Nafazatrom
Basic information
- CAS
59040-30-1- Standard SMILES
CC1=NN(CCOc2ccc3ccccc3c2)C(=O)C1- InChIKey
ISBUYSPRIJRBKX-UHFFFAOYSA-N- Molecular formula
- C16H16N2O2
- Average molar mass
- 268.31 g/mol
- Monoisotopic mass
- 268.12117776
Overview
Nafazatrom is a pyrazolinone derivative with potential antimetastatic activities. Nafazatrom, originally developed as an antithrombotic agent, inhibits the key prostaglandin catabolic enzyme, 15-hydroxyprostaglandin dehydrogenase, which prolongs the biological half-life of prostacyclin (prostaglandin I2; PGI2) and prevents intravascular coagulation. This agent also serves as a reducing cofactor with the hydroperoxidase moiety of cyclooxygenase and accelerates the conversion of arachidonic acid into precursors of PGI2. An elevated level of PGI2 prevents aggregation of platelets; subsequently it decreases the formation of tumor cell-platelet aggregates as well as their sequestration in blood vessels, which is an important initiating step in the development of metastasis.
Names & identifiers
- Preferred name
- Nafazatrom
- IUPAC
- 5-methyl-2-(2-naphthalen-2-yloxyethyl)-4H-pyrazol-3-one
- English name
- nafazatrom
- Molecular formula
- C16H16N2O2
- Molecular weight
- 268.31
Names & synonyms
NAFAZATROM59040-30-1Bay-g-6575Bay-g 6575BAY g 6575DTXSID002077942,4-Dihydro-5-methyl-2-(2-(2-naphthalenyloxy)ethyl)-3H-pyrazol-3-one3H-Pyrazol-3-one, 2,4-dihydro-5-methyl-2-(2-(2-naphthalenyloxy)ethyl)-K94216221BRefChem:927431DTXCID501302851-(2-(beta-naphthyloxy)ethyl)-3-methyl-2-pyrazolin-5-one
Show more names
2,4-Dihydro-5-methyl-2-[2-(2-naphtyloxy)ethyl]-3H-pyrazol-3-one2,4-Dihydro-5-methyl-2-[2-(2-naphthalenyloxy)ethyl]-3H-pyrazol-3-one3H-Pyrazol-3-one, 2,4-dihydro-5-methyl-2-[2-(2-naphthalenyloxy)ethyl]-
3H-pyrazol-3-one,2,4-dihydro-5-methyl-2-(2-(2-naphthalenyloxy)ethyl)261-571-15-methyl-2-(2-naphthalen-2-yloxyethyl)-4H-pyrazol-3-oneNafazatromumNafazatromum [INN-Latin]Nafazatrom [INN:BAN]EINECS 261-571-1BRN 0665222
Database identifiers
- CAS
59040-30-1- PubChem CID
- 42923
- DTXSID
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 41.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 394
Experimental & physicochemical properties
LogP2.74
Physicochemical properties
- Boiling point
- 441.5 · 441.5±47.0 °C(Predicted)
- Density
- 1.2 · 1.20±0.1 g/cm3(Predicted)
- pka
- 3.21 · 3.21±0.50(Predicted)
- FDA UNII
- 94216221 B · K94216221B
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Fibrinolysin or agents that convert plasminogen to FIBRINOLYSIN.
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.
Applications
UsesNafazatrom (Bay g 6575) is an orally active cardioprotective agent that protects against ischemic damage. Nafazatrom dose-dependently inhibits neutrophil aggregation, superoxide anion generation, arachidonic acid metabolism, and to a lesser extent the release of β-glucosidase, platelet aggregation or arachidonic acid in vitro. Acid metabolism has no significant effect. In a dog ischemia-reperfusion model, Nafazatrom (10 mg/kg; po) reduced infarct size and the occurrence of arrhythmias and rescued ischemic myocardial function without affecting any hemodynamic changes. The basis of Nafazatrom's cardioprotection may be inhibition of neutrophil function and cellular infiltration in vitro[1].
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