1.0 2010-04-08 22:10:02 UTC 2025-11-18 23:34:44 UTC FDB012192 Azelaic acid Azelaic acid, also known as 1,9-nonanedioate, AZA or azelex, is a saturated nine-carbon dicarboxylic acid. It ocurrs in all living organisms, ranging from bacteria to humans. AZA possesses a variety of in vitro and in vivo biological activities. 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. It is currently used as a topical treatment of mild to moderate inflammatory acne vulgaris, due to its antibiotic effects on skin bacteria. Its effectiveness is similar to that of other agents without the systemic side effects of oral antibiotics or the allergic sensitization of topical benzoyl peroxide and with less irritation than tretinoin. Azelaic acid is less expensive than certain other prescription acne preparations, but it is much more expensive than nonprescription benzoyl peroxide preparations. Whether it is safe and effective when used in combination with other agents is not known. (PMID: 7737781, 8961845). In plants, azelaic acid serves as a "distress flare" involved in defense responses after infection. It serves as a signal that induces the accumulation of salicylic acid, an important component of the plants defensive response (PMID: 19342588). AZA is found in high abundance in several crop plants including wheat, rye, and barley. Azelaic acid has been detected, but not quantified in, a few different foods, such as asparagus, common beans, and potato. This could make azelaic acid a potential biomarker for the consumption of these foods. Azelaic acid is a precursor to a number of industrial products including polymers and plasticizers, as well as being a component of a number of hair and skin conditioners. 1, 9-Nonanedioic acid 1,7-Dicarboxyheptane 1,7-Heptanedicarboxylate 1,7-Heptanedicarboxylic acid 1,9-Nonanedioate 1,9-Nonanedioic acid 1tuf Acide azelaique Acido azelaico Acidum azelaicum Anchoate Anchoic acid Azalaic acid Azelaate Azelaic acid Azelaic acid (usan/inn) Azelaic acid [usan:inn] Azelaic acid polyanhydride AZELAIC ACID, 95% Azelaic acid, INN, USAN Azelaic polyanhydride Azelaicacidtech Azelainic acid Azelainsaeure Azelate Azelex Azelex (TN) Azleaic acid Emerox 1110 Emerox 1144 Emery's L-110 Finacea Finacea (TN) Finevin Heptanedicarboxylic acid Lepargylate Lepargylic acid N-nonanedioate N-nonanedioic acid Nonandisaeure Nonanedioate Nonanedioic acid Nonanedioic acid azelaic acid Nonanedioic acid homopolymer Nonanedioic acid, homopolymer Poly(azelaic anhydride) Polyazelaic anhydride Skinorem Skinoren ZK 62498 C9H16O4 188.2209 188.104859 nonanedioic acid azelaic acid 123-99-9 OC(=O)CCCCCCCC(O)=O InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13) BDJRBEYXGGNYIS-UHFFFAOYSA-N belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Medium-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Hydrocarbon derivative Medium-chain fatty acid Organic oxide Organic oxygen compound Organooxygen compound Dicarboxylic acids Dicarboxylic acids alpha,omega-dicarboxylic acid Solid logp 1.37 ALOGPS logs -1.92 ALOGPS solubility 2.28e+00 g/l ALOGPS melting_point Mp 106.5° logp 1.82 ChemAxon pka_strongest_acidic 4.15 ChemAxon iupac nonanedioic acid ChemAxon average_mass 188.2209 ChemAxon mono_mass 188.104859 ChemAxon smiles OC(=O)CCCCCCCC(O)=O ChemAxon formula C9H16O4 ChemAxon inchi InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13) ChemAxon inchikey BDJRBEYXGGNYIS-UHFFFAOYSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 46.54 ChemAxon polarizability 20.5 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::EiMs 1170 Specdb::MsIr 855 Specdb::MsIr 856 Specdb::MsIr 857 Specdb::NmrTwoD 1485 Specdb::CMs 1478 Specdb::CMs 11300 Specdb::CMs 31229 Specdb::CMs 32377 Specdb::CMs 37762 Specdb::CMs 146197 Specdb::CMs 1076071 Specdb::CMs 1076073 Specdb::CMs 1076075 Specdb::NmrOneD 1540 Specdb::NmrOneD 2204 Specdb::NmrOneD 2898 Specdb::NmrOneD 145390 Specdb::NmrOneD 145391 Specdb::NmrOneD 145392 Specdb::NmrOneD 145393 Specdb::NmrOneD 145394 Specdb::NmrOneD 145395 Specdb::NmrOneD 145396 Specdb::NmrOneD 145397 Specdb::NmrOneD 145398 Specdb::NmrOneD 145399 Specdb::NmrOneD 145400 Specdb::NmrOneD 145401 Specdb::NmrOneD 145402 Specdb::NmrOneD 145403 Specdb::NmrOneD 145404 Specdb::NmrOneD 145405 Specdb::NmrOneD 145406 Specdb::NmrOneD 145407 Specdb::NmrOneD 145408 Specdb::NmrOneD 145409 Specdb::MsMs 1119 Specdb::MsMs 1120 Specdb::MsMs 1121 Specdb::MsMs 4664 Specdb::MsMs 4665 Specdb::MsMs 4666 Specdb::MsMs 4667 Specdb::MsMs 4668 Specdb::MsMs 7841 Specdb::MsMs 7842 Specdb::MsMs 7843 Specdb::MsMs 14513 Specdb::MsMs 14514 Specdb::MsMs 14515 Specdb::MsMs 437178 Specdb::MsMs 437179 Specdb::MsMs 437180 Specdb::MsMs 437181 Specdb::MsMs 437182 Specdb::MsMs 439668 Specdb::MsMs 439669 Specdb::MsMs 439670 Specdb::MsMs 439822 Specdb::MsMs 439823 Specdb::MsMs 440160 HMDB00784 48131 AZ1 #<Reference:0x000055ce31c67b18> #<Reference:0x000055ce31c678e8> #<Reference:0x000055ce31c67640> #<Reference:0x000055ce31c67370> #<Reference:0x000055ce31c671b8> #<Reference:0x000055ce31c66f88> #<Reference:0x000055ce31c66d58> #<Reference:0x000055ce31c66b78> #<Reference:0x000055ce31c66948> #<Reference:0x000055ce31c66718> #<Reference:0x000055ce31c664c0> #<Reference:0x000055ce31c66290> #<Reference:0x000055ce31c66088> #<Reference:0x000055ce31c65ea8> #<Reference:0x000055ce31c65c78> #<Reference:0x000055ce31c65ac0> #<Reference:0x000055ce31c658e0> #<Reference:0x000055ce31c65688> #<Reference:0x000055ce31c654d0> #<Reference:0x000055ce31c652f0> #<Reference:0x000055ce31c65048> #<Reference:0x000055ce31c64e18> #<Reference:0x000055ce31c64c60> #<Reference:0x000055ce31c64a58> #<Reference:0x000055ce31c64800> #<Reference:0x000055ce31c64620> #<Reference:0x000055ce31c643c8> #<Reference:0x000055ce31c64170> #<Reference:0x000055ce31c64f08> #<Reference:0x000055ce31c63f90> #<Reference:0x000055ce31c63d88> #<Reference:0x000055ce31c63b30> #<Reference:0x000055ce31c638d8> #<Reference:0x000055ce31c63680> #<Reference:0x000055ce31c634c8> #<Reference:0x000055ce31c632e8> #<Reference:0x000055ce31c63040> Anatidae Type 1 specific Anatidae 8830 Asparagus Type 1 specific Asparagus officinalis 4686 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Common bean Type 1 specific Phaseolus vulgaris 3885 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Potato Type 1 specific Solanum tuberosum 4113 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 3-oxo-5-alpha-steroid 4-dehydrogenase 2 P31213 SRD5A2 3-oxo-5-beta-steroid 4-dehydrogenase P51857 AKR1D1 Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti hyperpigmentative 351 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti leukemic 393 A substance that inhibits or prevents the proliferation of neoplasms. Anti-acne 78 A drug used to treat or prevent skin disorders or for the routine care of skin. Anti-melanomic 425 A substance that inhibits or prevents the proliferation of neoplasms. Anti-melasmic 426 Anti-proliferative 548 Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Cytotoxic 859 A role played by the molecular entity or part thereof which causes the development of a pathological process.