U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H14O4.2Na
Molecular Weight 232.1846
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DISODIUM AZELATE

SMILES

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

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

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 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
Amelanotic lentigo maligna melanoma: report of a case and review of the literature.
1999 Jul
Unraveling the patterns of subclinical pheomelanin-enriched facial hyperpigmentation: effect of depigmenting agents.
2000
Influence of drug treatment on the microacidity in rat and human skin--an in vitro electron spin resonance imaging study.
2001 Apr
Comparison of combined azelaic acid cream plus oral minocycline with oral isotretinoin in severe acne.
2001 Nov-Dec
A comparative study of 20% azelaic acid cream monotherapy versus a sequential therapy in the treatment of melasma in dark-skinned patients.
2002
Assessment of topical hypopigmenting agents on solar lentigines of Asian women.
2002
Sensitive and accurate quantitation of monoepoxy fatty acids in thermoxidized oils by gas-liquid chromatography.
2002 Dec 20
Recurrent lentigo maligna melanoma: regression associated with local azelaic acid 20%.
2002 Jan-Feb
Structure of a novel diterpenoid ester, fritillahupehin from bulbs of Fritillaria hupehensis Hsiao and K.C. Hsia.
2002 Jul
Cocrystal structures of diaminopimelate decarboxylase: mechanism, evolution, and inhibition of an antibiotic resistance accessory factor.
2002 Nov
Unknown peaks in GC-MS analyses of Guthrie cards blood samples might be the result of sample contamination by the black markings of the card.
2002 Oct
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
Urotropin azelate: a rather unwilling co-crystal.
2003 Feb
Gas chromatography-mass spectrometry profile of urinary organic acids of Wistar rats orally treated with ozonized unsaturated triglycerides and ozonized sunflower oil.
2003 Jan 15
Interaction between a capacitor electrolyte and gamma-aluminum oxide studied by Fourier transform infrared spectroscopy.
2003 Jun
Immunochemical detection of a novel lysine adduct using an antibody to linoleic acid hydroperoxide-modified protein.
2003 Jun
Investigation of surface changes of nanoparticles using TM-AFM phase imaging.
2003 Jun 15
A comparison of 15% azelaic acid gel and 0.75% metronidazole gel in the topical treatment of papulopustular rosacea: results of a randomized trial.
2003 Nov
Analgesic effects of intra-nasal enkephalins.
2003 Sep
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
Management of dyschromias in ethnic skin.
2004
Azelaic acid: a viewpoint by Susan Bershad.
2004
Interventions for rosacea.
2004
Diltiazem-induced hyperpigmentation.
2004 Apr
Rosacea. An overview of diagnosis and management.
2004 Dec
New rosacea drug gets the red out.
2004 Jan
The subtypes of rosacea: implications for treatment.
2004 Jan
Azelaic acid, a new treatment for rosacea.
2004 Jun
A case of idiopathic eruptive macular pigmentation.
2004 May
Proposal to accommodate Burkholderia cepacia genomovar VI as Burkholderia dolosa sp. nov.
2004 May
Diagnosis and treatment of acne.
2004 May 1
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
Considerations for treating acne in ethnic skin.
2005 Aug
Interventions for rosacea.
2005 Jul 20
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Evidence-based dermatology.
2005 Mar
Present and future rosacea therapy.
2005 Mar
Rosacea and its management: an overview.
2005 May
Case studies.
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 Dec 16 20:09:05 GMT 2023 , Edited by admin on Sat Dec 16 20:09:05 GMT 2023
NON-SPECIFIC STOICHIOMETRY
MESH
C010038
Created by admin on Sat Dec 16 20:09:05 GMT 2023 , Edited by admin on Sat Dec 16 20:09:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID40889659
Created by admin on Sat Dec 16 20:09:05 GMT 2023 , Edited by admin on Sat Dec 16 20:09:05 GMT 2023
PRIMARY
CAS
17265-13-3
Created by admin on Sat Dec 16 20:09:05 GMT 2023 , Edited by admin on Sat Dec 16 20:09:05 GMT 2023
PRIMARY
FDA UNII
0P4H8NH3UJ
Created by admin on Sat Dec 16 20:09:05 GMT 2023 , Edited by admin on Sat Dec 16 20:09:05 GMT 2023
PRIMARY
PUBCHEM
159815
Created by admin on Sat Dec 16 20:09:05 GMT 2023 , Edited by admin on Sat Dec 16 20:09:05 GMT 2023
PRIMARY
RXCUI
2117384
Created by admin on Sat Dec 16 20:09:05 GMT 2023 , Edited by admin on Sat Dec 16 20:09:05 GMT 2023
PRIMARY
ECHA (EC/EINECS)
241-298-4
Created by admin on Sat Dec 16 20:09:05 GMT 2023 , Edited by admin on Sat Dec 16 20:09:05 GMT 2023
PRIMARY