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Details

Stereochemistry ACHIRAL
Molecular Formula C9H14O4.2Na
Molecular Weight 232.185
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DISODIUM AZELATE

SMILES

C(CCCC(=O)[O-])CCCC(=O)[O-].[Na+].[Na+]

InChI

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

HIDE SMILES / InChI

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

1.04068802E12
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 unknown
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 unknown
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 unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Burkholderia cepacia complex genomovars: utilization of carbon sources, susceptibility to antimicrobial agents and growth on selective media.
2003
Transdermal penetration of topical drugs used in the treatment of acne.
2003
Interaction between a capacitor electrolyte and gamma-aluminum oxide studied by Fourier transform infrared spectroscopy.
2003 Jun
Efficacy and safety of azelaic acid (15%) gel as a new treatment for papulopustular rosacea: results from two vehicle-controlled, randomized phase III studies.
2003 Jun
Investigation of surface changes of nanoparticles using TM-AFM phase imaging.
2003 Jun 15
Analgesic effects of intra-nasal enkephalins.
2003 Sep
Azelaic acid (Finacea) for rosacea.
2003 Sep 15
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
Azelaic acid 15% gel: in the treatment of papulopustular rosacea.
2004
Interventions for rosacea.
2004
Rosacea. An overview of diagnosis and management.
2004 Dec
New rosacea drug gets the red out.
2004 Jan
The role of topical metronidazole in the treatment of rosacea.
2004 Jan
The subtypes of rosacea: implications for treatment.
2004 Jan
Medical treatment of rosacea with emphasis on topical therapies.
2004 Jan
Maintenance therapy for acne vulgaris: the fine balance between efficacy, cutaneous tolerability, and adherence.
2004 Jan-Feb
Phototoxic effects of topical azelaic acid, benzoyl peroxide and adapalene were not detected when applied immediately before UVB to normal skin.
2004 Jul-Aug
Topical agents used in the management of hyperpigmentation.
2004 Jun-Jul
A case of idiopathic eruptive macular pigmentation.
2004 May
Rosacea: where are we now?
2004 May-Jun
[Azelaic acid 15% gel in the treatment of acne vulgaris. Combined results of two double-blind clinical comparative studies].
2004 Oct
Hyperpigmentation: an overview of the common afflictions.
2004 Oct
Noxious sensory perceptions in patients with mild to moderate rosacea treated with azelaic acid 15% gel.
2004 Oct
Comparison of 15% azelaic acid gel and 0.75% metronidazole gel for the topical treatment of papulopustular rosacea.
2004 Oct
Azelaic acid as a new treatment for perioral dermatitis: results from an open study.
2004 Oct
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
Enhancement of the release of azelaic acid through the synthetic membranes by inclusion complex formation with hydroxypropyl-beta-cyclodextrin.
2005 Apr 11
Considerations for treating acne in ethnic skin.
2005 Aug
Chemical modification of proteins during peroxidation of phospholipids.
2005 Jul
Acne vulgaris.
2005 Jun
Lipid-derived modifications of plasma proteins in experimental and human diabetes.
2005 Jun
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
The pharmacologic therapy of rosacea: a paradigm shift in progress.
2005 Mar
Evidence-based dermatology.
2005 Mar
Present and future rosacea therapy.
2005 Mar
Cumulative irritation potential of metronidazole gel compared to azelaic acid gel after repeated applications to healthy skin.
2005 Nov-Dec
Face up to rosacea.
2005 Sep
Red facial rash with "granitos".
2005 Sep
[Rosacea. Clinical features, pathogenesis and therapy].
2005 Sep
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 Sep-Oct
The use of topical azelaic acid for common skin disorders other than inflammatory rosacea.
2006 Feb
Case studies.
2006 Feb
A clinical overview of azelaic acid.
2006 Feb
The rationale for advancing the formulation of azelaic acid vehicles.
2006 Feb
The evolution of azelaic acid.
2006 Feb
Topical therapies for rosacea.
2006 Jan
Treatment of melasma.
2006 May
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.
Name Type Language
DISODIUM AZELATE
INCI  
INCI  
Official Name English
DISODIUM NONANEDIOATE
Systematic Name English
SODIUM AZELATE (2:1)
Systematic Name English
NONANEDIOIC ACID, DISODIUM SALT
Common Name English
NONANEDIOIC ACID, SODIUM SALT (1:2)
Common Name English
DISODIUM AZELATE [INCI]
Common Name English
AZELAIC ACID, DISODIUM SALT
Common Name English
Code System Code Type Description
CAS
27825-99-6
Created by admin on Sat Jun 26 05:05:10 UTC 2021 , Edited by admin on Sat Jun 26 05:05:10 UTC 2021
NON-SPECIFIC STOICHIOMETRY
MESH
C010038
Created by admin on Sat Jun 26 05:05:10 UTC 2021 , Edited by admin on Sat Jun 26 05:05:10 UTC 2021
PRIMARY
CAS
17265-13-3
Created by admin on Sat Jun 26 05:05:10 UTC 2021 , Edited by admin on Sat Jun 26 05:05:10 UTC 2021
PRIMARY
FDA UNII
0P4H8NH3UJ
Created by admin on Sat Jun 26 05:05:10 UTC 2021 , Edited by admin on Sat Jun 26 05:05:10 UTC 2021
PRIMARY
PUBCHEM
159815
Created by admin on Sat Jun 26 05:05:10 UTC 2021 , Edited by admin on Sat Jun 26 05:05:10 UTC 2021
PRIMARY
RXCUI
2117384
Created by admin on Sat Jun 26 05:05:10 UTC 2021 , Edited by admin on Sat Jun 26 05:05:10 UTC 2021
PRIMARY
ECHA (EC/EINECS)
241-298-4
Created by admin on Sat Jun 26 05:05:10 UTC 2021 , Edited by admin on Sat Jun 26 05:05:10 UTC 2021
PRIMARY