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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 22.9898
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 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
Unraveling the patterns of subclinical pheomelanin-enriched facial hyperpigmentation: effect of depigmenting agents.
2000
Combination azelaic acid therapy for acne vulgaris.
2000 Aug
Characteristic urine organic acid profile in peroxisomal biogenesis disorders.
2000 Jun
Characterization of novel di- and tricarboxylic acids in fine tropical aerosols.
2001 Apr
Are 2 combined antimicrobial mechanisms better than 1 for the treatment of acne vulgaris? Clinical and antimicrobial results of a topical combination product containing 1% clindamycin and 5% benzoyl peroxide. Introduction.
2001 Feb
["Cleansing, topical treatment, oral administration". Controlling acne].
2001 Jul 26
Comparison of combined azelaic acid cream plus oral minocycline with oral isotretinoin in severe acne.
2001 Nov-Dec
The modern age of acne therapy: a review of current treatment options.
2001 Sep-Oct
A comparative study of 20% azelaic acid cream monotherapy versus a sequential therapy in the treatment of melasma in dark-skinned patients.
2002
Recurrent lentigo maligna melanoma: regression associated with local azelaic acid 20%.
2002 Jan-Feb
A status report on the medical management of rosacea: focus on topical therapies.
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
Guidelines for the management of acne vulgaris in adolescents.
2003
Topical treatment in acne: current status and future aspects.
2003
Urotropin azelate: a rather unwilling co-crystal.
2003 Feb
Management of acne.
2003 Jan
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
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
Azelaic acid 15% gel: in the treatment of papulopustular rosacea.
2004
Diltiazem-induced hyperpigmentation.
2004 Apr
The role of topical metronidazole in the treatment of rosacea.
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
Azelaic acid, a new treatment for rosacea.
2004 Jun
Differential conductance switching of planar tunnel junctions mediated by oxidation/reduction of functionally protected ferrocene.
2004 May 26
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
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
Rosacea: an update.
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
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Ion chromatographic analysis of amines, alkanolamines, and associated anions in concrete.
2005 Mar
Rosacea and its management: an overview.
2005 May
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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:26:06 GMT 2023
Edited
by admin
on Sat Dec 16 11:26:06 GMT 2023
Record UNII
5816841A8F
Record Status Validated (UNII)
Record Version
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Name Type Language
MONOSODIUM AZELATE
Systematic Name English
NONANEDIOIC ACID, SODIUM SALT (1:1)
Systematic Name English
SODIUM AZELATE (1:1)
Systematic Name English
AZELAIC ACID, MONOSODIUM SALT
Common Name English
Code System Code Type Description
CAS
17356-30-8
Created by admin on Sat Dec 16 11:26:06 GMT 2023 , Edited by admin on Sat Dec 16 11:26:06 GMT 2023
PRIMARY
EPA CompTox
DTXSID00884968
Created by admin on Sat Dec 16 11:26:06 GMT 2023 , Edited by admin on Sat Dec 16 11:26:06 GMT 2023
PRIMARY
PUBCHEM
23689125
Created by admin on Sat Dec 16 11:26:06 GMT 2023 , Edited by admin on Sat Dec 16 11:26:06 GMT 2023
PRIMARY
ECHA (EC/EINECS)
241-386-2
Created by admin on Sat Dec 16 11:26:06 GMT 2023 , Edited by admin on Sat Dec 16 11:26:06 GMT 2023
PRIMARY
FDA UNII
5816841A8F
Created by admin on Sat Dec 16 11:26:06 GMT 2023 , Edited by admin on Sat Dec 16 11:26:06 GMT 2023
PRIMARY