Identification
- Generic Name
- Aprindine
- DrugBank Accession Number
- DB01429
- Background
Aprindine is a cardiac depressant used in arrhythmias.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Aprindine (DB01429)
- Weight
- Average: 322.487
Monoisotopic: 322.24089897 - Chemical Formula
- C22H30N2
- Synonyms
- Aprindina
- Aprindine
- Aprindinum
- External IDs
- AC 1802
- Compound 99170
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 ASodium channel protein type 5 subunit alpha inhibitorHumans UCalmodulin inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hover over products below to view reaction partners
- 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 softwareAbatacept The metabolism of Aprindine can be increased when combined with Abatacept. Abiraterone The metabolism of Aprindine can be decreased when combined with Abiraterone. Acebutolol Acebutolol may increase the arrhythmogenic activities of Aprindine. Acetaminophen The metabolism of Aprindine can be decreased when combined with Acetaminophen. Acetyldigitoxin Acetyldigitoxin may increase the arrhythmogenic activities of Aprindine. Adalimumab The metabolism of Aprindine can be increased when combined with Adalimumab. Adenosine Adenosine may increase the arrhythmogenic activities of Aprindine. Ajmaline Ajmaline may increase the arrhythmogenic activities of Aprindine. Almotriptan The metabolism of Aprindine can be decreased when combined with Almotriptan. Alogliptin The metabolism of Alogliptin can be decreased when combined with Aprindine. 
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 Aprindine hydrochloride PB5EKT7Q2V 33237-74-0 KIPFVRHNAAZJOD-UHFFFAOYSA-N - International/Other Brands
- Aspenon / Fibocil (Lilly)
Categories
- ATC Codes
- C01BB04 — Aprindine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as indanes. These are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Indanes
- Sub Class
- Not Available
- Direct Parent
- Indanes
- Alternative Parents
- Dialkylarylamines / Aniline and substituted anilines / Aralkylamines / Trialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Amine / Aniline or substituted anilines / Aralkylamine / Aromatic homopolycyclic compound / Dialkylarylamine / Hydrocarbon derivative / Indane / Monocyclic benzene moiety / Organic nitrogen compound / Organonitrogen compound
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 5Y48085P9Q
- CAS number
- 37640-71-4
- InChI Key
- NZLBHDRPUJLHCE-UHFFFAOYSA-N
- InChI
- InChI=1S/C22H30N2/c1-3-23(4-2)15-10-16-24(21-13-6-5-7-14-21)22-17-19-11-8-9-12-20(19)18-22/h5-9,11-14,22H,3-4,10,15-18H2,1-2H3
- IUPAC Name
- N-[3-(diethylamino)propyl]-N-phenyl-2,3-dihydro-1H-inden-2-amine
- SMILES
- CCN(CC)CCCN(C1CC2=CC=CC=C2C1)C1=CC=CC=C1
References
- Synthesis Reference
Vanhoof, P. and Clarebout, P.; British Patent 1,321,424; June 27, 1973; assigned to Manufac- ture de Produits Pharmaceutiques A. Christiaens, SA
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015498
- KEGG Drug
- D01326
- PubChem Compound
- 2218
- PubChem Substance
- 46505478
- ChemSpider
- 2132
- 1054
- ChEBI
- 135370
- ChEMBL
- CHEMBL1213033
- ZINC
- ZINC000001420561
- Therapeutic Targets Database
- DAP000954
- PharmGKB
- PA164764496
- Wikipedia
- Aprindine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 120-121 °C Vanhoof, P. and Clarebout, P.; British Patent 1,321,424; June 27, 1973; assigned to Manufacture de Produits Pharmaceutiques A. Christiaens, SA logP 4.86 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.00782 mg/mL ALOGPS logP 5.58 ALOGPS logP 4.99 ChemAxon logS -4.6 ALOGPS pKa (Strongest Basic) 9.94 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 6.48 Å2 ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 105.22 m3·mol-1 ChemAxon Polarizability 40.02 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9925 Blood Brain Barrier + 0.9776 Caco-2 permeable + 0.7047 P-glycoprotein substrate Substrate 0.6441 P-glycoprotein inhibitor I Inhibitor 0.7951 P-glycoprotein inhibitor II Inhibitor 0.5188 Renal organic cation transporter Inhibitor 0.7209 CYP450 2C9 substrate Non-substrate 0.7897 CYP450 2D6 substrate Substrate 0.8918 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Inhibitor 0.7381 CYP450 2C9 inhibitor Non-inhibitor 0.7661 CYP450 2D6 inhibitor Inhibitor 0.5 CYP450 2C19 inhibitor Inhibitor 0.5287 CYP450 3A4 inhibitor Non-inhibitor 0.7571 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8111 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.6834 Biodegradation Not ready biodegradable 0.9961 Rat acute toxicity 2.4059 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7928 hERG inhibition (predictor II) Inhibitor 0.7202
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
- Yes
- Actions
- Inhibitor
- General Function
- Voltage-gated sodium channel activity involved in sa node cell action potential
- Specific Function
- This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the pr...
- Gene Name
- SCN5A
- Uniprot ID
- Q14524
- Uniprot Name
- Sodium channel protein type 5 subunit alpha
- Molecular Weight
- 226937.475 Da
References
- Sato R, Hisatome I, Tanaka Y, Sasaki N, Kotake H, Mashiba H, Katori R: Aprindine blocks the sodium current in guinea-pig ventricular myocytes. Naunyn Schmiedebergs Arch Pharmacol. 1991 Sep;344(3):331-6. [Article]
- Kamiya K, Kodama I, Toyama J: A combination of inactivated sodium channel blockers causes competitive interaction on dV/dtmax of single ventricular myocytes. Cardiovasc Res. 1991 Jun;25(6):516-22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Levine SN, Hollier B: Aprindine inhibits calmodulin-stimulated phosphodiesterase and Ca-ATPase activities. J Cardiovasc Pharmacol. 1983 Jan-Feb;5(1):151-6. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Ebner T, Eichelbaum M: The metabolism of aprindine in relation to the sparteine/debrisoquine polymorphism. Br J Clin Pharmacol. 1993 Apr;35(4):426-30. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
- Gene Name
- ORM1
- Uniprot ID
- P02763
- Uniprot Name
- Alpha-1-acid glycoprotein 1
- Molecular Weight
- 23511.38 Da
References
- Teirlynck O, Belpaire FM, Andreasen F: Binding of aprindine and moxaprindine to human serum, alpha 1-acid glycoprotein and serum of healthy and diseased humans. Eur J Clin Pharmacol. 1982;21(5):427-31. [Article]
Drug created at July 24, 2007 13:04 / Updated at April 03, 2021 10:01