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)
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 |
---|---|---|
Topical therapy for acne. | 2000 Jan 15 |
|
Characterization of novel di- and tricarboxylic acids in fine tropical aerosols. | 2001 Apr |
|
["Cleansing, topical treatment, oral administration". Controlling acne]. | 2001 Jul 26 |
|
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 |
|
Structure of a novel diterpenoid ester, fritillahupehin from bulbs of Fritillaria hupehensis Hsiao and K.C. Hsia. | 2002 Jul |
|
[Studies on chemical constituents of root of Cichorium intybus]. | 2002 Mar |
|
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 |
|
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 |
|
Analgesic effects of intra-nasal enkephalins. | 2003 Sep |
|
Azelaic acid 15% gel: in the treatment of papulopustular rosacea. | 2004 |
|
Interventions for rosacea. | 2004 |
|
Rosacea. An overview of diagnosis and management. | 2004 Dec |
|
Topical agents used in the management of hyperpigmentation. | 2004 Jun-Jul |
|
Proposal to accommodate Burkholderia cepacia genomovar VI as Burkholderia dolosa sp. nov. | 2004 May |
|
[Azelaic acid 15% gel in the treatment of acne vulgaris. Combined results of two double-blind clinical comparative studies]. | 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 |
|
Interventions for rosacea. | 2005 Jul 20 |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
A clinical overview of azelaic acid. | 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.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NDF-RT |
N0000008841
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
||
|
NDF-RT |
N0000008841
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
||
|
NDF-RT |
N0000009982
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
||
|
NCI_THESAURUS |
C28394
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
||
|
LOINC |
79495-8
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
||
|
WHO-ATC |
D10AX03
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
||
|
WHO-VATC |
QD10AX03
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
SUB05648MIG
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
19493
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
123-99-9
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
618278
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
ALTERNATIVE | |||
|
DB00548
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
100000091937
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
AZELAIC ACID
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
C47407
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
CHEMBL1238
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
F2VW3D43YT
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
18602
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
270
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
DTXSID8021640
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
204-669-1
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
m2168
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | Merck Index | ||
|
2266
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
7659
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
F2VW3D43YT
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
48131
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
HH-64
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
7484
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
Azelaic Acid
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY | |||
|
5883
Created by
admin on Fri Dec 15 15:26:07 GMT 2023 , Edited by admin on Fri Dec 15 15:26:07 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)