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Details

Stereochemistry ACHIRAL
Molecular Formula C9H16O4
Molecular Weight 188.2213
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZELAIC ACID

SMILES

C(CCCC(=O)O)CCCC(=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

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

1.04068802E12
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
Acne and its management beyond the age of 35 years.
2004
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
Management of dyschromias in ethnic skin.
2004
Diltiazem-induced hyperpigmentation.
2004 Apr
Evaluation of the antibacterial efficacy of diesters of azelaic acid.
2004 Apr
Rosacea. An overview of diagnosis and management.
2004 Dec
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
Topical agents used in the management of hyperpigmentation.
2004 Jun-Jul
A case of idiopathic eruptive macular pigmentation.
2004 May
Proposal to accommodate Burkholderia cepacia genomovar VI as Burkholderia dolosa sp. nov.
2004 May
Diagnosis and treatment of acne.
2004 May 1
Differential conductance switching of planar tunnel junctions mediated by oxidation/reduction of functionally protected ferrocene.
2004 May 26
Ethosomes and liposomes as topical vehicles for azelaic acid: a preformulation study.
2004 May-Jun
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
Hyperpigmentation: an overview of the common afflictions.
2004 Oct
Noxious sensory perceptions in patients with mild to moderate rosacea treated with azelaic acid 15% gel.
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
Comparison of azelaic acid and anthralin for the therapy of patchy alopecia areata: a pilot study.
2005
Aerosol products, mechanisms, and kinetics of heterogeneous reactions of ozone with oleic acid in pure and mixed particles.
2005
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
Interventions for rosacea.
2005 Jul 20
Acne vulgaris.
2005 Jun
Lipid-derived modifications of plasma proteins in experimental and human diabetes.
2005 Jun
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
The rigor of trials evaluating Rosacea treatments.
2005 Mar
Evidence-based dermatology.
2005 Mar
Present and future rosacea therapy.
2005 Mar
Alpha-adrenergic receptor-stimulated hypertrophy in adult rat ventricular myocytes is mediated via thioredoxin-1-sensitive oxidative modification of thiols on Ras.
2005 Mar 8
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
Red facial rash with "granitos".
2005 Sep
[Rosacea. Clinical features, pathogenesis and therapy].
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
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
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 [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
AZELAIC ACID [WHO-DD]
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 Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
NDF-RT N0000008841
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
NDF-RT N0000009982
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
NCI_THESAURUS C28394
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
LOINC 79495-8
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
WHO-ATC D10AX03
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
WHO-VATC QD10AX03
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
Code System Code Type Description
EVMPD
SUB05648MIG
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY
CAS
123-99-9
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY
RXCUI
618278
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
ALTERNATIVE
DRUG BANK
DB00548
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY
WIKIPEDIA
AZELAIC ACID
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY
NCI_THESAURUS
C47407
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY
ChEMBL
CHEMBL1238
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY
FDA UNII
F2VW3D43YT
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY
RXCUI
18602
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY
DRUG CENTRAL
270
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY
EPA CompTox
123-99-9
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-669-1
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY
MERCK INDEX
M2168
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY Merck Index
PUBCHEM
2266
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY
HSDB
7659
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY
IUPHAR
7484
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY
LACTMED
Azelaic Acid
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY
INN
5883
Created by admin on Sat Jun 26 15:51:27 UTC 2021 , Edited by admin on Sat Jun 26 15:51:27 UTC 2021
PRIMARY