Azelaic acid

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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
ECHA InfoCard
 100.004.246 Edit this at Wikidata
EC Number
  • 204-669-1
261342
IUPHAR/BPS
KEGG
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) checkY
    Key: BDJRBEYXGGNYIS-UHFFFAOYSA-N 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)
    Key: BDJRBEYXGGNYIS-UHFFFAOYAK
  • O=C(O)CCCCCCCC(=O)O
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
D10AX03 (WHO)
Topical
Pharmacokinetics:
Very low
12 h
Legal status
Hazards
GHS labelling:
GHS07: Exclamation mark
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).
checkY verify (what is checkY☒N ?)

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

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.

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

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. ^ a b Sigma-Aldrich catalog Archived April 9, 2008, at the Wayback Machine
  2. ^
    doi:10.1021/je060132t
    .
  3. PMID 16566285
    .
  4. ^
    ISBN 3527306730
    .
  5. ^
    PMID 28097901
    .
  6. OCLC 982188831.{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: others (link
    )
  7. doi:10.1021/cen-v089n005.p053
    .
  8. S2CID 206518245
    .
  9. PMID 22577261
    .
  10. ^ "Azelaic Acid for Acne". WebMD.
  11. ^ a b "Azelaic acid topical". Drugs.com.
  12. PMID 16924055
    .
  13. PMID 27484346
    .
  14. S2CID 8848543
    .
  15. S2CID 5750718
    .
  16. S2CID 58809558
    . Retrieved 2021-05-14.
  17. PMID 18246693
    .
  18. ^ "Azelaic Acid And Its Benefits". Chemist at Play. Retrieved 2022-03-10.
  19. ^
    S2CID 46960738
    .
  20. ^
    PMID 20493337
    .
  21. PMID 23652891
    .
  22. S2CID 222236883
    .
  23. S2CID 24913995
    .
  24. ISBN 978-0-7817-8403-0
    . Retrieved 9 August 2011.
  25. S2CID 28506969
    .
  26. PMID 4031538
    .
  27. PMID 8654129
    .
  28. ^ https://pharmaceutical.basf.com/en/APIs-Raw-Materials/Dermaz.html[full citation needed][permanent dead link]
  29. ^ "Azelaic Acid brands in Pakistan". www.druginfosys.com. Retrieved 2021-04-17.

External links

Retrieved from "https://en.wikipedia.org/w/index.php?title=Azelaic_acid&oldid=1193801078"