AZELAIC ACID
Azelaic acid is a naturally occurring saturated nine-carbon dicarboxylic acid (COOH (CH2)7-COOH).
Azelaic acid 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
Azelaic acid is an ingredient with antibacterial, skin cell regulating, anti-inflammatory and skin-lightening magic properties.
CAS Number: 123-99-9
EC Number: 204-669-1
Molecular formula: C9H16O4
Molar mass: 188.22 g/mol
Synonyms: 1,7-dicarboxyheptane, 1,7-Heptanedicarboxylic acid, 1,9-nonanedioic acid, acide azélaïque, acidum azelaicum, anchoic acid, Azelaic acid, AZELAIC ACID, azelaic acid, Azelainsäure Deutsch, lepargylic acid, n-nonanedioic acid, Nonandisäure Deutsch, Nonanedioic acid, 1,7-Heptanedicarboxylic acid, 1101094 [Beilstein], 123-99-9 [RN], 204-669-1 [EINECS], Acide azélaïque [French] [ACD/IUPAC Name], acide nonanedioïque [French], Acido azelaico [Spanish], anchoic acid, Azalaic Acid, Azelaate [ACD/IUPAC Name], Azelaic acid [ACD/IUPAC Name] [USAN] [Wiki], Azelainic acid, Azelainsäure [German] [ACD/IUPAC Name], Azelex [Trade name], Finaceae [Trade name], lepargylic acid, MFCD00004432 [MDL number], Nonandisäure [German], Nonanedioic acid [ACD/Index Name], Skinoren [Trade name], 1,7-dicarboxyheptane, 1,9-NONANEDIOIC ACID, 119176-67-9 [RN], acide azelaique [French], Acido azelaico [Spanish], Acidum acelaicum, Acidum azelaicum [Latin], AHI, AZ1, Azelaic acid,, azelaicacid, Azelainsäure [ACD/IUPAC Name], Azelate, DB00548, Emery's L-110, Finacea [Wiki], Heptanedicarboxylic acid, n-nonanedioic acid, Nonandisäure, Nonanedioate, Nonanedioic-D14 Acid, Nonanedionic acid, Skinorem, Water-soluble azelaic acid, Zumilin, азелаиновая кислота, حمض أزيلائيك, 壬二酸, azelaic acid, NONANEDIOIC ACID, 123-99-9, Finacea, Anchoic acid, Azelex, 1,7-Heptanedicarboxylic acid, Lepargylic acid, Skinoren, 1,9-Nonanedioic acid, Heptanedicarboxylic acid, n-Nonanedioic acid, Emerox 1110, Emerox 1144, acide azelaique, Finevin, Azelainic acid, acidum azelaicum, azelate, Polyazelaic anhydride, Skinorem, 1,7-Dicarboxyheptane, Azelaic acid, technical grade, Emery's L-110, azelaate, Poly(azelaic anhydride), ZK 62498, ZK-62498, UNII-F2VW3D43YT, NSC 19493, Azelaic acid 99%, Azelaic acid, 98%, CHEBI:48131, MFCD00004432, F2VW3D43YT, MLS000069659, 26776-28-3, NSC19493, NSC-19493, NCGC00014993-07, SMR000059164, Acido azelaico, Azalaic Acid, DSSTox_CID_1640, Acide azelaique [French], Acido azelaico [Spanish], Acidum azelaicum [Latin], DSSTox_RID_76254, DSSTox_GSID_21640, heptane-1,7-dicarboxylic acid, Azelaic acid [USAN:INN], Azelaic polyanhydride, Nonanedioic acid, homopolymer, Azelaic, Azelaic acid polyanhydride, CAS-123-99-9, Finacea (TN), Azelex (TN), SR-01000075671, EINECS 204-669-1, Azelaic acid (USAN/INN), BRN 1101094, Azelaicacidtech, Azelainsaeure, Lepargylate, Nonandisaeure, Anchoate, Nonanedioic acid, sodium salt, n-Nonanedioate, AI3-06299, nonanedionic acid, HSDB 7659, 1tuf, azelaic acid group, 1,9-Nonanedioate, SH-441, AGN-191861, Spectrum_000057, ACMC-1BTAP, Opera_ID_740, Polyazelaic Polyanhydride, 1,7-Heptanedicarboxylate, Spectrum2_000995, Spectrum3_000278, Spectrum4_000401, Spectrum5_001304, C9-120-alpha-polymorph, C9-140-alpha-polymorph, C9-180-alpha-polymorph, C9-220-alpha-polymorph, C9-260-alpha-polymorph, C9-298-alpha-polymorph, Epitope ID:187039, A-9800, EC 204-669-1, Nonanedioic acid homopolymer, Lopac-246379, SCHEMBL3887, CHEMBL1238, Lopac0_000051, BSPBio_001756, KBioGR_000662, KBioSS_000437, Nonanedioic acid Azelaic acid, 4-02-00-02055 (Beilstein Handbook Reference), 1-O-hexadecyl-2-(8-carboxyoctanoyl)-sn-glycero-3-phosphocholine has functional parent nonanedioic acid, 1-azelaoyl-sn-glycero-3-phosphocholine has functional parent nonanedioic acid, 1-palmitoyl-2-azelaoyl-sn-glycero-3-phosphocholine has functional parent nonanedioic acid, 2-azelaoyl-sn-glycero-3-phosphocholine has functional parent nonanedioic acid, nonanedioic acid monoglycoside has functional parent nonanedioic acid, azelaate is conjugate base of nonanedioic acid, azelaate(2−) is conjugate base of nonanedioic acid
Azelaic acid is a naturally occurring dicarboxylic acid produced by Malassezia furfur and found in whole grain cereals, rye, barley and animal products.
Azelaic acid possesses antibacterial, keratolytic, comedolytic, and anti-oxidant activity.
Azelaic acid is bactericidal against Proprionibacterium acnes and Staphylococcus epidermidis due to Azelaic acid inhibitory effect on the synthesis of microbial cellular proteins.
Azelaic acid exerts its keratolytic and comedolytic effects by reducing the thickness of the stratum corneum and decreasing the number of keratohyalin granules by reducing the amount and distribution of filaggrin in epidermal layers.
Azelaic acid also possesses a direct anti-inflammatory effect due to Azelaic acid scavenger activity of free oxygen radical.
This drug is used topically to reduce inflammation associated with acne and rosacea.
Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley.
Azelaic acid is also produced by Malassezia furfur, also known as Pityrosporum ovale, which is a species of fungus that is normally found on human skin.
Azelaic acid 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 works in part by stopping the growth of skin bacteria that cause acne, and by keeping skin pores clear.
Azelaic acid's antimicrobial action may be attributable to inhibition of microbial cellular protein synthesis.
Azelaic acid is a naturally occurring saturated nine-carbon dicarboxylic acid (COOH (CH2)7-COOH).
Azelaic acid possesses a variety of biological actions both in vitro and in vivo.
Interest in the biological activity of Azelaic acid arose originally out of studies of skin surface lipids and the pathogenesis of hypochromia in pityriasis versicolor infection.
Later, Azelaic acid was shown that Pityrosporum can oxidize unsaturated fatty acids to C8-C12 dicarboxylic acids that are cornpetitive inhibitors of tyrosinase in vitro.
Azelaic acid was chosen for further investigation and development of a new topical drug for treating hyperpigmentary disorders for the following reasons: Azelaic acid possesses a middle-range of antityrosinase activity, is inexpensive, and more soluble to be incorporated into a base cream than other dicarboxylic acids.
Azelaic acid is another option for the topical treatment of mild to moderate inflammatory acne vulgaris.
Azelaic acid offers effectiveness similar to that of other agents without the systemic side effects of oral antibiotics or the allergic sensitization of topical benzoyl peroxide and with less irritation than tretinoin.
Azelaic acid is less expensive than certain other prescription acne preparations, but Azelaic acid is much more expensive than nonprescription benzoyl peroxide preparations.
Whether Azelaic acid is safe and effective when used in combination with other agents is not known.
Azelaic acid is an organic compound with the formula HOOC(CH2)7COOH.
This saturated dicarboxylic acid exists as a white powder.
Azelaic acid is found in wheat, rye, and barley.
Azelaic acid 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
Azelaic acid has role antibacterial agent.
Azelaic acid has role antineoplastic agent.
Azelaic acid has role dermatologic drug.
Azelaic acid has role plant metabolite.
Azelaic acid is a α,ω-dicarboxylic acid.
Azelaic acid is conjugate acid of azelaate.
Azelaic acid is conjugate acid of azelaate(2−).
Azelaic acid is a dicarboxylic acid and is a white crystalline powder available in various purity grades depending on the final application.
The innovative production process achieves Azelaic acid with very high purity and low monocarboxylic content, fundamental features for Azelaic acid use as an intermediate in polymerization processes, typically as an alternative to sebacic acid and adipic acid.
The physiologic effect of Azelaic acid is by means of Decreased Protein Synthesis, and Decreased Sebaceous Gland Activity.
Azelaic acid is an ingredient with antibacterial, skin cell regulating, anti-inflammatory and skin-lightening magic properties.
Azelaic acid is especially useful for acne-prone or rosacea-prone skin types (in concentration 10% and up)
Azelaic acid is a prescription drug in the US but can be freely purchased in the EU in an up to 10% concentration.
Azelaic acid is a compound found in wheat, rye and barley that can help treat acne and rosacea because Azelaic acid soothes inflammation.
Azelaic acid treats sunspots and melasma because Azelaic acid blocks the production of abnormal pigmentation
Azelaic acid is also a tyrosinase inhibitor, meaning Azelaic acid can prevent hyperpigmentation because it interferes with melanin production.
Azelaic acid is anti-inflammatory for the acne and Azelaic acid is anti-pigment because it blocks tyrosinase.
Azelaic acid is a more gentle exfoliant than other alpha hydroxy acids (AHAs), including glycolic, lactic and mandelic acids
Chemically, Azelaic acid is a dicarboxylic acid.
Azelaic acid works on skin as a gentle leave-on exfoliant which helps unclog pores and refine skin's surface.
Azelaic acid also significantly lessens factors in skin that lead to sensitivity and bumps and delivers antioxidant benefits.
Azelaic acid can be derived from grains like barley, wheat, and rye, but it’s the lab-engineered form that is typically used in skincare products because of Azelaic acid stability and effectiveness.
Much of the research on this ingredient has looked at prescription-only topical products with concentrations between 15% and 20%, but there are incredible benefits to be seen even at lower concentrations.
Azelaic acid is a naturally occurring acid found in grains like barley, wheat, and rye.
Today's Azelaic acid is synthesized in a lab, though, to ensure Azelaic acid is uniform and stable.
Azelaic acid is an exfoliant that unclogs pores and also reduces pigmentation and the effects of scarring.
Azelaic acid manipulates the most upper layers in the cells which leaves you with a smooth and visibly healthier skin tone.
If you’re looking for a brighter skin tone with visibly improved evenness, skincare including Azelaic acid is a great choice.
Azelaic acid isn't an incredibly common skin care ingredient, but Azelaic acid can be found in some over-the-counter anti-aging and skin brightening products in strengths up to 10%.
For treating acne or rosacea, though, a prescription strength of at least 15% is needed.
Azelaic acid is relatively obscure when compared to some of the more trendy and well-known skin care acids like glycolic, lactic, salicylic, and even hyaluronic acid.
But Azelaic acid works slightly differently than other skin care acids.
Over-the-counter Azelaic acid can help improve minor blackheads, refine the pores, even out skin tone, and brighten the complexion.
Stronger, prescription Azelaic acid has even more benefits for the skin.
Topical Azelaic acid formulations have been used to address a wide range of physiological maladies including acne, hyperpigmentary dermatoses, hair loss, wrinkling, hyperhidrosis, non-acne inflammatory dermatoses, infectious cutaneous diseases and ichthyosis.
However, the only topical formulations of Azelaic acid presently known are dispersions.
Dispersions deliver Azelaic acid in an undissolved state.
When applied to the skin, undissolved Azelaic acid is not readily absorbed and as a result an excess of Azelaic acid must be present to be effective.
The higher the concentration of Azelaic acid, the more likely irritation (burning, stinging and redness) to the skin will occur.
What is needed is a completely solubilized topical Azelaic acid composition.
Solubilized Azelaic acid is much less likely to irritate the skin because Azelaic acid in a dissolved state is much more readily absorbed by the need be present in the formulation to be effective thereby lowering the risk of irritation to the skin.
While Azelaic acid is somewhat soluble in water, cosmetic oils and alcohols, each of these solvents has serious limitations.
Thus, water only marginally dissolves Azelaic acid so that a water and Azelaic acid solution would contain a maximum of about .24% by weight (w/w) Azelaic acid, not likely enough to be effective.
Azelaic acid has little or no solubility in cosmetic oils.
Alcohols are good solvents but are unsatisfactory because large amounts of alcohol e.g., isopropyl alcohol, in a topical composition has the undesirable side effect of drying the skin.
Indeed, some alcohols e.g., ethyl alcohol, render Azelaic acid unstable at normal temperatures and atmospheric pressures resulting in a totally ineffective composition
Azelaic acid is produced by a yeast (Malassezia fur fur, also known as Pityrosporum ovale) that is part of normal skin flora.
Azelaic acid can help in both acne vulgaris and acne rosacea as an antimicrobial, antiinflammatory, and comedolytic.
Azelaic acid can also be used for postinflammatory hyperpigmentation.
One study that compared results of European clinical trials showed Azelaic acid 20% cream is as effective as tretinoin 0.05%, benzoyl peroxide 5%, and topical erythromycin 2%.
Azelaic acid is similar to benzoyl peroxide, but there is less evidence of Azelaic acid usefulness.
Dosage:
Recommended dosage is 20% cream for acne vulgaris and 15% gel for acne rosacea, both applied one to two times a day.
Precautions:
Can cause hypopigmentation and some skin irritation but is usually well tolerated.
Topical Azelaic acid:
The topical application of Azelaic acid appears to be extremely effective in papulopustular rosacea.
Initially, Azelaic acid was released in a 20% cream formulation and was shown in this vehicle to be effective in the treatment of mild to moderate rosacea.
A 15% gel formulation of Azelaic acid vastly improved the delivery of Azelaic acid and has been shown to be superior in head-to-head studies to the 20% Azelaic acid cream.
Azelaic acid is equally as effective as metronidazole cream or gel.
In a meta-analysis of five double-blind trials involving topical Azelaic acid (cream or gel) for the treatment of rosacea compared with placebo or other topical treatments, four of five studies demonstrated significant decreases in mean inflammatory lesion count and erythema severity after treatment with Azelaic acid compared with placebo, and Azelaic acid was found to be equal to metronidazole in papulopustular rosacea.
However, no significant decrease in the severity of telangiectasia occurred in any treatment group.
Overexpression of cathelicidin peptide LL-37 has been implicated in the pathophysiology of rosacea, and Azelaic acid has been found to inhibit the pathological expression of cathelicidin, as well as the hyperactive protease activity that cleaves cathelicidin into LL-37.
A small, prospective, open-label, interventional study was performed to assess the effects of Azelaic acid 15% gel on inflammatory lesions of papulopustular rosacea.
Azelaic acid use was associated with a significant reduction in inflammatory lesions, and these results persisted beyond the active treatment phase.
Chemical peels:
Bleaching agents:
Hydroquinones are the most commonly used bleaching agents; other products include Azelaic acid, aloesin, vitamin C, arbutin, licorice extract, glabridin, mequinol (4-hydroxyanisol), melatonin, niacinamide, paper mulberry, soy, vitamin E, kojic acid, α- and β-hydroxy acids, and retinoids and retinoid combination therapy.
Azelaic acid is a prescription medication used to treat mild to moderate acne vulgaris, as well as rosacea.
Azelaic acid comes in a gel, lotion, and cream.
Azelaic acid is sold under the brand names Azelex, Finacea, and Finevin, as well as generic Azelaic acid.
Uses of Azelaic acid:
Azelaic acid is used in many pharmaceutical preparations as an active ingredient in acne rosacea, due to Azelaic acid therapeutic effectiveness.
The vegetable origin of Azelaic acid makes it particularly suitable also for other important applications such as the synthesis of complex esters.
Uses in Practice:
Topical Azelaic acid is Food and Drug Administration (FDA) approved for mild-moderate inflammatory acne vulgaris under the brand name Azelex as 20% cream.
Azelaic acid is also FDA approved for mild-to-moderate papulopustular rosacea under the brand name Finacea as 15% gel and 15% foam.
At this time, Azelaic acid is not approved for any other subtype of rosacea.
In clinical studies for Azelaic acid gel 15% (Finacea), there was some reduction of erythema noted in patients treated for papulopustular rosacea, but no specific clinical trials were performed to study erythema in rosacea in the absence of papules and pustules.
Azelaic acid is also used off-label for the treatment of hyperpigmentation disorders, including melasma, due to Azelaic acid inhibition of tyrosinase.
Pharmacokinetics:
Topical Azelaic acid has a bioavailability of up to 10% in the epidermis and dermis.
Approximately 4% of Azelaic acid cream or gel is absorbed systemically after topical application.
Azelaic acid is a saturated dicarboxylic acid (HOOC-(CH2)7-COOH) found in many foods, including animal products and whole grains.
Azelaic acid may undergo some beta-oxidation to shorter-chain dicarboxylic acids, but Azelaic acid is predominately excreted in its original form in urine.
The half-life of topical Azelaic acid is approximately 12 hours, and the patient should apply Azelaic acid to the area of concern twice daily.
Favorable results are typically seen within 4 weeks in patients with acne vulgaris and within 12 weeks in patients with papulopustular rosacea.
Uses of Azelaic acid for acne:
Azelaic acid works by:
Clearing your pores of bacteria that may be causing irritation or breakouts.
Reducing inflammation so acne becomes less visible, less red, and less irritated.
Gently encouraging cell turnover so your skin heals more quickly and scarring is minimized.
Azelaic acid can be used in gel, foam, or cream form.
All forms have the same basic instructions for use:
Wash the affected area thoroughly with warm water and pat dry.
Use a cleanser or mild soap to make sure the area is clean.
Wash your hands before applying the medication.
Apply a small amount of medication to the affected area, rub Azelaic acid in, and let it dry completely.
Once the medication has dried, you can apply cosmetics.
There’s no need to cover or bandage your skin.
Keep in mind that you should avoid using astringents or “deep-cleansing” cleansers while you use Azelaic acid.
Some people will need to apply the medication twice per day, but this will vary according to a doctor’s instructions.
Azelaic acid for acne scars:
Some people use azelaic to treat acne scarring in addition to active outbreaks.
Azelaic acid encourages cell turnover, which is a way to reduce how severe scarring appears.
Azelaic acid also prevents what’s known as melanin synthesis, the ability of your skin to produce pigments that can vary your skin’s tone.
If you’ve tried other topical medications to help with scarring or blemishes that’re slow to heal, Azelaic acid might help.
More research is needed to understand who this treatment works best for and how effective Azelaic acid can be.
Other uses:
Azelaic acid is also used for other skin conditions, such as hyperpigmentation, rosacea, and skin lightening.
Azelaic acid for hyperpigmentation:
After a breakout, inflammation can result in hyperpigmentation on some areas of your skin.
Azelaic acid stops discolored skin cells from populating.
A pilot study from 2011 showed Azelaic acid can treat acne while evening out hyperpigmentation triggered by acne.
Further research on skin of color has also shown that Azelaic acid is safe and beneficial for this use.
Azelaic acid for skin lightening:
The same property that makes Azelaic acid effective for the treatment of inflammatory hyperpigmentation also enables Azelaic acid to lighten skin that’s discolored by melanin.
Using Azelaic acid for skin lightening in patchy or blotchy areas of your skin due to melanin has been found effective, according to an older study.
Azelaic acid for rosacea:
Azelaic acid can reduce inflammation, making it an effective treatment for symptoms of rosacea.
Clinical studies demonstrate that Azelaic acid gel can continually improve the appearance of swelling and visible blood vessels caused by rosacea.
According to older research, Azelaic acid cream may be as effective as benzoyl peroxide and tretinoin (Retin-A) for the treatment of acne.
While Azelaic acid results are similar to those of benzoyl peroxide, it’s also more expensive.
Azelaic acid also works more gently than alpha hydroxy acid, glycolic acid, and salicylic acid.
While these other acids are strong enough to be used on their own in chemical peels, Azelaic acid isn’t.
This means that while Azelaic acid is less likely to irritate your skin, Azelaic acid also has to be used consistently and given time to take effect.
Takeaway:
Azelaic acid is a naturally occurring acid that’s milder than some more popular acids used to treat acne.
While the results of treatment with Azelaic acid might not be obvious right away, there is research that points to this ingredient as effective.
Acne, uneven skin tone, rosacea, and inflammatory skin conditions have all been shown to be effectively treated with Azelaic acid.
As with any medication, follow the dosing and application directions from your doctor closely.
Face acids, or skin acids, work by exfoliating, or shedding, the top layer of your skin.
Whenever you exfoliate your skin, new skin cells emerge to take the place of the old ones.
The process helps even out your skin tone and makes Azelaic acid smoother overall.
Many face acids are available OTC at beauty stores and drugstores.
Popular options include:
Alpha hydroxy acids, such as glycolic, lactic, citric, malic, or tartaric acid
Azelaic acid
Kojic acid
Salicylic acid
Vitamin C (in the form of l-ascorbic acid)
Main uses:
Fibres (E.g. Nylon 6,9 - Nylon 5,9 - Nylon 6,69)
Polyester Polyols (Polyurethanes and PUR Hotmelt)
Bioplastics (Polyesters)
Hot Melt Adhesives (Polyamides, Polyester)
Polyamide Hardeners (Epoxy Resins)
Low Temperature Plasticisers (Dioctyl Azelate DOZ)
Azelaic acid can also be used directly in other formulations such as:
Electrolytes for Capacitors
Lithium Complex Greases
Metalworking Fluids, Corrosion Inhibitors
Coating - Powder Resins (GMA)
Engine cooling fluids
Applications of Azelaic acid:
Azelaic acid is a naturally occurring acid found in grains such as barley, wheat, and rye.
Azelaic acid has antimicrobial and anti-inflammatory properties, which make Azelaic acid effective in the treatment of skin conditions like acne and rosacea.
Azelaic acid can prevent future outbreaks and clean bacteria from your pores that causes acne.
Azelaic acid is applied to your skin and is available in gel, foam, and cream form.
Azelex and Finacea are two brand names for prescription topical preparations.
They contain 15 percent or more of Azelaic acid. Some over-the-counter products contain smaller amounts.
Because Azelaic acid takes some time to take effect, Azelaic acid by itself isn’t typically a dermatologist’s first choice for treating acne.
Azelaic acid also has some side effects, such as skin burning, dryness, and peeling.
The antibacterial, antiphlogistic and keratolytic Azelaic acid is used in acne therapy.
Azelaic acid is also used for treatment of skin pigmentation including melasma and post-inflammatory hyperpigmentation, particularly in individuals with darker skin types.
Azelaic acid has been recommended as an alternative to hydroquinone.
As a tyrosinase inhibitor, Azelaic acid reduces synthesis of melanin.
About 4–8% of the topically applied substance is absorbed systemically.
In animal experiments Azelaic acid, even in high doses, is not teratogenic.
However, systematic studies on Azelaic acid use in humans are lacking.
Recommendation:
During pregnancy, Azelaic acid should only be used for strict indications on small skin surfaces, e.g. facial acne, preferably not in the first trimester.
Esters of this dicarboxylic acid find applications in lubrication and plasticizers.
In lubricant industries Azelaic acid 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
Medical:
Azelaic acid is used to treat mild to moderate acne, both comedonal acne and inflammatory acne.
Azelaic acid belongs to a class of medication called dicarboxylic acids.
Azelaic acid works by killing acne bacteria that infect skin pores.
Azelaic acid 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 Azelaic acid ability to reduce inflammation.
Azelaic acid 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.
Acne treatment:
In patients with moderate acne twice daily over 3 month topical 20% Azelaic acid reduced numbers of comedones, papules and pustules.
Along with retinoids Azelaic acid is considered to be effective in improving acne-treatment results.
The studies of latter though were admittedly limited.
In comparative review of effects of topical Azelaic acid, Salicylic acid, Nicotinamide, Sulfur, Zinc, and alpha-hydroxy acid Azelaic acid enjoyed more high-quality evidence of effectiveness than the rest.
Whitening agent:
Azelaic acid has been used for treatment of skin pigmentation including melasma and postinflammatory hyperpigmentation, particularly in those with darker skin types.
Azelaic acid has been recommended as an alternative to hydroquinone.
As a tyrosinase inhibitor, Azelaic acid reduces synthesis of melanin.
According to one report of 1988 Azelaic acid (in combination with zinc sulfate) in vitro showed to be a potent (90% inhibition) 5α-Reductase inhibitor, similar to the hair loss drugs finasteride and dutasteride.
Middle 80s in vitro research evaluating acid's depigmenting (whitening) capability concluded Azelaic acid is effective (cytotoxic to melanocytes) only at high concentrations.
More recent review claimed 20% Azelaic acid being more potent than 4% hydroquinon after period of application for three months without latter's adverse effects and even more effective if applied along with tretinoin for the same period of time.
Brand names:
Brand names for Azelaic acid include Dermaz 99, 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)
Topical Antibacterial Agents:
Disorders of Pigmentation:
Azelaic acid has no depigmenting activity on normal skin, solar freckles, senile freckles, lentigines, pigmented seborrheic keratoses, or nevi.
Azelaic acid has some activity against hypermelanosis caused by physical and chemical agents, postinflammatory hyperpigmentation, melasma, lentigo maligna, and lentigo maligna melanoma.
In melasma, treatment for 24 weeks with Azelaic acid 20% cream alone showed similar efficacy to treatment for 8 weeks with clobetasol 0.05% cream followed by 16 weeks with Azelaic acid 20% cream (90% vs. 96.7% improvement).
Benefits of Azelaic acid in Skin Care Products:
Azelaic acid products in concentrations of 10% or less aren’t easy to find, as very few brands have discovered Azelaic acid powerful skincare benefits, perhaps because it’s just such a tricky ingredient to formulate properly.
If not formulated properly, the texture may be grainy, which could be problematic for skin.
If you’re wondering whether to choose a cosmetic Azelaic acid skin care product or a prescription version, research has shown that a 10% concentration can still improve many of the visible imperfections some of us struggle with, from bumps to dull, uneven skin tone and various concerns related to aging.
But, there are some stubborn or advanced skin concerns where it’s best to consider one of the prescription products with Azelaic acid.
You and your dermatologist can discuss whether a prescription Azelaic acid product is right for you, and how to work Azelaic acid into your skincare routine.
The Science Behind Azelaic acid Skin Care Products:
Researchers have a theory on how Azelaic acid works its skin-improving magic.
What's suspected is that Azelaic acid works by inhibiting misbehaving elements on and within skin's uppermost layers.
Left unchecked, these troublemakers lead to persistent, visible skin imperfections (like brown patches and post-blemish marks), dull skin tone, and signs of sensitivities.
Azelaic acid seems Azelaic acid has a radar-like ability to interrupt or inhibit what's causing skin to act up.
Skin "hears" the message Azelaic acid sends and responds favorably, which leads to skin that looks remarkably better, no matter your age, skin type, or concerns.
The ongoing research on Azelaic acid led us to formulate our 10% Azelaic acid Booster.
The Azelaic acid within targets a wide range of skin imperfections and is formulated with 0.5% salicylic acid for a bit of a pore-refining nudge.
The 10% Azelaic acid Booster also contains a soothing complex of brightening plant extracts plus skin-restoring adenosine, an energizing ingredients that visibly reduces signs of aging.
Adding the 10% Azelaic acid Booster to your routine is easy: Azelaic acid can be applied once or twice daily after cleansing, toning, and exfoliating.
Apply on Azelaic acid own or mix with your favorite serum or moisturizer.
Azelaic acid is fine to apply it to the entire face, or you can target blemished areas as needed.
During the day, finish with a broad-spectrum sunscreen rated SPF 30 or greater.
The booster isn't an Azelaic acid cream or Azelaic acid gel; instead Azelaic acid is a gel-cream hybrid that's compatible with all skin types and can be used with any of our other products, including our exfoliants, which might lead you to wonder how Azelaic acid compares to AHA and BHA exfoliants.
Benefits of Azelaic acid for Skin:
Azelaic acid is a multifunctional skincare ingredient that tackles a multitude of concerns related to breakouts and inflammation.
Exfoliates gently:
Azelaic acid goes deep within the pores and removes dead skin cells that cause dull skin tone and clogged pores.
Fights acne:
Azelaic acid has antibacterial properties, and according to Fusco, Azelaic acid is reported to be bactericidal to P. acnes, which leads to acne.
Reduces inflammation:
Azelaic acid soothes irritation and helps to improve red bumps caused by inflammation.
Evens skin tone:
Azelaic acid inhibits tyrosinase, which is an enzyme that leads to hyperpigmentation.
Azelaic acid is effective on post-inflammatory hyperpigmentation from acne breakouts and can possibly have an effect on melasma as well.
Treats rosacea:
Azelaic acid could help with pore-clogging, inflammation, and secondary infections caused by rosacea.
Azelaic acid is a so-called carboxylic acid.
Azelaic acid is not an AHA or BHA but a distant relative to them (all being carboxylic acids).
Azelaic acid can be found naturally in wheat, rye, and barley.
Antibacterial effect → Anti-Acne:
Azelaic acid has a great antibacterial effect.
Azelaic acid works against multiple bacteriaS, acne-causing Propionibacterium acnes (P. acnes).
Very few ingredient are proven to work against P. acnes, so this alone makes Azelaic acid an awesome choice for acne-prone skin.
For acne treatment, 20% is the standard prescription strength choice.
Comparing 20% Azelaic acid to other acne treatments like 0.05% retinoic acid cream, 5% benzoyl peroxide cream or 2% erythromycin ointment Azelaic acid had nothing to be ashamed for as Azelaic acid showed similar effectiveness.
There is also a study that showed that 5% Azelaic acid is also somewhat effective (about 32% improvement) and Azelaic acid can be made much more effective by combining Azelaic acid with 2% clindamycin (about 64% improvement.)
Regulate the production of skin cells → Anti-Acne:
Azelaic acid also works on the cells that line hair follicles by changing the way they mature and proliferate, which decreases follicular ‘plugging’ and helps prevent blackheads, whiteheads, and inflamed acne lesions.
Azelaic acid helps with healthy skin cell production in the pores that is often problematic in acne and blackhead prone skin, which is nice!
Anti-inflammatory effect → Anti-rosacea, anti-acne:
The third magic property of Azelaic acid is that it is proven to ha an e anti-inflammatory effect.
This is cool not only for treating acne, but also for treating rosacea.
15% is the standard prescription strength dose for rosacea treatment.
Skin lightening effect → Anti-PIH, anti-melasma:
Last but not least Azelaic acid also shows skin lightening properties.
Azelaic acid seems to be especially effective for post-inflammatory hyperpigmentation (that often comes with acne) and melasma.
Studies have compared 20% Azelaic acid to 2% and 4% Hydroquinone and here again, Azelaic acid has nothing to be ashamed of, Azelaic acid showed similar skin lightening properties. (Though interestingly Azelaic acid did not seem to be effective for lightening age spots that are called solar lentigines.)
So the bottom line is that Azelaic acid can be a game changer (or rather skin changer) especially for acne-prone or rosacea skin types.
Azelaic acid is antibacterial, can regulate problematic skin cell production in pores, it’s anti-inflammatory and even helps with PIH and melasma.
Azelaic acid really can do a lot.
Azelaic acid keeps pores clear:
Azelaic acid is a comedolytic.
This means Azelaic acid helps break down existing pore blockages (AKA comedones) and keeps new ones from forming.
Clear pores and fewer pore blockages ultimately lead to fewer pimples.
Azelaic acid gently exfoliates:
Azelaic acid is also a keratolytic.
Keratolytics help your skin exfoliate by dissolving old, flaky skin cells.
Azelaic acid is a fairly gentle exfoliant, especially when compared to other acne treatments like topical retinoids.
Azelaic acid reduces acne-causing bacteria:
Azelaic acid kills Propionibacteria acnes, the bacteria that are responsible for inflamed acne breakouts.
This, in turn, reduces redness and inflammation.
Azelaic acid evens out your skin tone:
Another benefit of Azelaic acid Azelaic acid is ability to improve post-inflammatory hyperpigmentation, or those discolored spots pimples leave behind.
Complexions that are prone to hyperpigmentation will especially benefit from Azelaic acid.
Production of Azelaic acid:
Azelaic acid is industrially produced by the ozonolysis of oleic acid.
The side product is nonanoic acid.
Azelaic acid 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 of Azelaic acid:
In plants, Azelaic acid serves as a "distress flare" involved in defense responses after infection.
Azelaic acid serves as a signal that induces the accumulation of salicylic acid, an important component of a plant's defensive response.
Action Mechanism of Azelaic acid:
The mechanism of action of Azelaic acid is not well understood.
However, in vitro, Azelaic acid possesses antimicrobial activity against Propionibacterium acnes and Staphylococcus epidermidis, most likely through microbial cellular protein synthesis inhibition.
Microcomedones and comedones can arise because of hyperkeratinization.
Azelaic acid produces an anticomedonal effect by decreasing the amount of hyperkeratinization.
Biopsies have shown a decrease in stratum corneum thickness, keratohyalin granules, and filaggrin in patients treated with Azelaic acid cream.
Azelaic acid also competitively inhibits tyrosinase, an enzyme involved in the conversion of tyrosine to melanin.
Last, Azelaic acid mechanism of action also includes the inhibition of DNA synthesis and mitochondrial enzymes, thereby inducing direct cytotoxic effects on the melanocyte.
Therefore, Azelaic acid is thought to decrease postinflammatory hyperpigmentation.
Alternatives:
Currently, there are no other known drugs with the same mechanism of action as Azelaic acid.
On the other hand, there are many other drugs that can be used in the treatment of acne vulgaris, such as topical and oral retinoids, oral and topical antibiotics, benzoyl peroxide, topical dapsone, salicylic acid, photodynamic therapy, lasers, and peels.
Antibiotics develop resistance when not used in combination with benzoyl peroxide and therefore should not be used as monotherapy.
Azelaic acid is an effective monotherapy for acne vulgaris in pregnant women.
Handling and storage of Azelaic acid:
Conditions for safe storage, including any incompatibilities:
Storage conditions:
Tightly closed.
Dry.
Storage class:
Storage class (TRGS 510): 11: Combustible Solids
Stability and reactivity of Azelaic acid:
Reactivity
Forms explosive mixtures with air on intense heating.
A range from approx. 15 Kelvin below the flash point is to be rated as critical.
The following applies in general to flammable organic substances and mixtures: in correspondingly fine distribution, when whirled up a dust explosion potential may generally be assumed.
Chemical stability:
Azelaic acid is chemically stable under standard ambient conditions (room temperature).
Possibility of hazardous reactions:
No data available
Conditions to avoid:
Strong heating.
Incompatible materials:
Bases, Reducing agents, Oxidizing agents
Warnings And Precautions
Hypersensitivity reactions have been reported with the use of Azelaic acid.
Azelaic acid should be avoided in patients with known hypersensitivity reactions to Azelaic acid or its components.
Hypopigmentation has been reported with the use of Azelaic acid as well.
Skin should be monitored for signs of hypopigmentation, especially in patients with dark complexions.
In addition, contact with the eyes, mouth, and other mucous membranes should be avoided.
First aid measures of Azelaic acid:
General advice:
Show this material safety data sheet to the doctor in attendance.
If inhaled:
After inhalation:
Fresh air.
In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.
In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
Indication of any immediate medical attention and special treatment needed:
No data available
Firefighting measures of Azelaic acid:
Suitable extinguishing media:
Water Foam Carbon dioxide (CO2) Dry powder
Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
Special hazards arising from the substance or mixture:
Carbon oxides
Combustible.
Vapors are heavier than air and may spread along floors.
Forms explosive mixtures with air on intense heating.
Development of hazardous combustion gases or vapours possible in the event of fire.
Advice for firefighters:
Stay in danger area only with self-contained breathing apparatus.
Prevent skin contact by keeping a safe distance or by wearing suitable protective clothing.
Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
Accidental release measures of Azelaic acid:
Personal precautions, protective equipment and emergency procedures:
Advice for non-emergency personnel:
Avoid inhalation of dusts.
Avoid substance contact.
Ensure adequate ventilation.
Evacuate the danger area, observe emergency procedures, consult an expert.
Environmental precautions:
Do not let product enter drains.
Methods and materials for containment and cleaning up:
Cover drains. Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.
Avoidgeneration of dusts.
Identifiers of Azelaic acid:
CAS Number: 123-99-9
Beilstein Reference: 1101094
ChEBI: CHEBI:48131
ChEMBL: ChEMBL1238
ChemSpider: 2179
DrugBank: DB00548
ECHA InfoCard: 100.004.246
EC Number: 204-669-1
Gmelin Reference: 261342
IUPHAR/BPS: 7484
KEGG: D03034
PubChem CID: 2266
UNII: F2VW3D43YT
CompTox Dashboard (EPA): DTXSID8021640
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)
Key: BDJRBEYXGGNYIS-UHFFFAOYSA-N
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
CAS Number: 123-99-9
EC Number: 204-669-1
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
EC Number: 204-669-1
EC Name: Azelaic acid
CAS Number: 123-99-9
Molecular formula: C9H16O4
IUPAC Name: Azelaic acid
CAS number: 123-99-9
EC number: 204-669-1
Hill Formula: C₉H₁₆O₄
Chemical formula: HOOC(CH₂)₇COOH
Molar Mass: 188.22 g/mol
HS Code: 2917 13 90
Properties of Azelaic acid:
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
vapor density: 6.5 (vs air)
Quality Level: 200
vapor pressure: <1 mmHg ( 20 °C)
Assay: 98%
form: powder
bp: 286 °C/100 mmHg (lit.)
mp: 109-111 °C (lit.)
SMILES string: OC(=O)CCCCCCCC(O)=O
InChI: 1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
InChI key: BDJRBEYXGGNYIS-UHFFFAOYSA-N
Boiling point: 237 °C (20 hPa)
Density: 1.029 g/cm3 (20 °C)
Flash point: 215 °C
Melting Point: 107 °C
pH value: 3.5 (1 g/l, H₂O)
Vapor pressure: <1 hPa (20 °C)
Solubility: 2.4 g/l
Specifications of Azelaic acid:
Assay (GC, area%): ≥ 90.0 % (a/a)
Identity (IR): passes test
Pharmacology of Azelaic acid:
ATC code: D10AX03 (WHO)
Routes of
administration: Topical
Pharmacokinetics:
Bioavailability: Very low
Biological half-life: 12 h
Legal status:
AU: S2 (Pharmacy Only)
US: ℞-only
Names of Azelaic acid:
Preferred IUPAC name:
Nonanedioic acid
1,7-Heptanedicarboxylic acid
1,9-Nonanedioic acid
Acide azelaique
Acido azelaico
Acidum azelaicum
Anchoic acid
Azelaic acid, technical grade
Azelex
Emerox 1110
Emerox 1144
Finacea
Heptanedicarboxylic acid
Lepargylic acid
Skinoren
CAS name:
Nonanedioic acid
IUPAC names:
1,7-Heptanedicarboxylic acid
azelaic acid
Azelainsäure
Azeleic Acid
Nonanedioic acid
nonanedioic acid
Nonanedioic acid
Nonanedionic acid
Trade names:
Crodacid DC1195
Ácido Azelaico
