Azelaic acid

Last updated
Azelaic acid
Azelaic acid.png
Azelaic acid 3D ball.png
Names
Preferred IUPAC name
Nonanedioic acid
Identifiers
3D model (JSmol)
1101094
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.246 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-669-1
261342
KEGG
PubChem CID
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) Yes check.svgY
    Key: BDJRBEYXGGNYIS-UHFFFAOYSA-N Yes check.svgY
  • 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
Appearancewhite 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:
GHS-pictogram-exclam.svg
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Azelaic acid (AzA) is an organic compound with the formula HOOC(CH2)7 COOH. [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]

Contents

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. [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 30g azelaic acid cream tube.png
Azelaic acid cream labeled in Russian

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. [14] [15] [16] [17] In patients with moderate acne, twice daily application over 3 months of 20% AzA significantly reduced the number of comedones, papules, and pustules; [18] [19] at this strength, it’s considered to be as effective as benzoyl peroxide 5%, tretinoin 0.05%, erythromycin 2%, and oral tetracycline at 500 mg-1000 mg. [20] [21] In a comparative review of effects of topical AzA, Salicylic acid, Nicotinamide, Sulfur, Zinc, and 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 melasma and postinflammatory hyperpigmentation, particularly in those with darker skin types. It has been recommended as an alternative to hydroquinone. [23] As a tyrosinase inhibitor, [5] azelaic acid reduces synthesis of melanin. [24] According to one report in 1988, azelaic acid in combination with zinc sulfate in vitro was found to be a potent (90% inhibition) 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]

Related Research Articles

<span class="mw-page-title-main">Acne</span> Skin condition characterized by pimples

Acne also known as acne vulgaris, is a long-term skin condition that occurs when dead skin cells and oil from the skin clog hair follicles. Typical features of the condition include blackheads or whiteheads, pimples, oily skin, and possible scarring. It primarily affects skin with a relatively high number of oil glands, including the face, upper part of the chest, and back. The resulting appearance can lead to lack of confidence, anxiety, reduced self-esteem, and, in extreme cases, depression or thoughts of suicide.

<span class="mw-page-title-main">Tinea versicolor</span> Skin disease

Tinea versicolor is a condition characterized by a skin eruption on the trunk and proximal extremities. The majority of tinea versicolor is caused by the fungus Malassezia globosa, although Malassezia furfur is responsible for a small number of cases. These yeasts are normally found on the human skin and become troublesome only under certain conditions, such as a warm and humid environment, although the exact conditions that cause initiation of the disease process are poorly understood.

<span class="mw-page-title-main">Rosacea</span> Skin condition, usually on the face

Rosacea is a long-term skin condition that typically affects the face. It results in redness, pimples, swelling, and small and superficial dilated blood vessels. Often, the nose, cheeks, forehead, and chin are most involved. A red, enlarged nose may occur in severe disease, a condition known as rhinophyma.

<span class="mw-page-title-main">Benzoyl peroxide</span> Chemical compound with uses in industry and acne treatment

Benzoyl peroxide is a chemical compound (specifically, an organic peroxide) with structural formula (C6H5−C(=O)O−)2, often abbreviated as (BzO)2. In terms of its structure, the molecule can be described as two benzoyl (C6H5−C(=O)−, Bz) groups connected by a peroxide (−O−O−). It is a white granular solid with a faint odour of benzaldehyde, poorly soluble in water but soluble in acetone, ethanol, and many other organic solvents. Benzoyl peroxide is an oxidizer, which is principally used in the production of polymers.

<span class="mw-page-title-main">Adapalene</span> Third-generation topical retinoid

Adapalene is a third-generation topical retinoid primarily used in the treatment of mild-moderate acne, and is also used off-label to treat keratosis pilaris as well as other skin conditions. Studies have found adapalene is as effective as other retinoids, while causing less irritation. It also has several advantages over other retinoids. The adapalene molecule is more stable compared to tretinoin and tazarotene, which leads to less concern for photodegradation. It is also chemically more stable compared to the other two retinoids, allowing it to be used in combination with benzoyl peroxide. Due to its effects on keratinocyte proliferation and differentiation, adapalene is superior to tretinoin for the treatment of comedonal acne and is often used as a first-line agent. The Swiss company Galderma sells adapalene under the brand name Differin.

<span class="mw-page-title-main">Hyperpigmentation</span> Darkening of an area of skin or nails due to increased melanin

Hyperpigmentation is the darkening of an area of skin or nails caused by increased melanin.

<span class="mw-page-title-main">Melasma</span> Medical condition

Melasma is a tan or dark skin discoloration. Melasma is thought to be caused by sun exposure, genetic predisposition, hormone changes, and skin irritation. Although it can affect anyone, it is particularly common in women, especially pregnant women and those who are taking oral or patch contraceptives or hormone replacement therapy medications.

<span class="mw-page-title-main">Ammonium bituminosulfonate</span> Chemical compound

Ichthammol or ammonium bituminosulfonate, also known as black ointment, is a medication derived from sulfur-rich oil shale. It is used as a treatment for different skin diseases, including eczema and psoriasis. It is applied on the skin as an ointments, most commonly containing 10% or 20% ichthammol.

<span class="mw-page-title-main">Perioral dermatitis</span> Medical condition

Perioral dermatitis, also known as periorificial dermatitis, is a common type of inflammatory skin rash. Symptoms include multiple small (1–2 mm) bumps and blisters sometimes with background redness and scale, localized to the skin around the mouth and nostrils. Less commonly, the eyes and genitalia may be involved. It can be persistent or recurring, and resembles particularly rosacea and to some extent acne and allergic dermatitis. The term "dermatitis" is a misnomer because this is not an eczematous process.

<span class="mw-page-title-main">Lentigo</span> Small pigment spots on skin

A lentigo is a small pigmented spot on the skin with a clearly defined edge, surrounded by normal-appearing skin. It is a harmless (benign) hyperplasia of melanocytes which is linear in its spread. This means the hyperplasia of melanocytes is restricted to the cell layer directly above the basement membrane of the epidermis where melanocytes normally reside. This is in contrast to the "nests" of multi-layer melanocytes found in moles. Because of this characteristic feature, the adjective "lentiginous" is used to describe other skin lesions that similarly proliferate linearly within the basal cell layer.

<span class="mw-page-title-main">Liver spot</span> Age-related skin blemish

Liver spots are blemishes on the skin associated with aging and exposure to ultraviolet radiation from the sun. They range in color from light brown to red or black and are located in areas most often exposed to the sun, particularly the hands, face, shoulders, arms and forehead, and the scalp if bald.

<span class="mw-page-title-main">Arbutin</span> Glycoside

β-arbutin, also known by its International Nomenclature of Cosmetic Ingredients (INCI) name, arbutin, is a glycosylated derivative of hydroquinone. β-Arbutin is naturally present in the leaves and bark of a variety of plants, notably the bearberry plant, Arctostaphylos uva-ursi. Utilized as a biosynthetic active ingredient in topical treatments for skin lightening, β-arbutin is aimed at addressing hyperpigmentation issues. Its mechanism of action involves inhibiting the activity of tyrosinase, an essential enzyme for melanin synthesis in the human skin, thereby leading to a reduction in hyperpigmentation. It is important to distinguish β-arbutin from its structurally similar stereoisomer, α-arbutin, which exhibits similar effects in clinical applications.

Hidradenitis is any disease in which the histologic abnormality is primarily an inflammatory infiltrate around the eccrine glands. This group includes neutrophilic eccrine hidradenitis and recurrent palmoplantar hidradenitis.

<span class="mw-page-title-main">Pimple</span> Type of comedo

A pimple or zit is a kind of comedo that results from excess sebum and dead skin cells getting trapped in the pores of the skin. In its aggravated state, it may evolve into a pustule or papule. Pimples can be treated by acne medications, antibiotics, and anti-inflammatories prescribed by a physician, or various over the counter remedies purchased at a pharmacy.

Infantile acne is a form of acne that begins in very young children. Typical symptoms include inflammatory and noninflammatory lesions, papules and pustules most commonly present on the face. No cause of infantile acne has been established but it may be caused by increased sebaceous gland secretions due to elevated androgens, genetics and the fetal adrenal gland causing increased sebum production. Infantile acne can resolve by itself by age 1 or 2. However, treatment options include topical benzyl peroxide, topical retinoids and topical antibiotics in most cases.

<span class="mw-page-title-main">Azerizin</span> Dietary supplement

Azerizin is claimed to be a proprietary blend of the natural ingredients nicotinamide, azelaic acid, quercetin and curcumin that purportedly combine the anti-inflammatory and antimicrobial properties, along with inhibiting effects on sebum production.

<span class="mw-page-title-main">Medical uses of salicylic acid</span> Overview of a common topical medication

Salicylic acid is used as a medicine to help remove the outer layer of the skin. As such it is used to treat warts, skin tags, calluses, psoriasis, dandruff, acne, ringworm, and ichthyosis. For conditions other than warts, it is often used together with other medications. It is applied to the area affected.

<span class="mw-page-title-main">Glyceryl octyl ascorbic acid</span> Chemical compound

Glyceryl octyl ascorbic acid (GO-VC) is an amphipathic derivative of vitamin C consisting of two ether linkages: a 1-octyl at position 2 and a glycerin at position 3. The chemical name is 2-glyceryl-3-octyl ascorbic acid. The isomer in which these two groups are swapped is also known.

Postinflammatory hyperpigmentation (PIH) is a skin condition characterized by the darkening of the skin (hyperpigmentation) following an inflammatory injury, such as acne, dermatitis, infectious disease, or trauma. Less frequently, it may occur as a complication of a medical procedure performed on the skin. It is a common cause of skin discoloration and can affect individuals of all skin types.

Cetyl tranexamate mesylate is a bioavailable derivative of tranexamic acid for use in cosmetic formulations. Its primary use is in skincare products aimed at enhancing appearance by targeting hyperpigmentation, uneven skin tone, inflammation, dark spots, UV induced erythema, acne scars, and overall skin clarity.

References

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