AZ1

AZELAIC ACID


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Chemical Component Summary

NameAZELAIC ACID
Identifiersnonanedioic acid
FormulaC9 H16 O4
Molecular Weight188.221
TypeNON-POLYMER
Isomeric SMILESC(CCCC(=O)O)CCCC(=O)O
InChIInChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
InChIKeyBDJRBEYXGGNYIS-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count29
Chiral Atom Count0
Bond Count28
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB00548 
NameAzelaic acid
Groups approved
DescriptionAzelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is also produced by _Malassezia furfur_, also known as _Pityrosporum ovale_, which is a species of fungus that is normally found on human skin. Azelaic acid 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.
Synonyms
  • 1,9-nonanedioic acid
  • Ácido azelaico
  • Acidum acelaicum
  • n-nonanedioic acid
  • Anchoic acid
Brand Names
  • Tri-Zel
  • Azelaic Acid Gel
  • Finacea Foam
  • AnubisMed
  • Finacea
IndicationFor the topical treatment of mild-to-moderate inflammatory acne vulgaris.
Categories
  • Acids, Acyclic
  • Anti-Acne Preparations
  • Anti-Acne Preparations for Topical Use
  • Decreased Protein Synthesis
  • Decreased Sebaceous Gland Activity
ATC-CodeD10AX03
CAS number123-99-9

Drug Targets

NameTarget SequencePharmacological ActionActions
Thioredoxin reductaseMTEIDFDIAIIGAGPAGMTAAVYASRANLKTVMIERGIPGGQMANTEEVE...unknowninhibitor
3-oxo-5-beta-steroid 4-dehydrogenaseMDLSAASHRIPLSDGNSIPIIGLGTYSEPKSTPKGACATSVKVAIDTGYR...unknowninhibitor
3-oxo-5-alpha-steroid 4-dehydrogenase 2MQVQCQQSPVLAGSATLVALGALALYVAKPSGYGKHTESLKPAATRLPAR...unknowninhibitor
TyrosinaseMLLAVLYCLLWSFQTSAGHFPRACVSSKNLMEKECCPPWSGDRSPCGQLS...unknowninhibitor
DNA polymerase IMVQIPQNPLILVDGSSYLYRAYHAFPPLTNSAGEPTGAMYGVLNMLRSLI...unknowninhibitor
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 2266, 19347555
ChEMBL CHEMBL1238
ChEBI CHEBI:48131
CCDC/CSD LEXQIQ, AZELAC03, KECKEL, QEQZAO, AZELAC17, NUKZID, NEQPAD, TACBIK, AZELAC04, LEXQOW, KAYGOI, XUNHUJ, AZELAC05, UNEGEZ, NAQPIH, KAYJAX, AZELAC16, HOFYUZ, AZELAC15, KEFCAA, AZELAC14, AZELAC13, RUYXAM, ISIJAW, AZELAC12, AZELAC11, AZELAC01, TATNOV, DALJIN, KEBLOW, KAXMOP, GEHXEA, DALJOT
COD 2200095, 7200295, 4119600, 4508027, 4508028, 4508029, 4508030, 4513714, 7205992, 4508031, 4508032