| 词条 | Azelaic acid |
| 释义 |
| Watchedfields = changed | verifiedrevid = 458792195 | ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile = Azelaic acid.png | ImageSize = 255px | ImageAlt = Skeletal formula of azelaic acid | ImageFile1 = Azelaic acid 3D ball.png | ImageSize1 = 255px | ImageAlt1 = Ball-and-stick model of the azelaic acid molecule | IUPACName = nonanedioic acid | OtherNames = |Section1={{Chembox Identifiers | IUPHAR_ligand = 7484 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1238 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00548 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = F2VW3D43YT | InChIKey = BDJRBEYXGGNYIS-UHFFFAOYAK | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = BDJRBEYXGGNYIS-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 123-99-9 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 2179 | PubChem = 2266 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D03034 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 48131 | SMILES = O=C(O)CCCCCCCC(=O)O | InChI = 1/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13) }} |Section2={{Chembox Properties | C=9 | H=16 | O=4 | MolarMass = 188.22 g/mol | Appearance = white solid | Density = 1.443 g/mL | MeltingPtC = 109 to 111 | MeltingPt_ref = [1] | BoilingPtC = 286 | BoilingPt_notes = at 100 mmHg[1] | Solubility = 2.14 g/L[2] | pKa = 4.550, 5.498[2] }} |Section6={{Chembox Pharmacology | ATCCode_prefix = D10 | ATCCode_suffix = AX03 | AdminRoutes = Topical | Bioavail = Very low | Metabolism = | HalfLife = 12 h | ProteinBound = | Excretion = | Legal_status = | Legal_US = Rx-only | Legal_UK = | Legal_AU = S2 (Pharmacy Only) | Legal_CA = | Pregnancy_category = | Pregnancy_AU = | Pregnancy_US = }}Azelaic 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 a number of hair and skin conditioners.[5] ProductionAzelaic acid is industrially produced by the ozonolysis of oleic acid. The side product is nonanoic acid. It is produced naturally by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. The bacterial degradation of nonanoic acid gives azelaic acid. Biological functionIn plants, azelaic acid serves as a "distress flare" involved in defense responses after infection.[3] It serves as a signal that induces the accumulation of salicylic acid, an important component of a plant's defensive response.[4] ApplicationsPolymers and related materialsEsters of this dicarboxylic acid find applications in lubrication and plasticizers. In lubricant industries it is used as a thickening agent in lithium complex grease. With hexamethylenediamine, azelaic acid forms Nylon-6,9, which finds specialized uses as a plastic.[5] MedicalAzelaic acid is used to treat mild to moderate acne, both comedonal acne and inflammatory acne.[6][7] It belongs to a class of medication called dicarboxylic acids. It works by killing acne bacteria that infect skin pores. It also decreases the production of keratin, which is a natural substance that promotes the growth of acne bacteria.[8] Azelaic acid is also used as a topical gel treatment for rosacea, due to its ability to reduce inflammation.[7] It clears the bumps and swelling caused by rosacea. The mechanism of action is thought to be through the inhibition of hyperactive protease activity that converts cathelicidin into the antimicrobial skin peptide LL-37.[9] Azelaic acid has been used for treatment of skin pigmentation including melasma and postinflammatory hyperpigmentation, particularly in those with darker skin types. It has been recommended as an alternative to hydroquinone.[10] As a tyrosinase inhibitor, azelaic acid reduces synthesis of melanin.[11] Azelaic acid is also a potent 5ar-inhibitor, similar to the hair loss drugs finasteride and dutasteride.[12] Brand namesBrand names for azelaic acid include Dermaz 99,[13] Crema Pella Perfetta (micronized azelaic acid, kojic dipalmitate, and liquorice extract), Azepur99, Azetec99, Azaclear (azelaic acid and niacinamide), AzClear Action, Azelex, White Action cream, Finacea, Finevin, Melazepam, Skinoren, Ezanic, Azelac, Azaderm, and others. References1. ^1 Sigma-Aldrich catalog {{webarchive |url=https://web.archive.org/web/20080409115856/http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/11470 |date=April 9, 2008 }} 2. ^1 {{cite journal |title=Solubility and Activity Coefficients of Acidic and Basic Nonelectrolytes in Aqueous Salt Solutions. 2. Solubility and Activity Coefficients of Suberic, Azelaic, and Sebacic Acids in NaCl(aq), (CH3)4NCl(aq), and (C2H5)4NI(aq) at Different Ionic Strengths and at t = 25 °C |last1=Bretti|first1=C.|last2=Crea|first2=F.|last3=Foti|first3=C.|last4=Sammartano|first4=S. |journal=J. Chem. Eng. Data |year=2006 |volume=51 |issue=5 |pages=1660–1667 |doi=10.1021/je060132t}} 3. ^{{cite journal | author = Sarah Everts | title = Vegetative Warfare | journal = Chemical & Engineering News | date=January 31, 2011 | volume = 89 | issue = 5 | pages = 53–55 | url=http://cen.acs.org/articles/89/i5/Vegetative-Warfare.html | subscription=yes }} 4. ^{{Cite journal | last1 = Jung | first1 = H. W. | last2 = Tschaplinski | first2 = T. J. | last3 = Wang | first3 = L. | last4 = Glazebrook | first4 = J. | last5 = Greenberg | first5 = J. T. | title = Priming in Systemic Plant Immunity | journal = Science | volume = 324 | issue = 5923 | pages = 89–91 | year = 2009 | pmid = 19342588 | doi = 10.1126/science.1170025| bibcode = 2009Sci...324...89W }} 5. ^1 {{cite encyclopedia|first1=Boy |last1=Cornils |first2=Peter |last2=Lappe |title=Dicarboxylic Acids, Aliphatic |encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry |date=2006 |publisher=Wiley-VCH |location=Weinheim |DOI=10.1002/14356007.a08_523}} 6. ^{{cite web|url=http://www.webmd.com/skin-problems-and-treatments/acne/azelaic-acid-for-acne-vulgaris |title=Azelaic Acid for Acne|website=WebMD}} 7. ^1 {{cite web|url=https://www.drugs.com/mtm/azelaic-acid-topical.html |title=Azelaic acid topical|website=Drugs.com}} 8. ^{{cite journal | title = Azelaic acid in the treatment of papulopustular rosacea – A systematic review of randomized controlled trials | last1 = Liu | first1 = R. H. | last2 = Smith | first2 = M. K. | last3 = Basta | first3 = S. A. | last4 = Farmer | first4 = E. R. | journal = Arch. Dermatol. | volume = 142 | issue = 8 | pages = 1047–1052 | year = 2006 | doi =10.1001/archderm.142.8.1047 | pmid = 16924055 }} 9. ^{{cite journal | pmc=3346901| year=2012| author1=Reinholz| first1=M.| title=Cathelicidin LL-37: An Antimicrobial Peptide with a Role in Inflammatory Skin Disease| journal=Annals of Dermatology| volume=24| issue=2| pages=126–135| last2=Ruzicka| first2=T.| last3=Schauber| first3=J.| doi=10.5021/ad.2012.24.2.126| pmid=22577261}} 10. ^{{cite journal | last= Draelos |first=Z. | title = Skin lightening preparations and the hydroquinone controversy. | journal = Dermatol. Ther. | volume = 20 | issue = 5 | pages = 308–313 | date = Sep–Oct 2007 | pmid = 18045355 | doi=10.1111/j.1529-8019.2007.00144.x}} 11. ^{{cite book|last=Grimes|first=Pearl E.|title=Aesthetics and Cosmetic Surgery for Darker Skin Types|url=https://books.google.com/books?id=ALt93yGZccQC&pg=PA74|accessdate=9 August 2011|date=2007-07-01|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-8403-0|pages=74 ff.}} 12. ^{{cite journal |doi=10.1111/j.1365-2133.1988.tb03474.x |pmid=3207614 |title=Inhibition of 5α-reductase activity in human skin by zinc and azelaic acid |journal=British Journal of Dermatology |volume=119 |issue=5 |pages=627–32 |year=1988 |last1=Stamatiadis |first1=D |last2=Bulteau-Portois |first2=Marie-Claire |last3=Mowszowicz |first3=Irene }} 13. ^https://pharmaceutical.basf.com/en/APIs-Raw-Materials/Dermaz.html{{full citation needed|date=September 2018}} External links
3 : 5α-Reductase inhibitors|Dicarboxylic acids|Anti-acne preparations |
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