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
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
DescriptionCurator'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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2505463
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P14679 Gene ID: 7299.0 Gene Symbol: TYR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2114832 |
2.73 mM [Ki] | ||
Target ID: CHEMBL2096978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2114832 |
125.0 mM [Ki] | ||
Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20967185 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | FINACEA Approved UseFINACEA® (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 Date2002 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Title | Date | PubMed |
---|---|---|
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7640879
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 | ||
---|---|---|---|---|
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
SUBSTANCE RECORD