Human Metabolome Database Version 3.5

Showing metabocard for Azelaic acid (HMDB00784)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:29:03 -0600
HMDB ID HMDB00784
Secondary Accession Numbers None
Metabolite Identification
Common Name Azelaic acid
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 Link_out, 8961845 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1,7-Dicarboxyheptane
  2. 1,7-Heptanedicarboxylate
  3. 1,7-Heptanedicarboxylic acid
  4. 1,9-Nonanedioate
  5. 1,9-Nonanedioic acid
  6. Anchoate
  7. Anchoic acid
  8. Azalaic acid
  9. Azelaic acid
  10. Azelaicacidtech
  11. Azelainic acid
  12. Azelate
  13. Azelex
  14. Emerox 1110
  15. Emerox 1144
  16. Emery'S L-110
  17. Finacea
  18. Finevin
  19. Heptanedicarboxylic acid
  20. Lepargylate
  21. Lepargylic acid
  22. N-Nonanedioate
  23. N-Nonanedioic acid
  24. Nonanedioate
  25. Nonanedioic acid
  26. Nonanedioic acid azelaic acid
  27. Nonanedioic acid homopolymer
  28. Poly(azelaic anhydride)
  29. Polyazelaic anhydride
  30. Skinorem
  31. Skinoren
Chemical Formula C9H16O4
Average Molecular Weight 188.2209
Monoisotopic Molecular Weight 188.104859
IUPAC Name nonanedioic acid
Traditional IUPAC Name azelaic acid
CAS Registry Number 123-99-9
SMILES OC(=O)CCCCCCCC(O)=O
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)
InChI Key BDJRBEYXGGNYIS-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Carboxylic Acids and Derivatives
Sub Class Dicarboxylic Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Dicarboxylic acids(KEGG)
  • Dicarboxylic acids(Lipidmaps)
  • Fatty Acids and Conjugates
  • alpha,omega-dicarboxylic acid(ChEBI)
Substituents
  • Carboxylic Acid
Direct Parent Dicarboxylic Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 106.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 2.4 mg/mL Not Available
LogP 1.57 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 2.28 g/L ALOGPS
LogP 1.37 ALOGPS
LogP 1.82 ChemAxon
LogS -1.92 ALOGPS
pKa (strongest acidic) 4.15 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 74.6 A2 ChemAxon
Rotatable Bond Count 8 ChemAxon
Refractivity 46.54 ChemAxon
Polarizability 20.51 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Prostate
  • Skin
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
27.0 (0.0-58.0) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
17.0 +/- 17.0 uM Adult (>18 years old) Not Specified Normal
Urine Detected and Quantified
2.5 (0.1-12.3) umol/mmol creatinine Newborn (0-30 days old) Both Normal
Urine Detected and Quantified
3.6 (0.1-4.4) umol/mmol creatinine Infant (0-1 year old) Both Normal
Urine Detected and Quantified
4.3 (1.0-11.7) umol/mmol creatinine Children (1-13 year old) Both Comment Normal
Urine Detected and Quantified
3.7 (0.6-17.6) umol/mmol creatinine Adolescent (13-18 years old) Both Comment Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected and Quantified
2.21 +/- 1.67 umol/mmol creatinine Adult (>18 years old) Both Not Available
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
4.8 (1.3-15) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
2.8 (1.8-4.8) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
1.9 (1.2-3.2) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00548 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB012192
KNApSAcK ID Not Available
Chemspider ID 2179 Link_out
KEGG Compound ID C08261 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Nonanedioic acid Link_out
NuGOwiki Link HMDB00784 Link_out
Metagene Link HMDB00784 Link_out
METLIN ID 5750 Link_out
PubChem Compound 2266 Link_out
PDB ID AZ1 Link_out
ChEBI ID 48131 Link_out
References
Synthesis Reference Chen, Song; Yan, Jinlong. Synthesis of azelaic acid by chemical oxidation with oleic acid. Pige Huagong (2003), 20(6), 31-35.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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 Link_out
  2. 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 Link_out
  3. 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. Pubmed: 8412012 Link_out
  4. 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. Pubmed: 10896310 Link_out
  5. 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 Link_out
  6. Russell JJ: Topical therapy for acne. Am Fam Physician. 2000 Jan 15;61(2):357-66. Pubmed: 10670502 Link_out
  7. Webster G: Combination azelaic acid therapy for acne vulgaris. J Am Acad Dermatol. 2000 Aug;43(2 Pt 3):S47-50. Pubmed: 10898830 Link_out
  8. Del Rosso JQ: A status report on the medical management of rosacea: focus on topical therapies. Cutis. 2002 Nov;70(5):271-5. Pubmed: 12469780 Link_out
  9. Liao DC: Management of acne. J Fam Pract. 2003 Jan;52(1):43-51. Pubmed: 12540312 Link_out
  10. Del Rosso JQ: Medical treatment of rosacea with emphasis on topical therapies. Expert Opin Pharmacother. 2004 Jan;5(1):5-13. Pubmed: 14680431 Link_out
  11. Wolf JE Jr: The role of topical metronidazole in the treatment of rosacea. Cutis. 2004 Jan;73(1 Suppl):19-28. Pubmed: 14959942 Link_out
  12. 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 Link_out
  13. Halder RM, Richards GM: Management of dyschromias in ethnic skin. Dermatol Ther. 2004;17(2):151-7. Pubmed: 15113282 Link_out
  14. Halder RM, Richards GM: Topical agents used in the management of hyperpigmentation. Skin Therapy Lett. 2004 Jun-Jul;9(6):1-3. Pubmed: 15334278 Link_out
  15. Lindow KB: Rosacea. An overview of diagnosis and management. Adv Nurse Pract. 2004 Dec;12(12):27-32. Pubmed: 15615217 Link_out
  16. 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. Pubmed: 15624705 Link_out
  17. Wolf JE Jr: Present and future rosacea therapy. Cutis. 2005 Mar;75(3 Suppl):4-7; discussion 33-6. Pubmed: 15810803 Link_out
  18. 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 Link_out
  19. Purdy S: Acne vulgaris. Clin Evid. 2005 Jun;(13):2038-59. Pubmed: 16135322 Link_out
  20. Roebuck HL: Face up to rosacea. Nurse Pract. 2005 Sep;30(9):24-30, 35; quiz 36-7. Pubmed: 16151303 Link_out
  21. Callender VD: Considerations for treating acne in ethnic skin. Cutis. 2005 Aug;76(2 Suppl):19-23. Pubmed: 16164153 Link_out
  22. Nally JB, Berson DS: Topical therapies for rosacea. J Drugs Dermatol. 2006 Jan;5(1):23-6. Pubmed: 16468288 Link_out
  23. Fleischer AB Jr: The evolution of azelaic acid. Cutis. 2006 Feb;77(2 Suppl):4-6. Pubmed: 16566281 Link_out
  24. Draelos ZD: The rationale for advancing the formulation of azelaic acid vehicles. Cutis. 2006 Feb;77(2 Suppl):7-11. Pubmed: 16566282 Link_out
  25. Elewski B, Thiboutot D: A clinical overview of azelaic acid. Cutis. 2006 Feb;77(2 Suppl):12-6. Pubmed: 16566283 Link_out
  26. 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 Link_out
  27. 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 Link_out
  28. 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 Link_out
  29. Goodman G: Managing acne vulgaris effectively. Aust Fam Physician. 2006 Sep;35(9):705-9. Pubmed: 16969442 Link_out
  30. Purdy S: Acne vulgaris. Clin Evid. 2006 Jun;(15):2183-201. Pubmed: 16973084 Link_out
  31. 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 Link_out
  32. 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 Link_out
  33. 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 Link_out
  34. 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 Link_out
  35. 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. Pubmed: 19212411 Link_out
  36. 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 Link_out
  37. Mackrides PS, Shaughnessy AF: Azelaic acid therapy for acne. Am Fam Physician. 1996 Dec;54(8):2457-9. Pubmed: 8961845 Link_out

Enzymes
Name: Tyrosinase
Reactions: Not Available
Gene Name: TYR
Uniprot ID: P14679 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3-oxo-5-beta-steroid 4-dehydrogenase
Reactions: Not Available
Gene Name: AKR1D1
Uniprot ID: P51857 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3-oxo-5-alpha-steroid 4-dehydrogenase 2
Reactions: Not Available
Gene Name: SRD5A2
Uniprot ID: P31213 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA