Details
Stereochemistry | ACHIRAL |
Molecular Formula | C9H16O4 |
Molecular Weight | 188.2209 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCCCCCCC(O)=O
InChI
InChIKey=BDJRBEYXGGNYIS-UHFFFAOYSA-N
InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
Molecular Formula | C9H16O4 |
Molecular Weight | 188.2209 |
Charge | 0 |
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 |
---|---|---|
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 |
|
Topical therapy for acne. | 2000 Jan 15 |
|
Characterization of novel di- and tricarboxylic acids in fine tropical aerosols. | 2001 Apr |
|
A comparative study of 20% azelaic acid cream monotherapy versus a sequential therapy in the treatment of melasma in dark-skinned patients. | 2002 |
|
The management of rosacea. | 2002 |
|
Assessment of topical hypopigmenting agents on solar lentigines of Asian women. | 2002 |
|
Total synthesis of (-)-minquartynoic acid: an anti-cancer, anti-HIV natural product. | 2002 Jul 25 |
|
[Studies on chemical constituents of root of Cichorium intybus]. | 2002 Mar |
|
Azelaic acid (20%) cream in the treatment of acne vulgaris. | 2002 Mar |
|
Fluid shear stress attenuates hydrogen peroxide-induced c-Jun NH2-terminal kinase activation via a glutathione reductase-mediated mechanism. | 2002 Oct 18 |
|
Transdermal penetration of topical drugs used in the treatment of acne. | 2003 |
|
Management of acne. | 2003 Jan |
|
Atmospheric pressure mass spectrometry: a new analytical chemical characterization method for dissolved organic matter in rainwater. | 2003 Jan 1 |
|
Interaction between a capacitor electrolyte and gamma-aluminum oxide studied by Fourier transform infrared spectroscopy. | 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 |
|
Azelaic acid (Finacea) for rosacea. | 2003 Sep 15 |
|
Photoelectron resonance capture ionization mass spectrometry: a soft ionization source for mass spectrometry of particle-phase organic compounds. | 2004 |
|
Azelaic acid 15% gel: in the treatment of papulopustular rosacea. | 2004 |
|
Interventions for rosacea. | 2004 |
|
Rosacea. An overview of diagnosis and management. | 2004 Dec |
|
Medical treatment of rosacea with emphasis on topical therapies. | 2004 Jan |
|
Azelaic acid, a new treatment for rosacea. | 2004 Jun |
|
Topical agents used in the management of hyperpigmentation. | 2004 Jun-Jul |
|
Conformationally constrained dipeptide surrogates with aromatic side-chains: synthesis of 4-aryl indolizidin-9-one amino acids by conjugate addition to a common alpha,omega-diaminoazelate enone intermediate. | 2004 Mar 5 |
|
Diagnosis and treatment of acne. | 2004 May 1 |
|
Ethosomes and liposomes as topical vehicles for azelaic acid: a preformulation study. | 2004 May-Jun |
|
Noxious sensory perceptions in patients with mild to moderate rosacea treated with azelaic acid 15% gel. | 2004 Oct |
|
Azelaic acid as a new treatment for perioral dermatitis: results from an open study. | 2004 Oct |
|
Enhancement of the release of azelaic acid through the synthetic membranes by inclusion complex formation with hydroxypropyl-beta-cyclodextrin. | 2005 Apr 11 |
|
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 |
|
Evidence-based dermatology. | 2005 Mar |
|
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 |
|
Case studies. | 2006 Feb |
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
Fri Dec 15 15:26:07 GMT 2023
by
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on
Fri Dec 15 15:26:07 GMT 2023
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Record UNII |
F2VW3D43YT
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000008841
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N0000008841
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N0000009982
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NCI_THESAURUS |
C28394
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79495-8
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D10AX03
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QD10AX03
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SUB05648MIG
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19493
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DB00548
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100000091937
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AZELAIC ACID
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C47407
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m2168
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7484
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Azelaic Acid
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Related Record | Type | Details | ||
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ACTIVE MOIETY |