Masoprocol
Grundinformationen
- CAS
741285-10-9- Standard-SMILES
C[C@H](Cc1ccc(O)c(O)c1)[C@@H](C)Cc1ccc(O)c(O)c1- InChIKey
HCZKYJDFEPMADG-TXEJJXNPSA-N- Summenformel
- C18H22O4
- Durchschnittliche Molmasse
- 302,4 g/mol
Überblick
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 a metabolite, a hypoglycemic agent, an antineoplastic agent and a lipoxygenase inhibitor.
Namen und Bezeichner
- Bevorzugter Name
- Masoprocol
- IUPAC
- 4-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
- Englischer Name
- 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-, (R*,S*)-
- Summenformel
- C18H22O4
- Molmasse
- 302.36
Namen und Synonyme
Masoprocol27686-84-6meso-NDGAmeso-Nordihydroguaiaretic acidActinexMasoprocolumCHX 100CHX-100meso-4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-, (R*,S*)-ORISTAR NHGADTXSID5045178
Weitere Namen anzeigen
Einecs 248-606-6Masoprocolum [inn-latin]1,2-Benzenediol, 4,4'-((2R,3S)-2,3-dimethyl-1,4-butanediyl)bis-, rel-
4-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol7BO8G1BYQUINSM-18erythro-nordihydroguaiaretic acidNSC-4291(R*,S*)-4,4'-(2,3-Dimethylbutane-1,4-diyl)bispyrocatecholNSC-682984DTXCID3025178
Datenbank-Bezeichner
- CAS
741285-10-9- ChEMBL
CHEMBL313972- ChEBI
CHEBI:73468- UNII
- 7BO8G1BYQU
- EC Number
- 248-606-6
- Nikkaji
- J257.424A
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,3
- Polarare Oberfläche (TPSA)
- 80,9 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 22
- Formalladung
- 0
- Komplexität
- 303
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
LogP5.8
Solubility1.36e-02 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point185.5 °C
Physical DescriptionSolid
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Gefahrenhinweise
Other Safety InformationIMAP assessments - 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-, (R*,S*)-: Environment tier I assessment
Toxikologische Informationen
Exposure RoutesLess than 1%-2% is absorbed through the skin over a 4-day period following application.
Toxicity Summary
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.
Signs and SymptomsSymptoms of overdose or allergic reaction include bluish coloration of skin, dizziness, severe, or feeling faint, wheezing or trouble in breathing.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemie und Industrie
Pharmakologische Informationen
ATC Code
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
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.
MeSH Pharmacological Classification
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
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.
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.
Absorption, Distribution and ExcretionLess than 1%-2% is absorbed through the skin over a 4-day period following application.
Cellular LocationsCytoplasm
Verwendung und Herstellung
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