Azelaic acid

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Azelaic acid

Names
IUPAC name nonanedioic acid
Identifiers
CAS Number	123-99-9 Y
ChEBI	CHEBI:48131 Y
ChEMBL	ChEMBL1238 Y
ChemSpider	2179 Y
DrugBank	DB00548 Y
IUPHAR/BPS	7484
Jmol 3D model	Interactive image
KEGG	D03034 Y
PubChem	2266
UNII	F2VW3D43YT Y
InChI InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13) Y Key: BDJRBEYXGGNYIS-UHFFFAOYSA-N Y 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
SMILES O=C(O)CCCCCCCC(=O)O
Properties
Chemical formula	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)
Boiling point	286 °C (547 °F; 559 K) at 100 mmHg
Solubility in water	2.14 g/L
Acidity (pKa)	4.550, 5.498
Pharmacology
ATC code	D10AX03
Legal status	US: ℞-only
Routes of administration	Topical
Pharmacokinetics:
Bioavailability	Very low
Biological half-life	12 hours
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 is an organic compound with the formula (CH₂)₇(CO₂H)2. 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, plasticizers, as well as being a component of a number of hair and skin conditioners.

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.

Biological function

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

Applications

Polymers and related materials

Esters of this dicarboxylic acid find applications in lubrication and plasticizers. With hexamethylenediamine azelaic acid forms Nylon-6,9, which finds specialized uses as a plastic.

Medical

Azelaic acid is used to treat mild to moderate acne, both comedonal acne and inflammatory acne. 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. Azelaic acid is also used as a topical gel treatment for rosacea, due to its ability to reduce inflammation. 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. Azelaic acid has been used for treatment of skin pigmentation including melasma and post inflammatory hyperpigmentation, particularly in those with darker skin types. It has been recommended as an alternative to hydroquinone (HQ). As a tyrosinase inhibitor, azelaic acid reduces synthesis of melanin.

Brand names

Brand names for azelaic acid include Azepur99 (Azelaic Products), Azetec99 (Azeco Technologies USA), Azaclear (azelaic acid and niacinamide, Epikintics), AzClear Action (Ego Pharmaceuticals), Azelex (Allergan), White Action cream (SynCare), Finacea (Intendis/Berlex Laboratories), Finevin (Intendis/Berlex Laboratories), Melazepam (Strata Dermatologics), Skinoren (Intendis), Ezanic (Intas), and Azaderm (MUP) .

External links

• Azelaic Acid side effects
• DermNet treatments/azelaic-acid

• Azelaic Acid Topical, MedlinePlus