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Namespace Prefixes

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Statements

Subject Item
n2:DB00548
rdf:type
n3:Drug
n3:description
Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is a natural substance that is produced by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. It is effective against a number of skin conditions, such as mild to moderate acne, when applied topically in a cream formulation of 20%. It works in part by stopping the growth of skin bacteria that cause acne, and by keeping skin pores clear. Azelaic acid's antimicrobial action may be attributable to inhibition of microbial cellular protein synthesis.
n3:dosage
n24:271B4454-363D-11E5-9242-09173F13E4C5 n24:271B4455-363D-11E5-9242-09173F13E4C5 n24:271B4456-363D-11E5-9242-09173F13E4C5 n24:271B4457-363D-11E5-9242-09173F13E4C5
n3:group
approved
n3:halfLife
The observed half-lives in healthy subjects are approximately 45 minutes after oral dosing and 12 hours after topical dosing, indicating percutaneous absorption rate-limited kinetics.
n3:indication
For the topical treatment of mild-to-moderate inflammatory acne vulgaris.
n3:manufacturer
n4:271B444C-363D-11E5-9242-09173F13E4C5 n4:271B444B-363D-11E5-9242-09173F13E4C5
owl:sameAs
n12:DB00548 n31:DB00548
dcterms:title
Azelaic Acid
adms:identifier
n8:PA164754850 n10:2266 n13:10922-825-02 n14:AZ1 n15:46506284 n18:48131 n19:C08261 n20:D03034 n21:2179 n22:DB00548
n3:mechanismOfAction
The exact mechanism of action of azelaic acid is not known. It is thought that azelaic acid manifests its antibacterial effects by inhibiting the synthesis of cellular protein in anaerobic and aerobic bacteria, especially <i>Staphylococcus epidermidis</i> and <i>Propionibacterium acnes</i>. In aerobic bacteria, azelaic acid reversibly inhibits several oxidoreductive enzymes including tyrosinase, mitochondrial enzymes of the respiratory chain, thioredoxin reductase, 5-alpha-reductase, and DNA polymerases. In anaerobic bacteria, azelaic acid impedes glycolysis. Along with these actions, azelaic acid also improves acne vulgaris by normalizing the keratin process and decreasing microcomedo formation. Azelaic acid may be effective against both inflamed and noninflamed lesions. Specifically, azelaic acid reduces the thickness of the stratum corneum, shrinks keratohyalin granules by reducing the amount and distribution of filaggrin (a component of keratohyalin) in epidermal layers, and lowers the number of keratohyalin granules.
n3:packager
n4:271B4448-363D-11E5-9242-09173F13E4C5 n4:271B4449-363D-11E5-9242-09173F13E4C5 n4:271B4446-363D-11E5-9242-09173F13E4C5 n4:271B4447-363D-11E5-9242-09173F13E4C5 n4:271B444A-363D-11E5-9242-09173F13E4C5
n3:patent
n6:6534070 n6:2311128
n3:routeOfElimination
Azelaic acid is mainly excreted unchanged in the urine, but undergoes some ß-oxidation to shorter chain dicarboxylic acids.
n3:synonym
Nonandisaeure 1,7-Heptanedicarboxylic acid Skinoren Finacea Azelaic acid Acidum azelaicum Acide azélaïque Azelainsäure Anchoic acid Azelainsaeure Nonanedioic acid N-Nonanedioic acid 1,7-Dicarboxyheptane Lepargylic acid Ácido azelaico Acidum acelaicum Azelex Nonandisäure 1,9-Nonanedioic acid
n3:toxicity
Oral LD50 in rat: >5 g/kg
n3:mixture
n27:271B4445-363D-11E5-9242-09173F13E4C5
n3:synthesisReference
Abdul Malek, Clevys J. Monasterios, G. Ronald Brown, Ved P. Gupta, "Two step oxidation process for the production of carboxylic acids such as azelaic acid from unsaturated substrates." U.S. Patent US5380928, issued October, 1981.
n16:hasConcept
n17:M0055275
foaf:page
n26:azelex.htm n28:aze1043.shtml n32:azelaic-acid-cream.html
n3:IUPAC-Name
n5:271B445C-363D-11E5-9242-09173F13E4C5
n3:InChI
n5:271B4462-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n5:271B4461-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n5:271B445E-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n5:271B445F-363D-11E5-9242-09173F13E4C5
n3:SMILES
n5:271B4460-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n5:271B445A-363D-11E5-9242-09173F13E4C5 n5:271B4471-363D-11E5-9242-09173F13E4C5
n3:logP
n5:271B445B-363D-11E5-9242-09173F13E4C5 n5:271B4458-363D-11E5-9242-09173F13E4C5 n5:271B4474-363D-11E5-9242-09173F13E4C5
n3:logS
n5:271B4459-363D-11E5-9242-09173F13E4C5 n5:271B4475-363D-11E5-9242-09173F13E4C5
n3:pKa
n5:271B4476-363D-11E5-9242-09173F13E4C5
n29:hasATCCode
n30:D10AX03
n3:H-Bond-Acceptor-Count
n5:271B4468-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n5:271B4469-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n5:271B4463-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n5:271B4464-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n5:271B4466-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n5:271B4465-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n5:271B4467-363D-11E5-9242-09173F13E4C5
n3:absorption
Approximately 4% of the topically applied azelaic acid is systemically absorbed.
n3:affectedOrganism
Various aerobic and anaerobic microorganisms
n3:casRegistryNumber
123-99-9
n3:category
n3:containedIn
n9:271B444D-363D-11E5-9242-09173F13E4C5 n9:271B4452-363D-11E5-9242-09173F13E4C5 n9:271B4453-363D-11E5-9242-09173F13E4C5 n9:271B4450-363D-11E5-9242-09173F13E4C5 n9:271B4451-363D-11E5-9242-09173F13E4C5 n9:271B444E-363D-11E5-9242-09173F13E4C5 n9:271B444F-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n5:271B446D-363D-11E5-9242-09173F13E4C5
n3:Boiling-Point
n5:271B4473-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n5:271B446F-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n5:271B4470-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n5:271B4472-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n5:271B446C-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n5:271B446B-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n5:271B446E-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n5:271B445D-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n5:271B446A-363D-11E5-9242-09173F13E4C5