Identification
- Generic Name
- Prenylamine
- DrugBank Accession Number
- DB04825
- Background
Prenylamine was withdrawn from the Canadian, US, and UK markets in 1988 due to concerns regarding cardiac arrhythmias.
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Prenylamine (DB04825)
- Weight
- Average: 329.4779
Monoisotopic: 329.214349869 - Chemical Formula
- C24H27N
- Synonyms
- 1-Phenyl-2-(1',1'-diphenylpropyl-3'-amino)propane
- DL-prenylamine
- N-(1-Methyl-2-phenylethyl)-gamma-phenylbenzenepropanamine
- N-(3,3-Diphenylpropyl)-alpha-methylphenaethylamin
- N-(3,3-Diphenylpropyl)-alpha-methylphenethylamine
- Prenilamina
- Prenylamine
- Prenylaminum
- External IDs
- B-436
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UCalmodulin Not Available Humans UMyosin light chain kinase 2, skeletal/cardiac muscle inhibitorHumans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Prenylamine can be increased when it is combined with Abametapir. Acarbose The risk or severity of hypoglycemia can be increased when Prenylamine is combined with Acarbose. Acebutolol Acebutolol may increase the arrhythmogenic activities of Prenylamine. Aceclofenac The risk or severity of hyperkalemia can be increased when Prenylamine is combined with Aceclofenac. Acemetacin The risk or severity of hyperkalemia can be increased when Prenylamine is combined with Acemetacin. Acetohexamide The risk or severity of hypoglycemia can be increased when Prenylamine is combined with Acetohexamide. Acetyldigitoxin Acetyldigitoxin may increase the arrhythmogenic activities of Prenylamine. Acetylsalicylic acid The risk or severity of hyperkalemia can be increased when Acetylsalicylic acid is combined with Prenylamine. Acrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Prenylamine. Adenosine Adenosine may increase the arrhythmogenic activities of Prenylamine. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Prenylamine lactate 6J3J6SXI7V 69-43-2 QPOFIDVRLWJICD-UHFFFAOYSA-N - International/Other Brands
- Bismethin / Corontin / Corpax / Elecor / Falliocor / Hostaginan / Segontin / Synadrin / Valecor
Categories
- ATC Codes
- C01DX52 — Prenylamine, combinations
- C01DX — Other vasodilators used in cardiac diseases
- C01D — VASODILATORS USED IN CARDIAC DISEASES
- C01 — CARDIAC THERAPY
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- Adrenergic Agents
- Agents causing hyperkalemia
- Amines
- Antiarrhythmic agents
- Bradycardia-Causing Agents
- Calcium Channel Blockers
- Calcium-Regulating Hormones and Agents
- Calmodulin, antagonists & inhibitors
- Cardiac Therapy
- Cardiovascular Agents
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Ethylamines
- Hydroxy Acids
- Membrane Transport Modulators
- Moderate Risk QTc-Prolonging Agents
- Neurotransmitter Agents
- Phenethylamines
- QTc Prolonging Agents
- Vasodilating Agents
- Vasodilators Used in Cardiac Diseases
- Chemical TaxonomyProvided by Classyfire
- 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
- Amine / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Diphenylmethane / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Phenylpropane
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- K2OH82Z000
- CAS number
- 390-64-7
- 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
References
- Synthesis Reference
- US3152173
- General References
- Not Available
- External Links
- KEGG Drug
- D02383
- PubChem Compound
- 9801
- PubChem Substance
- 46508663
- ChemSpider
- 9418
- BindingDB
- 50017723
- 8674
- ChEBI
- 8397
- ChEMBL
- CHEMBL24072
- Wikipedia
- Prenylamine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, film coated Oral 25 MG Tablet, film coated Oral 50 MG - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 36.5 °C PhysProp water solubility 50 mg/L (at 37 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) - Predicted Properties
Property Value Source Water Solubility 3.54e-05 mg/mL ALOGPS logP 5.89 ALOGPS logP 6.12 ChemAxon logS -7 ALOGPS pKa (Strongest Basic) 10.48 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 12.03 Å2 ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 107.09 m3·mol-1 ChemAxon Polarizability 39.76 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9774 Caco-2 permeable + 0.8194 P-glycoprotein substrate Substrate 0.5313 P-glycoprotein inhibitor I Inhibitor 0.59 P-glycoprotein inhibitor II Non-inhibitor 0.7214 Renal organic cation transporter Inhibitor 0.6263 CYP450 2C9 substrate Non-substrate 0.7387 CYP450 2D6 substrate Substrate 0.8796 CYP450 3A4 substrate Non-substrate 0.6941 CYP450 1A2 substrate Inhibitor 0.8455 CYP450 2C9 inhibitor Non-inhibitor 0.9304 CYP450 2D6 inhibitor Inhibitor 0.927 CYP450 2C19 inhibitor Inhibitor 0.6787 CYP450 3A4 inhibitor Non-inhibitor 0.6841 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6512 Ames test Non AMES toxic 0.8094 Carcinogenicity Non-carcinogens 0.8812 Biodegradation Not ready biodegradable 0.86 Rat acute toxicity 3.0889 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7311 hERG inhibition (predictor II) Inhibitor 0.7538
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
Drug created at September 11, 2007 20:28 / Updated at February 21, 2021 18:51