Record Information |
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Version | 2.0 |
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Creation Date | 2014-09-11 05:17:08 UTC |
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Update Date | 2014-12-24 20:26:57 UTC |
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Accession Number | T3D4799 |
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Identification |
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Common Name | Azelaic Acid |
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Class | Small Molecule |
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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. |
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Compound Type | - Antineoplastic Agent
- Dermatologic Agent
- Drug
- Food Toxin
- Metabolite
- Natural Compound
- Organic Compound
- Plant Toxin
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Chemical Structure | |
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Synonyms | Synonym | 1,7-Dicarboxyheptane | 1,7-Heptanedicarboxylate | 1,7-Heptanedicarboxylic acid | 1,9-Nonanedioate | 1,9-Nonanedioic acid | Acide azélaïque | Ácido azelaico | Acidum acelaicum | Acidum azelaicum | Acne-Derm | Acnean | Acnederm | Acnesafe | Aknoren | Ami | Anchoate | Anchoic acid | Arbonid | Azalaic acid | Azelaate | Azelaic acid | Azelaicacidtech | Azelainic acid | Azelainsaeure | Azelainsäure | Azelate | Azelex | Emerox 1110 | Emerox 1144 | Emery'S L-110 | Finacea | Finevin | Heptanedicarboxylic acid | Lepargylate | Lepargylic acid | N-Nonanedioate | N-Nonanedioic acid | Nonandisaeure | Nonandisäure | Nonanedioate | Nonanedioic acid | Nonanedioic acid azelaic acid | Nonanedioic acid homopolymer | Poly(azelaic anhydride) | Polyazelaic anhydride | Skinorem | Skinoren | Zumilin |
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Chemical Formula | C9H16O4 |
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Average Molecular Mass | 188.221 g/mol |
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Monoisotopic Mass | 188.105 g/mol |
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CAS Registry Number | 123-99-9 |
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IUPAC Name | nonanedioic acid |
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Traditional Name | azelaic acid |
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SMILES | OC(=O)CCCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13) |
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InChI Key | InChIKey=BDJRBEYXGGNYIS-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | 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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Medium-chain fatty acids |
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Alternative Parents | |
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Substituents | - Medium-chain fatty acid
- Dicarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Endogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 106.5°C | Boiling Point | 286.5°C at 1.00E+02 mm Hg | Solubility | 2400 mg/L (at 20°C) | LogP | 1.57 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0v0r-4920000000-5a3ed693b1c4083f1f15 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0v0r-4920000000-5a3ed693b1c4083f1f15 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00mk-1910000000-83ba58dac4b0698643d0 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-000f-9600000000-24638c458fa83f47c259 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00y0-9740000000-d157d08c3a7c87244190 | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-000i-0900000000-a118e433f0bd27a95b89 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-006t-9600000000-93b3a375b722791cb5c9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-052k-9500000000-6b069f2fed947651b284 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-000i-0900000000-7980b5eadcca6ee1eadd | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-0900000000-462585874f7661d40d5b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-004j-4900000000-0f65eeeed8c8a6ff3cc9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0002-9300000000-d654ca3c764066f98358 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0002-9000000000-60a08bb384f2b4cbfca8 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-0900000000-7980b5eadcca6ee1eadd | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-0900000000-462585874f7661d40d5b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004j-4900000000-0f65eeeed8c8a6ff3cc9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-9300000000-fcefbd80852c2625bc0e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-9000000000-60a08bb384f2b4cbfca8 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-004i-0900000000-26216115e75cad833509 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-004i-0900000000-7bef8272c481ea57a60b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-004i-0900000000-751bf479539d4bd2b5e1 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-00di-0900000000-9a056a45b27896966bf9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-00di-0900000000-3155fd845eec8f32ce93 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-004r-0900000000-544110f97ebc0f97e15b | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00dr-0900000000-b1b7c1ab57d58a2405a8 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00g3-2900000000-d0ba7fbbe987efa4c818 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05qd-9100000000-8d65a19b998d18ad08ac | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-a7edc3ac66d27685b9d1 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00kr-1900000000-c56b9d972f88c58dc65b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9300000000-47cbefe19a788d7f36b9 | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-06rx-9100000000-6db2acb47ad4c6163063 | JSpectraViewer | MoNA | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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Toxicity Profile |
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Route of Exposure | Approximately 4% of the topically applied azelaic acid is systemically absorbed. |
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Mechanism of Toxicity | 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 Staphylococcus epidermidis and Propionibacterium acnes. 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. |
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Metabolism | Mainly excreted unchanged in the urine but undergoes some b-oxidation to shorter chain dicarboxylic acids.
Route of Elimination: Azelaic acid is mainly excreted unchanged in the urine, but undergoes some нф-oxidation to shorter chain dicarboxylic acids.
Half Life: 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. |
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Toxicity Values | Oral LD50 in rat: >5 g/kg |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | For the topical treatment of mild-to-moderate inflammatory acne vulgaris. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB00548 |
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HMDB ID | HMDB00784 |
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PubChem Compound ID | 2266 |
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ChEMBL ID | CHEMBL1238 |
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ChemSpider ID | 2179 |
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KEGG ID | C08261 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 48131 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | AZ1 |
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ACToR ID | Not Available |
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Wikipedia Link | Nonanedioic acid |
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References |
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Synthesis Reference | 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. |
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MSDS | Link |
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General References | - Mayer-da-Silva A, Gollnick H, Detmar M, Gassmuller J, Parry A, Muller R, Orfanos CE: Effects of azelaic acid on sebaceous gland, sebum excretion rate and keratinization pattern in human skin. An in vivo and in vitro study. Acta Derm Venereol Suppl (Stockh). 1989;143:20-30. [2475995 ]
- Hermanns JF, Petit L, Martalo O, Pierard-Franchimont C, Cauwenbergh G, Pierard GE: Unraveling the patterns of subclinical pheomelanin-enriched facial hyperpigmentation: effect of depigmenting agents. Dermatology. 2000;201(2):118-22. [11053913 ]
- Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [8412012 ]
- Korman SH, Mandel H, Gutman A: Characteristic urine organic acid profile in peroxisomal biogenesis disorders. J Inherit Metab Dis. 2000 Jun;23(4):425-8. [10896310 ]
- Rocamora V, Puig L, Romani J, de Moragas JM: Amelanotic lentigo maligna melanoma: report of a case and review of the literature. Cutis. 1999 Jul;64(1):53-6. [10431675 ]
- Russell JJ: Topical therapy for acne. Am Fam Physician. 2000 Jan 15;61(2):357-66. [10670502 ]
- Webster G: Combination azelaic acid therapy for acne vulgaris. J Am Acad Dermatol. 2000 Aug;43(2 Pt 3):S47-50. [10898830 ]
- Del Rosso JQ: A status report on the medical management of rosacea: focus on topical therapies. Cutis. 2002 Nov;70(5):271-5. [12469780 ]
- Liao DC: Management of acne. J Fam Pract. 2003 Jan;52(1):43-51. [12540312 ]
- Del Rosso JQ: Medical treatment of rosacea with emphasis on topical therapies. Expert Opin Pharmacother. 2004 Jan;5(1):5-13. [14680431 ]
- Wolf JE Jr: The role of topical metronidazole in the treatment of rosacea. Cutis. 2004 Jan;73(1 Suppl):19-28. [14959942 ]
- Frampton JE, Wagstaff AJ: Azelaic acid 15% gel: in the treatment of papulopustular rosacea. Am J Clin Dermatol. 2004;5(1):57-64. [14979745 ]
- Halder RM, Richards GM: Management of dyschromias in ethnic skin. Dermatol Ther. 2004;17(2):151-7. [15113282 ]
- Halder RM, Richards GM: Topical agents used in the management of hyperpigmentation. Skin Therapy Lett. 2004 Jun-Jul;9(6):1-3. [15334278 ]
- Lindow KB: Rosacea. An overview of diagnosis and management. Adv Nurse Pract. 2004 Dec;12(12):27-32. [15615217 ]
- Cayce KA, McMichael AJ, Feldman SR: Hyperpigmentation: an overview of the common afflictions. Dermatol Nurs. 2004 Oct;16(5):401-6, 413-6; quiz 417. [15624705 ]
- Wolf JE Jr: Present and future rosacea therapy. Cutis. 2005 Mar;75(3 Suppl):4-7; discussion 33-6. [15810803 ]
- van Zuuren EJ, Graber MA: The rigor of trials evaluating Rosacea treatments. Cutis. 2005 Mar;75(3 Suppl):13-6; discussion 33-6. [15810805 ]
- Purdy S: Acne vulgaris. Clin Evid. 2005 Jun;(13):2038-59. [16135322 ]
- Roebuck HL: Face up to rosacea. Nurse Pract. 2005 Sep;30(9):24-30, 35; quiz 36-7. [16151303 ]
- Callender VD: Considerations for treating acne in ethnic skin. Cutis. 2005 Aug;76(2 Suppl):19-23. [16164153 ]
- Nally JB, Berson DS: Topical therapies for rosacea. J Drugs Dermatol. 2006 Jan;5(1):23-6. [16468288 ]
- Fleischer AB Jr: The evolution of azelaic acid. Cutis. 2006 Feb;77(2 Suppl):4-6. [16566281 ]
- Draelos ZD: The rationale for advancing the formulation of azelaic acid vehicles. Cutis. 2006 Feb;77(2 Suppl):7-11. [16566282 ]
- Elewski B, Thiboutot D: A clinical overview of azelaic acid. Cutis. 2006 Feb;77(2 Suppl):12-6. [16566283 ]
- Del Rosso JQ: The use of topical azelaic acid for common skin disorders other than inflammatory rosacea. Cutis. 2006 Feb;77(2 Suppl):22-4. [16566285 ]
- Worret WI, Fluhr JW: [Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid]. J Dtsch Dermatol Ges. 2006 Apr;4(4):293-300. [16638058 ]
- Liu RH, Smith MK, Basta SA, Farmer ER: Azelaic acid in the treatment of papulopustular rosacea: a systematic review of randomized controlled trials. Arch Dermatol. 2006 Aug;142(8):1047-52. [16924055 ]
- Goodman G: Managing acne vulgaris effectively. Aust Fam Physician. 2006 Sep;35(9):705-9. [16969442 ]
- Purdy S: Acne vulgaris. Clin Evid. 2006 Jun;(15):2183-201. [16973084 ]
- Gupta AK, Gover MD, Nouri K, Taylor S: The treatment of melasma: a review of clinical trials. J Am Acad Dermatol. 2006 Dec;55(6):1048-65. Epub 2006 Sep 28. [17097400 ]
- Fitton A, Goa KL: Azelaic acid. A review of its pharmacological properties and therapeutic efficacy in acne and hyperpigmentary skin disorders. Drugs. 1991 May;41(5):780-98. [1712709 ]
- van Zuuren EJ, Gupta AK, Gover MD, Graber M, Hollis S: Systematic review of rosacea treatments. J Am Acad Dermatol. 2007 Jan;56(1):107-15. Epub 2006 Nov 7. [17190628 ]
- Gupta AK, Gover MD: Azelaic acid (15% gel) in the treatment of acne rosacea. Int J Dermatol. 2007 May;46(5):533-8. [17472690 ]
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [19212411 ]
- Nguyen QH, Bui TP: Azelaic acid: pharmacokinetic and pharmacodynamic properties and its therapeutic role in hyperpigmentary disorders and acne. Int J Dermatol. 1995 Feb;34(2):75-84. [7737781 ]
- Mackrides PS, Shaughnessy AF: Azelaic acid therapy for acne. Am Fam Physician. 1996 Dec;54(8):2457-9. [8961845 ]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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