Identification
- Generic Name
- Masoprocol
- DrugBank Accession Number
- DB00179
- Background
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]
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Masoprocol (DB00179)
- Weight
- Average: 302.3649
Monoisotopic: 302.151809192 - Chemical Formula
- C18H22O4
- Synonyms
- erythro-nordihydroguaiaretic acid
- Masoprocol
- 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
- Nordihydroguaiaretic acid
- External IDs
- CHX 100
- CHX-100
- INSM-18
- INSM18
- NSC-4291
Pharmacology
- Indication
Used for the treatment of actinic keratoses (precancerous skin growths that can become malignant if left untreated).
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Masoprocol 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 Masoprocol was withdrawn from the U.S. market in June 1996.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 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.
Target Actions Organism AArachidonate 5-lipoxygenase inhibitorHumans USex hormone-binding globulin Not Available Humans ATransient receptor potential cation channel subfamily M member 7 inhibitorHumans - Absorption
Less than 1%-2% is absorbed through the skin over a 4-day period following application.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms of overdose or allergic reaction include bluish coloration of skin, dizziness, severe, or feeling faint, wheezing or trouble in breathing.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareArticaine The risk or severity of methemoglobinemia can be increased when Masoprocol is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Masoprocol is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Masoprocol is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Masoprocol is combined with Bupivacaine. Butacaine The risk or severity of methemoglobinemia can be increased when Masoprocol is combined with Butacaine. Butamben The risk or severity of methemoglobinemia can be increased when Masoprocol is combined with Butamben. Capsaicin The risk or severity of methemoglobinemia can be increased when Masoprocol is combined with Capsaicin. Chloroprocaine The risk or severity of methemoglobinemia can be increased when Masoprocol is combined with Chloroprocaine. Cinchocaine The risk or severity of methemoglobinemia can be increased when Masoprocol is combined with Cinchocaine. Cocaine The risk or severity of methemoglobinemia can be increased when Masoprocol is combined with Cocaine. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Actinex
Categories
- ATC Codes
- L01XX10 — Masoprocol
- Drug Categories
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Antioxidants
- Benzene Derivatives
- Benzyl Compounds
- Biological Factors
- Catechols
- Compounds used in a research, industrial, or household setting
- Cyclooxygenase Inhibitors
- Enzyme Inhibitors
- Lignans
- Lipoxygenase Inhibitors
- Peripheral Nervous System Agents
- Phenols
- Protective Agents
- Sensory System Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.
- Kingdom
- Organic compounds
- Super Class
- Lignans, neolignans and related compounds
- Class
- Dibenzylbutane lignans
- Sub Class
- Not Available
- Direct Parent
- Dibenzylbutane lignans
- Alternative Parents
- Phenylpropanes / Catechols / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Organooxygen compounds / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homomonocyclic compound / Benzenoid / Catechol / Dibenzylbutane lignan skeleton / Hydrocarbon derivative / Monocyclic benzene moiety / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- nordihydroguaiaretic acid (CHEBI:73468) / Lignans (C10719)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 7BO8G1BYQU
- CAS number
- 27686-84-6
- InChI Key
- 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)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
- SMILES
- C[C@@H](CC1=CC(O)=C(O)C=C1)[C@H](C)CC1=CC(O)=C(O)C=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014325
- KEGG Drug
- D04862
- KEGG Compound
- C10719
- PubChem Compound
- 71398
- PubChem Substance
- 46508042
- ChemSpider
- 64490
- BindingDB
- 22372
- 227239
- ChEBI
- 73468
- ChEMBL
- CHEMBL313972
- ZINC
- ZINC000000012342
- Therapeutic Targets Database
- DNC001037
- PharmGKB
- PA164746493
- Guide to Pharmacology
- GtP Drug Page
- Wikipedia
- Masoprocol
- MSDS
- Download (69 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Terminated Treatment Prostate Cancer 1 1 Active Not Recruiting Treatment High Grade Glioma (III or IV) 1 1 Completed Treatment Head and Neck Neoplasms 1 1 Terminated Treatment Acute Lymphoblastic Leukemia (ALL) / Acute Myeloid Leukemia / Adult T-Cell Leukemia (ATL) / Chronic Lymphocytic Leukemia / Chronic Myeloid Leukemia (CML-BP) / Chronic Myelomonocytic Leukemia / Leukemias / Myelodysplastic Syndrome 1 1 Terminated Treatment Lymphoma / Refractory Solid Tumors 1 1 Terminated Treatment Prostate Cancer 1 1, 2 Completed Treatment Cervical Intraepithelial Neoplasia (CIN) 1
Pharmacoeconomics
- Manufacturers
- Univ arizona cancer center
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 185.5 °C PhysProp logP 5.8 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0136 mg/mL ALOGPS logP 3.44 ALOGPS logP 4.76 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) 9.21 Chemaxon pKa (Strongest Basic) -6.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 80.92 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 86.62 m3·mol-1 Chemaxon Polarizability 33.63 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.935 Blood Brain Barrier - 0.5361 Caco-2 permeable + 0.6215 P-glycoprotein substrate Substrate 0.6654 P-glycoprotein inhibitor I Non-inhibitor 0.9519 P-glycoprotein inhibitor II Non-inhibitor 0.9144 Renal organic cation transporter Non-inhibitor 0.886 CYP450 2C9 substrate Non-substrate 0.7194 CYP450 2D6 substrate Non-substrate 0.8261 CYP450 3A4 substrate Non-substrate 0.5171 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Inhibitor 0.8891 CYP450 2D6 inhibitor Inhibitor 0.8262 CYP450 2C19 inhibitor Inhibitor 0.8628 CYP450 3A4 inhibitor Non-inhibitor 0.5833 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5322 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.8614 Biodegradation Not ready biodegradable 0.9632 Rat acute toxicity 2.1491 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9462 hERG inhibition (predictor II) Non-inhibitor 0.6288
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Mass Spectrum (Electron Ionization) MS splash10-00di-0901000000-c0d0caa2c363f17f6c94 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTOF , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-00di-0911000000-ad449f20d75c55f665cc 1H NMR Spectrum 1D NMR Not Applicable 13C NMR Spectrum 1D NMR Not Applicable
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Arachidonate 5-lipoxygenase
- Molecular Weight
- 77982.595 Da
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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Chen HC, Xie J, Zhang Z, Su LT, Yue L, Runnels LW: Blockade of TRPM7 channel activity and cell death by inhibitors of 5-lipoxygenase. PLoS One. 2010 Jun 17;5(6):e11161. doi: 10.1371/journal.pone.0011161. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Androgen binding
- Specific Function
- Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
- Gene Name
- SHBG
- Uniprot ID
- P04278
- Uniprot Name
- Sex hormone-binding globulin
- Molecular Weight
- 43778.755 Da
References
- Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Protein serine/threonine kinase activity
- Specific Function
- Essential ion channel and serine/threonine-protein kinase. Divalent cation channel permeable to calcium and magnesium. Has a central role in magnesium ion homeostasis and in the regulation of anoxi...
- Gene Name
- TRPM7
- Uniprot ID
- Q96QT4
- Uniprot Name
- Transient receptor potential cation channel subfamily M member 7
- Molecular Weight
- 212695.37 Da
References
- Chen HC, Xie J, Zhang Z, Su LT, Yue L, Runnels LW: Blockade of TRPM7 channel activity and cell death by inhibitors of 5-lipoxygenase. PLoS One. 2010 Jun 17;5(6):e11161. doi: 10.1371/journal.pone.0011161. [Article]
Drug created at June 13, 2005 13:24 / Updated at January 03, 2023 04:16