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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

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
Influence of drug treatment on the microacidity in rat and human skin--an in vitro electron spin resonance imaging study.
2001 Apr
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
Azelaic acid (20%) cream in the treatment of acne vulgaris.
2002 Mar
Urotropin azelate: a rather unwilling co-crystal.
2003 Feb
Management of acne.
2003 Jan
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
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
Acne and its management beyond the age of 35 years.
2004
Management of dyschromias in ethnic skin.
2004
Rosacea. An overview of diagnosis and management.
2004 Dec
New rosacea drug gets the red out.
2004 Jan
[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
Aerosol products, mechanisms, and kinetics of heterogeneous reactions of ozone with oleic acid in pure and mixed particles.
2005
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
The rigor of trials evaluating Rosacea treatments.
2005 Mar
Face up to rosacea.
2005 Sep
Red facial rash with "granitos".
2005 Sep
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
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