AZELAIC ACID
AZELAIC ACID
Display Name:Azelaic acid
EC Number: 204-669-1
EC Name: Azelaic acid
CAS Number: 123-99-9
Molecular formula: C9H16O4
IUPAC Name: 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 its 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 its scavenger activity of free oxygen radical.
This drug is used topically to reduce inflammation associated with acne and rosacea.
NCI Thesaurus (NCIt)
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 (AZA) is a naturally occurring saturated nine-carbon dicarboxylic acid (COOH (CH2)7-COOH).
It possesses a variety of biological actions both in vitro and in vivo.
Interest in the biological activity of AZA arose originally out of studies of skin surface lipids and the pathogenesis of hypochromia in pityriasis versicolor infection.
Later, it 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: it 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.
It 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 it is much more expensive than nonprescription benzoyl peroxide preparations.
Whether it is safe and effective when used in combination with other agents is not known.
Azelaic acid (nonanedioic 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 its use as an intermediate in polymerization processes, typically as an alternative to sebacic acid and adipic 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
Azelaic acid is used in many pharmaceutical preparations as an active ingredient in acne rosacea, due to its therapeutic effectiveness.
The vegetable origin of azelaic acid makes it particularly suitable also for other important applications such as the synthesis of complex esters.
Names
Preferred IUPAC name
Nonanedioic acid
Identifiers
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
Value
1,7-Dicarboxyheptane
1,7-Heptanedicarboxylic acid
1,9-Nonanedioic acid
Acide azelaique ChEBI
Acidum azelaicum
Anchoic acid
The physiologic effect of azelaic acid is by means of Decreased Protein Synthesis, and Decreased Sebaceous Gland Activity.
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
http://www.hmdb.ca/metabolites/HMDB0000784
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:48131
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 (AzA) is an organic compound with the formula HOOC(CH2)7COOH.
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
nonanedioic acid has role antibacterial agent
nonanedioic acid has role antineoplastic agent
nonanedioic acid has role dermatologic drug
nonanedioic acid has role plant metabolite
nonanedioic acid is a α,ω-dicarboxylic acid
nonanedioic acid is conjugate acid of azelaate
nonanedioic acid is conjugate acid of azelaate(2−)
Incoming
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
IUPAC Name
nonanedioic acid
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
Brand Names
Azelex
Finacea
Skinoren
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
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.[5]
Biological function
In plants, azelaic acid serves as a “distress flare” involved in defense responses after infection.
It serves as a signal that induces the accumulation of salicylic acid, an important component of a plant’s defensive response.
Applications
Azelaic acid cream labeled in Russian.
Polymers and related materials
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
Medical
Azelaic acid is used to treat mild to moderate acne, both comedonal acne and inflammatory acne.
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 of acne bacteria.
Azelaic acid is also used as a topical gel treatment for rosacea, due to its ability to reduce inflammation.
It 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% AzA reduced numbers of comedones, papules and pustules.
Along with retinoids AzA 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 AzA, Salicylic acid, Nicotinamide, Sulfur, Zinc, and alpha-hydroxy acid AzA 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.
It 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 it is effective (cytotoxic to melanocytes) only at high concentrations.
More recent review claimed 20% AzA 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)[21]
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).
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)
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 it soothes inflammation.
Azelaic acid treats sunspots and melasma because it blocks the production of abnormal pigmentation
Azelaic acid is also a tyrosinase inhibitor, meaning it can prevent hyperpigmentation because it interferes with melanin production.
It’s anti-inflammatory for the acne and it’s 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
Treating Acne with Azelaic Acid
What is 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 it 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 it 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.
Azelaic acid
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 (Akhavan 2003).
However, systematic studies on its 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.
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 it 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 it can be.
Other uses for azelaic acid
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 it 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.
Azelaic acid side effects and precautions
Azelaic acid can cause side effects, including:
burning or tingling on your skin
peeling skin at the site of application
skin dryness or redness
Less-common side effects include:
blistering or flaking skin
irritation and swelling
tightness or pain in your joints
hives and itching
fever
difficulty breathing
If you experience any of these side effects, stop using azelaic acid and see a doctor.
It’s always important to wear sunscreen when you go outside, but be especially mindful to wear SPF products when you’re using azelaic acid.
Since it can thin your skin, your skin is more sensitive and prone to sun damage.
How azelaic acid compares with other treatments
Azelaic acid isn’t for everyone.
The effectiveness of the treatment may depend on your:
symptoms
skin type
expectations
Since it works slowly, azelaic acid is often prescribed along with other forms of acne treatment.
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, it 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.
Medically reviewed by Dena Westphalen, Pharm.D. — Written by Kathryn Watson on December 19, 2018
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 it 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)
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 its 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.
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 its 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 it 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. It 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: it can be applied once or twice daily after cleansing, toning, and exfoliating.
Apply on its own or mix with your favorite serum or moisturizer.
It’s 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 it’s 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.
How Does Azelaic Acid Compare to Alpha Hydroxy Acids (AHAs) or Salicylic Acid (BHA)?
These three ingredients have similarities, but also some interesting differences.
Although azelaic acid can exfoliate skin when properly formulated (just like for AHAs and BHA, the product’s pH range matters), it doesn’t exfoliate the same way or with the same level of effectiveness as ingredients like glycolic acid and lactic acid (AHAs) or salicylic acid (BHA).
On the other hand, azelaic acid offers additional benefits that AHA and BHA ingredients don’t provide, especially when it comes to improving a markedly uneven skin tone and certain other skin issues.
There’s no reason you can’t use an AHA or BHA exfoliant along with an azelaic acid product.
In fact, this combination can be ideal for addressing the look of multiple skin concerns, from bumps to uneven skin tone to age-related concerns you may be struggling with.
Some skin care ingredients seem to have everything going for them – and azelaic acid is one of those mighty few.
Produced naturally by yeast that lives on healthy skin, this anything but ordinary acid brightens skin’s tone while visibly boosting texture and minimising blemishes.
What’s more, unlike many acids, this one does not cause irritation – in fact, it’s been shown to reduce redness and rosacea.
Delivered as a lightweight cream-gel suitable for all skin types, this is a beauty no-brainer.
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: It goes deep within the pores and removes dead skin cells that cause dull skin tone and clogged pores.
Fights acne: It has antibacterial properties, and according to Fusco, it’s reported to be bactericidal to P. acnes, which leads to acne.
Reduces inflammation: It soothes irritation and helps to improve red bumps caused by inflammation.
Evens skin tone: It inhibits tyrosinase, which is an enzyme that leads to hyperpigmentation.
It’s 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. It’s not an AHA or BHA but a distant relative to them (all being carboxylic acids). It can be found naturally in wheat, rye, and barley.
property no.1: Antibacterial effect → Anti-Acne
Azelaic acid has a great antibacterial effect. It 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 it showed similar effectiveness.
There is also a study that showed that 5% azelaic acid is also somewhat effective (about 32% improvement) and it can be made much more effective by combining it with 2% clindamycin (about 64% improvement.)
property no. 2: 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.
It helps with healthy skin cell production in the pores that is often problematic in acne and blackhead prone skin, which is nice!
Magic property no. 3: 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.
Magic property no. 4: Skin lightening effect → Anti-PIH, anti-melasma
Last but not least azelaic acid also shows skin lightening properties. It 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, it 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. It’s antibacterial, can regulate problematic skin cell production in pores, it’s anti-inflammatory and even helps with PIH and melasma. It really can do a lot.
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%.
It is similar to benzoyl peroxide, but there is less evidence of its 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.
Michael T. Murray ND, John Nowicki ND, in Textbook of Natural Medicine (Fifth Edition), 2020
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.
It 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.
It 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.
Azelaic acid can also be found in some over-the-counter skin care products, but in lower concentrations
What Is Azelaic Acid?
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 it’s uniform and stable.
Azelaic acid isn’t an incredibly common skin care ingredient, but it 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.1
How Azelaic Acid Works
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.
It keeps pores clear: Azelaic acid is a comedolytic. This means it 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.
It 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.
It 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.
It evens out your skin tone: Another benefit of azelaic acid it’s it’s 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
Other names: Nonanedioic acid; Anchoic acid; Emerox 1144; Lepargylic acid; 1,7-Heptanedicarboxylic acid; Heptanedicarboxylic acid; Azelainic acid; Azelaic acid, technical grade; Emerox 1110; 1,9-Nonanedioic acid; 1,7-Dicarboxyheptane; n-Nonanedioic acid; Emery’s L-110; Skinoren; ZK-62498; Finacea; NSC 19493
Without a stable, completely solubilized formula of azelaic acid, the benefits of azelaic acid are unavailable to many users who experience the burning, stinging and redness of the skin associated with exposure to high levels of undissolved azelaic acid in dispersions
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.
• Azelex®
• Finacea®
• ZK-62498
• Azelate
• Nonanedioic acid azelaic acid
• Nonanedioic acid homopolymer
• Azelainic acid
• Emerox 1110
• Polyazelaic anhydride
• Nonanedioate
• Heptanedicarboxylic acid
• Anchoate
• Finevin
• N-Nonanedioate
• Emerox 1144
• Poly(azelaic anhydride)
• Azelex
• Skinoren
• 1,7-Heptanedicarboxylate
• Finacea
• Azalaic acid
• 1,9-Nonanedioate
• Emery’S L-110
• Lepargylate
• Azelaicacidtech
• Skinorem
• Acidum acelaicum
• N-Nonanedioic acid
• Ácido azelaico
• 1,7-Dicarboxyheptane
• Azelaic acid
• Nonandisäure
• Azelainsäure
• 1,9-Nonanedioic acid
• Azelainsaeure
• Acidum azelaicum
• Nonanedioic acid
• 1,7-Heptanedicarboxylic acid
• Acide azélaïque
• Lepargylic acid
• Anchoic acid
• Nonandisaeure
• Azelaic 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
http://www.hmdb.ca/metabolites/HMDB0000784
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:48131
n-nonanedioic acid
Nonandisäure
Nonanedioate
Nonanedioic-D14 Acid
Nonanedionic acid
Skinorem
Water-soluble azelaic acid
Zumilin
азелаиновая кислота
حمض أزيلائيك
壬二酸
MECHANISM OF ACTION
The mechanism of action of azelaic acid is not well understood.
However, in vitro, it possesses antimicrobial activity against Propionibacterium acnes and Staphylococcus epidermidis, most likely through microbial cellular protein synthesis inhibition (Allergan, Inc., 2003).
Microcomedones and comedones can arise because of hyperkeratinization.
Azelaic acid produces an anticomedonal effect by decreasing the amount of hyperkeratinization (Allergan, Inc., 2003).
Biopsies have shown a decrease in stratum corneum thickness, keratohyalin granules, and filaggrin in patients treated with azelaic acid cream (Allergan, Inc., 2003).
Azelaic acid also competitively inhibits tyrosinase, an enzyme involved in the conversion of tyrosine to melanin.
Last, its mechanism of action also includes the inhibition of DNA synthesis and mitochondrial enzymes, thereby inducing direct cytotoxic effects on the melanocyte (Sarkar et al., 2016).
Therefore, azelaic acid is thought to decrease postinflammatory hyperpigmentation (Zaenglein et al., 2016).
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 (Allergan, Inc., 2003). It is also FDA approved for mild-to-moderate papulopustular rosacea under the brand name Finacea as 15% gel and 15% foam (Bayer HealthCare Pharmaceuticals Inc., 2015). 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 (Bayer HealthCare Pharmaceuticals Inc., 2015). Azelaic acid is also used off-label for the treatment of hyperpigmentation disorders, including melasma, due to its inhibition of tyrosinase (Figure 1; Mazurek & Pierzchala, 2016).
PHARMACOKINETICS
Topical azelaic acid has a bioavailability of up to 10% in the epidermis and dermis (Allergan, Inc., 2003). Approximately 4% of azelaic acid cream or gel is absorbed systemically after topical application (Allergan, Inc., 2003; Bayer HealthCare Pharmaceuticals Inc., 2015). Azelaic acid is a saturated dicarboxylic acid (HOOC-(CH2)7-COOH) found in many foods, including animal products and whole grains. It may undergo some beta-oxidation to shorter-chain dicarboxylic acids, but it is predominately excreted in its original form in urine (Allergan, Inc., 2003). The half-life of topical azelaic acid is approximately 12 hours, and the patient should apply it 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 (Allergan, Inc., 2003; Bayer HealthCare Pharmaceuticals Inc., 2015).
ADVERSE EFFECTS
Mild, transient adverse effects have been reported with topical azelaic acid. Adverse effects of the 15% gel (Finacea gel) used for rosacea include burning/stinging/tingling (29%), pruritis (11%), scaling/dry skin (8%), and erythema/irritation (4%; Bayer HealthCare Pharmaceuticals Inc., 2015). Adverse effects of the 20% cream (Azelex) used for acne vulgaris are similar but less commonly noted in the clinical trials. They include pruritus, burning, stinging, and tingling in 1%-5% of patients and erythema, dryness, rash, peeling, irritation, dermatitis, and contact dermatitis in less than 1% of patients (Allergan, Inc., 2003). Clinical trials of the 15% foam (Finacea foam) reported similar adverse reactions. All three formulations of topical azelaic acid mention that hypopigmentation has been reported and recommend monitoring for this in patients with dark complexions, as this has not been well studied in this population. Azelaic acid can also cause ocular and mucous membrane irritation; thus, contact should be avoided (Bayer HealthCare Pharmaceuticals Inc., 2015). It should be noted that hypersensitivity reactions to azelaic acid or its components have also been reported.
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 (Chien, Qi, Rainer, Sachs, & Helfrich, 2016).
WARNINGS AND PRECAUTIONS
Hypersensitivity reactions have been reported with the use of azelaic acid. It 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.
1,7-Heptanedicarboxylic acid
1,9-Nonanedioic acid
Acide azelaique
Acido azelaico
Acidum azelaicum
Anchoic acid
Azelaic acid
Azelaic acid
azelaic acid
Azelaic acid, technical grade
Azelex
Other
Emerox 1110
Other
Emerox 1144
Other
Finacea
Other
Heptanedicarboxylic acid
Other
Lepargylic acid
Other
Skinoren
Other
CAS names
Nonanedioic acid
IUPAC names
1,7-Heptanedicarboxylic acid
AZELAIC ACID
Azelaic Acid
Azelaic acid
azelaic acid
Azelaic acid
azelaic acid
Azelainsäure
Azeleic Acid
Nonanedioic acid
nonanedioic acid
Nonanedioic acid
Nonanedionic acid
Trade names
Crodacid DC1195
Ácido Azelaico