Chemistry:Azelaic acid

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Short description: Organic chemical compound
Azelaic acid
Skeletal formula of azelaic acid
Ball-and-stick model of the azelaic acid molecule
Names
Preferred IUPAC name
Nonanedioic acid
Identifiers
3D model (JSmol)
1101094
ChEBI
ChEMBL
ChemSpider
DrugBank
EC Number
  • 204-669-1
261342
KEGG
UNII
Properties
C9H16O4
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]
Pharmacology
1=ATC code }} D10AX03 (WHO)
Topical
Pharmacokinetics:
Very low
12 h
Legal status
Hazards
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
Tracking categories (test):

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.[5]

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.[6]

Biological function

Plants biology

In plants, azelaic acid serves as a "distress flare" involved in defense responses after infection.[7] It serves as a signal that induces the accumulation of salicylic acid, an important component of a plant's defensive response.[8]

Human biology

The mechanism of action in humans is thought to be through the inhibition of hyperactive protease activity that converts cathelicidin into the antimicrobial skin peptide LL-37.[9]

Applications

Azelaic acid cream labeled in Russian

Polymers and related materials

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]

Medical

Azelaic acid is used to treat mild to moderate acne, both comedonal acne and inflammatory acne.[10][11] 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[clarification needed] of acne bacteria.[12] Azelaic acid is also used as a topical gel treatment for rosacea, due to its ability to reduce inflammation.[11] 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 has the potential to be fully comparable to that of some 20% creams.[13]

Acne treatment

Azelaic acid is effective for mild to moderate acne when applied topically at a 15%-20% concentration.[14][15][16][17] In patients with moderate acne, twice daily application over 3 months of 20% AzA significantly reduced the number of comedones, papules, and pustules[18];[19] at this strength, it’s considered to be as effective as benzoyl peroxide 5%, tretinoin 0.05%, erythromycin 2%, and oral tetracycline at 500mg-1000mg.[20][21] 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.[22] 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.[20]

Whitening agent

Azelaic acid is 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.[23] As a tyrosinase inhibitor,[5] azelaic acid reduces synthesis of melanin.[24] 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.[25] In vitro research during mid-1980s evaluating azelaic acid's depigmenting (whitening) capability concluded it is effective (cytotoxic to melanocytes) at only high concentrations.[26]

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.[27][19]

Brand names

Brand names for azelaic acid include Dermaz 99,[28] 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)[29]

References

  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. ↑ 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. https://pubmed.ncbi.nlm.nih.gov/16566285/. 
  4. ↑ 4.0 4.1 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. ↑ 5.0 5.1 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. PMID 28097901. 
  6. ↑ Integrative medicine. David Rakel (Fourth ed.). Philadelphia, PA. 2018. ISBN 978-0-323-35868-2. OCLC 982188831. https://www.worldcat.org/oclc/982188831. 
  7. ↑ Sarah Everts (January 31, 2011). "Vegetative Warfare". Chemical & Engineering News 89 (5): 53–55. doi:10.1021/cen-v089n005.p053. http://cen.acs.org/articles/89/i5/Vegetative-Warfare.html. 
  8. ↑ Jung, H. W.; Tschaplinski, T. J.; Wang, L.; Glazebrook, J.; Greenberg, J. T. (2009). "Priming in Systemic Plant Immunity". Science 324 (5923): 89–91. doi:10.1126/science.1170025. PMID 19342588. Bibcode: 2009Sci...324...89W. 
  9. ↑ 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. PMID 22577261. 
  10. ↑ "Azelaic Acid for Acne". http://www.webmd.com/skin-problems-and-treatments/acne/azelaic-acid-for-acne-vulgaris. 
  11. ↑ 11.0 11.1 "Azelaic acid topical". https://www.drugs.com/mtm/azelaic-acid-topical.html. 
  12. ↑ 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". Archives of Dermatology 142 (8): 1047–1052. doi:10.1001/archderm.142.8.1047. PMID 16924055. 
  13. ↑ Burchacka, E.; Potaczek, P.; Paduszyński, P.; Karłowicz-Bodalska, K.; Han, T.; Han, S. (2016-10-01). "New effective azelaic acid liposomal gel formulation of enhanced pharmaceutical bioavailability" (in en). Biomedicine & Pharmacotherapy 83: 771–775. doi:10.1016/j.biopha.2016.07.014. ISSN 0753-3322. PMID 27484346. https://www.sciencedirect.com/science/article/abs/pii/S0753332216306278. 
  14. ↑ "Azelaic acid: Properties and mode of action". Skin Pharmacology and Physiology 27 Suppl 1 (Supplement 1): 9–17. November 2013. doi:10.1159/000354888. PMID 24280644. 
  15. ↑ "Treatment of acne vulgaris in pregnant patients". Dermatologic Therapy 26 (4): 302–11. July 2013. doi:10.1111/dth.12077. PMID 23914887. 
  16. ↑ Gollnick, H. P.; Graupe, K.; Zaumseil, R. P. (2004). "15% Azelainsauregel in der Behandlung der Akne. Zwei doppelblinde klinische Vergleichsstudien". Journal der Deutschen Dermatologischen Gesellschaft 2 (10): 841–847. doi:10.1046/j.1439-0353.2004.04731.x. PMID 16281587. http://europepmc.org/article/med/16281587. Retrieved 2021-05-14. 
  17. ↑ 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. https://pubmed.ncbi.nlm.nih.gov/18246693/. 
  18. ↑ "Azelaic Acid And Its Benefits" (in en). https://chemistatplay.com/blogs/news/azelaic-acid-and-its-benefits. 
  19. ↑ 19.0 19.1 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. https://pubmed.ncbi.nlm.nih.gov/1712709/. 
  20. ↑ 20.0 20.1 "Alternative therapies for common dermatologic disorders, part 2". Primary Care 37 (2): 285–96. June 2010. doi:10.1016/j.pop.2010.02.005. PMID 20493337. 
  21. ↑ 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. https://pubmed.ncbi.nlm.nih.gov/23652891/. 
  22. ↑ 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. https://pubmed.ncbi.nlm.nih.gov/33034949/. 
  23. ↑ Draelos, Z. (Sep–Oct 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. 
  24. ↑ 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. https://books.google.com/books?id=ALt93yGZccQC&pg=PA74. Retrieved 9 August 2011. 
  25. ↑ 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. 
  26. ↑ 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. 
  27. ↑ 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. https://pubmed.ncbi.nlm.nih.gov/8654129/. 
  28. ↑ https://pharmaceutical.basf.com/en/APIs-Raw-Materials/Dermaz.html[full citation needed][yes|permanent dead link|dead link}}]
  29. ↑ "Azelaic Acid brands in Pakistan". http://www.druginfosys.com/availablebrands.aspx?query=20%2520%25w/w&form=Cream&drugCode=807&drugName=Azelaic%2520Acid&type=1&Ing==1. 

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