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Withdrawn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Prenylamine was withdrawn from the Canadian, US, and UK markets in 1988 due to concerns regarding cardiac arrhythmias.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
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCalmodulinNot AvailableHuman
UMyosin light chain kinase 2, skeletal/cardiac muscle
inhibitor
Human
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
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Prenylamine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Prenylamine.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Prenylamine is combined with 2,4-thiazolidinedione.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Prenylamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Prenylamine.
5-androstenedioneThe metabolism of Prenylamine can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of Prenylamine can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Prenylamine.
AbafunginThe therapeutic efficacy of Abafungin can be increased when used in combination with Prenylamine.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Prenylamine.
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
Wikipedia
Prenylamine
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
Actions
Inhibitor
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]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [PubMed:22039822]

Drug created on September 11, 2007 14:28 / Updated on November 02, 2018 06:06