Azelaic acid
Chemical name	nonanedioic acid
Other names	1,7-heptanedicarboxylic acid
Chemical formula	C9H16O4
Molecular mass	188.22 g/mol
CAS number	[123-99-9]
Melting point	98-103 °C
Boiling point	237 °C at 20 mmHg
SMILES	OC(CCCCCCCC(O)=O)=O
Disclaimer and 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 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. Image File history File links Azelaic_acid. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass (abbreviated MM) of a substance, called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A dicarboxylic acid is an organic compound where each molecule contains two carboxylic acid functional groups, often written -COOH. Dicarboxylic acids can be used to prepare copolymers such as nylon and polyethylene terephthalate. ... Species T. boeoticum T. compactum T. dicoccoides T. dicoccon T. durum T. monococcum T. spelta T. sphaerococcum References:   ITIS 42236 2002-09-22 Wheat (Triticum spp. ... Binomial name Secale cereale M.Bieb. ... Binomial name Hordeum vulgare L. Barley (Hordeum vulgare) is a major food and animal feed crop, a member of the grass family Poaceae. ... Malassezia furfur (formerly known as Pityrosporum ovale) is one species of a group of related fungi (yeasts) naturally found on the skin surfaces of many animals and humans, and primarily known as the most common cause of dandruff. ... Yeasts are single-celled (unicellular) fungi, a few species of which are commonly used to leaven bread, ferment alcoholic beverages, and even drive experimental fuel cells. ... A close-up of human skin. ... In medicine, a topical medication is applied to body surfaces such as the skin or mucous membranes such as the vagina, nasopharynx, or the eye. ... Cream is a dairy product that is composed of the higher-butterfat layer skimmed from the top of raw milk before homogenization. ... Young Girl Fixing her Hair, by Sophie Gengembre Anderson Hair is a filamentous outgrowth from the skin, found mainly in mammals. ... A stimulant is a drug that increases the activity of the sympathetic nervous system and produces a sense of euphoria or the feeling of being more awake. ...

Properties

Azelaic acid is:

• Antibacterial: it reduces the growth of bacteria in the follicle (Proprionibacterium acnes and Staphylococcus epidermidis);
• Keratolytic & comedolytic: it returns to normal, the disordered growth of the skin cells, lining the follicle; and
• Scavenger of free radicals: it reduces inflammation.
• Reduces pigmentation: it is particularly useful for darker-skinned patients, who have melasma, or whose acne spots leave persistent brown marks; (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: Subgroups Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular: bacterium) are a major group of living organisms. ... In botany, a follicle is a type of simple dry fruit produced by certain flowering plants. ... Staphyloccus epidermidis is a member of the bacterial genus Staphylococcus, consisting of Gram-positive cocci arranged in clusters. ... Keratolytic (ker-uh-toe-lih-tik) therapy is treatment to remove warts. ... This article is about skin in the biological sense. ... In chemistry free radicals are uncharged atomic or molecular species with unpaired electrons or an otherwise open shell configuration. ... Inflammation is the first response of the immune system to infection or irritation and may be referred to as the innate cascade. ... Melasma on adult females cheek. ...

• bacterial resistance to antibiotics
• reduction in sebum production
• photosensitivity (easy sunburn)
• staining of skin or clothing
• 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. An antibiotic is a drug that kills or slows the growth of bacteria. ... The sebaceous glands are glands found in the skin of mammals. ... Photosensitivity is the amount to which an object reacts upon receiving photons of light. ... In chemistry, to bleach something generally means to whiten it or oxidize it. ... The word irritant may refer to: Something that causes irritation, often a chemical substance. ... Physician examining a child A physician is a person who practices medicine. ...

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.

Hair loss

Azelaic acid may be very 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 male prostrate enlargement (benign prostatic hyperplasia, BPH) and to damage hair follicles. 1988 (MCMLXXXVIII) was a leap year starting on Friday of the Gregorian calendar. ... General Name, Symbol, Number zinc, Zn, 30 Chemical series transition metals Group, Period, Block 12, 4, d Appearance bluish pale gray Atomic mass 65. ... // An ion is an atom or a group of atoms (a chemical substance), or subatomic particle, with a net electric charge. ... Pyridoxine Vitamin B-6 is a water-soluble vitamin. ... 5-alpha reductase is an enzyme (EC 1. ... Ribbon diagram of the enzyme TIM. TIM is catalytically perfect, meaning its conversion rate is limited, or nearly limited to its substrate diffusion rate. ... Testosterone is a steroid hormone from the androgen group. ... Dihydrotestosterone (DHT) is a biologically active metabolite of the hormone testosterone, formed primarily in the prostate gland, testes, hair follicles, and adrenal glands by the enzyme 5α-reductase by means of reducing the Δ4,5 double-bond. ... DHT is an acronym with several meanings. ... Male Anatomy The prostate is a gland that is part of male mammalian sex organs. ... BPH redirects here, It can also refer to the Break Permitted Here character in the C1 control code set. ...

External links

• http://dermnetnz.org/treatments/azelaic-acid.html
• http://www.nlm.nih.gov/medlineplus/druginfo/uspdi/202783.html