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Identification
NamePrenylamine
Accession NumberDB04825
TypeSmall Molecule
GroupsWithdrawn
DescriptionPrenylamine was withdrawn from the Canadian, US, and UK markets in 1988 due to concerns regarding cardiac arrhythmias.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
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not 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
UNIIK2OH82Z000
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
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+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 CodesC01DX52C01DX02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
2-HYDROXY-1,4-NAPHTHOQUINONEThe risk or severity of adverse effects can be increased when 2-HYDROXY-1,4-NAPHTHOQUINONE is combined with Prenylamine.
2-mercaptobenzothiazoleThe risk or severity of adverse effects can be increased when 2-mercaptobenzothiazole is combined with Prenylamine.
AlfuzosinAlfuzosin may increase the hypotensive activities of Prenylamine.
AmobarbitalThe metabolism of Prenylamine can be increased when combined with Amobarbital.
AmorolfineThe risk or severity of adverse effects can be increased when Amorolfine is combined with Prenylamine.
Amphotericin BThe risk or severity of adverse effects can be increased when Amphotericin B is combined with Prenylamine.
AN2690The risk or severity of adverse effects can be increased when AN2690 is combined with Prenylamine.
AnidulafunginThe risk or severity of adverse effects can be increased when Anidulafungin is combined with Prenylamine.
ArtemetherThe risk or severity of adverse effects can be increased when Artemether is combined with Prenylamine.
AtosibanThe risk or severity of adverse effects can be increased when Prenylamine is combined with Atosiban.
Atracurium besylatePrenylamine may increase the neuromuscular blocking activities of Atracurium besylate.
Bafilomycin A1The risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Prenylamine.
BarbitalThe metabolism of Prenylamine can be increased when combined with Barbital.
Benzoic AcidThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Prenylamine.
BifonazoleThe risk or severity of adverse effects can be increased when Bifonazole is combined with Prenylamine.
ButenafineThe risk or severity of adverse effects can be increased when Butenafine is combined with Prenylamine.
ButoconazoleThe risk or severity of adverse effects can be increased when Butoconazole is combined with Prenylamine.
CandicidinThe risk or severity of adverse effects can be increased when Candicidin is combined with Prenylamine.
CarvedilolCarvedilol may increase the hypotensive activities of Prenylamine.
CaspofunginThe risk or severity of adverse effects can be increased when Caspofungin is combined with Prenylamine.
CeruleninThe risk or severity of adverse effects can be increased when Cerulenin is combined with Prenylamine.
ChloroxineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Prenylamine.
CiclopiroxThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Prenylamine.
CimetidineThe serum concentration of Prenylamine can be increased when it is combined with Cimetidine.
ClopidogrelThe therapeutic efficacy of Clopidogrel can be decreased when used in combination with Prenylamine.
ClotrimazoleThe risk or severity of adverse effects can be increased when Clotrimazole is combined with Prenylamine.
CyclosporineThe risk or severity of adverse effects can be increased when Cyclosporine is combined with Prenylamine.
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Prenylamine.
Decanoic AcidThe risk or severity of adverse effects can be increased when Decanoic Acid is combined with Prenylamine.
DoxazosinDoxazosin may increase the hypotensive activities of Prenylamine.
EconazoleThe risk or severity of adverse effects can be increased when Econazole is combined with Prenylamine.
EfavirenzThe serum concentration of Prenylamine can be decreased when it is combined with Efavirenz.
EfinaconazoleThe risk or severity of adverse effects can be increased when Efinaconazole is combined with Prenylamine.
FluconazoleThe serum concentration of Prenylamine can be increased when it is combined with Fluconazole.
FlucytosineThe risk or severity of adverse effects can be increased when Flucytosine is combined with Prenylamine.
FosphenytoinThe serum concentration of Fosphenytoin can be increased when it is combined with Prenylamine.
GlyphosateThe risk or severity of adverse effects can be increased when Glyphosate is combined with Prenylamine.
GriseofulvinThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Prenylamine.
HaloproginThe risk or severity of adverse effects can be increased when Haloprogin is combined with Prenylamine.
HexetidineThe risk or severity of adverse effects can be increased when Hexetidine is combined with Prenylamine.
HexobarbitalThe metabolism of Prenylamine can be increased when combined with Hexobarbital.
IndoraminIndoramin may increase the hypotensive activities of Prenylamine.
IsoconazoleThe risk or severity of adverse effects can be increased when Isoconazole 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.
LabetalolLabetalol may increase the hypotensive activities of Prenylamine.
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.
MethylphenobarbitalThe metabolism of Prenylamine can be increased when combined with Methylphenobarbital.
MevastatinThe risk or severity of adverse effects can be increased when Mevastatin is combined with Prenylamine.
MicafunginThe risk or severity of adverse effects can be increased when Micafungin is combined with Prenylamine.
MiconazoleThe risk or severity of adverse effects can be increased when Miconazole is combined with Prenylamine.
MiltefosineThe risk or severity of adverse effects can be increased when Miltefosine is combined with Prenylamine.
MivacuriumPrenylamine may increase the neuromuscular blocking activities of Mivacurium.
MonensinThe risk or severity of adverse effects can be increased when Monensin is combined with Prenylamine.
MyxothiazolThe risk or severity of adverse effects can be increased when Myxothiazol is combined with Prenylamine.
NafcillinThe metabolism of Prenylamine can be increased when combined with Nafcillin.
NaftifineThe risk or severity of adverse effects can be increased when Naftifine is combined with Prenylamine.
NatamycinThe risk or severity of adverse effects can be increased when Natamycin is combined with Prenylamine.
NitroprussidePrenylamine may increase the hypotensive activities of Nitroprusside.
NitroxolineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Prenylamine.
NystatinThe risk or severity of adverse effects can be increased when Nystatin is combined with Prenylamine.
OxiconazoleThe risk or severity of adverse effects can be increased when Oxiconazole is combined with Prenylamine.
pafuramidineThe risk or severity of adverse effects can be increased when pafuramidine is combined with Prenylamine.
PentamidineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Prenylamine.
PentobarbitalThe metabolism of Prenylamine can be increased when combined with Pentobarbital.
PhenobarbitalThe metabolism of Prenylamine can be increased when combined with Phenobarbital.
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.
PrimidoneThe metabolism of Prenylamine can be increased when combined with Primidone.
RadicicolThe risk or severity of adverse effects can be increased when Radicicol is combined with Prenylamine.
RapacuroniumPrenylamine may increase the neuromuscular blocking activities of Rapacuronium.
Salicylhydroxamic AcidThe risk or severity of adverse effects can be increased when Salicylhydroxamic Acid is combined with Prenylamine.
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Prenylamine.
SecobarbitalThe metabolism of Prenylamine can be increased when combined with Secobarbital.
SertaconazoleThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Prenylamine.
SilodosinSilodosin may increase the hypotensive activities of Prenylamine.
SinefunginThe risk or severity of adverse effects can be increased when Sinefungin is combined with Prenylamine.
SirolimusThe risk or severity of adverse effects can be increased when Sirolimus is combined with Prenylamine.
SulconazoleThe risk or severity of adverse effects can be increased when Sulconazole is combined with Prenylamine.
TamsulosinTamsulosin may increase the hypotensive activities of Prenylamine.
TavaboroleThe risk or severity of adverse effects can be increased when Tavaborole is combined with Prenylamine.
TerazosinTerazosin may increase the hypotensive activities of Prenylamine.
TerbinafineThe risk or severity of adverse effects can be increased when Terbinafine is combined with Prenylamine.
TerconazoleThe risk or severity of adverse effects can be increased when Terconazole is combined with Prenylamine.
ThiamylalThe metabolism of Prenylamine can be increased when combined with Thiamylal.
ThiopentalThe metabolism of Prenylamine can be increased when combined with Thiopental.
ThymolThe risk or severity of adverse effects can be increased when Thymol is combined with Prenylamine.
TioconazoleThe risk or severity of adverse effects can be increased when Tioconazole is combined with Prenylamine.
TolnaftateThe risk or severity of adverse effects can be increased when Tolnaftate is combined with Prenylamine.
TrimazosinTrimazosin may increase the hypotensive activities of Prenylamine.
TrimetrexateThe risk or severity of adverse effects can be increased when Trimetrexate is combined with Prenylamine.
VoriconazoleThe risk or severity of adverse effects can be increased when Voriconazole is combined with Prenylamine.
Food InteractionsNot 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 of protein kinases and phosphatases. Together with CCP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis.
Gene Name:
CALM1
Uniprot ID:
P62158
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
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 ]
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Drug created on September 11, 2007 14:28 / Updated on August 17, 2016 12:24