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Identification
NamePrenylamine
Accession NumberDB04825
TypeSmall Molecule
GroupsWithdrawn
Description

Prenylamine was withdrawn from the Canadian, US, and UK markets in 1988 due to concerns regarding cardiac arrhythmias.

Structure
Thumb
Synonyms
1-Phenyl-2-(1',1'-diphenylpropyl-3'-amino)propane
DL-prenylamine
N-(1-Methyl-2-phenylethyl)-3,3-diphenyl-1-propanamine
N-(1-Methyl-2-phenylethyl)-gamma-phenylbenzenepropanamine
N-(3,3-Diphenylpropyl)-alpha-methylphenaethylamin
N-(3,3-Diphenylpropyl)-alpha-methylphenethylamine
N-(3'-Phenyl-2-propyl)-1,1-diphenyl-3-propyloamine
Prenilamina
Prenylaminum
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
BismethinNot Available
CarditinNot Available
CorontinNot Available
CorpaxNot Available
ElecorNot Available
FalliocorNot Available
HostaginanNot Available
SegontinNot Available
SynadrinNot Available
ValecorNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number390-64-7
WeightAverage: 329.4779
Monoisotopic: 329.214349869
Chemical FormulaC24H27N
InChI KeyInChIKey=IFFPICMESYHZPQ-UHFFFAOYSA-N
InChI
InChI=1S/C24H27N/c1-20(19-21-11-5-2-6-12-21)25-18-17-24(22-13-7-3-8-14-22)23-15-9-4-10-16-23/h2-16,20,24-25H,17-19H2,1H3
IUPAC Name
(3,3-diphenylpropyl)(1-phenylpropan-2-yl)amine
SMILES
CC(CC1=CC=CC=C1)NCCC(C1=CC=CC=C1)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Phenylpropylamine
  • Amphetamine or derivatives
  • Phenylpropane
  • Aralkylamine
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
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+1.0
Blood Brain Barrier+0.9774
Caco-2 permeable+0.8194
P-glycoprotein substrateSubstrate0.5313
P-glycoprotein inhibitor IInhibitor0.59
P-glycoprotein inhibitor IINon-inhibitor0.7214
Renal organic cation transporterInhibitor0.6263
CYP450 2C9 substrateNon-substrate0.7387
CYP450 2D6 substrateSubstrate0.8796
CYP450 3A4 substrateNon-substrate0.6941
CYP450 1A2 substrateInhibitor0.8455
CYP450 2C9 inhibitorNon-inhibitor0.9304
CYP450 2D6 inhibitorInhibitor0.927
CYP450 2C19 inhibitorInhibitor0.6787
CYP450 3A4 inhibitorNon-inhibitor0.6841
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6512
Ames testNon AMES toxic0.8094
CarcinogenicityNon-carcinogens0.8812
BiodegradationNot ready biodegradable0.86
Rat acute toxicity3.0889 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7311
hERG inhibition (predictor II)Inhibitor0.7538
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point36.5 °CPhysProp
water solubility50 mg/L (at 37 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
Water Solubility3.54e-05 mg/mLALOGPS
logP5.89ALOGPS
logP6.12ChemAxon
logS-7ALOGPS
pKa (Strongest Basic)10.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity107.09 m3·mol-1ChemAxon
Polarizability39.76 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US3152173
General ReferencesNot Available
External Links
ATC CodesC01DX02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcetaminophenThe metabolism of Prenylamine can be increased when combined with Acetaminophen.
AmobarbitalThe metabolism of Prenylamine can be increased when combined with Amobarbital.
Atracurium besylatePrenylamine may increase the neuromuscular blocking activities of Atracurium besylate.
ButabarbitalThe metabolism of Prenylamine can be increased when combined with Butabarbital.
ButalbitalThe metabolism of Prenylamine can be increased when combined with Butalbital.
CaffeineThe metabolism of Prenylamine can be increased when combined with Caffeine.
Calcium AcetateThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium Acetate.
Calcium carbonateThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium carbonate.
Calcium ChlorideThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium Chloride.
Calcium citrateThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium citrate.
Calcium gluconateThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium gluconate.
CimetidineThe serum concentration of Prenylamine can be increased when it is combined with Cimetidine.
Cisatracurium besylatePrenylamine may increase the neuromuscular blocking activities of Cisatracurium besylate.
ClarithromycinThe metabolism of Prenylamine can be decreased when combined with Clarithromycin.
ClopidogrelThe therapeutic efficacy of Clopidogrel can be decreased when used in combination with Prenylamine.
DoxazosinDoxazosin may increase the hypotensive activities of Prenylamine.
EfavirenzThe serum concentration of Prenylamine can be decreased when it is combined with Efavirenz.
ErythromycinThe metabolism of Prenylamine can be decreased when combined with Erythromycin.
FluconazoleThe serum concentration of Prenylamine can be increased when it is combined with Fluconazole.
FosphenytoinThe serum concentration of Fosphenytoin can be increased when it is combined with Prenylamine.
ItraconazoleThe risk or severity of adverse effects can be increased when Itraconazole is combined with Prenylamine.
KetoconazoleThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Prenylamine.
Magnesium chlorideThe risk or severity of adverse effects can be increased when Prenylamine is combined with Magnesium chloride.
Magnesium citrateThe risk or severity of adverse effects can be increased when Prenylamine is combined with Magnesium citrate.
Magnesium hydroxideThe risk or severity of adverse effects can be increased when Prenylamine is combined with Magnesium hydroxide.
Magnesium oxideThe risk or severity of adverse effects can be increased when Prenylamine is combined with Magnesium oxide.
Magnesium salicylateThe risk or severity of adverse effects can be increased when Prenylamine is combined with Magnesium salicylate.
Magnesium SulfateThe risk or severity of adverse effects can be increased when Prenylamine is combined with Magnesium Sulfate.
MethohexitalThe metabolism of Prenylamine can be increased when combined with Methohexital.
NafcillinThe metabolism of Prenylamine can be increased when combined with Nafcillin.
NitroprussidePrenylamine may increase the hypotensive activities of Nitroprusside.
PancuroniumPrenylamine may increase the neuromuscular blocking activities of Pancuronium.
PentobarbitalThe metabolism of Prenylamine can be increased when combined with Pentobarbital.
PhenobarbitalThe metabolism of Prenylamine can be increased when combined with Phenobarbital.
PhenoxybenzaminePhenoxybenzamine may increase the hypotensive activities of Prenylamine.
PhentolaminePhentolamine may increase the hypotensive activities of Prenylamine.
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Prenylamine.
PosaconazoleThe risk or severity of adverse effects can be increased when Posaconazole is combined with Prenylamine.
PrazosinPrazosin may increase the hypotensive activities of Prenylamine.
RifabutinThe serum concentration of Prenylamine can be decreased when it is combined with Rifabutin.
RifampicinThe serum concentration of Prenylamine can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Prenylamine can be decreased when it is combined with Rifapentine.
RocuroniumPrenylamine may increase the neuromuscular blocking activities of Rocuronium.
SecobarbitalThe metabolism of Prenylamine can be increased when combined with Secobarbital.
SilodosinSilodosin may increase the hypotensive activities of Prenylamine.
SulfisoxazoleThe metabolism of Prenylamine can be decreased when combined with Sulfisoxazole.
TamsulosinTamsulosin may increase the hypotensive activities of Prenylamine.
TelithromycinThe metabolism of Prenylamine can be decreased when combined with Telithromycin.
TerazosinTerazosin may increase the hypotensive activities of Prenylamine.
VecuroniumPrenylamine may increase the neuromuscular blocking activities of Vecuronium.
VoriconazoleThe risk or severity of adverse effects can be increased when Voriconazole is combined with Prenylamine.
Food InteractionsNot Available

Targets

1. Calmodulin

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Calmodulin P62158 Details

References:

  1. Lamers JM, Cysouw KJ, Verdouw PD: Slow calcium channel blockers and calmodulin. Effect of felodipine, nifedipine, prenylamine and bepridil on cardiac sarcolemmal calcium pumping ATPase. Biochem Pharmacol. 1985 Nov 1;34(21):3837-43. Pubmed

2. Myosin light chain kinase 2, skeletal/cardiac muscle

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Myosin light chain kinase 2, skeletal/cardiac muscle Q9H1R3 Details

References:

  1. Lamers JM, Cysouw KJ, Verdouw PD: Slow calcium channel blockers and calmodulin. Effect of felodipine, nifedipine, prenylamine and bepridil on cardiac sarcolemmal calcium pumping ATPase. Biochem Pharmacol. 1985 Nov 1;34(21):3837-43. Pubmed

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Drug created on September 11, 2007 14:28 / Updated on October 08, 2013 14:25