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Details

Stereochemistry ACHIRAL
Molecular Formula C9H15O4.Na
Molecular Weight 210.2028
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MONOSODIUM AZELATE

SMILES

[Na+].OC(=O)CCCCCCCC([O-])=O

InChI

InChIKey=KITSBOHZGUHIOU-UHFFFAOYSA-M
InChI=1S/C9H16O4.Na/c10-8(11)6-4-2-1-3-5-7-9(12)13;/h1-7H2,(H,10,11)(H,12,13);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C9H15O4
Molecular Weight 187.213
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/?term=2114832 https://www.ncbi.nlm.nih.gov/pubmed/18803456

Azelaic acid, a naturally occurring saturated dicarboxylic acid found in wheat, rye, and barley, possesses antimicrobial activity, affects keratin production, and reduces inflammation. One of the brand name for azelaic acid is FINACEA,Gel, 15% is indicated for topical treatment of the inflammatory papules and pustules of mild to moderate rosacea. Although some reduction of erythema, which was present in patients with papules, and pustules of rosacea occurred in clinical studies, efficacy for treatment of erythema in rosacea in the absence of papules and pustules has not been evaluated. Rosacea is a common skin condition thought to be primarily an inflammatory disorder. Neutrophils, in particular, have been implicated in the inflammation associated with rosacea and mediate many of their effects through the release of reactive oxygen species. Many effective agents for rosacea, including topical azelaic acid have anti-inflammatory properties. Azelaic acid per se has multiple modes of action in rosacea, but an anti-inflammatory effect achieved by reducing reactive oxygen species appears to be the main pharmacological action. A possible mechanism of action for azelaic acid in the human epidermis includes its possibility to inhibit tyrosinase and of membrane-associated thioredoxin reductase enzymes, this enzyme is shown to regulate tyrosinase through a feedback mechanism involving electron transfer to intracellular thioredoxin, followed by a specific interaction between reduced thioredoxin and tyrosinase.

CNS Activity

Curator's Comment: Azelaic acid is capable of crossing the blood-brain barrier: its concentration in the cerebrospinal fluid is normally in the range of 2-5% of the values in the serum.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P14679
Gene ID: 7299.0
Gene Symbol: TYR
Target Organism: Homo sapiens (Human)
2.73 mM [Ki]
125.0 mM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
FINACEA

Approved Use

FINACEA® (azelaic acid) Gel, 15% is indicated for topical treatment of the inflammatory papules and pustules of mild to moderate rosacea. Although some reduction of erythema which was present in patients with papules and pustules of rosacea occurred in clinical studies, efficacy for treatment of erythema in rosacea in the absence of papules and pustules has not been evaluated.

Launch Date

2002
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
112 ng/mL
1 g single, topical
dose: 1 g
route of administration: Topical
experiment type: SINGLE
co-administered:
AZELAIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
136 ng/mL
1 g 2 times / day steady-state, topical
dose: 1 g
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
AZELAIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
613 ng × h/mL
1 g single, topical
dose: 1 g
route of administration: Topical
experiment type: SINGLE
co-administered:
AZELAIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
686 ng × h/mL
1 g 2 times / day steady-state, topical
dose: 1 g
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
AZELAIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12 h
1 g single, topical
dose: 1 g
route of administration: Topical
experiment type: SINGLE
co-administered:
AZELAIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Treatment of melasma.
2006-05
The use of topical azelaic acid for common skin disorders other than inflammatory rosacea.
2006-02
Case studies.
2006-02
A clinical overview of azelaic acid.
2006-02
The rationale for advancing the formulation of azelaic acid vehicles.
2006-02
The evolution of azelaic acid.
2006-02
Topical therapies for rosacea.
2006-01
Cumulative irritation potential of metronidazole gel compared to azelaic acid gel after repeated applications to healthy skin.
2005-11-24
The face and mind evaluation study: an examination of the efficacy of rosacea treatment using physician ratings and patients' self-reported quality of life.
2005-09-20
Face up to rosacea.
2005-09
Red facial rash with "granitos".
2005-09
[Rosacea. Clinical features, pathogenesis and therapy].
2005-09
Considerations for treating acne in ethnic skin.
2005-08
Interventions for rosacea.
2005-07-20
Chemical modification of proteins during peroxidation of phospholipids.
2005-07
Acne vulgaris.
2005-06
Lipid-derived modifications of plasma proteins in experimental and human diabetes.
2005-06
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005-06
Rosacea and its management: an overview.
2005-05
Enhancement of the release of azelaic acid through the synthetic membranes by inclusion complex formation with hydroxypropyl-beta-cyclodextrin.
2005-04-11
Alpha-adrenergic receptor-stimulated hypertrophy in adult rat ventricular myocytes is mediated via thioredoxin-1-sensitive oxidative modification of thiols on Ras.
2005-03-08
Ion chromatographic analysis of amines, alkanolamines, and associated anions in concrete.
2005-03
The pharmacologic therapy of rosacea: a paradigm shift in progress.
2005-03
The rigor of trials evaluating Rosacea treatments.
2005-03
Evidence-based dermatology.
2005-03
Present and future rosacea therapy.
2005-03
Comparison of azelaic acid and anthralin for the therapy of patchy alopecia areata: a pilot study.
2005
Aerosol products, mechanisms, and kinetics of heterogeneous reactions of ozone with oleic acid in pure and mixed particles.
2005
Rosacea: an update.
2005
Rosacea. An overview of diagnosis and management.
2004-12
[Azelaic acid 15% gel in the treatment of acne vulgaris. Combined results of two double-blind clinical comparative studies].
2004-10
Hyperpigmentation: an overview of the common afflictions.
2004-10
Noxious sensory perceptions in patients with mild to moderate rosacea treated with azelaic acid 15% gel.
2004-10
Comparison of 15% azelaic acid gel and 0.75% metronidazole gel for the topical treatment of papulopustular rosacea.
2004-10
Azelaic acid as a new treatment for perioral dermatitis: results from an open study.
2004-10
Topical agents used in the management of hyperpigmentation.
2004-08-31
Phototoxic effects of topical azelaic acid, benzoyl peroxide and adapalene were not detected when applied immediately before UVB to normal skin.
2004-08-21
Rosacea: where are we now?
2004-06-05
Azelaic acid, a new treatment for rosacea.
2004-06
Differential conductance switching of planar tunnel junctions mediated by oxidation/reduction of functionally protected ferrocene.
2004-05-26
Diagnosis and treatment of acne.
2004-05-01
A case of idiopathic eruptive macular pigmentation.
2004-05
Proposal to accommodate Burkholderia cepacia genomovar VI as Burkholderia dolosa sp. nov.
2004-05
Ethosomes and liposomes as topical vehicles for azelaic acid: a preformulation study.
2004-04-06
Diltiazem-induced hyperpigmentation.
2004-04
Evaluation of the antibacterial efficacy of diesters of azelaic acid.
2004-04
Acne and its management beyond the age of 35 years.
2004
Photoelectron resonance capture ionization mass spectrometry: a soft ionization source for mass spectrometry of particle-phase organic compounds.
2004
Optimal management of recalcitrant disorders of hyperpigmentation in dark-skinned patients.
2004
Management of dyschromias in ethnic skin.
2004
Patents

Sample Use Guides

Apply and gently massage into the affected areas on the face twice daily (morning and evening). Patients should be reassessed if no improvement is observed upon completing 12 weeks of therapy.
Route of Administration: Topical
In Vitro Use Guide
Using a clonogenic assay in vitro, it has been shown that exposure to azelaic acid (1-100 mM) for 24 hours has a dose-dependent effect on the survival of the colony-forming ability of murine (B16) and human (HMB2, and SK23) melanoma cells as compared with a non-melanotic non-tumoral Chinese hamster cell line (CHO). Both human cell lines were more sensitive to the diacid than the murine cells, and the HMB2 cells were more sensitive than the SK23 cells.
Substance Class Chemical
Created
by admin
on Tue Apr 01 16:25:47 GMT 2025
Edited
by admin
on Tue Apr 01 16:25:47 GMT 2025
Record UNII
5816841A8F
Record Status Validated (UNII)
Record Version
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Name Type Language
MONOSODIUM AZELATE
Systematic Name English
AZELAIC ACID, MONOSODIUM SALT
Preferred Name English
NONANEDIOIC ACID, SODIUM SALT (1:1)
Systematic Name English
SODIUM AZELATE (1:1)
Systematic Name English
Code System Code Type Description
CAS
17356-30-8
Created by admin on Tue Apr 01 16:25:47 GMT 2025 , Edited by admin on Tue Apr 01 16:25:47 GMT 2025
PRIMARY
EPA CompTox
DTXSID00884968
Created by admin on Tue Apr 01 16:25:47 GMT 2025 , Edited by admin on Tue Apr 01 16:25:47 GMT 2025
PRIMARY
PUBCHEM
23689125
Created by admin on Tue Apr 01 16:25:47 GMT 2025 , Edited by admin on Tue Apr 01 16:25:47 GMT 2025
PRIMARY
ECHA (EC/EINECS)
241-386-2
Created by admin on Tue Apr 01 16:25:47 GMT 2025 , Edited by admin on Tue Apr 01 16:25:47 GMT 2025
PRIMARY
FDA UNII
5816841A8F
Created by admin on Tue Apr 01 16:25:47 GMT 2025 , Edited by admin on Tue Apr 01 16:25:47 GMT 2025
PRIMARY