| Azelaic acid | |
|---|---|
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nonanedioic acid |
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| Identifiers | |
| CAS number | 123-99-9 |
| PubChem | 2266 |
| ChemSpider | 2179 |
| UNII | F2VW3D43YT |
| DrugBank | APRD00812 |
| KEGG | D03034 |
| ChEBI | CHEBI:48131 |
| ChEMBL | CHEMBL1238 |
| ATC code | D10 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C9H16O4 |
| Molar mass | 188.22 g mol−1 |
| Melting point |
109-111 °C[1] |
| Boiling point |
286 °C at 100 mmHg[1] |
| Solubility in water | 2.14 g/L[2] |
| Acidity (pKa) | 4.550, 5.498[2] |
| Pharmacology | |
| Bioavailability | Very low |
| Routes of administration |
Topical |
| Elimination half-life |
12 hours |
| Legal status |
℞-only(US) |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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 component of a number of hair and skin conditioners.
Contents |
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.
In plants, azelaic acid serves as a "distress flare" involved in defense responses after infection.[3] It serves as a signal that induces the accumulation of salicylic acid, an important component of a plant's defensive response.[4]
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.[5]
Azelaic acid is used to treat mild to moderate acne; i.e. both comedonal acne and inflammatory acne. It works in part by stopping the growth of skin bacteria that cause acne, and by keeping skin pores clear.[6]
Azelaic acid is also used as a topical gel treatment for rosacea, due to its ability to reduce inflammation. In some cases, females have reported hair growth on face and neck.
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), the current gold standard for skin lightening, as countries such as Japan and the EU have questioned the safety of HQ.[7]
It is a Tyrosinase inhibitor. This reduces synthesis of melanin.[8]
Azelaic acid may be useful as a hair growth stimulant. A research report by Stamatiadis in 1988 suggested that azelaic acid (and combinations of it, with zinc ion and vitamin B6) was a strong type I 5-alpha reductase (5-AR) inhibitor.[9] The enzyme, 5-AR (both Types I and II) convert testosterone to dihydrotestosterone (DHT). DHT has been shown to contribute to prostate enlargement (benign prostatic hyperplasia, BPH) and to damage hair follicles. However, no clinical studies have confirmed its efficacy in helping with hair loss.
AzClear Action (20% lotion, Ego Pharmaceuticals), Azelex (20% cream, Allergan), White Action cream (20% cream,2% glycolic acid), SynCare), Finacea (15% gel, Intendis/Berlex Laboratories, subsidiaries of Bayer AG), Finevin (20% cream, Intendis/Berlex Laboratories), Skinoren (20% cream or 15% gel, Intendis), and Azaclear (azelaic acid and niacinamide, Epikinetics LLC).
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