Identification

Name
Azelaic Acid
Accession Number
DB00548  (APRD00812, EXPT00598)
Type
Small Molecule
Groups
Approved
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.

Structure
Thumb
Synonyms
  • 1,7-Dicarboxyheptane
  • 1,7-Heptanedicarboxylic acid
  • 1,9-Nonanedioic acid
  • Acide azélaïque
  • Ácido azelaico
  • Acidum acelaicum
  • Acidum azelaicum
  • Anchoic acid
  • Azelaic acid
  • Azelainsaeure
  • Azelainsäure
  • Lepargylic acid
  • N-Nonanedioic acid
  • Nonandisaeure
  • Nonandisäure
  • Nonanedioic acid
  • Skinoren
External IDs
UNII-F2VW3D43YT / ZK 62498 / ZK-62498
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Azelaic AcidGel.15 g/gTopicalAlvogen, Inc.2015-07-08Not applicableUs
AzelexCream.2 g/gCutaneousAllergan1996-03-21Not applicableUs
AzelexCream.2 g/gCutaneousPhysicians Total Care, Inc.2007-05-31Not applicableUs
FinaceaKitIntendis Inc.2011-04-12Not applicableUs
FinaceaGel15 %TopicalBayer2010-06-15Not applicableCanada
FinaceaGel.15 g/gTopicalBayer2002-12-24Not applicableUs
FinaceaGel.15 g/gTopicalIntendis Inc.2004-12-24Not applicableUs
FinaceaGel.15 g/gTopicalPhysicians Total Care, Inc.2005-03-03Not applicableUs
Finacea FoamAerosol, foam.15 g/gTopicalBayer2015-08-03Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ELCURE AC-LEX SerumLiquid2.5 mL/50mLTopicalElcure Co., Ltd.2011-11-242017-05-24Us
International/Other Brands
Acne-Derm (Unia) / Acnean (Newai Chem) / Acnederm (Ego) / Acnesafe (Z-Jans Pharma) / Aknoren (Herbacos Recordati) / Ami (Everest) / Arbonid (Intermed) / Azelex / Finacea / Finevin (Berlex) / Skinoren (Bayer) / Zumilin (Farmedia)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
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 Pharmaceuticals2012-03-012017-11-10Us
Categories
UNII
F2VW3D43YT
CAS number
123-99-9
Weight
Average: 188.2209
Monoisotopic: 188.104859
Chemical Formula
C9H16O4
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

Pharmacology

Indication

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

Structured Indications
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
Human
A3-oxo-5-alpha-steroid 4-dehydrogenase 2
inhibitor
Human
ATyrosinase
inhibitor
Human
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
Toxicity

Oral LD50 in rat: >5 g/kg

Affected organisms
  • Various aerobic and anaerobic microorganisms
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Azelaic Acid.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Azelaic Acid.Experimental
BevacizumabBevacizumab may increase the cardiotoxic activities of Azelaic Acid.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Azelaic Acid.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Azelaic Acid.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Azelaic Acid.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of Azelaic Acid.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Azelaic Acid.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Azelaic Acid.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Azelaic Acid.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Azelaic Acid.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Azelaic Acid.Experimental
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Azelaic Acid.Experimental
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Azelaic Acid.Experimental
OleandrinOleandrin may decrease the cardiotoxic activities of Azelaic Acid.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Azelaic Acid.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Azelaic Acid.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Azelaic Acid.Experimental
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Azelaic Acid.Experimental
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Azelaic Acid.Approved, Investigational
Food Interactions
Not Available

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
External Links
Human Metabolome Database
HMDB00784
KEGG Drug
D03034
KEGG Compound
C08261
PubChem Compound
2266
PubChem Substance
46506284
ChemSpider
2179
ChEBI
48131
ChEMBL
CHEMBL1238
Therapeutic Targets Database
DAP000889
PharmGKB
PA164754850
HET
AZ1
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
ATC Codes
D10AX03 — Azelaic acid
AHFS Codes
  • 84:92.00 — Misc. Skin and Mucous Membrane Agents
PDB Entries
1tuf / 5izf / 5izj / 5j5x
FDA label
Download (389 KB)
MSDS
Download (72.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentPapulopustular Rosacea1
1CompletedTreatmentRosaceas1
2CompletedTreatmentPapulopustular Rosacea1
2CompletedTreatmentPerioral Dermatitis1
2CompletedTreatmentSeborrheic Dermatitis on the Face1
2, 3CompletedTreatmentRosaceas1
3CompletedTreatmentAcne Vulgaris1
3CompletedTreatmentErythemas / Rosaceas1
3CompletedTreatmentPapulopustular Rosacea1
3CompletedTreatmentPapulopustular Rosacea (PPR)1
3CompletedTreatmentRosaceas2
3RecruitingTreatmentHypertensive / Sleep Apnea Syndrome1
4CompletedTreatmentAcne Rosacea1
4CompletedTreatmentAcne Vulgaris2
4CompletedTreatmentAcne Vulgaris / Post Inflammatory Hyperpigmentation1
4CompletedTreatmentPapulopustular Rosacea2
4CompletedTreatmentSkin Manifestations2
4Unknown StatusTreatmentMelanosis1
Not AvailableActive Not RecruitingNot AvailableRosaceas1
Not AvailableCompletedNot AvailableRosaceas1
Not AvailableCompletedTreatmentRosaceas1
Not AvailableUnknown StatusDiagnosticAcne / Quality of Life1

Pharmacoeconomics

Manufacturers
  • Allergan inc
  • Intendis inc
Packagers
Dosage forms
FormRouteStrength
GelTopical.15 g/g
CreamCutaneous.2 g/g
LiquidTopical2.5 mL/50mL
GelTopical15 %
Kit
Aerosol, foamTopical.15 g/g
Tablet, coatedOral
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)
CA2311128No2008-01-292018-11-18Canada
US6730288No1999-09-082019-09-08Us
US6534070No1998-11-182018-11-18Us
US9211259No2009-01-262029-01-26Us
US8435498No2004-03-012024-03-01Us
US9265725No2007-12-082027-12-08Us
US8900554No2003-10-242023-10-24Us
US8722021No2003-10-242023-10-24Us
US7700076No2007-09-182027-09-18Us

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-MSNot Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dr-0900000000-b1b7c1ab57d58a2405a8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00g3-2900000000-d0ba7fbbe987efa4c818
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05qd-9100000000-8d65a19b998d18ad08ac
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-a7edc3ac66d27685b9d1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kr-1900000000-c56b9d972f88c58dc65b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9300000000-47cbefe19a788d7f36b9
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
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
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
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
alpha,omega-dicarboxylic acid (CHEBI:48131) / Dicarboxylic acids (C08261) / Dicarboxylic acids (LMFA01170054)

Targets

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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:3652030]
  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. [PubMed:12386148]
  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. [PubMed:2114832]
Kind
Protein
Organism
Human
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. [PubMed:3207614]
Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:3207614]
Kind
Protein
Organism
Human
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. [PubMed:2114832]
  2. Nazzaro-Porro M: Azelaic acid. J Am Acad Dermatol. 1987 Dec;17(6):1033-41. [PubMed:2963038]
  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. [PubMed:4004885]
  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. [PubMed:448162]
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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. Galhaup I: Azelaic acid: mode of action at cellular and subcellular levels. Acta Derm Venereol Suppl (Stockh). 1989;143:75-82. [PubMed:2475996]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:34