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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
Structure of 9-PHENANTHROL

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

HIDE SMILES / InChI

Molecular Formula C14H10O
Molecular Weight 194.2286
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
17.0 µM [IC50]
12.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
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
Record UNII
9FYU45OV9H
Record Status Validated (UNII)
Record Version