Azelaic acid

Identification

Summary

Azelaic acid is a saturated dicarboxylic acid used to treat mild to moderate acne vulgaris.

Brand Names
Azelex, Finacea
Generic Name
Azelaic acid
DrugBank Accession Number
DB00548
Background

Azelaic 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.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 188.2209
Monoisotopic: 188.104859
Chemical Formula
C9H16O4
Synonyms
  • 1,7-dicarboxyheptane
  • 1,7-Heptanedicarboxylic acid
  • 1,9-nonanedioic acid
  • Acide azélaïque
  • Ácido azelaico
  • Acidum acelaicum
  • Acidum azelaicum
  • Anchoic acid
  • Azelaic acid
  • Azelainsäure
  • Lepargylic acid
  • n-nonanedioic acid
  • Nonandisäure
  • Nonanedioic acid
External IDs
  • ZK 62498
  • ZK-62498

Pharmacology

Indication

For the topical treatment of mild-to-moderate inflammatory acne vulgaris.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAcne vulgaris•••••••••••••••••
Treatment ofInflammatory lesions caused by rosacea•••••••••••••••••••• ••••
Treatment ofInflammatory lesions caused by rosacea•••••••••••••••
Treatment ofSusceptible bacterial infections••••••••••••••••••• ••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

Mechanism of action

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.

TargetActionsOrganism
AThioredoxin reductase
inhibitor
Staphylococcus aureus (strain Mu50 / ATCC 700699)
A3-oxo-5-beta-steroid 4-dehydrogenase
inhibitor
Humans
A3-oxo-5-alpha-steroid 4-dehydrogenase 2
inhibitor
Humans
ATyrosinase
inhibitor
Humans
ADNA polymerase I
inhibitor
Escherichia coli (strain K12)
Absorption

Approximately 4% of the topically applied azelaic acid is systemically absorbed.

Volume of distribution

Not Available

Protein binding

Not Available

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 ß-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.

Clearance

Not Available

Adverse Effects
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Toxicity

Oral LD50 in rat: >5 g/kg

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAzelaic acid may decrease the excretion rate of Abacavir which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Azelaic acid which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Azelaic acid which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Azelaic acid which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Azelaic acid which could result in a lower serum level and potentially a reduction in efficacy.
Food Interactions
  • Avoid alcohol. Alcohol may cause flushing; therefore, it may worsen rosacea.
  • Take with or without food. Food and drink, which have a high temperature or are spicy, may exacerbate flushing and rosacea, avoid if possible.

Products

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International/Other Brands
Acne-Derm (Unia) / Acnean (Newai Chem) / Acnederm (Ego) / Acnesafe (Z-Jans Pharma) / Aknoren (Herbacos Recordati) / Ami (Everest) / Arbonid (Intermed) / Finevin (Berlex) / Skinoren (Bayer) / Zumilin (Farmedia)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AzelexCream0.2 g/1gCutaneousAlmirall, LLC2018-09-24Not applicableUS flag
AzelexCream0.2 g/1gCutaneousAllergan, Inc.1996-03-21Not applicableUS flag
AzelexCream0.2 g/1gCutaneousPhysicians Total Care, Inc.2007-05-31Not applicableUS flag
FinaceaGel15 % w/wTopicalLeo Pharma2010-06-15Not applicableCanada flag
FinaceaKit0.15 g/1gTopicalIntendis Inc.2011-04-12Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Azelaic AcidGel0.15 g/1gTopicalActavis Pharma, Inc.2018-11-19Not applicableUS flag
Azelaic AcidGel0.15 g/1gTopicalAlvogen, Inc.2015-07-082018-04-27US flag
Azelaic AcidGel0.15 g/1gTopicalAmneal Pharmaceuticals of New York Llc2018-11-19Not applicableUS flag
Azelaic AcidGel0.15 g/1gTopicalTaro Pharmaceuticals U.S.A., Inc.2019-08-23Not applicableUS flag
Azelaic AcidGel0.15 g/1gTopicalGlenmark Pharmaceuticals Inc., USA2018-11-19Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ELCURE AC-LEX SerumLiquid2.5 g/50mLTopicalElcure Co., Ltd.2011-11-242017-04-20US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
2% Salicylic Acid FACIAL CLEANSERAzelaic acid (10 mg/236mL) + Glycerin (50 mg/236mL) + Kaolin (20 mg/236mL) + Zinc pidolate (10 mg/236mL) + Salicylic acid (20 mg/236mL)LiquidTopicalVolans Epic LLC2023-04-06Not applicableUS flag
AnubisMedAzelaic acid (7 g/50mL) + Ethanol (22.68 mL/50mL) + Isopropyl alcohol (2.7 g/50mL) + Polyethylene glycol 400 (4.9965 g/50mL) + Propylene glycol (10 g/50mL) + Salicylic acid (1 g/50mL) + Water (1.62 mL/50mL)LiquidTopicalANUBIS COSMETICS SL2022-10-262027-09-08US flag
FIXAMICIN DEXACIPRO GOTAS OTICASAzelaic acid (3 mg) + Dexamethasone (1 mg)SuspensionAuricular (otic)TECNOFAR TQ S.A.S2009-05-18Not applicableColombia flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Azelaic Acid 15% / Niacinamide 4%Azelaic acid (15 g/100g) + Nicotinamide (4 g/100g)CreamTopicalSincerus Florida, LLC2019-05-01Not applicableUS flag
ELCURE AC-LEX SerumAzelaic acid (2.5 g/50mL)LiquidTopicalElcure Co., Ltd.2011-11-242017-04-20US flag
Tri-ZelAzelaic acid (5 mg/1) + Cupric oxide (1.5 mg/1) + Folic acid (500 ug/1) + Nicotinamide (600 mg/1) + Pyridoxine (5 mg/1) + Zinc oxide (10 mg/1)TabletOralRochester Pharmaceuticals2012-09-102014-03-06US flag
Vp-zelAzelaic acid (5 mg/1) + Cupric oxide (1.5 mg/1) + Folic acid (500 ug/1) + Nicotinamide (600 mg/1) + Pyridoxine (5 mg/1) + Zinc (10 mg/1)Tablet, coatedOralVirtus Pharmaceuticals2012-03-012016-09-30US flag

Categories

ATC Codes
D10AX03 — Azelaic acid
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Medium-chain fatty acids
Alternative Parents
Dicarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
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
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
alpha,omega-dicarboxylic acid (CHEBI:48131) / Dicarboxylic acids (C08261) / Dicarboxylic acids (LMFA01170054)
Affected organisms
  • Various aerobic and anaerobic microorganisms

Chemical Identifiers

UNII
F2VW3D43YT
CAS number
123-99-9
InChI Key
BDJRBEYXGGNYIS-UHFFFAOYSA-N
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)
IUPAC Name
nonanedioic acid
SMILES
OC(=O)CCCCCCCC(O)=O

References

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.

US5380928
General References
Not Available
Human Metabolome Database
HMDB0000784
KEGG Drug
D03034
KEGG Compound
C08261
PubChem Compound
2266
PubChem Substance
46506284
ChemSpider
2179
RxNav
18602
ChEBI
48131
ChEMBL
CHEMBL1238
ZINC
ZINC000001531036
Therapeutic Targets Database
DAP000889
PharmGKB
PA164754850
PDBe Ligand
AZ1
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Azelaic_acid
PDB Entries
1tuf / 5izf / 7oow
FDA label
Download (389 KB)
MSDS
Download (72.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceRosacea1
4CompletedTreatmentAcne Vulgaris2
4CompletedTreatmentAcne Vulgaris / Postinflammatory Hyperpigmentation1
4CompletedTreatmentDermal manifestations2
4CompletedTreatmentPapulopustular Rosacea (PPR)3

Pharmacoeconomics

Manufacturers
  • Allergan inc
  • Intendis inc
Packagers
  • Allergan Inc.
  • Bayer Healthcare
  • Intendis Inc.
  • Physicians Total Care Inc.
  • Professional Co.
Dosage Forms
FormRouteStrength
CreamTopical
LiquidTopical
Cream20 %
LotionCutaneous
CreamTopical
GelTopical
CreamCutaneous0.2 g/1g
Tablet, film coatedOral500 mg
Tablet, coatedOral500 mg
TabletOral250 mg
TabletOral500 mg
Tablet, film coatedOral250 mg
CreamTopical20 g
LiquidTopical2.5 g/50mL
GelCutaneous15.000 g
GelTopical0.15 g/1g
GelTopical15 % w/w
GelTopical15 %
KitTopical0.15 g/1g
GelTopical150 mg/g
Aerosol, foamTopical.15 g/1g
GelTopical15 g
SuspensionAuricular (otic)
SolutionAuricular (otic)
Tablet, coatedOral250 mg
CreamTopical20 %
CreamCutaneous
CreamTopical20 g/100g
TabletOral
Tablet, coatedOral
Cream
CreamTopical20 %w/w
Prices
Unit descriptionCostUnit
Azelex 20% Cream 50 gm Tube262.74USD tube
Azelex 20% Cream 30 gm Tube181.32USD tube
Finacea 15% Gel 50 gm Tube162.28USD tube
Finacea plus kit143.15USD kit
Azelex 20% cream5.21USD g
Finacea 15% gel2.86USD g
Azelaic acid flakes1.05USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2311128No2008-01-292018-11-18Canada flag
US6730288No2004-05-042019-09-08US flag
US6534070No2003-03-182018-11-18US flag
US9211259No2015-12-152029-01-26US flag
US8435498No2013-05-072024-03-01US flag
US9265725No2016-02-232027-12-08US flag
US8900554No2014-12-022023-10-24US flag
US8722021No2014-05-132023-10-24US flag
US7700076No2010-04-202027-09-18US flag
US10117812No2018-11-062027-10-18US flag
US10322085No2019-06-182023-10-24US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)106.5 °CPhysProp
boiling point (°C)286.5 °C at 1.00E+02 mm HgPhysProp
water solubility2400 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.57HANSCH,C ET AL. (1995)
logS-1.89ADME Research, USCD
pKa4.55 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility2.28 mg/mLALOGPS
logP1.37ALOGPS
logP1.82Chemaxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.15Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area74.6 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity46.54 m3·mol-1Chemaxon
Polarizability20.5 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5731
Blood Brain Barrier+0.7397
Caco-2 permeable-0.6412
P-glycoprotein substrateNon-substrate0.6969
P-glycoprotein inhibitor INon-inhibitor0.9845
P-glycoprotein inhibitor IINon-inhibitor0.9229
Renal organic cation transporterNon-inhibitor0.9359
CYP450 2C9 substrateNon-substrate0.8447
CYP450 2D6 substrateNon-substrate0.905
CYP450 3A4 substrateNon-substrate0.7534
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.939
CYP450 2D6 inhibitorNon-inhibitor0.9729
CYP450 2C19 inhibitorNon-inhibitor0.9762
CYP450 3A4 inhibitorNon-inhibitor0.96
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9927
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.8382
BiodegradationReady biodegradable0.8506
Rat acute toxicity1.3577 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9348
hERG inhibition (predictor II)Non-inhibitor0.9602
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (10.6 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0v0r-4920000000-5a3ed693b1c4083f1f15
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000f-9600000000-24638c458fa83f47c259
GC-MS Spectrum - GC-MSGC-MSsplash10-0v0r-4920000000-5a3ed693b1c4083f1f15
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00mk-1910000000-83ba58dac4b0698643d0
Mass Spectrum (Electron Ionization)MSsplash10-06rx-9100000000-6db2acb47ad4c6163063
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-000i-0900000000-a118e433f0bd27a95b89
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-006t-9600000000-93b3a375b722791cb5c9
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-052k-9500000000-6b069f2fed947651b284
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-000i-0900000000-7980b5eadcca6ee1eadd
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-004i-0900000000-462585874f7661d40d5b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-004j-4900000000-0f65eeeed8c8a6ff3cc9
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0002-9300000000-d654ca3c764066f98358
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0002-9000000000-60a08bb384f2b4cbfca8
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-0900000000-7980b5eadcca6ee1eadd
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-462585874f7661d40d5b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004j-4900000000-0f65eeeed8c8a6ff3cc9
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-9300000000-fcefbd80852c2625bc0e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-9000000000-60a08bb384f2b4cbfca8
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-004i-0900000000-26216115e75cad833509
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-004i-0900000000-7bef8272c481ea57a60b
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-004i-0900000000-751bf479539d4bd2b5e1
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00di-0900000000-9a056a45b27896966bf9
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00di-0900000000-3155fd845eec8f32ce93
MS/MS Spectrum - , negativeLC-MS/MSsplash10-004r-0900000000-544110f97ebc0f97e15b
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00dj-1900000000-3ecb6548dc8d9f033502
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00dj-1900000000-54ce98f98b693cf612f8
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00dj-0900000000-a60da08a98e28b13862b
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0900000000-d0d2d4d3afb06cc7f975
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0900000000-cabc8bfaec299b9fc983
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0900000000-33b811157e88db52f81f
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0900000000-7438aeab6e2a8446cd58
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-003r-9500000000-93ca14ea208dc4bbd259
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-a50b78d01655149ad2c4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-9100000000-a50484281f393d34b377
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-4900000000-f6e4a4417cd845ab8c90
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-066u-9000000000-ef25b669012b8e67365e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4m-9100000000-992726fa4680ecbb3f34
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-149.0660438
predicted
DarkChem Lite v0.1.0
[M-H]-134.744286
predicted
DarkChem Lite v0.1.0
[M-H]-148.9474438
predicted
DarkChem Lite v0.1.0
[M-H]-138.19588
predicted
DeepCCS 1.0 (2019)
[M+H]+141.96379
predicted
DeepCCS 1.0 (2019)
[M+Na]+150.78783
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Staphylococcus aureus (strain Mu50 / ATCC 700699)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Thioredoxin-disulfide reductase activity
Specific Function
Not Available
Gene Name
trxB
Uniprot ID
P66010
Uniprot Name
Thioredoxin reductase
Molecular Weight
33615.84 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Schallreuter KU, Wood JM: Azelaic acid as a competitive inhibitor of thioredoxin reductase in human melanoma cells. Cancer Lett. 1987 Sep;36(3):297-305. [Article]
  4. Hojo Y, Saito Y, Tanimoto T, Hoefen RJ, Baines CP, Yamamoto K, Haendeler J, Asmis R, Berk BC: Fluid shear stress attenuates hydrogen peroxide-induced c-Jun NH2-terminal kinase activation via a glutathione reductase-mediated mechanism. Circ Res. 2002 Oct 18;91(8):712-8. [Article]
  5. Schallreuter KU, Wood JW: A possible mechanism of action for azelaic acid in the human epidermis. Arch Dermatol Res. 1990;282(3):168-71. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Steroid binding
Specific Function
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihyd...
Gene Name
AKR1D1
Uniprot ID
P51857
Uniprot Name
3-oxo-5-beta-steroid 4-dehydrogenase
Molecular Weight
37376.615 Da
References
  1. Stamatiadis D, Bulteau-Portois MC, Mowszowicz I: Inhibition of 5 alpha-reductase activity in human skin by zinc and azelaic acid. Br J Dermatol. 1988 Nov;119(5):627-32. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Sterol 5-alpha reductase activity
Specific Function
Converts testosterone (T) into 5-alpha-dihydrotestosterone (DHT) and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation...
Gene Name
SRD5A2
Uniprot ID
P31213
Uniprot Name
3-oxo-5-alpha-steroid 4-dehydrogenase 2
Molecular Weight
28393.015 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Stamatiadis D, Bulteau-Portois MC, Mowszowicz I: Inhibition of 5 alpha-reductase activity in human skin by zinc and azelaic acid. Br J Dermatol. 1988 Nov;119(5):627-32. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Protein homodimerization activity
Specific Function
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA ...
Gene Name
TYR
Uniprot ID
P14679
Uniprot Name
Tyrosinase
Molecular Weight
60392.69 Da
References
  1. Schallreuter KU, Wood JW: A possible mechanism of action for azelaic acid in the human epidermis. Arch Dermatol Res. 1990;282(3):168-71. [Article]
  2. Nazzaro-Porro M: Azelaic acid. J Am Acad Dermatol. 1987 Dec;17(6):1033-41. [Article]
  3. Picardo M, Passi S, Sirianni MC, Fiorilli M, Russo GD, Cortesi E, Barile G, Breathnach AS, Nazzaro-Porro M: Activity of azelaic acid on cultures of lymphoma- and leukemia-derived cell lines, normal resting and stimulated lymphocytes and 3T3 fibroblasts. Biochem Pharmacol. 1985 May 15;34(10):1653-8. [Article]
  4. Nazzaro-Porro M, Passi S, Balus L, Breathnach A, Martin B, Morpurgo G: Effect of dicarboxylic acids on lentigo maligna. J Invest Dermatol. 1979 Jun;72(6):296-305. [Article]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Dna-directed dna polymerase activity
Specific Function
In addition to polymerase activity, this DNA polymerase exhibits 3' to 5' and 5' to 3' exonuclease activity. It is able to utilize nicked circular duplex DNA as a template and can unwind the parent...
Gene Name
polA
Uniprot ID
P00582
Uniprot Name
DNA polymerase I
Molecular Weight
103117.145 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Galhaup I: Azelaic acid: mode of action at cellular and subcellular levels. Acta Derm Venereol Suppl (Stockh). 1989;143:75-82. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48