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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
Structure of Azelaic acid

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)

HIDE SMILES / InChI

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

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
Combination azelaic acid therapy for acne vulgaris.
2000 Aug
Topical therapy for acne.
2000 Jan 15
Characteristic urine organic acid profile in peroxisomal biogenesis disorders.
2000 Jun
Sensitive and accurate quantitation of monoepoxy fatty acids in thermoxidized oils by gas-liquid chromatography.
2002 Dec 20
Recurrent lentigo maligna melanoma: regression associated with local azelaic acid 20%.
2002 Jan-Feb
Structure of a novel diterpenoid ester, fritillahupehin from bulbs of Fritillaria hupehensis Hsiao and K.C. Hsia.
2002 Jul
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
Guidelines for the management of acne vulgaris in adolescents.
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
Gas chromatography-mass spectrometry profile of urinary organic acids of Wistar rats orally treated with ozonized unsaturated triglycerides and ozonized sunflower oil.
2003 Jan 15
Interaction between a capacitor electrolyte and gamma-aluminum oxide studied by Fourier transform infrared spectroscopy.
2003 Jun
New rosacea drug gets the red out.
2004 Jan
Medical treatment of rosacea with emphasis on topical therapies.
2004 Jan
Differential conductance switching of planar tunnel junctions mediated by oxidation/reduction of functionally protected ferrocene.
2004 May 26
[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
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
The pharmacologic therapy of rosacea: a paradigm shift in progress.
2005 Mar
Cumulative irritation potential of metronidazole gel compared to azelaic acid gel after repeated applications to healthy skin.
2005 Nov-Dec
Red facial rash with "granitos".
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
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
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 Fri Dec 15 15:26:07 GMT 2023
Edited
by admin
on Fri Dec 15 15:26:07 GMT 2023
Record UNII
F2VW3D43YT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Azelaic acid
HSDB   INCI   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INCI   USAN   INN  
Official Name English
ZK-62498
Code English
AZELATE
Systematic Name English
AZELAIC ACID [INCI]
Common Name English
AZELAIC ACID [MART.]
Common Name English
AZELAIC ACID [VANDF]
Common Name English
Azelaic acid [WHO-DD]
Common Name English
azelaic acid [INN]
Common Name English
AZELEX
Brand Name English
NONANEDIOIC ACID
Systematic Name English
NSC-19493
Code English
1,7-HEPTANEDICARBOXYLIC ACID
Systematic Name English
AZELAIC ACID [HSDB]
Common Name English
FINACEA
Brand Name English
ZK 62498
Code English
AZELAIC ACID [USAN]
Common Name English
AZELAIC ACID [ORANGE BOOK]
Common Name English
ANCHOIC ACID
Common Name English
LEPARGYLIC ACID
Common Name English
AZELAIC ACID [MI]
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
EVMPD
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
NSC
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
CAS
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
RXCUI
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
DRUG BANK
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
SMS_ID
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
WIKIPEDIA
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
NCI_THESAURUS
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
ChEMBL
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
FDA UNII
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
RXCUI
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
DRUG CENTRAL
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
EPA CompTox
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
ECHA (EC/EINECS)
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
MERCK INDEX
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
PUBCHEM
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
HSDB
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
DAILYMED
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
CHEBI
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
USAN
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
IUPHAR
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
LACTMED
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
INN
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
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ACTIVE MOIETY