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Identification
NameTridihexethyl
Accession NumberDB00505  (APRD00286)
TypeSmall Molecule
GroupsWithdrawn
Description

Tridihexethyl is a synthetic anticholinergic agent which has been shown in experimental and clinical studies to have a pronounced antispasmodic and antisecretory effect on the gastrointestinal tract. Tridihexethyl is an antimuscarinic, anticholinergic drug. Tridihexethyl is no longer available in the US market.

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
PathilonNot Available
PropethonumNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Tridihexethyl chloride
ThumbNot applicableDBSALT001377
Categories
UNII7HE50A367X
CAS number60-49-1
WeightAverage: 318.5166
Monoisotopic: 318.279689779
Chemical FormulaC21H36NO
InChI KeyInChIKey=NPRHVSBSZMAEIN-UHFFFAOYSA-N
InChI
InChI=1S/C21H36NO/c1-4-22(5-2,6-3)18-17-21(23,19-13-9-7-10-14-19)20-15-11-8-12-16-20/h7,9-10,13-14,20,23H,4-6,8,11-12,15-18H2,1-3H3/q+1
IUPAC Name
(3-cyclohexyl-3-hydroxy-3-phenylpropyl)triethylazanium
SMILES
CC[N+](CC)(CC)CCC(O)(C1CCCCC1)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropylamines. These are compounds containing a phenylpropylamine moiety, which consists of a phenyl group substituted at the third carbon by an propan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropylamines
Direct ParentPhenylpropylamines
Alternative Parents
Substituents
  • Phenylpropylamine
  • Aralkylamine
  • Tertiary alcohol
  • Quaternary ammonium salt
  • 1,3-aminoalcohol
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Organic cation
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed as an adjunct in the treatment of peptic ulcer disease and in Acquired nystagmus
PharmacodynamicsTridihexethyl is a synthetic anticholinergic agent which has been shown in experimental and clinical studies to have a pronounced antispasmodic and antisecretory effect on the gastrointestinal tract. Tridihexethyl is an antimuscarinic, anticholinergic drug.
Mechanism of actionTridihexethyl binds the muscarinic acetylcholine receptor. It may block all three types of muscarinic receptors including M-1 receptors in the CNS and ganglia, M-2 receptors in the heart (vagus) and M-3 receptors at the parasympathetic NEJ system. The muscarinic acetylcholine receptors mediate various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Tridihexethyl inhibits vagally mediated reflexes by antagonizing the action of acetylcholine. This in turn reduces the secretion of gastric acids in the stomach.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8291
Blood Brain Barrier+0.9277
Caco-2 permeable+0.6969
P-glycoprotein substrateSubstrate0.7363
P-glycoprotein inhibitor INon-inhibitor0.7804
P-glycoprotein inhibitor IINon-inhibitor0.6714
Renal organic cation transporterInhibitor0.5622
CYP450 2C9 substrateNon-substrate0.7795
CYP450 2D6 substrateNon-substrate0.5453
CYP450 3A4 substrateSubstrate0.5728
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9072
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9163
Ames testNon AMES toxic0.8549
CarcinogenicityNon-carcinogens0.5749
BiodegradationNot ready biodegradable0.9515
Rat acute toxicity2.5261 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5444
hERG inhibition (predictor II)Inhibitor0.8856
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Lederle laboratories div american cyanamid co
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point181.5 °CNot Available
water solubility11 mg/mLNot Available
logP1.17Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.68e-05 mg/mLALOGPS
logP2.31ALOGPS
logP0.29ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)13.69ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity111.22 m3·mol-1ChemAxon
Polarizability39.17 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesA03AB08
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular Weight:
66127.445 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular Weight:
51420.375 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
G-protein coupled acetylcholine receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then trigge...
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23