Prenylamine

Identification

Name
Prenylamine
Accession Number
DB04825
Type
Small Molecule
Groups
Withdrawn
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Prenylamine was withdrawn from the Canadian, US, and UK markets in 1988 due to concerns regarding cardiac arrhythmias.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
International/Other Brands
Bismethin / Carditin / Corontin / Corpax / Elecor / Falliocor / Hostaginan / Segontin / Synadrin / Valecor
Categories
UNII
K2OH82Z000
CAS number
390-64-7
Weight
Average: 329.4779
Monoisotopic: 329.214349869
Chemical Formula
C24H27N
InChI Key
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCalmodulinNot AvailableHuman
UMyosin light chain kinase 2, skeletal/cardiac muscleNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2-HYDROXY-1,4-NAPHTHOQUINONEThe risk or severity of adverse effects can be increased when 2-HYDROXY-1,4-NAPHTHOQUINONE is combined with Prenylamine.Experimental
2-mercaptobenzothiazoleThe risk or severity of adverse effects can be increased when 2-mercaptobenzothiazole is combined with Prenylamine.Vet Approved
AlfuzosinAlfuzosin may increase the hypotensive activities of Prenylamine.Approved, Investigational
AmobarbitalThe metabolism of Prenylamine can be increased when combined with Amobarbital.Approved, Illicit
AmorolfineThe risk or severity of adverse effects can be increased when Amorolfine is combined with Prenylamine.Approved, Investigational
Amphotericin BThe risk or severity of adverse effects can be increased when Amphotericin B is combined with Prenylamine.Approved, Investigational
AnidulafunginThe risk or severity of adverse effects can be increased when Anidulafungin is combined with Prenylamine.Approved, Investigational
ArtemetherThe risk or severity of adverse effects can be increased when Artemether is combined with Prenylamine.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Prenylamine is combined with Atorvastatin.Approved
AtosibanThe risk or severity of adverse effects can be increased when Prenylamine is combined with Atosiban.Approved, Investigational
Bafilomycin A1The risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Prenylamine.Experimental
BarbexacloneThe metabolism of Prenylamine can be increased when combined with Barbexaclone.Experimental
BarbitalThe metabolism of Prenylamine can be increased when combined with Barbital.Illicit
Benzoic AcidThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Prenylamine.Approved
BifonazoleThe risk or severity of adverse effects can be increased when Bifonazole is combined with Prenylamine.Approved, Investigational
Brefeldin AThe risk or severity of adverse effects can be increased when Brefeldin A is combined with Prenylamine.Experimental
BucindololBucindolol may increase the hypotensive activities of Prenylamine.Investigational
BunazosinBunazosin may increase the hypotensive activities of Prenylamine.Investigational
ButenafineThe risk or severity of adverse effects can be increased when Butenafine is combined with Prenylamine.Approved
ButoconazoleThe risk or severity of adverse effects can be increased when Butoconazole is combined with Prenylamine.Approved
Calcium AcetateThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium Acetate.Approved
Calcium CarbonateThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium Carbonate.Approved
Calcium ChlorideThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium Chloride.Approved
Calcium CitrateThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium Citrate.Approved
Calcium glubionateThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium glubionate.Approved
Calcium GluceptateThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium Gluceptate.Approved
Calcium gluconateThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium gluconate.Approved, Vet Approved
Calcium lactateThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium lactate.Approved, Experimental, Investigational, Vet Approved
Calcium lactate gluconateThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium lactate gluconate.Experimental
Calcium laevulateThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium laevulate.Experimental
Calcium pangamateThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium pangamate.Experimental
Calcium PhosphateThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Calcium Phosphate.Approved
CandicidinThe risk or severity of adverse effects can be increased when Candicidin is combined with Prenylamine.Withdrawn
Capric acidThe risk or severity of adverse effects can be increased when Capric acid is combined with Prenylamine.Experimental
CarbomycinThe metabolism of Prenylamine can be decreased when combined with Carbomycin.Vet Approved
CarvedilolCarvedilol may increase the hypotensive activities of Prenylamine.Approved, Investigational
CaseinThe therapeutic efficacy of Prenylamine can be decreased when used in combination with Casein.Approved
CaspofunginThe risk or severity of adverse effects can be increased when Caspofungin is combined with Prenylamine.Approved
CerivastatinThe risk or severity of adverse effects can be increased when Prenylamine is combined with Cerivastatin.Withdrawn
CeruleninThe risk or severity of adverse effects can be increased when Cerulenin is combined with Prenylamine.Approved
ChloroxineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Prenylamine.Approved
CiclopiroxThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Prenylamine.Approved, Investigational
CimetidineThe serum concentration of Prenylamine can be increased when it is combined with Cimetidine.Approved
ClarithromycinThe metabolism of Prenylamine can be decreased when combined with Clarithromycin.Approved
ClopidogrelThe therapeutic efficacy of Clopidogrel can be decreased when used in combination with Prenylamine.Approved
ClotrimazoleThe risk or severity of adverse effects can be increased when Clotrimazole is combined with Prenylamine.Approved, Vet Approved
CordycepinThe risk or severity of adverse effects can be increased when Cordycepin is combined with Prenylamine.Investigational
CyclosporineThe risk or severity of adverse effects can be increased when Cyclosporine is combined with Prenylamine.Approved, Investigational, Vet Approved
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Prenylamine.Investigational
DichloropheneThe risk or severity of adverse effects can be increased when Dichlorophene is combined with Prenylamine.Vet Approved
DoxazosinDoxazosin may increase the hypotensive activities of Prenylamine.Approved
EconazoleThe risk or severity of adverse effects can be increased when Econazole is combined with Prenylamine.Approved
EfavirenzThe serum concentration of Prenylamine can be decreased when it is combined with Efavirenz.Approved, Investigational
EfinaconazoleThe risk or severity of adverse effects can be increased when Efinaconazole is combined with Prenylamine.Approved
ErythromycinThe metabolism of Prenylamine can be decreased when combined with Erythromycin.Approved, Vet Approved
FenticonazoleThe risk or severity of adverse effects can be increased when Fenticonazole is combined with Prenylamine.Experimental
FluconazoleThe serum concentration of Prenylamine can be increased when it is combined with Fluconazole.Approved
FlucytosineThe risk or severity of adverse effects can be increased when Flucytosine is combined with Prenylamine.Approved
FlutrimazoleThe risk or severity of adverse effects can be increased when Flutrimazole is combined with Prenylamine.Experimental
FluvastatinThe risk or severity of adverse effects can be increased when Prenylamine is combined with Fluvastatin.Approved
FosphenytoinThe serum concentration of Fosphenytoin can be increased when it is combined with Prenylamine.Approved
GlyphosateThe risk or severity of adverse effects can be increased when Glyphosate is combined with Prenylamine.Experimental
GriseofulvinThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Prenylamine.Approved, Vet Approved
HachimycinThe risk or severity of adverse effects can be increased when Hachimycin is combined with Prenylamine.Experimental
HaloproginThe risk or severity of adverse effects can be increased when Haloprogin is combined with Prenylamine.Approved, Withdrawn
HexetidineThe risk or severity of adverse effects can be increased when Hexetidine is combined with Prenylamine.Approved, Investigational
HexobarbitalThe metabolism of Prenylamine can be increased when combined with Hexobarbital.Approved
IndoraminIndoramin may increase the hypotensive activities of Prenylamine.Withdrawn
IsoconazoleThe risk or severity of adverse effects can be increased when Isoconazole is combined with Prenylamine.Approved
ItraconazoleThe risk or severity of adverse effects can be increased when Itraconazole is combined with Prenylamine.Approved, Investigational
JosamycinThe metabolism of Prenylamine can be decreased when combined with Josamycin.Approved, Investigational
KetoconazoleThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Prenylamine.Approved, Investigational
KitasamycinThe metabolism of Prenylamine can be decreased when combined with Kitasamycin.Experimental
LabetalolLabetalol may increase the hypotensive activities of Prenylamine.Approved
LovastatinThe risk or severity of adverse effects can be increased when Prenylamine is combined with Lovastatin.Approved, Investigational
MepartricinThe risk or severity of adverse effects can be increased when Mepartricin is combined with Prenylamine.Experimental
MethohexitalThe metabolism of Prenylamine can be increased when combined with Methohexital.Approved
MethylphenobarbitalThe metabolism of Prenylamine can be increased when combined with Methylphenobarbital.Approved
MevastatinThe risk or severity of adverse effects can be increased when Mevastatin is combined with Prenylamine.Experimental
MicafunginThe risk or severity of adverse effects can be increased when Micafungin is combined with Prenylamine.Approved, Investigational
MiconazoleThe risk or severity of adverse effects can be increased when Miconazole is combined with Prenylamine.Approved, Investigational, Vet Approved
MiltefosineThe risk or severity of adverse effects can be increased when Miltefosine is combined with Prenylamine.Approved
MonensinThe risk or severity of adverse effects can be increased when Monensin is combined with Prenylamine.Vet Approved
MyxothiazolThe risk or severity of adverse effects can be increased when Myxothiazol is combined with Prenylamine.Experimental
NafcillinThe metabolism of Prenylamine can be increased when combined with Nafcillin.Approved
NaftifineThe risk or severity of adverse effects can be increased when Naftifine is combined with Prenylamine.Approved
NatamycinThe risk or severity of adverse effects can be increased when Natamycin is combined with Prenylamine.Approved
NifuratelThe risk or severity of adverse effects can be increased when Nifuratel is combined with Prenylamine.Experimental
Nikkomycin ZThe risk or severity of adverse effects can be increased when Nikkomycin Z is combined with Prenylamine.Investigational
NitroprussidePrenylamine may increase the hypotensive activities of Nitroprusside.Approved
NitroxolineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Prenylamine.Approved
NystatinThe risk or severity of adverse effects can be increased when Nystatin is combined with Prenylamine.Approved, Vet Approved
OleandomycinThe metabolism of Prenylamine can be decreased when combined with Oleandomycin.Vet Approved
OmoconazoleThe risk or severity of adverse effects can be increased when Omoconazole is combined with Prenylamine.Experimental
OxiconazoleThe risk or severity of adverse effects can be increased when Oxiconazole is combined with Prenylamine.Approved
PafuramidineThe risk or severity of adverse effects can be increased when Pafuramidine is combined with Prenylamine.Investigational
PentamidineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Prenylamine.Approved
PentobarbitalThe metabolism of Prenylamine can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe metabolism of Prenylamine can be increased when combined with Phenobarbital.Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Prenylamine.Approved, Vet Approved
PitavastatinThe risk or severity of adverse effects can be increased when Prenylamine is combined with Pitavastatin.Approved
PosaconazoleThe risk or severity of adverse effects can be increased when Posaconazole is combined with Prenylamine.Approved, Investigational, Vet Approved
PravastatinThe risk or severity of adverse effects can be increased when Prenylamine is combined with Pravastatin.Approved
PrazosinPrazosin may increase the hypotensive activities of Prenylamine.Approved
PrimidoneThe metabolism of Prenylamine can be increased when combined with Primidone.Approved, Vet Approved
PyrrolnitrinThe risk or severity of adverse effects can be increased when Pyrrolnitrin is combined with Prenylamine.Experimental
RadicicolThe risk or severity of adverse effects can be increased when Radicicol is combined with Prenylamine.Experimental
RifabutinThe serum concentration of Prenylamine can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Prenylamine can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Prenylamine can be decreased when it is combined with Rifapentine.Approved
RifaximinThe serum concentration of Prenylamine can be decreased when it is combined with Rifaximin.Approved, Investigational
RosuvastatinThe risk or severity of adverse effects can be increased when Prenylamine is combined with Rosuvastatin.Approved
Salicylhydroxamic AcidThe risk or severity of adverse effects can be increased when Salicylhydroxamic Acid is combined with Prenylamine.Experimental
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Prenylamine.Approved, Vet Approved
SecobarbitalThe metabolism of Prenylamine can be increased when combined with Secobarbital.Approved, Vet Approved
SertaconazoleThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Prenylamine.Approved
SilodosinSilodosin may increase the hypotensive activities of Prenylamine.Approved
SimvastatinThe risk or severity of adverse effects can be increased when Prenylamine is combined with Simvastatin.Approved
SinefunginThe risk or severity of adverse effects can be increased when Sinefungin is combined with Prenylamine.Experimental
SirolimusThe risk or severity of adverse effects can be increased when Sirolimus is combined with Prenylamine.Approved, Investigational
SolithromycinThe metabolism of Prenylamine can be decreased when combined with Solithromycin.Investigational
SulconazoleThe risk or severity of adverse effects can be increased when Sulconazole is combined with Prenylamine.Approved
TamsulosinTamsulosin may increase the hypotensive activities of Prenylamine.Approved, Investigational
TavaboroleThe risk or severity of adverse effects can be increased when Tavaborole is combined with Prenylamine.Approved
TelithromycinThe metabolism of Prenylamine can be decreased when combined with Telithromycin.Approved
TerazosinTerazosin may increase the hypotensive activities of Prenylamine.Approved
TerbinafineThe risk or severity of adverse effects can be increased when Terbinafine is combined with Prenylamine.Approved, Investigational, Vet Approved
TerconazoleThe risk or severity of adverse effects can be increased when Terconazole is combined with Prenylamine.Approved
ThiamylalThe metabolism of Prenylamine can be increased when combined with Thiamylal.Approved, Vet Approved
ThiopentalThe metabolism of Prenylamine can be increased when combined with Thiopental.Approved, Vet Approved
ThymolThe risk or severity of adverse effects can be increased when Thymol is combined with Prenylamine.Approved
TioconazoleThe risk or severity of adverse effects can be increased when Tioconazole is combined with Prenylamine.Approved
TolciclateThe risk or severity of adverse effects can be increased when Tolciclate is combined with Prenylamine.Experimental
TolnaftateThe risk or severity of adverse effects can be increased when Tolnaftate is combined with Prenylamine.Approved, Vet Approved
TrimazosinTrimazosin may increase the hypotensive activities of Prenylamine.Experimental
TrimetrexateThe risk or severity of adverse effects can be increased when Trimetrexate is combined with Prenylamine.Approved, Investigational
TylosinThe metabolism of Prenylamine can be decreased when combined with Tylosin.Vet Approved
UbidecarenoneThe risk or severity of adverse effects can be increased when Prenylamine is combined with Ubidecarenone.Approved, Investigational, Nutraceutical
UrapidilUrapidil may increase the hypotensive activities of Prenylamine.Investigational
VoriconazoleThe risk or severity of adverse effects can be increased when Voriconazole is combined with Prenylamine.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference
US3152173
General References
Not Available
External Links
PubChem Compound
9801
PubChem Substance
46508663
ChemSpider
9418
BindingDB
50017723
ChEBI
8397
ChEMBL
CHEMBL24072
ATC Codes
C01DX52 — Prenylamine, combinationsC01DX02 — Prenylamine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)36.5 °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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Amphetamines and derivatives / Phenylpropanes / Aralkylamines / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Diphenylmethane / Amphetamine or derivatives / Phenylpropane / Aralkylamine / Secondary amine / Secondary aliphatic amine / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Titin binding
Specific Function
Calmodulin mediates the control of a large number of enzymes, ion channels, aquaporins and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number...
Gene Name
CALM1
Uniprot ID
P0DP23
Uniprot Name
Calmodulin
Molecular Weight
16837.47 Da
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:2933041]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Myosin light chain kinase activity
Specific Function
Implicated in the level of global muscle contraction and cardiac function. Phosphorylates a specific serine in the N-terminus of a myosin light chain.
Gene Name
MYLK2
Uniprot ID
Q9H1R3
Uniprot Name
Myosin light chain kinase 2, skeletal/cardiac muscle
Molecular Weight
64684.295 Da
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:2933041]

Drug created on September 11, 2007 14:28 / Updated on December 01, 2017 15:33