Azelaic acid

Azelaic acid
File:Azelaic acid.png
File:Azelaic-acid-3D-balls.png
IUPAC name nonanedioic acid
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number	123-99-9 Y
PubChem	2266
ChemSpider	2179
DrugBank	APRD00812
ATC code	D10AX03
SMILES
InChI
InChI key	BDJRBEYXGGNYIS-UHFFFAOYAK
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula	C9H16O4
Molar mass	188.22 g mol−1
Melting point	109-111 °C
Boiling point	286 °C at 100 mmHg
Solubility in water	2.14 g/L
Acidity (pKa)	4.550, 5.598
style="background: #F8EABA; text-align: center;" colspan="2" | Pharmacology
Bioavailability	Very low
Routes of administration	Topical
Elimination half-life	12 hours
Legal status	℞-only(US)
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is a natural substance that is produced by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. It is industrially produced by the ozonolysis of oleic acid. It is effective against a number of skin conditions, such as mild to moderate acne, when applied topically in a cream formulation of 20%. Azelaic acid may be useful as a hair growth stimulant, although at present there are no clinical studies to confirm its efficacy.

Brand names: Acnederm (20% lotion, Ego Pharmaceuticals), Azelex (20% cream, Allergan), Finacea (15% gel, Intendis/Berlex Laboratories, subsidiaries of Bayer AG), Finevin (20% cream, Intendis/Berlex Laboratories), Skinoren (20% cream or 15% gel, Intendis).

Properties

• Antibacterial: it reduces the growth of bacteria in the follicle (Propionibacterium acnes and Staphylococcus epidermidis).
• Keratolytic & comedolytic: it returns to normal the disordered growth of the skin cells, lining the follicle.
• Scavenger of free radicals and reduces inflammation.
• Reduces pigmentation: it is particularly useful for darker-skinned patients, who have melasma, or whose acne spots leave persistent brown marks known as actinic lentigines. (per the product insert: "There have been reports of hypopigmentation after use of azelaic acid. Since azelaic acid has not been well studied in patients with dark complexions, these patients should be monitored for early signs of hypopigmentation.")
• Non-toxic, and is well tolerated by most patients.

Azelaic acid does not result in bacterial resistance to antibiotics, reduction in sebum production, photosensitivity (easy sunburn), staining of skin or clothing, or bleaching of normal skin or clothing.

Because 20% azelaic acid can be a skin irritant, it should be used only when prescribed by a physician.

Uses of azelaic acid

Acne treatment

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.

Rosacea treatment

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.

Hair loss

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. 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.

External links

• DermNet treatments/azelaic-acid
• http://www.nlm.nih.gov/medlineplus/druginfo/meds/a603020.html

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