharmaceutical preparations and scientific research AzA is typically used in concentrations between 15% and 20% but some research demonstrates that in certain vehicle formulations, the pharmaceutical effects of 10% Azelaic acid have the potential to be fully comparable to that of some 20% creams. [19]

Acne treatment

Azelaic acid is effective for mild to moderate acne when applied topically at a 15%-20% concentration. [20] [21] [22] [23] In patients with moderate acne, twice daily application over 3 months of 20% AzA significantly reduced the number of comedones, papules, and pustules; [24] [25] at this strength, it’s considered to be as effective as benzoyl peroxide 5%, tretinoin 0.05%, erythromycin 2%, and oral tetracycline at 500 mg-1000 mg. [26] [27] In a comparative review of effects of topical AzA, Salicylic acid, Nicotinamide, Sulfur, Zinc, and alpha-hydroxy acid, AzA had more high-quality evidence of effectiveness than the rest. [28] 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. [26]

Whitening agent

Azelaic acid is used for the 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. [29] As a tyrosinase inhibitor, [9] azelaic acid reduces synthesis of melanin. [30] According to one report in 1988, azelaic acid in combination with zinc sulfate in vitro was found to be a potent (90% inhibition) 5α-reductase inhibitor, similar to the hair loss drugs finasteride and dutasteride. [31] In vitro research during mid-1980s evaluating azelaic acid's depigmenting (whitening) capability concluded it is effective (cytotoxic to melanocytes) at only high concentrations. [32]

A 1996 review claimed 20% AzA is as potent as 4% hydroquinone after a period of application of three months without the latter's adverse effects and even more effective if applied along with tretinoin for the same period of time. [33] [25]

Brand names

Brand names for azelaic acid include Dermaz 99, [34] 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, Azelan, Azaderm, (Acnegen, Eziderm, Acnicam, Azelexin in Pakistan) [35]

References

  1. 1 2 Sigma-Aldrich catalog Archived 9 April 2008 at the Wayback Machine
  2. 1 2 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. ↑ "The Poisons Standard (the SUSMP)". Therapeutic Goods Administration (TGA). 22 August 2022. Retrieved 31 August 2025.
  4. ↑ "Finacea- azelaic acid gel; Finacea- azelaic acid kit". DailyMed. 12 April 2011. Retrieved 1 September 2025.
  5. ↑ Del Rosso JQ (February 2006). "The use of topical azelaic acid for common skin disorders other than inflammatory rosacea". Cutis. 77 (2 Suppl): 22–24. PMID   16566285.
  6. 1 2 Cornils B, Lappe P (2006). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523. ISBN   978-3-527-30673-2.
  7. 1 2 Feng X, Shang J, Gu Z, Gong J, Chen Y, Liu Y (2024). "Azelaic Acid: Mechanisms of Action and Clinical Applications". Clinical, Cosmetic and Investigational Dermatology. 17: 2359–2371. doi: 10.2147/CCID.S485237 . PMC   11512533 . PMID   39464747.
  8. ↑ Jung HW, Tschaplinski TJ, Wang L, Glazebrook J, Greenberg JT (April 2009). "Priming in systemic plant immunity". Science. 324 (5923): 89–91. Bibcode:2009Sci...324...89W. doi:10.1126/science.1170025. PMID   19342588. S2CID   206518245.
  9. 1 2 Pillaiyar T, Manickam M, Namasivayam V (December 2017). "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. PMC   6010116 . PMID   28097901.
  10. ↑ Rakel D (2018). Integrative medicine (Fourth ed.). Philadelphia, PA: Elsevier Inc. ISBN   978-0-323-35868-2. OCLC   982188831.
  11. ↑ Everts S (31 January 2011). "Vegetative Warfare" . Chemical & Engineering News . 89 (5): 53–55. doi:10.1021/cen-v089n005.p053.
  12. ↑ Jung HW, Tschaplinski TJ, Wang L, Glazebrook J, Greenberg JT (April 2009). "Priming in systemic plant immunity". Science. 324 (5923): 89–91. Bibcode:2009Sci...324...89W. doi:10.1126/science.1170025. PMID   19342588. S2CID   206518245.
  13. ↑ Priya Reddy YN, Oelmüller R (February 2024). "Lipid peroxidation and stress-induced signalling molecules in systemic resistance mediated by azelaic acid/AZELAIC ACID INDUCED1: signal initiation and propagation". Physiology and Molecular Biology of Plants. 30 (2): 305–316. Bibcode:2024PMBP...30..305P. doi:10.1007/s12298-024-01420-1. PMC   11016046 . PMID   38623172.
  14. ↑ Schulte BC, Wu W, Rosen T (September 2015). "Azelaic Acid: Evidence-based Update on Mechanism of Action and Clinical Application". Journal of Drugs in Dermatology. 14 (9): 964–968. PMID   26355614.
  15. ↑ "Azelate Drug Usage Statistics, United States, 2013 - 2023". ClinCalc. Retrieved 21 August 2025.
  16. ↑ "Azelaic Acid for Acne". WebMD .
  17. 1 2 "Azelaic acid topical". Drugs.com.
  18. ↑ Liu RH, Smith MK, Basta SA, Farmer ER (August 2006). "Azelaic acid in the treatment of papulopustular rosacea: a systematic review of randomized controlled trials". Archives of Dermatology. 142 (8): 1047–1052. doi:10.1001/archderm.142.8.1047. PMID   16924055.
  19. ↑ Burchacka E, Potaczek P, Paduszyński P, Karłowicz-Bodalska K, Han T, Han S (October 2016). "New effective azelaic acid liposomal gel formulation of enhanced pharmaceutical bioavailability". Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie. 83: 771–775. doi:10.1016/j.biopha.2016.07.014. PMID   27484346.
  20. ↑ Sieber MA, Hegel JK (November 2013). "Azelaic acid: Properties and mode of action". Skin Pharmacology and Physiology (Review). 27 (Supplement 1): 9–17. doi:10.1159/000354888. PMID   24280644. S2CID   8848543.
  21. ↑ Pugashetti R, Shinkai K (July 2013). "Treatment of acne vulgaris in pregnant patients". Dermatologic Therapy (Review). 26 (4): 302–311. doi: 10.1111/dth.12077 . PMID   23914887. S2CID   5750718.
  22. ↑ Gollnick HP, Graupe K, Zaumseil RP (October 2004). "[Azelaic acid 15% gel in the treatment of acne vulgaris. Combined results of two double-blind clinical comparative studies]" [Azelaic acid 15% gel in the treatment of acne vulgaris. Combined results of two double-blind clinical comparative studies]. Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology. 2 (10): 841–847. doi:10.1046/j.1439-0353.2004.04731.x. PMID   16281587. S2CID   58809558.
  23. ↑ Thiboutot D (January 2008). "Versatility of azelaic acid 15% gel in treatment of inflammatory acne vulgaris". Journal of Drugs in Dermatology. 7 (1): 13–16. PMID   18246693.
  24. ↑ "Azelaic Acid And Its Benefits". Chemist at Play. Retrieved 10 March 2022.
  25. 1 2 Fitton A, Goa KL (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. PMID   1712709. S2CID   46960738.
  26. 1 2 Morelli V, Calmet E, Jhingade V (June 2010). "Alternative therapies for common dermatologic disorders, part 2". Primary Care (Review). 37 (2): 285–296. doi:10.1016/j.pop.2010.02.005. PMID   20493337.
  27. ↑ Woolery-Lloyd HC, Keri J, Doig S (April 2013). "Retinoids and azelaic acid to treat acne and hyperpigmentation in skin of color". Journal of Drugs in Dermatology. 12 (4): 434–437. PMID   23652891.
  28. ↑ Liu H, Yu H, Xia J, Liu L, Liu G, Sang H, et al. (November 2020). "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. PMID   33034949. S2CID   222236883.
  29. ↑ Draelos ZD (September–October 2007). "Skin lightening preparations and the hydroquinone controversy". Dermatologic Therapy. 20 (5): 308–313. doi: 10.1111/j.1529-8019.2007.00144.x . PMID   18045355. S2CID   24913995.
  30. ↑ Grimes PE (1 July 2007). Aesthetics and Cosmetic Surgery for Darker Skin Types. Lippincott Williams & Wilkins. pp. 74 ff. ISBN   978-0-7817-8403-0 . Retrieved 9 August 2011.
  31. ↑ Stamatiadis D, Bulteau-Portois MC, Mowszowicz I (November 1988). "Inhibition of 5 alpha-reductase activity in human skin by zinc and azelaic acid". The British Journal of Dermatology. 119 (5): 627–632. doi:10.1111/j.1365-2133.1988.tb03474.x. PMID   3207614. S2CID   28506969.
  32. ↑ Pathak MA, Ciganek ER, Wick M, Sober AJ, Farinelli WA, Fitzpatrick TB (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 . PMID   4031538.
  33. ↑ Breathnach AS (January 1996). "Melanin hyperpigmentation of skin: melasma, topical treatment with azelaic acid, and other therapies". Cutis. 57 (1 Suppl): 36–45. PMID   8654129.
  34. ↑ https://pharmaceutical.basf.com/en/APIs-Raw-Materials/Dermaz.html%5B%5D%5B%5D
  35. ↑ "Azelaic Acid brands in Pakistan". www.druginfosys.com. Retrieved 17 April 2021.
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