Enzacamene
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Grundinformationen
- CAS
1782069-81-1- Standard-SMILES
Cc1ccc(/C=C2/C(=O)C3(C)CCC2C3(C)C)cc1- InChIKey
HEOCBCNFKCOKBX-SDNWHVSQSA-N- Summenformel
- C18H22O
- Durchschnittliche Molmasse
- 254,4 g/mol
- Monoisotopische Masse
- 254,16706532
Namen und Bezeichner
- Bevorzugter Name
- Enzacamene
- IUPAC
- (3E)-1,7,7-trimethyl-3-[(4-methylphenyl)methylidene]bicyclo[2.2.1]heptan-2-one
- Englischer Name
- Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-3-[(4-methylphenyl)methylene]-, (3E)-
- Summenformel
- C18H22O
- Molmasse
- 254.37
Namen und Synonyme
Enzacamene4-Methylbenzylidene camphorEnzacamenoMETHYL BENZYLIDENE CAMPHOR3-(4-Methylbenzylidene)camphor(3E)-1,7,7-trimethyl-3-[(4-methylphenyl)methylidene]bicyclo[2.2.1]heptan-2-oneDTXSID8047896enzacamenum(3E)-1,7,7-trimethyl-3-((4-methylphenyl)methylidene)bicyclo(2.2.1)heptan-2-oneEusolex-63004-MBC cpdRefChem:920992
Weitere Namen anzeigen
Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-3-[(4-methylphenyl)methylene]-, (3E)-
DTXCID308142588I3XWY40L91782069-81-1Enzacamene D-L form4-MethylbenzylidenecamphorParsol 50003-(p-Methylbenzylidene)-DL-camphor3-(4-METHYLBENZYLIDENE)-CAMPHOR
Datenbank-Bezeichner
- CAS
1782069-81-1、36861-47-9- PubChem CID
- 6434217
- DTXSID
DTXSID201348972- ChEMBL
CHEMBL2104261- ChEBI
CHEBI:135937- Nikkaji
- J2.361.347F、J475.334H
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 4,5
- Polarare Oberfläche (TPSA)
- 17,1 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 19
- Formalladung
- 0
- Komplexität
- 423
Experimentelle und physikochemische Eigenschaften
LogP5.14
SolubilityPoorly soluble
Melting Point66-69
Physikochemische Eigenschaften
- Siedepunkt
- 357 · 357-358℃ at 101.3kPa
- Dichte
- 1.108 at · 1.108 at 20℃
- Dampfdruck
- 0 · 0-0.029Pa at 20-50℃
- Aggregatzustand
- Solid:crystalline
- LogP
- 5.1 · 5.1-5.6 at 23℃ and pH7
Chemie und Industrie
Pharmakologische Informationen
Protein BindingNo pharmacokinetic data available.
Pharmacodynamics
Several studies suggest that enzacamene elicit estrogen-like effects. In prepubertal male rats exposed to enzacamene during embryonic and fetal development, decrease in testicular weight with decreased levels of LH, GnRH, and glutamate were observed; in comparison, there was an increase in LH, GnRH, and aspartate levels in peripubertal rats. These findings suggest that high concentrations of enzacamene during embryonic and fetal stage inhibits the testicular axis in male rats during the prepubertal stage and stimulates it during peripubertad stage. In a study of zebrafish (Danio rerio) embryo, exposure to enzacamene during early vertebrate development was associated with muscular and neuronal defects that may result in developmental defects, including a reduction in AChE activity, disorganized pattern of slow muscle fibers, and axon pathfinding errors during motor neuron innervation. Enzacamene displays a weak binding activity in receptors binding assays using the mammalian estrogen receptor (ER).
Mechanism of Action
Enzacamene absorbs UV-B rays. It is proposed that enzacamene exerts estrogen-like activities in the same direction as endogenous estrogens via nonclassical estrogen signaling mechanisms that do not involve gene regulation by the nuclear ER. It binds to cytosolic estradiol binding sites of estrogen receptors with low to moderate affinity compared to that of the endogenous agonist. Based on the findings of a study with _Xenopus_ hepatocytes in culture, enzacamene has a potential to induce the ER gene only at higher concentrations (10–100 μmol/L). While enzacamene was not shown to activate estrogen-dependent gene transcription when tested in an ER reporter gene assay in yeast cells, it was demonstrated in _Xenopus_ hepatocytes cultures that activate ER-dependent signaling mechanisms leading to altered gene expression. In micromolar concentrations, enzacamene accelerates cell proliferation rate in MCF-7 human breast cancer cells.
Biological Half-LifeThe half life of enzacamene (4-MBC) and its main metabolite, 3-(4-carboxybenzylidene)camphor, displayed half-lives of approximately 15 h after reaching peak plasma concentrations after oral administration in rats.
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