DT-Web

DB00179 - Masoprocol


Identification
Name Masoprocol
Accession Number DB00179 (APRD01084)
Type small molecule
Description A 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
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 302.3649
Groups approved
Monoisotopic Weight 302.151809192
Pharmacology
Indication Used for the treatment of actinic keratoses (precancerous skin growths that can become malignant if left untreated).
Mechanism of action Although 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.
Absorption Less than 1%-2% is absorbed through the skin over a 4-day period following application.
Protein binding Not Available
Biotransformation Not Available
Route of elimination Not Available
Toxicity Symptoms 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
Interactions
Drug Interactions Not Available
Food Interactions Not Available

Targets


Arachidonate 5-lipoxygenase
Name Arachidonate 5-lipoxygenase
Gene Name ALOX5
Pharmacological action yes
Actions inhibitor
References
  • 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
  • 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
  • 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
  • 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
  • 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
  • Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. - Pubmed
DTHybrid score 0.3224

Enzymes


Cytochrome P450 2J2
Name Cytochrome P450 2J2
Gene Name CYP2J2
Actions inhibitor
References
  • 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. Epub 2009 Nov 24. - Pubmed
DTHybrid score 0.3156

Predictions


Id Partner name Gene Name Score
20 Prostaglandin G/H synthase 1 PTGS1 0.0831
4512 Cytochrome P450 3A4 CYP3A4 0.0619
290 Prostaglandin G/H synthase 2 PTGS2 0.0517
1588 Multidrug resistance protein 1 ABCB1 0.0509
4118 Cytochrome P450 3A5 CYP3A5 0.048
4924 Cytochrome P450 2C8 CYP2C8 0.0412
239 Coagulation factor X F10 0.0405
4757 Cytochrome P450 2C9 CYP2C9 0.0358
4119 Cytochrome P450 2D6 CYP2D6 0.0317
238 Peroxisome proliferator-activated receptor gamma PPARG 0.0311
61 2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinase folK 0.0304
2644 2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinase folK 0.0304
2710 2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinase folK 0.0304
703 NADPH azoreductase azr 0.0295
1757 Myeloperoxidase MPO 0.0282
101 Potassium voltage-gated channel subfamily H member 2 KCNH2 0.0277
2038 Inhibitor of nuclear factor kappa-B kinase subunit beta IKBKB 0.027
6016 Cytochrome P450 2C19 CYP2C19 0.0262
1284 Nuclear receptor subfamily 1 group I member 2 NR1I2 0.0217
492 Histamine H1 receptor HRH1 0.0216
4162 Potassium voltage-gated channel subfamily KQT member 3 KCNQ3 0.021
3923 Cholinesterase BCHE 0.0201
1086 Potassium voltage-gated channel subfamily KQT member 2 KCNQ2 0.0196
6107 Cytochrome P450 3A7 CYP3A7 0.0192
4200 Cytochrome P450 1A2 CYP1A2 0.0173
6270 Group IIE secretory phospholipase A2 PLA2G2E 0.017
1735 Canalicular multispecific organic anion transporter 1 ABCC2 0.0167
606 Cytochrome P450 27, mitochondrial CYP27A1 0.0162
581 Cytochrome P450 2R1 CYP2R1 0.0158
1992 Vitamin D-binding protein GC 0.0156
1732 ATP-binding cassette sub-family G member 2 ABCG2 0.015
6158 Solute carrier organic anion transporter family member 1C1 SLCO1C1 0.0143
824 Sodium-dependent serotonin transporter SLC6A4 0.0142
540 Sodium-dependent noradrenaline transporter SLC6A2 0.0141
1729 Solute carrier family 22 member 6 SLC22A6 0.0137
78 Acetyl-CoA acetyltransferase, mitochondrial ACAT1 0.0133
778 Cysteinyl leukotriene receptor 1 CYSLTR1 0.0124
1490 Solute carrier organic anion transporter family member 1B1 SLCO1B1 0.0122
6018 UDP-glucuronosyltransferase 1-9 UGT1A9 0.012
856 Vitamin D3 receptor VDR 0.0119
6017 Cholesterol side-chain cleavage enzyme, mitochondrial CYP11A1 0.0103
1654 Interleukin-1 beta IL1B 0.01
51 Muscarinic acetylcholine receptor M3 CHRM3 0.0096
1650 Heme carrier protein 1 SLC46A1 0.0096
6030 Cytochrome P450 2B6 CYP2B6 0.0094
6024 Cytochrome P450 1A1 CYP1A1 0.0093
1632 Solute carrier organic anion transporter family member 2B1 SLCO2B1 0.0087
1507 Cytochrome c CYCS 0.0086
33 Cystine/glutamate transporter SLC7A11 0.0084
494 Caspase-1 CASP1 0.0083
183 Vascular endothelial growth factor A VEGFA 0.008
22 30S ribosomal protein S4 rpsD 0.0076
6714 30S ribosomal protein S4 rpsD 0.0076
1024 Solute carrier family 22 member 11 SLC22A11 0.0076
86 SEC14-like protein 4 SEC14L4 0.0075
4077 Serine/threonine-protein phosphatase 2A catalytic subunit beta isoform PPP2CB 0.0075
375 SEC14-like protein 3 SEC14L3 0.0075
4076 Diacylglycerol kinase alpha DGKA 0.0075
5718 Cytochrome P450 2A6 CYP2A6 0.0073
140 30S ribosomal protein S9 rpsI 0.0072
6719 30S ribosomal protein S9 rpsI 0.0072
6725 30S ribosomal protein S9 rpsI 0.0072
2077 Caspase-3 CASP3 0.0069
65 Matrix metalloproteinase-9 Not Available 0.0068
708 Alpha-tocopherol transfer protein TTPA 0.0065
6142 Solute carrier family 22 member 8 SLC22A8 0.0065
283 SEC14-like protein 2 SEC14L2 0.0064
905 Glutathione transferase omega-1 GSTO1 0.0063
899 Glutathione S-transferase Mu 3 GSTM3 0.0063
4078 Serine/threonine-protein phosphatase 2A catalytic subunit alpha isoform PPP2CA 0.0061
997 Protein kinase C beta type PRKCB 0.0059
186 Glutamate--cysteine ligase catalytic subunit GCLC 0.0057
810 Heme oxygenase 1 HMOX1 0.0056
3391 Heme oxygenase 1 pbsA1 0.0056
1970 Protein kinase C alpha type PRKCA 0.0055
4152 Superoxide dismutase [Cu-Zn] SOD1 0.0051
6143 Solute carrier family 22 member 7 SLC22A7 0.0051
3932 Glutathione S-transferase A2 GSTA2 0.0049
389 Amiloride-sensitive cation channel 2, neuronal ACCN2 0.0043
2157 NAD(P)H dehydrogenase [quinone] 1 NQO1 0.0042
904 Glutathione S-transferase P GSTP1 0.004
3804 Sodium channel protein type 4 subunit alpha SCN4A 0.0038
6106 Cytochrome P450 2C18 CYP2C18 0.0032
2981 Phospholipase A2, membrane associated PLA2G2A 0.0031
6178 UDP-glucuronosyltransferase 2B7 UGT2B7 0.0025
6022 UDP-glucuronosyltransferase 1-1 UGT1A1 0.0024
373 Transthyretin TTR 0.0024
2164 Multidrug resistance-associated protein 4 ABCC4 0.0023
587 Serum albumin ALB 0.0023
862 Multidrug resistance-associated protein 1 ABCC1 0.0022
6013 Cytochrome P450 2E1 CYP2E1 0.0019
4943 Cytochrome c6 petJ 0.0018
4934 Cytochrome c-551 nirM 0.0018
5218 Cytochrome c-551 nirM 0.0018
4905 Cytochrome c2 Not Available 0.0018
4939 Cytochrome c2 cycA 0.0018
4964 Cytochrome c2 cycA 0.0018
4979 Cytochrome c2 cycA 0.0018
6673 Cytochrome c2 cycA 0.0018
4947 Bacterial hemoglobin vhb 0.0018
4916 Cyanoglobin glbN 0.0018
4994 Hemoglobin-like protein HbO glbO 0.0018
4909 CooA protein cooA 0.0018
4975 Cytochrome c-556 RPA3973 0.0018
4942 Diheme cytochrome c napB napB 0.0018
3116 Bacterioferritin bfr 0.0018
4906 Bacterioferritin bfr 0.0018
4965 Bacterioferritin bfr 0.0018
4954 Soluble cytochrome b558 Not Available 0.0018
4907 Cytochrome c-L moxG 0.0018
6865 Cytochrome c-L moxG 0.0018
4981 Iron-starvation protein PigA pigA 0.0018
4989 Cytochrome c551 peroxidase ccp 0.0018
5222 Cytochrome c551 peroxidase ccpA 0.0018
4936 Cytochrome c2 iso-2 Not Available 0.0018
4915 Cytochrome c-550 psbV 0.0018
4959 Cytochrome c-550 psbV 0.0018
5216 Cytochrome c-550 psbV 0.0018
4925 Cytochrome c-type protein SHP shp 0.0018
5000 HemO hemO 0.0018
4998 Hemoglobin-like protein yjbI yjbI 0.0018
4935 Cytochrome c-554 cycA1 0.0018
644 Heme oxygenase 2 HMOX2 0.0018
4982 Heme oxygenase 2 pbsA2 0.0018
4999 Cytochrome P450 165B3 CYP165B3 0.0018
4764 Cytochrome P450 165C4 CYP165C4 0.0018
4984 Neuroglobin NGB 0.0018
4937 Cytochrome oxidase subunit II rcoxA 0.0018
4971 Nonaheme cytochrome c hmcA 0.0018
4961 Hemophore HasA hasA 0.0018
4910 Cytoglobin CYGB 0.0018
4976 Apocytochrome f petA 0.0018
6407 Apocytochrome f petA 0.0018
4904 Cytochrome c family protein GSU1996 0.0018
4903 Methyl-accepting chemotaxis protein Tar4 0.0018
4931 Cytochrome P450 167A1 CYP167A1 0.0018
4972 P450cin cinA 0.0018
4960 Putative cytochrome P450-family protein SCO7417 0.0018
4926 Heme-based aerotactic transducer hemAT hemAT 0.0018
4922 Cytochrome c, putative SO_4144 0.0018
4952 Catalase/peroxidase katA 0.0018
4970 Cytochrome c nitrite reductase catalytic subunit nrfA 0.0018
4993 Hydroxylamine oxidoreductase hao1 0.0018
3093 Catalase HPII katE 0.0018
4908 Heme-regulated cyclic AMP phosphodiesterase dosP 0.0018
4920 Peroxidase/catalase katG 0.0013
4956 Quinohemoprotein alcohol dehydrogenase ADH IIB qbdA 0.0013
4037 Hypothetical protein GPX1 0.0013
4297 Hypothetical protein SP_1951 0.0013
4521 Hypothetical protein BC_2969 0.0013
4540 Hypothetical protein TM_1070 0.0013
4555 Hypothetical protein MT1739 0.0013
4569 Hypothetical protein mshD 0.0013
4578 Hypothetical protein PA3270 0.0013
4747 Hypothetical protein PA3967 0.0013
5177 Hypothetical protein TM_0096 0.0013
5194 Hypothetical protein PA1204 0.0013
5240 Hypothetical protein Rv2991 0.0013
5370 Hypothetical protein TM_1158 0.0013
5710 Hypothetical protein Tb927.5.1360 0.0013
2119 Cytochrome b5 CYB5A 0.0013
4990 PpcA ppcA 0.0013
4948 Cytochrome c-553 Not Available 0.0013
4923 Cytochrome c3 DvMF_2499 0.0013
4945 Cytochrome c3 Not Available 0.0013
4949 Cytochrome c3 DVU_3171 0.0013
4968 Cytochrome c3 cytc3 0.0013
4997 Cytochrome c3 SO_2727 0.0013
5219 Cytochrome c3 cyd 0.0013
4902 Nine-heme cytochrome c Ddes_2038 0.0013
3570 Cytochrome P450 152A1 cypC 0.0013
4289 Cytochrome P450 TT_P0059 0.0013
6262 Cytochrome P450 staP 0.0013
3189 High-molecular-weight cytochrome c hmcA 0.0013
4992 Cytochrome c peroxidase Not Available 0.0013
4988 Sulfite oxidase, mitochondrial SUOX 0.0013
2915 Sensor protein fixL fixL 0.0013
4944 Sensor protein fixL fixL 0.0013
4385 Cytochrome c' Not Available 0.0013
4967 Cytochrome c' cycA 0.0013
5038 Cytochrome c' Not Available 0.0013
5223 Cytochrome c' cycP 0.0013
3375 Acidic cytochrome c3 Not Available 0.0013
4813 Heme oxygenase hmuO 0.0013
5769 Heme oxygenase Not Available 0.0013
2230 Catalase CAT 0.0013
3249 Catalase katA 0.0013
3625 Catalase katA 0.0013
4539 Catalase katA 0.0013
4941 Catalase katB 0.0013
3670 Soluble cytochrome b562 precursor cybC 0.0011
3411 Cytochrome P450 121 cyp121 0.0011
2617 Nitric oxide synthase oxygenase nos 0.0011
2701 Nitric oxide synthase oxygenase nos 0.0011
3291 Cytochrome c-552 cycA 0.0011
4927 Cytochrome c-552 nrfA 0.0011
4938 Cytochrome c-552 cycA 0.0011
4953 Cytochrome c-552 nrfA 0.0011
5217 Cytochrome c-552 cycM 0.0011
518 Peroxidase/catalase T katG 0.0011
4386 Hemoglobin-like protein HbN glbN 0.0011
3102 Flavohemoprotein hmp 0.0011
4969 Flavohemoprotein hmp 0.0011
605 Fumarate reductase flavoprotein subunit frdA 0.001
2709 Fumarate reductase flavoprotein subunit SO_0970 0.001
3673 Fumarate reductase flavoprotein subunit fccA 0.001
4912 Fumarate reductase flavoprotein subunit ifcA 0.001
6549 Fumarate reductase flavoprotein subunit frdA 0.001
2845 Bifunctional P-450:NADPH-P450 reductase CYP102A1 0.001
3127 Nitrite reductase nirS 0.001
3284 Nitrite reductase nirS 0.001
2972 6-deoxyerythronolide B hydroxylase eryF 0.001
3221 Cytochrome c4 cc4 0.001
4608 Putative cytochrome P450 SCO1207 0.001
4963 Putative cytochrome P450 SCO2884 0.001
6254 Putative cytochrome P450 SCO6998 0.001
358 Cystathionine beta-synthase CBS 0.0009
260 Cytochrome P450 51 ERG11 0.0009
761 Cytochrome P450 51 ERG11 0.0009
3163 Cytochrome P450 51 cyp51 0.0009
693 Hemoglobin subunit beta HBB 0.0009
6268 Hydroxyacid oxidase 1 HAO1 0.0008
2298 Cytochrome P450-cam camC 0.0007
76 Nitric-oxide synthase, brain NOS1 0.0007
7 Nitric oxide synthase, inducible NOS2 0.0006
291 Nitric-oxide synthase, endothelial NOS3 0.0006
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