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
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 |
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 |
---|---|---|
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
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 11:26:06 GMT 2023
by
admin
on
Sat Dec 16 11:26:06 GMT 2023
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Record UNII |
5816841A8F
|
Record Status |
Validated (UNII)
|
Record Version |
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-
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241-386-2
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5816841A8F
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