Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2024-09-03 04:18:55 UTC |
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NP-MRD ID | NP0000459 |
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Natural Product DOI | https://doi.org/10.57994/1562 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Azelaic acid |
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Description | Azelaic acid (AZA) is a naturally occurring saturated nine-carbon dicarboxylic acid (COOH (CH2)7-COOH). It possesses a variety of biological actions both in vitro and in vivo. Interest in the biological activity of AZA arose originally out of studies of skin surface lipids and the pathogenesis of hypochromia in pityriasis versicolor infection. Later, it was shown that Pityrosporum can oxidize unsaturated fatty acids to C8-C12 dicarboxylic acids that are cornpetitive inhibitors of tyrosinase in vitro. Azelaic acid was chosen for further investigation and development of a new topical drug for treating hyperpigmentary disorders for the following reasons: It possesses a middle-range of antityrosinase activity, is inexpensive, and more soluble to be incorporated into a base cream than other dicarboxylic acids. Azelaic acid is another option for the topical treatment of mild to moderate inflammatory acne vulgaris. It offers effectiveness 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 ). |
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Structure | 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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Synonyms | Value | Source |
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1,7-Dicarboxyheptane | ChEBI | 1,7-Heptanedicarboxylic acid | ChEBI | 1,9-Nonanedioic acid | ChEBI | Acide azelaique | ChEBI | Acidum azelaicum | ChEBI | Anchoic acid | ChEBI | Azelainsaeure | ChEBI | Azelex | ChEBI | Finacea | ChEBI | Lepargylic acid | ChEBI | N-Nonanedioic acid | ChEBI | Nonandisaeure | ChEBI | Skinoren | ChEBI | Nonanedioic acid | Kegg | 1,7-Heptanedicarboxylate | Generator | 1,9-Nonanedioate | Generator | Anchoate | Generator | Lepargylate | Generator | N-Nonanedioate | Generator | Nonanedioate | Generator | Azelaate | Generator | Azalaic acid | HMDB | Azelaicacidtech | HMDB | Azelainic acid | HMDB | Azelate | HMDB | Emerox 1110 | HMDB | Emerox 1144 | HMDB | Emery'S L-110 | HMDB | Finevin | HMDB | Heptanedicarboxylic acid | HMDB | Nonanedioic acid azelaic acid | HMDB | Nonanedioic acid homopolymer | HMDB | Poly(azelaic anhydride) | HMDB | Polyazelaic anhydride | HMDB | Skinorem | HMDB | Azelaic acid, dilithium salt | HMDB | Azelaic acid, dipotassium salt | HMDB | Azelaic acid, disodium salt | HMDB | Azelaic acid, monosodium salt | HMDB | Azelaic acid, potassium salt | HMDB | Azelaic acid, sodium salt | HMDB | Monosodium azelate | HMDB | Azelic acid | HMDB | alpha,Omega-nonanedioic acid | HMDB | Α,ω-nonanedioic acid | HMDB | Azelaic acid | PhytoBank |
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Chemical Formula | C9H16O4 |
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Average Mass | 188.2209 Da |
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Monoisotopic Mass | 188.10486 Da |
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IUPAC Name | nonanedioic acid |
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Traditional Name | azelaic acid |
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CAS Registry Number | 123-99-9 |
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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 | BDJRBEYXGGNYIS-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | Not Available | Sumner lab, University of Missouri | Zach Tretter | 2024-01-10 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | Not Available | Sumner lab, University of Missouri | Zach Tretter | 2024-01-10 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | Not Available | Sumner lab, University of Missouri | Zach Tretter | 2024-01-10 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | Not Available | Sumner lab, University of Missouri | Zach Tretter | 2024-01-10 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental) | Not Available | Sumner lab, University of Missouri | Zach Tretter | 2024-01-10 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Species Where Detected | |
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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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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 106.5 °C | Not Available | Boiling Point | 356.00 to 357.00 °C. @ 760.00 mm Hg | The Good Scents Company Information System | Water Solubility | 2.4 mg/mL | Not Available | LogP | 1.57 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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Predicted Properties | |
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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. [PubMed: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. [PubMed:11053913 ]
- 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. [PubMed:10431675 ]
- Russell JJ: Topical therapy for acne. Am Fam Physician. 2000 Jan 15;61(2):357-66. [PubMed:10670502 ]
- Webster G: Combination azelaic acid therapy for acne vulgaris. J Am Acad Dermatol. 2000 Aug;43(2 Pt 3):S47-50. [PubMed:10898830 ]
- Del Rosso JQ: Medical treatment of rosacea with emphasis on topical therapies. Expert Opin Pharmacother. 2004 Jan;5(1):5-13. [PubMed:14680431 ]
- Frampton JE, Wagstaff AJ: Azelaic acid 15% gel: in the treatment of papulopustular rosacea. Am J Clin Dermatol. 2004;5(1):57-64. [PubMed:14979745 ]
- Halder RM, Richards GM: Topical agents used in the management of hyperpigmentation. Skin Therapy Lett. 2004 Jun-Jul;9(6):1-3. [PubMed:15334278 ]
- Wolf JE Jr: Present and future rosacea therapy. Cutis. 2005 Mar;75(3 Suppl):4-7; discussion 33-6. [PubMed:15810803 ]
- van Zuuren EJ, Graber MA: The rigor of trials evaluating Rosacea treatments. Cutis. 2005 Mar;75(3 Suppl):13-6; discussion 33-6. [PubMed:15810805 ]
- Nally JB, Berson DS: Topical therapies for rosacea. J Drugs Dermatol. 2006 Jan;5(1):23-6. [PubMed:16468288 ]
- Fleischer AB Jr: The evolution of azelaic acid. Cutis. 2006 Feb;77(2 Suppl):4-6. [PubMed:16566281 ]
- Draelos ZD: The rationale for advancing the formulation of azelaic acid vehicles. Cutis. 2006 Feb;77(2 Suppl):7-11. [PubMed:16566282 ]
- Elewski B, Thiboutot D: A clinical overview of azelaic acid. Cutis. 2006 Feb;77(2 Suppl):12-6. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:16924055 ]
- 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. [PubMed: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. [PubMed: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. [PubMed:17190628 ]
- Gupta AK, Gover MD: Azelaic acid (15% gel) in the treatment of acne rosacea. Int J Dermatol. 2007 May;46(5):533-8. [PubMed:17472690 ]
- 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. [PubMed:7737781 ]
- Mackrides PS, Shaughnessy AF: Azelaic acid therapy for acne. Am Fam Physician. 1996 Dec;54(8):2457-9. [PubMed:8961845 ]
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