azelaic acid

Also known as Azelex®, Finacea®, ZK-62498, Azelate, Nonanedioic acid azelaic acid, Nonanedioic acid homopolymer, Azelainic acid, Emerox 1110

chemical compound

In the Vinony graph

Vinony's link graph records 103 inbound references to azelaic acid, and connects out to antibiotic, acne and comedo.

Vinony files it under 5α-Reductase inhibitors, Anti-acne preparations and Chembox having GHS data.

Vinony links it to 33 Wikipedia language editions.

Key facts

Medlineplus: a603020
License data: United States</span>"}]]}'>US DailyMed : Azelaic acid
Comptox dashboard u s environmental prot: DTXSID8021640
Echa infocard: 100.004.246

via Wikipedia infobox

Chemical data

Formula: C9H16O4
Molecular weight: 188.22 g/mol
IUPAC name: nonanedioic acid
SMILES: C(CCCC(=O)O)CCCC(=O)O
InChIKey: BDJRBEYXGGNYIS-UHFFFAOYSA-N
XLogP: 1.6
Polar surface area: 74.6 Å²
H-bond donors: 2
H-bond acceptors: 4
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1995
Admin. routes: topical
Indications: rosacea, acne, seborrheic dermatitis, Dermatitis, Perioral

via ChEMBL · EBI

Research

1,120 papers

The versatility of azelaic acid in dermatology.The Journal of dermatological treatment · 2022
Azelaic Acid: Mechanisms of Action and Clinical Applications.Clinical, cosmetic and investigational dermatology · 2024
Topical azelaic acid, salicylic acid, nicotinamide, sulphur, zinc and fruit acid (alpha-hydroxy acid) for acne.The Cochrane database of systematic reviews · 2020
Azelaic Acid.2006
Azelaic acid.Journal of the American Academy of Dermatology · 1987

via PubMed

Wikidata facts

Subclass of: fatty acid
Has part: carbon
Mass: 188.105
Has use: medication

Show 10 more facts

combustion enthalpy: -4777
found in taxon: tomato
chemical formula: C₉H₁₆O₄
electric dipole moment: 0.00000000000000000000000000000817
medical condition treated: rosacea
canonical SMILES: C(CCCC(=O)O)CCCC(=O)O
density: 1.251
melting point: 102
subject has role: 5-alpha-reductase inhibitors
Commons category: Azelaic acid

Sources (4)

via Wikidata · CC0

~6 min read

Encyclopedic overview

Azelaic acid (AzA), or nonanedioic acid, is an organic compound with the formula HOOC(CH2)7COOH. This saturated dicarboxylic acid exists as a white powder. It is found in wheat, rye, and barley. It is a precursor to diverse industrial products including polymers and plasticizers, as well as being a component of several hair and skin conditioners. In medicine, topical formulations of AzA are used in the treatment of acne vulgaris, where they exert antimicrobial and keratolytic effects that reduce clogged hair follicles and inflammation. In plants, AzA functions as a mobile signaling molecule that primes systemic acquired resistance against pathogens by inducing the accumulation of salicylic acid. AzA also inhibits tyrosinase.

Production

Excerpted from Wikipedia’s “azelaic acid” article, available under the CC BY-SA 4.0 licence.