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Identification
NameMasoprocol
Accession NumberDB00179  (APRD01084)
TypeSmall Molecule
GroupsApproved
DescriptionA potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils. [PubChem]
Structure
Thumb
Synonyms
CHX 100
CHX-100
erythro-nordihydroguaiaretic acid
Masoprocolum
meso-1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane
meso-2,3-bis(3,4-dihydroxyphenylmethyl)butane
meso-4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
meso-4,4'-(2,3-dimethyl-1,4-butanediyl)bis(pyrocatechol)
meso-4,4'-(2,3-dimethyltetramethylene)dipyrocatechol
meso-NDGA
meso-nordihydroguaiaretic acid
meso-β,γ-dimethyl-α,δ-bis(3,4-dihydroxyphenyl)butan
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ActinexNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII7BO8G1BYQU
CAS number27686-84-6
WeightAverage: 302.3649
Monoisotopic: 302.151809192
Chemical FormulaC18H22O4
InChI KeyInChIKey=HCZKYJDFEPMADG-TXEJJXNPSA-N
InChI
InChI=1S/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3/t11-,12+
IUPAC Name
4-[(2S,3R)-3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl]benzene-1,2-diol
SMILES
C[C@@H](CC1=CC(O)=C(O)C=C1)[[email protected]](C)CC1=CC(O)=C(O)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassDibenzylbutane lignans
Sub ClassNot Available
Direct ParentDibenzylbutane lignans
Alternative Parents
Substituents
  • Dibenzylbutane lignan skeleton
  • Phenylpropane
  • 1,2-diphenol
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationUsed for the treatment of actinic keratoses (precancerous skin growths that can become malignant if left untreated).
PharmacodynamicsMasoprocol is a novel antineoplastic agent. It is not known exactly how masoprocol works. Laboratory experiments have shown that masoprocol prevents cells similar to the ones found in actinic keratoses from multiplying. Masoprocol was withdrawn from the U.S. market in June 1996.
Mechanism of actionAlthough the exact mechanism of action is not known, studies have shown that masoprocol is a potent 5-lipoxygenase inhibitor and has antiproliferative activity against keratinocytes in tissue culture, but the relationship between this activity and its effectiveness in actinic keratoses is unknown. Masoprocol also inhibits prostaglandins but the significance of this action is not yet known.
Related Articles
AbsorptionLess than 1%-2% is absorbed through the skin over a 4-day period following application.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of overdose or allergic reaction include bluish coloration of skin, dizziness, severe, or feeling faint, wheezing or trouble in breathing.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.935
Blood Brain Barrier-0.5361
Caco-2 permeable+0.6215
P-glycoprotein substrateSubstrate0.6654
P-glycoprotein inhibitor INon-inhibitor0.9519
P-glycoprotein inhibitor IINon-inhibitor0.9144
Renal organic cation transporterNon-inhibitor0.886
CYP450 2C9 substrateNon-substrate0.7194
CYP450 2D6 substrateNon-substrate0.8261
CYP450 3A4 substrateNon-substrate0.5171
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8891
CYP450 2D6 inhibitorInhibitor0.8262
CYP450 2C19 inhibitorInhibitor0.8628
CYP450 3A4 inhibitorNon-inhibitor0.5833
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5322
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.8614
BiodegradationNot ready biodegradable0.9632
Rat acute toxicity2.1491 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9462
hERG inhibition (predictor II)Non-inhibitor0.6288
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Univ arizona cancer center
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point185.5 °CPhysProp
logP5.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0136 mg/mLALOGPS
logP3.44ALOGPS
logP4.76ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity86.62 m3·mol-1ChemAxon
Polarizability33.63 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-00di-0901000000-c0d0caa2c363f17f6c94View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesL01XX10
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (69 KB)
Interactions
Drug Interactions
Drug
AbciximabMasoprocol may increase the anticoagulant activities of Abciximab.
AcebutololMasoprocol may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Masoprocol is combined with Aceclofenac.
AcenocoumarolMasoprocol may increase the anticoagulant activities of Acenocoumarol.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Masoprocol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Masoprocol is combined with Acetylsalicylic acid.
AdapaleneThe risk or severity of adverse effects can be increased when Masoprocol is combined with Adapalene.
Alendronic acidThe risk or severity of adverse effects can be increased when Masoprocol is combined with Alendronic acid.
AliskirenMasoprocol may decrease the antihypertensive activities of Aliskiren.
AlprenololMasoprocol may decrease the antihypertensive activities of Alprenolol.
AlprostadilThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Masoprocol.
AmikacinMasoprocol may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
AmilorideMasoprocol may decrease the antihypertensive activities of Amiloride.
AncrodMasoprocol may increase the anticoagulant activities of Ancrod.
AntipyrineThe risk or severity of adverse effects can be increased when Masoprocol is combined with Antipyrine.
Antithrombin III humanMasoprocol may increase the anticoagulant activities of Antithrombin III human.
ApixabanMasoprocol may increase the anticoagulant activities of Apixaban.
ApremilastThe risk or severity of adverse effects can be increased when Masoprocol is combined with Apremilast.
ArdeparinMasoprocol may increase the anticoagulant activities of Ardeparin.
ArgatrobanMasoprocol may increase the anticoagulant activities of Argatroban.
ArotinololMasoprocol may decrease the antihypertensive activities of Arotinolol.
AtenololMasoprocol may decrease the antihypertensive activities of Atenolol.
AzapropazoneThe risk or severity of adverse effects can be increased when Masoprocol is combined with Azapropazone.
AzelastineThe risk or severity of adverse effects can be increased when Masoprocol is combined with Azelastine.
Azilsartan medoxomilThe risk or severity of adverse effects can be increased when Azilsartan medoxomil is combined with Masoprocol.
BalsalazideMasoprocol may increase the nephrotoxic activities of Balsalazide.
BalsalazideThe risk or severity of adverse effects can be increased when Balsalazide is combined with Masoprocol.
BecaplerminMasoprocol may increase the anticoagulant activities of Becaplermin.
BefunololMasoprocol may decrease the antihypertensive activities of Befunolol.
BenazeprilThe risk or severity of adverse effects can be increased when Benazepril is combined with Masoprocol.
BendroflumethiazideThe therapeutic efficacy of Bendroflumethiazide can be decreased when used in combination with Masoprocol.
BenoxaprofenThe risk or severity of adverse effects can be increased when Masoprocol is combined with Benoxaprofen.
BetaxololMasoprocol may decrease the antihypertensive activities of Betaxolol.
BevacizumabBevacizumab may increase the cardiotoxic activities of Masoprocol.
BevantololMasoprocol may decrease the antihypertensive activities of Bevantolol.
BimatoprostThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Masoprocol.
BisoprololMasoprocol may decrease the antihypertensive activities of Bisoprolol.
BivalirudinMasoprocol may increase the anticoagulant activities of Bivalirudin.
BopindololMasoprocol may decrease the antihypertensive activities of Bopindolol.
BromfenacThe risk or severity of adverse effects can be increased when Masoprocol is combined with Bromfenac.
BufuralolMasoprocol may decrease the antihypertensive activities of Bufuralol.
BumetanideMasoprocol may decrease the diuretic activities of Bumetanide.
BupranololMasoprocol may decrease the antihypertensive activities of Bupranolol.
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Masoprocol.
CandesartanThe risk or severity of adverse effects can be increased when Candesartan is combined with Masoprocol.
CandoxatrilThe risk or severity of adverse effects can be increased when Candoxatril is combined with Masoprocol.
CaptoprilThe risk or severity of adverse effects can be increased when Captopril is combined with Masoprocol.
Carboprost TromethamineThe therapeutic efficacy of Carboprost Tromethamine can be decreased when used in combination with Masoprocol.
CarprofenThe risk or severity of adverse effects can be increased when Masoprocol is combined with Carprofen.
CarteololMasoprocol may decrease the antihypertensive activities of Carteolol.
CarvedilolMasoprocol may decrease the antihypertensive activities of Carvedilol.
CastanospermineThe risk or severity of adverse effects can be increased when Masoprocol is combined with Castanospermine.
CelecoxibThe risk or severity of adverse effects can be increased when Masoprocol is combined with Celecoxib.
CeliprololMasoprocol may decrease the antihypertensive activities of Celiprolol.
CertoparinMasoprocol may increase the anticoagulant activities of Certoparin.
ChloroquineThe risk or severity of adverse effects can be increased when Masoprocol is combined with Chloroquine.
ChlorothiazideThe therapeutic efficacy of Chlorothiazide can be decreased when used in combination with Masoprocol.
ChlorthalidoneThe therapeutic efficacy of Chlorthalidone can be decreased when used in combination with Masoprocol.
CholestyramineCholestyramine can cause a decrease in the absorption of Masoprocol resulting in a reduced serum concentration and potentially a decrease in efficacy.
CilazaprilThe risk or severity of adverse effects can be increased when Cilazapril is combined with Masoprocol.
Citric AcidMasoprocol may increase the anticoagulant activities of Citric Acid.
ClodronateThe risk or severity of adverse effects can be increased when Masoprocol is combined with Clodronate.
ClonixinThe risk or severity of adverse effects can be increased when Masoprocol is combined with Clonixin.
CloprostenolThe therapeutic efficacy of Cloprostenol can be decreased when used in combination with Masoprocol.
ColesevelamColesevelam can cause a decrease in the absorption of Masoprocol resulting in a reduced serum concentration and potentially a decrease in efficacy.
ColestipolColestipol can cause a decrease in the absorption of Masoprocol resulting in a reduced serum concentration and potentially a decrease in efficacy.
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Masoprocol.
CyclosporineMasoprocol may increase the nephrotoxic activities of Cyclosporine.
D-LimoneneThe risk or severity of adverse effects can be increased when Masoprocol is combined with D-Limonene.
Dabigatran etexilateMasoprocol may increase the anticoagulant activities of Dabigatran etexilate.
DalteparinMasoprocol may increase the anticoagulant activities of Dalteparin.
DanaparoidMasoprocol may increase the anticoagulant activities of Danaparoid.
DaunorubicinMasoprocol may decrease the excretion rate of Daunorubicin which could result in a lower serum level and potentially a reduction in efficacy.
DeferasiroxThe risk or severity of adverse effects can be increased when Masoprocol is combined with Deferasirox.
DesirudinMasoprocol may increase the anticoagulant activities of Desirudin.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Masoprocol.
DesmopressinThe risk or severity of adverse effects can be increased when Masoprocol is combined with Desmopressin.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Masoprocol.
DextranMasoprocol may increase the anticoagulant activities of Dextran.
Dextran 40Masoprocol may increase the anticoagulant activities of Dextran 40.
Dextran 70Masoprocol may increase the anticoagulant activities of Dextran 70.
Dextran 75Masoprocol may increase the anticoagulant activities of Dextran 75.
DiclofenacThe risk or severity of adverse effects can be increased when Masoprocol is combined with Diclofenac.
DicoumarolMasoprocol may increase the anticoagulant activities of Dicoumarol.
DiflunisalThe risk or severity of adverse effects can be increased when Masoprocol is combined with Diflunisal.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Masoprocol.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Masoprocol.
DigoxinDigoxin may decrease the cardiotoxic activities of Masoprocol.
DihydrostreptomycinMasoprocol may decrease the excretion rate of Dihydrostreptomycin which could result in a lower serum level and potentially a reduction in efficacy.
DinoprostoneThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Masoprocol.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Masoprocol.
DoxorubicinMasoprocol may decrease the excretion rate of Doxorubicin which could result in a lower serum level and potentially a reduction in efficacy.
DrospirenoneMasoprocol may increase the hyperkalemic activities of Drospirenone.
DroxicamThe risk or severity of adverse effects can be increased when Masoprocol is combined with Droxicam.
Edetic AcidMasoprocol may increase the anticoagulant activities of Edetic Acid.
EdoxabanMasoprocol may increase the anticoagulant activities of Edoxaban.
EnalaprilThe risk or severity of adverse effects can be increased when Enalapril is combined with Masoprocol.
EnalaprilatThe risk or severity of adverse effects can be increased when Enalaprilat is combined with Masoprocol.
EnoxaparinMasoprocol may increase the anticoagulant activities of Enoxaparin.
EpirizoleThe risk or severity of adverse effects can be increased when Masoprocol is combined with Epirizole.
EpirubicinMasoprocol may decrease the excretion rate of Epirubicin which could result in a lower serum level and potentially a reduction in efficacy.
EplerenoneMasoprocol may decrease the antihypertensive activities of Eplerenone.
EpoprostenolThe therapeutic efficacy of Epoprostenol can be decreased when used in combination with Masoprocol.
EprosartanThe risk or severity of adverse effects can be increased when Eprosartan is combined with Masoprocol.
EsmololMasoprocol may decrease the antihypertensive activities of Esmolol.
Etacrynic acidMasoprocol may decrease the diuretic activities of Etacrynic acid.
EtanerceptThe risk or severity of adverse effects can be increased when Etanercept is combined with Masoprocol.
Ethyl biscoumacetateMasoprocol may increase the anticoagulant activities of Ethyl biscoumacetate.
Etidronic acidThe risk or severity of adverse effects can be increased when Masoprocol is combined with Etidronic acid.
EtodolacThe risk or severity of adverse effects can be increased when Masoprocol is combined with Etodolac.
EtofenamateThe risk or severity of adverse effects can be increased when Masoprocol is combined with Etofenamate.
EtoricoxibThe risk or severity of adverse effects can be increased when Masoprocol is combined with Etoricoxib.
Evening primrose oilThe risk or severity of adverse effects can be increased when Masoprocol is combined with Evening primrose oil.
exisulindThe risk or severity of adverse effects can be increased when Masoprocol is combined with exisulind.
FenbufenThe risk or severity of adverse effects can be increased when Masoprocol is combined with Fenbufen.
FenoprofenThe risk or severity of adverse effects can be increased when Masoprocol is combined with Fenoprofen.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Masoprocol.
FlunixinThe risk or severity of adverse effects can be increased when Masoprocol is combined with Flunixin.
FlurbiprofenThe risk or severity of adverse effects can be increased when Masoprocol is combined with Flurbiprofen.
Folic AcidThe therapeutic efficacy of Folic Acid can be decreased when used in combination with Masoprocol.
Fondaparinux sodiumMasoprocol may increase the anticoagulant activities of Fondaparinux sodium.
ForasartanThe risk or severity of adverse effects can be increased when Forasartan is combined with Masoprocol.
FosinoprilThe risk or severity of adverse effects can be increased when Fosinopril is combined with Masoprocol.
FramycetinMasoprocol may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
FurosemideMasoprocol may decrease the diuretic activities of Furosemide.
GemeprostThe therapeutic efficacy of Gemeprost can be decreased when used in combination with Masoprocol.
GentamicinMasoprocol may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
HaloperidolThe risk or severity of adverse effects can be increased when Masoprocol is combined with Haloperidol.
HeparinMasoprocol may increase the anticoagulant activities of Heparin.
HirulogMasoprocol may increase the anticoagulant activities of Hirulog.
HMPL-004The risk or severity of adverse effects can be increased when Masoprocol is combined with HMPL-004.
HydralazineMasoprocol may decrease the antihypertensive activities of Hydralazine.
HydrochlorothiazideThe therapeutic efficacy of Hydrochlorothiazide can be decreased when used in combination with Masoprocol.
HydroflumethiazideThe therapeutic efficacy of Hydroflumethiazide can be decreased when used in combination with Masoprocol.
Hygromycin BMasoprocol may decrease the excretion rate of Hygromycin B which could result in a lower serum level and potentially a reduction in efficacy.
IbandronateThe risk or severity of adverse effects can be increased when Masoprocol is combined with Ibandronate.
IbuprofenThe risk or severity of adverse effects can be increased when Masoprocol is combined with Ibuprofen.
IbuproxamThe risk or severity of adverse effects can be increased when Masoprocol is combined with Ibuproxam.
IcatibantThe risk or severity of adverse effects can be increased when Masoprocol is combined with Icatibant.
IdarubicinMasoprocol may decrease the excretion rate of Idarubicin which could result in a lower serum level and potentially a reduction in efficacy.
IloprostThe therapeutic efficacy of Iloprost can be decreased when used in combination with Masoprocol.
IndapamideThe therapeutic efficacy of Indapamide can be decreased when used in combination with Masoprocol.
IndenololMasoprocol may decrease the antihypertensive activities of Indenolol.
IndomethacinThe risk or severity of adverse effects can be increased when Masoprocol is combined with Indomethacin.
IndoprofenThe risk or severity of adverse effects can be increased when Masoprocol is combined with Indoprofen.
IrbesartanThe risk or severity of adverse effects can be increased when Irbesartan is combined with Masoprocol.
IsoxicamThe risk or severity of adverse effects can be increased when Masoprocol is combined with Isoxicam.
KanamycinMasoprocol may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
KebuzoneThe risk or severity of adverse effects can be increased when Masoprocol is combined with Kebuzone.
KetoprofenThe risk or severity of adverse effects can be increased when Masoprocol is combined with Ketoprofen.
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Masoprocol.
LabetalolMasoprocol may decrease the antihypertensive activities of Labetalol.
LeflunomideThe risk or severity of adverse effects can be increased when Masoprocol is combined with Leflunomide.
LepirudinMasoprocol may increase the anticoagulant activities of Lepirudin.
LevobunololMasoprocol may decrease the antihypertensive activities of Levobunolol.
LisinoprilThe risk or severity of adverse effects can be increased when Lisinopril is combined with Masoprocol.
LithiumThe serum concentration of Lithium can be increased when it is combined with Masoprocol.
LornoxicamThe risk or severity of adverse effects can be increased when Masoprocol is combined with Lornoxicam.
LosartanThe risk or severity of adverse effects can be increased when Losartan is combined with Masoprocol.
LoxoprofenThe risk or severity of adverse effects can be increased when Masoprocol is combined with Loxoprofen.
LubiprostoneThe therapeutic efficacy of Lubiprostone can be decreased when used in combination with Masoprocol.
LumiracoxibThe risk or severity of adverse effects can be increased when Masoprocol is combined with Lumiracoxib.
Magnesium salicylateThe risk or severity of adverse effects can be increased when Masoprocol is combined with Magnesium salicylate.
Meclofenamic acidThe risk or severity of adverse effects can be increased when Masoprocol is combined with Meclofenamic acid.
Mefenamic acidThe risk or severity of adverse effects can be increased when Masoprocol is combined with Mefenamic acid.
MeloxicamThe risk or severity of adverse effects can be increased when Masoprocol is combined with Meloxicam.
MesalazineMasoprocol may increase the nephrotoxic activities of Mesalazine.
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Masoprocol.
MetamizoleThe risk or severity of adverse effects can be increased when Masoprocol is combined with Metamizole.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Masoprocol.
MethyclothiazideThe therapeutic efficacy of Methyclothiazide can be decreased when used in combination with Masoprocol.
MetipranololMasoprocol may decrease the antihypertensive activities of Metipranolol.
MetolazoneThe therapeutic efficacy of Metolazone can be decreased when used in combination with Masoprocol.
MetoprololMasoprocol may decrease the antihypertensive activities of Metoprolol.
MetrizamideMasoprocol may decrease the excretion rate of Metrizamide which could result in a lower serum level and potentially a reduction in efficacy.
MisoprostolThe therapeutic efficacy of Misoprostol can be decreased when used in combination with Masoprocol.
MoexiprilThe risk or severity of adverse effects can be increased when Moexipril is combined with Masoprocol.
MorniflumateThe risk or severity of adverse effects can be increased when Morniflumate is combined with Masoprocol.
Mycophenolate mofetilThe risk or severity of adverse effects can be increased when Masoprocol is combined with Mycophenolate mofetil.
Mycophenolic acidThe risk or severity of adverse effects can be increased when Masoprocol is combined with Mycophenolic acid.
NabumetoneThe risk or severity of adverse effects can be increased when Masoprocol is combined with Nabumetone.
NadololMasoprocol may decrease the antihypertensive activities of Nadolol.
NadroparinMasoprocol may increase the anticoagulant activities of Nadroparin.
NaftifineThe risk or severity of adverse effects can be increased when Masoprocol is combined with Naftifine.
NaproxenThe risk or severity of adverse effects can be increased when Masoprocol is combined with Naproxen.
NCX 4016The risk or severity of adverse effects can be increased when Masoprocol is combined with NCX 4016.
NeomycinMasoprocol may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
NepafenacThe risk or severity of adverse effects can be increased when Masoprocol is combined with Nepafenac.
NetilmicinMasoprocol may decrease the excretion rate of Netilmicin which could result in a lower serum level and potentially a reduction in efficacy.
Niflumic AcidThe risk or severity of adverse effects can be increased when Masoprocol is combined with Niflumic Acid.
NimesulideThe risk or severity of adverse effects can be increased when Masoprocol is combined with Nimesulide.
OlmesartanThe risk or severity of adverse effects can be increased when Olmesartan is combined with Masoprocol.
OlopatadineThe risk or severity of adverse effects can be increased when Masoprocol is combined with Olopatadine.
OlsalazineMasoprocol may increase the nephrotoxic activities of Olsalazine.
OlsalazineThe risk or severity of adverse effects can be increased when Olsalazine is combined with Masoprocol.
Omacetaxine mepesuccinateThe risk or severity of adverse effects can be increased when Masoprocol is combined with Omacetaxine mepesuccinate.
OmapatrilatThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Masoprocol.
OrgoteinThe risk or severity of adverse effects can be increased when Masoprocol is combined with Orgotein.
OtamixabanMasoprocol may increase the anticoagulant activities of Otamixaban.
OuabainOuabain may decrease the cardiotoxic activities of Masoprocol.
OxaprozinThe risk or severity of adverse effects can be increased when Masoprocol is combined with Oxaprozin.
OxprenololMasoprocol may decrease the antihypertensive activities of Oxprenolol.
OxyphenbutazoneThe risk or severity of adverse effects can be increased when Masoprocol is combined with Oxyphenbutazone.
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Masoprocol.
PamidronateThe risk or severity of adverse effects can be increased when Masoprocol is combined with Pamidronate.
ParecoxibThe risk or severity of adverse effects can be increased when Masoprocol is combined with Parecoxib.
ParomomycinMasoprocol may decrease the excretion rate of Paromomycin which could result in a lower serum level and potentially a reduction in efficacy.
PenbutololMasoprocol may decrease the antihypertensive activities of Penbutolol.
Pentosan PolysulfateMasoprocol may increase the anticoagulant activities of Pentosan Polysulfate.
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Masoprocol.
PhenindioneMasoprocol may increase the anticoagulant activities of Phenindione.
PhenprocoumonMasoprocol may increase the anticoagulant activities of Phenprocoumon.
PhenylbutazoneThe risk or severity of adverse effects can be increased when Masoprocol is combined with Phenylbutazone.
PimecrolimusThe risk or severity of adverse effects can be increased when Masoprocol is combined with Pimecrolimus.
PindololMasoprocol may decrease the antihypertensive activities of Pindolol.
PiretanideMasoprocol may decrease the diuretic activities of Piretanide.
PirfenidoneThe risk or severity of adverse effects can be increased when Masoprocol is combined with Pirfenidone.
PiroxicamThe risk or severity of adverse effects can be increased when Masoprocol is combined with Piroxicam.
PlicamycinMasoprocol may decrease the excretion rate of Plicamycin which could result in a lower serum level and potentially a reduction in efficacy.
PolythiazideThe therapeutic efficacy of Polythiazide can be decreased when used in combination with Masoprocol.
PractololMasoprocol may decrease the antihypertensive activities of Practolol.
PralatrexateThe serum concentration of Pralatrexate can be increased when it is combined with Masoprocol.
ProbenecidThe serum concentration of Masoprocol can be increased when it is combined with Probenecid.
PropacetamolThe risk or severity of adverse effects can be increased when Masoprocol is combined with Propacetamol.
PropranololMasoprocol may decrease the antihypertensive activities of Propranolol.
Prostaglandin D2The therapeutic efficacy of Prostaglandin D2 can be decreased when used in combination with Masoprocol.
Protein CMasoprocol may increase the anticoagulant activities of Protein C.
ProtocatechualdehydeMasoprocol may increase the anticoagulant activities of Protocatechualdehyde.
PTC299The risk or severity of adverse effects can be increased when Masoprocol is combined with PTC299.
PuromycinMasoprocol may decrease the excretion rate of Puromycin which could result in a lower serum level and potentially a reduction in efficacy.
QuinaprilThe risk or severity of adverse effects can be increased when Quinapril is combined with Masoprocol.
QuinethazoneThe therapeutic efficacy of Quinethazone can be decreased when used in combination with Masoprocol.
RamiprilThe risk or severity of adverse effects can be increased when Ramipril is combined with Masoprocol.
RescinnamineThe risk or severity of adverse effects can be increased when Rescinnamine is combined with Masoprocol.
ResveratrolThe risk or severity of adverse effects can be increased when Masoprocol is combined with Resveratrol.
ReviparinMasoprocol may increase the anticoagulant activities of Reviparin.
RibostamycinMasoprocol may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
RisedronateThe risk or severity of adverse effects can be increased when Masoprocol is combined with Risedronate.
RivaroxabanMasoprocol may increase the anticoagulant activities of Rivaroxaban.
RofecoxibThe risk or severity of adverse effects can be increased when Masoprocol is combined with Rofecoxib.
SalicylamideThe risk or severity of adverse effects can be increased when Masoprocol is combined with Salicylamide.
Salicylic acidThe risk or severity of adverse effects can be increased when Masoprocol is combined with Salicylic acid.
SalsalateThe risk or severity of adverse effects can be increased when Masoprocol is combined with Salsalate.
SaprisartanThe risk or severity of adverse effects can be increased when Saprisartan is combined with Masoprocol.
SaralasinThe risk or severity of adverse effects can be increased when Saralasin is combined with Masoprocol.
SeratrodastThe risk or severity of adverse effects can be increased when Masoprocol is combined with Seratrodast.
SotalolMasoprocol may decrease the antihypertensive activities of Sotalol.
SpectinomycinMasoprocol may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
SpiraprilThe risk or severity of adverse effects can be increased when Spirapril is combined with Masoprocol.
SpironolactoneMasoprocol may decrease the antihypertensive activities of Spironolactone.
SRT501The risk or severity of adverse effects can be increased when Masoprocol is combined with SRT501.
StreptomycinMasoprocol may decrease the excretion rate of Streptomycin which could result in a lower serum level and potentially a reduction in efficacy.
StreptozocinMasoprocol may decrease the excretion rate of Streptozocin which could result in a lower serum level and potentially a reduction in efficacy.
SulfasalazineMasoprocol may increase the nephrotoxic activities of Sulfasalazine.
SulfasalazineThe risk or severity of adverse effects can be increased when Sulfasalazine is combined with Masoprocol.
SulindacThe risk or severity of adverse effects can be increased when Masoprocol is combined with Sulindac.
SulodexideMasoprocol may increase the anticoagulant activities of Sulodexide.
SuprofenThe risk or severity of adverse effects can be increased when Masoprocol is combined with Suprofen.
TacrolimusMasoprocol may increase the nephrotoxic activities of Tacrolimus.
TalniflumateThe risk or severity of adverse effects can be increased when Talniflumate is combined with Masoprocol.
TasosartanThe risk or severity of adverse effects can be increased when Tasosartan is combined with Masoprocol.
Technetium Tc-99m MedronateThe risk or severity of adverse effects can be increased when Masoprocol is combined with Technetium Tc-99m Medronate.
TelmisartanThe risk or severity of adverse effects can be increased when Telmisartan is combined with Masoprocol.
TemocaprilThe risk or severity of adverse effects can be increased when Temocapril is combined with Masoprocol.
TenofovirThe risk or severity of adverse effects can be increased when Masoprocol is combined with Tenofovir.
TenoxicamThe risk or severity of adverse effects can be increased when Masoprocol is combined with Tenoxicam.
TepoxalinThe risk or severity of adverse effects can be increased when Masoprocol is combined with Tepoxalin.
TeriflunomideThe risk or severity of adverse effects can be increased when Masoprocol is combined with Teriflunomide.
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Masoprocol is combined with Tiaprofenic acid.
TiludronateThe risk or severity of adverse effects can be increased when Masoprocol is combined with Tiludronate.
TimololMasoprocol may decrease the antihypertensive activities of Timolol.
TobramycinMasoprocol may decrease the excretion rate of Tobramycin which could result in a lower serum level and potentially a reduction in efficacy.
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Masoprocol is combined with Tolfenamic Acid.
TolmetinThe risk or severity of adverse effects can be increased when Masoprocol is combined with Tolmetin.
TorasemideMasoprocol may decrease the diuretic activities of Torasemide.
TrandolaprilThe risk or severity of adverse effects can be increased when Trandolapril is combined with Masoprocol.
TranilastThe risk or severity of adverse effects can be increased when Masoprocol is combined with Tranilast.
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Masoprocol.
TravoprostThe therapeutic efficacy of Travoprost can be decreased when used in combination with Masoprocol.
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Masoprocol.
TriamtereneMasoprocol may decrease the antihypertensive activities of Triamterene.
TrichlormethiazideThe therapeutic efficacy of Trichlormethiazide can be decreased when used in combination with Masoprocol.
Trisalicylate-cholineThe risk or severity of adverse effects can be increased when Masoprocol is combined with Trisalicylate-choline.
ValdecoxibThe risk or severity of adverse effects can be increased when Masoprocol is combined with Valdecoxib.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Masoprocol.
VancomycinThe serum concentration of Vancomycin can be increased when it is combined with Masoprocol.
WarfarinMasoprocol may increase the anticoagulant activities of Warfarin.
XimelagatranMasoprocol may increase the anticoagulant activities of Ximelagatran.
ZaltoprofenThe risk or severity of adverse effects can be increased when Masoprocol is combined with Zaltoprofen.
ZileutonThe risk or severity of adverse effects can be increased when Masoprocol is combined with Zileuton.
Zoledronic acidThe risk or severity of adverse effects can be increased when Masoprocol is combined with Zoledronic acid.
ZomepiracThe risk or severity of adverse effects can be increased when Masoprocol is combined with Zomepirac.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Iron ion binding
Specific Function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
ALOX5
Uniprot ID:
P09917
Molecular Weight:
77982.595 Da
References
  1. Audouin C, Mestdagh N, Lassoie MA, Houssin R, Henichart JP: N-Aminoindoline derivatives as inhibitors of 5-lipoxygenase. Bioorg Med Chem Lett. 2001 Mar 26;11(6):845-8. [PubMed:11277534 ]
  2. Lambert JD, Meyers RO, Timmermann BN, Dorr RT: Pharmacokinetic analysis by high-performance liquid chromatography of intravenous nordihydroguaiaretic acid in the mouse. J Chromatogr B Biomed Sci Appl. 2001 Apr 15;754(1):85-90. [PubMed:11318430 ]
  3. Azadzoi KM, Heim VK, Tarcan T, Siroky MB: Alteration of urothelial-mediated tone in the ischemic bladder: role of eicosanoids. Neurourol Urodyn. 2004;23(3):258-64. [PubMed:15098224 ]
  4. West M, Mhatre M, Ceballos A, Floyd RA, Grammas P, Gabbita SP, Hamdheydari L, Mai T, Mou S, Pye QN, Stewart C, West S, Williamson KS, Zemlan F, Hensley K: The arachidonic acid 5-lipoxygenase inhibitor nordihydroguaiaretic acid inhibits tumor necrosis factor alpha activation of microglia and extends survival of G93A-SOD1 transgenic mice. J Neurochem. 2004 Oct;91(1):133-43. [PubMed:15379894 ]
  5. Jeon SB, Ji KA, You HJ, Kim JH, Jou I, Joe EH: Nordihydroguaiaretic acid inhibits IFN-gamma-induced STAT tyrosine phosphorylation in rat brain astrocytes. Biochem Biophys Res Commun. 2005 Mar 11;328(2):595-600. [PubMed:15694390 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible for the epoxidation of endogenous cardiac arachidonic acid pools.
Gene Name:
CYP2J2
Uniprot ID:
P51589
Molecular Weight:
57610.165 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23