Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H29N2O.C2H3O2.H2O |
| Molecular Weight | 402.5271 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.CC([O-])=O.CC[N+](CC)(CC(=O)NC1=C(C)C=CC=C1C)CC2=CC=CC=C2
InChI
InChIKey=GNXLNAUMSDPCGP-UHFFFAOYSA-N
InChI=1S/C21H28N2O.C2H4O2.H2O/c1-5-23(6-2,15-19-13-8-7-9-14-19)16-20(24)22-21-17(3)11-10-12-18(21)4;1-2(3)4;/h7-14H,5-6,15-16H2,1-4H3;1H3,(H,3,4);1H2
Denatonium, usually available as denatonium benzoate (trade names Bitrex) is the most bitter chemical compound known, with bitterness thresholds of 0.05 ppm for the benzoate and 0.01 ppm for the saccharide. Scientists at Macfarlan Smith, Ltd. of Edinburgh, Scotland discovered Bitrex during research on derivatives of the anesthetic lidocaine. The extremely bitter taste proved effective in reducing ingestion by humans and animals. Denatonium is commonly included in placebo medications used in clinical trials to match the bitter taste of certain medications. Denatonium activates bitter taste receptor, mainly, TAS2R4, TAS2R8, TAS2R10, TAS2R13 on many cell types and plays important roles in chemical release, ciliary beating and smooth muscle relaxation through intracellular Ca(2+)-dependent pathways.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q9NYW5 Gene ID: 50832.0 Gene Symbol: TAS2R4 Target Organism: Homo sapiens (Human) |
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Target ID: Q9NYV9 Gene ID: 50838.0 Gene Symbol: TAS2R13 Target Organism: Homo sapiens (Human) |
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Target ID: Q9NYW0 Gene ID: 50839.0 Gene Symbol: TAS2R10 Target Organism: Homo sapiens (Human) |
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Target ID: Q9NYW2 Gene ID: 50836.0 Gene Symbol: TAS2R8 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
Doses
| Dose | Population | Adverse events |
|---|---|---|
300 ppm single, ophthalmic Dose: 300 ppm Route: ophthalmic Route: single Dose: 300 ppm Sources: |
healthy, 27 years (range: 22–33 years) Health Status: healthy Age Group: 27 years (range: 22–33 years) Sex: M+F Sources: |
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1 umol/kg single, intragastric Dose: 1 umol/kg Route: intragastric Route: single Dose: 1 umol/kg Sources: |
healthy, 29 years |
|
1.69 mg/mL single, respiratory Dose: 1.69 mg/mL Route: respiratory Route: single Dose: 1.69 mg/mL Sources: |
healthy, 34 years |
Other AEs: Asthma... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Asthma | 1 patient | 1.69 mg/mL single, respiratory Dose: 1.69 mg/mL Route: respiratory Route: single Dose: 1.69 mg/mL Sources: |
healthy, 34 years |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Bitter taste transduced by PLC-beta(2)-dependent rise in IP(3) and alpha-gustducin-dependent fall in cyclic nucleotides. | 2001 Apr |
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| Soa genotype selectively affects mouse gustatory neural responses to sucrose octaacetate. | 2001 Apr 27 |
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| Haplotypes at the Tas2r locus on distal chromosome 6 vary with quinine taste sensitivity in inbred mice. | 2005 Jun 6 |
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| G-protein signaling: back to the future. | 2005 Mar |
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| Bitterness suppression with zinc sulfate and na-cyclamate: a model of combined peripheral and central neural approaches to flavor modification. | 2005 Nov |
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| PLCbeta2-independent behavioral avoidance of prototypical bitter-tasting ligands. | 2005 Sep |
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| Mouse taste cells with G protein-coupled taste receptors lack voltage-gated calcium channels and SNAP-25. | 2006 Mar 30 |
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| Exploratory behaviour in NO-dependent cyclase mutants of Drosophila shows defects in coincident neuronal signalling. | 2007 Aug 6 |
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| Broad tuning of the human bitter taste receptor hTAS2R46 to various sesquiterpene lactones, clerodane and labdane diterpenoids, strychnine, and denatonium. | 2007 Jul 25 |
|
| Functional characterization of human bitter taste receptors. | 2007 May 1 |
|
| Characterization of ligands for fish taste receptors. | 2007 May 23 |
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| The neural processing of taste. | 2007 Sep 18 |
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| Behavioral genetics and taste. | 2007 Sep 18 |
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| Predators' toxin burdens influence their strategic decisions to eat toxic prey. | 2007 Sep 4 |
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| Adverse reactions associated with respirator fit testing of healthcare workers in British Columbia, Canada: a review of compensation claim cases. | 2007 Winter |
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| Final report of the safety assessment of Alcohol Denat., including SD Alcohol 3-A, SD Alcohol 30, SD Alcohol 39, SD Alcohol 39-B, SD Alcohol 39-C, SD Alcohol 40, SD Alcohol 40-B, and SD Alcohol 40-C, and the denaturants, Quassin, Brucine Sulfate/Brucine, and Denatonium Benzoate. | 2008 |
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| Role of CCK1 and Y2 receptors in activation of hindbrain neurons induced by intragastric administration of bitter taste receptor ligands. | 2008 Jan |
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| Gustation in fish: search for prototype of taste perception. | 2009 |
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| A Drosophila gustatory receptor essential for aversive taste and inhibiting male-to-male courtship. | 2009 Oct 13 |
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| Ghrelin is produced in taste cells and ghrelin receptor null mice show reduced taste responsivity to salty (NaCl) and sour (citric acid) tastants. | 2010 Sep 14 |
Patents
Sample Use Guides
1 µmol/kg bodyweight (10mM) was administered as a bolus into the stomach through a nasogastric feeding tube.
Route of Administration:
Other
Denatonium inhibits growth and induces apoptosis of airway epithelial cells. After treatment with 2 mM denatonium for 24 h, the expression of the anti-apoptotic protein Bcl-2 was significantly reduced and the release of cytochrome c and Smac/DIABLO from the mitochondria to the cytoplasm was drastically increased in human bronchial epithelial cell lines 16HBE. To examine whether denatonium induces mitochondrial damage in airway epithelial cells, was used transmission electron microscopy to examine the ultrastructures of human lung cancer cell line A549 treated with 2 mM denatonium. The control cells appeared to have normal mitochondria and mostly homogeneous cytoplasms, while A549 cells treated with denatonium showed large amplitude swelling of mitochondria.
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Preferred Name | English |
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FDA ORPHAN DRUG |
942123
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168429466
Created by
admin on Wed Apr 02 08:03:49 GMT 2025 , Edited by admin on Wed Apr 02 08:03:49 GMT 2025
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ACTIVE MOIETY
SUBSTANCE RECORD
