Masoprocol
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Masoprocol
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CAS No:
27686-84-6
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Formula:
C18H22O4
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Chemical Name:
Masoprocol
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Synonyms:
1,2-Benzenediol,4,4′-[(2R,3S)-2,3-dimethyl-1,4-butanediyl]bis-,rel-;Pyrocatechol,4,4′-(2,3-dimethyltetramethylene)di-,meso-;1,2-Benzenediol,4,4′-(2,3-dimethyl-1,4-butanediyl)bis-,(R*,S*)-;rel-4,4′-[(2R,3S)-2,3-Dimethyl-1,4-butanediyl]bis[1,2-benzenediol];meso-Nordihydroguaiaretic acid;CHX 100;meso-NDGA;Masoprocol;Actinex;334707-72-1;741285-10-9;1050512-02-1
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CAS No:
Description
Solid
Masoprocol is the meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase. It has a role as an antineoplastic agent, a lipoxygenase inhibitor, a hypoglycemic agent and a metabolite.|Masoprocol is a naturally occurring antioxidant dicatechol originally derived from the creosote bush Larrea divaricatta with antipromoter, anti-inflammatory, and antineoplastic activities. Masoprocol directly inhibits activation of two receptor tyrosine kinases (RTKs), the insulin-like growth factor receptor (IGF-1R) and the c-erbB2/HER2/neu receptor, resulting in decreased proliferation of susceptible tumor cell populations. This agent may induce apoptosis in susceptible tumor cell populations as a result of disruption of the actin cytoskeleton in association with the activation of stress activated protein kinases (SAPKs). In addition, masoprocol inhibits arachidonic acid 5-lipoxygenase (5LOX), resulting in diminished synthesis of inflammatory mediators such as prostaglandins and leukotrienes. It may prevent leukocyte infiltration into tissues and the release of reactive oxygen species.|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.
Masoprocol Basic Attributes
302.36500
302.36
248-606-6
7BO8G1BYQU
DTXSID5045178
C701
L - Antineoplastic and immunomodulating agents
Characteristics
80.92000
3.56640
crystals
1.241g/cm3
185-186 °C
526.5ºC
247.8ºC
1.626
1.36e-02 g/L
1.06E-11mmHg at 25°C
Toxicity
Symptoms of overdose or allergic reaction include bluish coloration of skin, dizziness, severe, or feeling faint, wheezing or trouble in breathing.
Drug Information
Used for the treatment of actinic keratoses (precancerous skin growths that can become malignant if left untreated).
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.
Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)|Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)|Compounds that bind to and inhibit that enzymatic activity of LIPOXYGENASES. Included under this category are inhibitors that are specific for lipoxygenase subtypes and act to reduce the production of LEUKOTRIENES. (See all compounds classified as Lipoxygenase Inhibitors.)
Less than 1%-2% is absorbed through the skin over a 4-day period following application.
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.
(R*,S*)-4,4'-(2,3-Dimethylbutane-1,4-diyl)bispyrocatechol
Masoprocol Use and Manufacturing
1,2-Benzenediol, 4,4'-[(2R,3S)-2,3-dimethyl-1,4-butanediyl]bis-, rel-: INACTIVE
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Computed Properties
Molecular Weight:302.4
XLogP3:4.3
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:302.15180918
Monoisotopic Mass:302.15180918
Topological Polar Surface Area:80.9
Heavy Atom Count:22
Complexity:303
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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