Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H10O |
| Molecular Weight | 194.2286 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC2=C(C=CC=C2)C3=C1C=CC=C3
InChI
InChIKey=DZKIUEHLEXLYKM-UHFFFAOYSA-N
InChI=1S/C14H10O/c15-14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-9,15H
| Molecular Formula | C14H10O |
| Molecular Weight | 194.2286 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
9-Phenanthrol is a small molecule capable of modulating vascular and smooth muscle contractility through inhibition of the TRMP4 and Anoctamin-1 Ca(2+) channels. This mechanism of action has suggested implications for ischemic injuries to the heart and brain, as well as control over the excitability of vascular smooth muscle and urinary bladder smooth muscle.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q8TD43 Gene ID: 54795.0 Gene Symbol: TRPM4 Target Organism: Homo sapiens (Human) |
17.0 µM [IC50] | ||
Target ID: Q5XXA6 Gene ID: 55107.0 Gene Symbol: ANO1 Target Organism: Homo sapiens (Human) |
12.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Metabolism of phenanthrene by Phanerochaete chrysosporium. | 1991 Nov |
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| Initial oxidative and subsequent conjugative metabolites produced during the metabolism of phenanthrene by fungi. | 1996 Apr |
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| Liquid chromatography-mass spectrometry analysis of hydroxylated polycyclic aromatic hydrocarbons, formed in a simulator of the human gastrointestinal tract. | 2004 Jul 5 |
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| The importance of both charge exchange and proton transfer in the analysis of polycyclic aromatic compounds using atmospheric pressure chemical ionization mass spectrometry. | 2004 Mar |
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| A different route to the synthesis of 9,10-disubstituted phenanthrenes. | 2005 Aug 5 |
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| Proteasome-dependent pharmacological rescue of cystic fibrosis transmembrane conductance regulator revealed by mutation of glycine 622. | 2008 Apr |
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| Facilitating effects of metal cations on phenanthrone sorption in soils. | 2008 Apr 1 |
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| Enhanced reactivity of hydroxylated polycyclic aromatic hydrocarbons to birnessite in soil: reaction kinetics and nonextractable residue formation. | 2008 May |
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| Direct quantification of monohydroxy-polycyclic aromatic hydrocarbons in synthetic urine samples via solid-phase extraction-room-temperature fluorescence excitation-emission matrix spectroscopy. | 2008 May 15 |
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| Involuntary tobacco smoke exposure and urinary levels of polycyclic aromatic hydrocarbons in the United States, 1999 to 2002. | 2009 Mar |
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| Ca2+ release from the sarcoplasmic reticulum is required for sustained TRPM4 activity in cerebral artery smooth muscle cells. | 2010 Aug |
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| Differential action of monohydroxylated polycyclic aromatic hydrocarbons with estrogen receptors α and β. | 2013 Apr |
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| The TRPM4 channel inhibitor 9-phenanthrol. | 2014 Apr |
Sample Use Guides
Tetracycline-inducible HEK-293 cells were transfected to express the human TRPM4 channel and cultured in DMEM supplemented with 10% fetal bovine serum and 2 mM glutamine under a 5% CO2 atmosphere at 37 deg-C. The growth media was further supplemented with 5 micro-g/mL S-blasticidin and 0.4 mg/mL Zeocin. Cells were resuspended in media containing 1 micro-g/mL tetracycline 18 - 22 hours before experimentation. Whole-cell currents were recorded using the inside out configuration of the voltage patch-clamp technique. TRPM4 currents were monitored with seven doses of 9-phenanthrol between 10^-8 to 10^-4 M. At 10^-4 M 9-phenanthrol almost totally inhibited the channel current. The fitting of the dose-response curves with the Hill equation yielded an IC50 in the range of 2 × 10−5 m and showed no voltage dependence of the drug effect.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 02:16:12 GMT 2023
by
admin
on
Sat Dec 16 02:16:12 GMT 2023
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| Record UNII |
9FYU45OV9H
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| Record Status |
Validated (UNII)
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| Record Version |
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207-602-4
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28820
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DTXSID9047592
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50554
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9-Phenanthrol
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484-17-3
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10229
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9FYU45OV9H
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