Identification

Name
Amiodarone
Accession Number
DB01118  (APRD00288)
Type
Small Molecule
Groups
Approved, Investigational
Description

An antianginal and antiarrhythmic drug. It increases the duration of ventricular and atrial muscle action by inhibiting Na,K-activated myocardial adenosine triphosphatase. There is a resulting decrease in heart rate and in vascular resistance.

Structure
Thumb
Synonyms
  • 2-Butyl-3-(3,5-diiodo-4-(2-diethylaminoethoxy)benzoyl)benzofuran
  • 2-Butyl-3-benzofuranyl 4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl ketone
  • 2-n-Butyl-3',5'-diiodo-4'-N-diethylaminoethoxy-3-benzoylbenzofuran
  • Amiodarona
  • Amiodaronum
Product Ingredients
IngredientUNIICASInChI Key
Amiodarone hydrochloride976728SY6Z19774-82-4ITPDYQOUSLNIHG-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AmiodaroneTablet200 mgOralSivem Pharmaceuticals Ulc2012-06-10Not applicableCanada
AmiodaroneTablet200 mgOralSorres Pharma Inc2009-06-232014-06-20Canada
AmiodaroneTablet200 mgOralSanis Health Inc2011-06-10Not applicableCanada
Amiodarone for Injection 50mg/mlSolution50 mgIntravenousTeva2004-04-21Not applicableCanada
Amiodarone HydrochlorideInjection50 mg/1mLIntravenousAmphastar Pharmaceuticals, Inc.2004-02-112008-01-24Us
Amiodarone HydrochlorideInjection50 mg/1mLIntravenousAmphastar Pharmaceuticals, Inc.2004-02-112008-01-24Us
Amiodarone HydrochlorideInjection50 mg/1mLIntravenousAmphastar Pharmaceuticals, Inc.2004-02-112008-01-24Us
Amiodarone Hydrochloride for InjectionLiquid50 mgIntravenousSandoz Canada Incorporated2000-06-14Not applicableCanada
Amiodarone Hydrochloride for InjectionSolution50 mgIntravenousHospira, Inc.2002-08-29Not applicableCanada
Amiodarone Hydrochloride InjectionSolution50 mgIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amiodarone HClTablet400 mg/1OralCameron Pharmaceuticals2013-01-01Not applicableUs
Amiodarone HClTablet400 mg/1OralMayne Pharma2013-01-01Not applicableUs
Amiodarone HClTablet100 mg/1OralCameron Pharmaceuticals2017-01-01Not applicableUs
Amiodarone HClTablet200 mg/1OralMayne Pharma2013-01-01Not applicableUs
Amiodarone HClTablet100 mg/1OralMayne Pharma2017-01-01Not applicableUs
Amiodarone HClTablet200 mg/1OralCameron Pharmaceuticals2013-01-01Not applicableUs
Amiodarone HydrochlorideInjection, solution50 mg/1mLIntravenousGeneral Injectables & Vaccines2014-09-022018-12-31Us
Amiodarone hydrochlorideTablet200 mg/1OralREMEDYREPACK INC.2018-10-22Not applicableUs
Amiodarone HydrochlorideInjection, solution50 mg/1mLIntravenousMylan Institutional LLC2002-10-14Not applicableUs
Amiodarone HydrochlorideTablet200 mg/1OralLake Erie Medical Dba Quality Care Produts Llc1998-11-302017-06-01Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Amiodarone HClAmiodarone hydrochloride (1.8 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2013-10-18Not applicableUs
International/Other Brands
Amio-Aqueous IV / Aratac / Arycor / Atlansil / Tachyra
Categories
UNII
N3RQ532IUT
CAS number
1951-25-3
Weight
Average: 645.3116
Monoisotopic: 645.023680639
Chemical Formula
C25H29I2NO3
InChI Key
IYIKLHRQXLHMJQ-UHFFFAOYSA-N
InChI
InChI=1S/C25H29I2NO3/c1-4-7-11-22-23(18-10-8-9-12-21(18)31-22)24(29)17-15-19(26)25(20(27)16-17)30-14-13-28(5-2)6-3/h8-10,12,15-16H,4-7,11,13-14H2,1-3H3
IUPAC Name
{2-[4-(2-butyl-1-benzofuran-3-carbonyl)-2,6-diiodophenoxy]ethyl}diethylamine
SMILES
CCCCC1=C(C(=O)C2=CC(I)=C(OCCN(CC)CC)C(I)=C2)C2=C(O1)C=CC=C2

Pharmacology

Indication

Intravenously, for initiation of treatment and prophylaxis of frequently recurring ventricular fibrillation and hemodynamically unstable ventricular tachycardia in patients refractory to other therapy. Orally, for the treatment of life-threatening recurrent ventricular arrhythmias such as recurrent ventricular fibrillation and recurrent hemodynamically unstable ventricular tachycardia.

Associated Conditions
Pharmacodynamics

Amiodarone belongs to a class of drugs called Vaughan-Williams Class III antiarrhythmic agents. It is used in the treatment of a wide range of cardiac tachyarhthmias, including both ventricular and supraventricular (atrial) arrhythmias. After intravenous administration in man, amiodarone relaxes vascular smooth muscle, reduces peripheral vascular resistance (afterload), and slightly increases cardiac index. Amiodarone prolongs phase 3 of the cardiac action potential. It has numerous other effects however, including actions that are similar to those of antiarrhythmic classes Ia, II, and IV. Amiodarone shows beta blocker-like and calcium channel blocker-like actions on the SA and AV nodes, increases the refractory period via sodium- and potassium-channel effects, and slows intra-cardiac conduction of the cardiac action potential, via sodium-channel effects.

Mechanism of action

The antiarrhythmic effect of amiodarone may be due to at least two major actions. It prolongs the myocardial cell-action potential (phase 3) duration and refractory period and acts as a noncompetitive a- and b-adrenergic inhibitor.

TargetActionsOrganism
APotassium voltage-gated channel subfamily H member 2
inhibitor
Human
ABeta-1 adrenergic receptor
antagonist
Human
UVoltage-dependent T-type calcium channel subunit alpha-1H
inhibitor
Human
AVoltage-dependent calcium channel subunit alpha-2/delta-2
inhibitor
Human
UThyroid hormone receptor alphaNot AvailableHuman
UThyroid hormone receptor betaNot AvailableHuman
UPeroxisome proliferator-activated receptor gammaNot AvailableHuman
Absorption

Slow and variable (about 20 to 55% of an oral dose is absorbed).

Volume of distribution
Not Available
Protein binding

>96%

Metabolism

Amiodarone is extensively metabolized in the liver via CYP2C8 (under 1% unchanged in urine), and can effect the metabolism of numerous other drugs. The major metabolite of amiodarone is desethylamiodarone (DEA), which also has antiarrhythmic properties. The metabolism of amiodarone is inhibited by grapefruit juice, leading to elevated serum levels of amiodarone.

Route of elimination

Amiodarone is eliminated primarily by hepatic metabolism and biliary excretion and there is negligible excretion of amiodarone or DEA in urine.

Half life

58 days (range 15-142 days)

Clearance
  • 90-158 mL/h/kg [Healthy with a single dose IV (5 mg/kg over 15 min)]
  • 100 mL/h/kg [Normal subjects > 65 yrs]
  • 150 mL/h/kg [younger subjects]
  • 220 and 440 mL/h/kg [patients with VT and VF]
Toxicity

Intravenous, mouse: LD50 = 178 mg/kg. Some side effects have a significant mortality rate: specifically, hepatitis, exacerbation of asthma and congestive failure, and pneumonitis.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Amiodarone Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Potassium voltage-gated channel subfamily H member 2MiRP1Not AvailableKCNE2ADR Directly StudiedThe presence of polymorphisms in KCNH2 and KCNE2 may potentially be associated with increased susceptibility to long Q-T syndrome or cardiac arrhytmia when treated with amiodarone.Details

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of Amiodarone can be decreased when combined with (R)-warfarin.
(S)-WarfarinThe metabolism of Amiodarone can be decreased when combined with (S)-Warfarin.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Amiodarone is combined with 2,4-thiazolidinedione.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Amiodarone.
3,5-diiodothyropropionic acidThe metabolism of Amiodarone can be decreased when combined with 3,5-diiodothyropropionic acid.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Amiodarone.
4-MethoxyamphetamineThe metabolism of Amiodarone can be decreased when combined with 4-Methoxyamphetamine.
5-androstenedioneThe metabolism of Amiodarone can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of Amiodarone can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of Amiodarone can be decreased when combined with 6-O-benzylguanine.
Food Interactions
  • Grapefruit and grapefruit juice should be avoided throughout treatment.
  • Grapefruit can significantly increase serum levels of this product.
  • Take without regard to meals.

References

Synthesis Reference
US3248401
General References
  1. DELTOUR G, BINON F, TONDEUR R, GOLDENBERG C, HENAUX F, SION R, DERAY E, CHARLIER R: [Studies in the benzofuran series. VI. Coronary-dilating activity of alkylated and aminoalkylated derivatives of 3-benzoylbenzofuran]. Arch Int Pharmacodyn Ther. 1962 Sep 1;139:247-54. [PubMed:14026835]
  2. CHARLIER R, DELTOUR G, TONDEUR R, BINON F: [Studies in the benzofuran series. VII. Preliminary pharmacological study of 2-butyl-3-(3,5-diiodo-4-beta-N-diethylaminoethoxybenzoyl)-benzofuran]. Arch Int Pharmacodyn Ther. 1962 Sep 1;139:255-64. [PubMed:14020244]
  3. Singh BN, Vaughan Williams EM: The effect of amiodarone, a new anti-anginal drug, on cardiac muscle. Br J Pharmacol. 1970 Aug;39(4):657-67. [PubMed:5485142]
  4. Rosenbaum MB, Chiale PA, Halpern MS, Nau GJ, Przybylski J, Levi RJ, Lazzari JO, Elizari MV: Clinical efficacy of amiodarone as an antiarrhythmic agent. Am J Cardiol. 1976 Dec;38(7):934-44. [PubMed:793369]
  5. Rosenbaum MB, Chiale PA, Haedo A, Lazzari JO, Elizari MV: Ten years of experience with amiodarone. Am Heart J. 1983 Oct;106(4 Pt 2):957-64. [PubMed:6613843]
  6. Electronic Medicines Compendium Amiodarone 100mg Tablets [Link]
External Links
Human Metabolome Database
HMDB0015250
KEGG Drug
D02910
KEGG Compound
C06823
PubChem Compound
2157
PubChem Substance
46507387
ChemSpider
2072
BindingDB
18957
ChEBI
2663
ChEMBL
CHEMBL633
Therapeutic Targets Database
DAP000496
PharmGKB
PA448383
IUPHAR
2566
Guide to Pharmacology
GtP Drug Page
HET
BBI
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Amiodarone
ATC Codes
C01BD01 — Amiodarone
AHFS Codes
  • 24:04.04.20 — Class III Antiarrythmics
PDB Entries
4o8z / 5h4d
FDA label
Download (545 KB)
MSDS
Download (51.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Unknown StatusPreventionPatients With Coronary Artery Disease Scheduled for by Pass Surgery1
1CompletedTreatmentHealthy Volunteers2
2CompletedPreventionArrhythmia of ventricular origin / Prophylaxis of perioperative arrhythmia1
2CompletedTreatmentCardiac Arrest1
2WithdrawnTreatmentBlood Pressures1
3CompletedPreventionArrythmias / Cardiovascular Disease (CVD) / Heart Arrest / Heart Diseases / Myocardial Infarction / Ventricular Fibrillation1
3CompletedPreventionAtrial Flutter / Nonvalvular Atrial Fibrillation1
3CompletedPreventionNonvalvular Atrial Fibrillation2
3CompletedTreatmentArrythmias / Cardiovascular Disease (CVD) / Congestive Heart Failure (CHF) / Death, Sudden,Cardiac / Heart Diseases / Heart Failure, Unspecified1
3CompletedTreatmentArrythmias / Cardiovascular Disease (CVD) / Heart Diseases / Nonvalvular Atrial Fibrillation1
3CompletedTreatmentCardiac Arrest1
3CompletedTreatmentCerebrovascular Accidents / Nonvalvular Atrial Fibrillation / Sudden Death1
3CompletedTreatmentNonvalvular Atrial Fibrillation3
3CompletedTreatmentPostoperative Atrial Fibrillation1
3Not Yet RecruitingPreventionNonvalvular Atrial Fibrillation1
3Not Yet RecruitingTreatmentAtrial Fibrillation Rapid / Nonvalvular Atrial Fibrillation / Sepsis / Shock, Septic / Ventricular Fibrillation1
3RecruitingTreatmentAtrial Fibrillation in High Risk Patients / Thoracic Surgery1
3RecruitingTreatmentChagas Cardiomyopathy1
3RecruitingTreatmentHeart Diseases / Prophylaxis of cardiomyopathy / Ventricular Premature Complexes1
3SuspendedTreatmentNonvalvular Atrial Fibrillation1
3TerminatedTreatmentDefibrillators, Implantable / Ventricular Tachycardia (VT)1
3TerminatedTreatmentHeart Failure, Unspecified / Nonvalvular Atrial Fibrillation1
3Unknown StatusPreventionLung Cancers / Nonvalvular Atrial Fibrillation1
3Unknown StatusTreatmentNonvalvular Atrial Fibrillation1
4Active Not RecruitingTreatmentHeart Failure, Unspecified1
4CompletedPreventionCoronary Artery Bypass Graft Surgery Patients / Nonvalvular Atrial Fibrillation1
4CompletedPreventionNonvalvular Atrial Fibrillation1
4CompletedPreventionNonvalvular Atrial Fibrillation / Oesophagectomy1
4CompletedPreventionNonvalvular Atrial Fibrillation / Surgery, Cardiac1
4CompletedTreatmentNonvalvular Atrial Fibrillation2
4CompletedTreatmentRecurrent Ventricular Tachycardia1
4Enrolling by InvitationTreatmentNew Onset Atrial Fibrillation / Severe Sepsis / Shock, Septic1
4Not Yet RecruitingTreatmentNonvalvular Atrial Fibrillation1
4Not Yet RecruitingTreatmentProphylaxis of cardiomyopathy / Ventricular Premature Beats, Contractions, or Systoles1
4RecruitingTreatmentArrhythmias Ventricular1
4RecruitingTreatmentHeart Failure, Unspecified / Nonvalvular Atrial Fibrillation1
4RecruitingTreatmentMyocardial Infarction / Ventricular Tachyarrhythmias1
4RecruitingTreatmentNonvalvular Atrial Fibrillation1
4Unknown StatusPreventionNonvalvular Atrial Fibrillation1
4WithdrawnTreatmentNonvalvular Atrial Fibrillation1
Not AvailableActive Not RecruitingTreatmentNonvalvular Atrial Fibrillation1
Not AvailableActive Not RecruitingTreatmentNonvalvular Atrial Fibrillation / Quality of Life1
Not AvailableCompletedNot AvailableAtrial Tachycardia / Nonvalvular Atrial Fibrillation1
Not AvailableCompletedNot AvailableDeath, Sudden,Cardiac / Heart Arrest1
Not AvailableCompletedPreventionNonvalvular Atrial Fibrillation1
Not AvailableCompletedPreventionOther Intraoperative Cardiac Functional Disturbances During Cardiac Surgery1
Not AvailableCompletedTreatmentArrythmias / Nonvalvular Atrial Fibrillation1
Not AvailableCompletedTreatmentMonomorphic Ventricular Tachycardia1
Not AvailableCompletedTreatmentNonvalvular Atrial Fibrillation2
Not AvailableCompletedTreatmentPersistant Atrial Fibrillation1
Not AvailableNot Yet RecruitingTreatmentAt Least 10 Points in Rassi Risk Score for Death / Chagas Cardiomyopathy / Non-sustained Ventricular Tachycardia1
Not AvailableRecruitingPreventionNonvalvular Atrial Fibrillation1
Not AvailableRecruitingTreatmentHeart Failure, Unspecified / Recurrent Atrial Fibrillation1
Not AvailableTerminatedTreatmentMitral Valvulopathy / Nonvalvular Atrial Fibrillation1
Not AvailableTerminatedTreatmentNonvalvular Atrial Fibrillation1
Not AvailableTerminatedTreatmentVentricular Tachycardia (VT)2
Not AvailableUnknown StatusTreatmentNonvalvular Atrial Fibrillation1
Not AvailableUnknown StatusTreatmentSurgery, Cardiac1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Alphapharm Party Ltd.
  • Amerisource Health Services Corp.
  • Amphastar Pharmaceuticals
  • Apotex Inc.
  • APP Pharmaceuticals
  • A-S Medication Solutions LLC
  • Aurolife Pharma LLC
  • Aurosal Pharmaceuticals LLC
  • Barr Pharmaceuticals
  • Baxter International Inc.
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Bioniche Pharma
  • Cadila Healthcare Ltd.
  • Cardinal Health
  • Caremark LLC
  • Diversified Healthcare Services Inc.
  • Eon Labs
  • General Injectables and Vaccines Inc.
  • Gland Pharma Ltd.
  • Heartland Repack Services LLC
  • Hikma Pharmaceuticals
  • Hospira Inc.
  • Mckesson Corp.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Murty Pharmaceuticals Inc.
  • Mylan
  • Neuman Distributors Inc.
  • Novex Pharma
  • Novopharm Ltd.
  • Par Pharmaceuticals
  • Physicians Total Care Inc.
  • Prepak Systems Inc.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sagent Pharmaceuticals
  • Sandhills Packaging Inc.
  • Sandoz
  • Sanofi-Aventis Inc.
  • Sicor Pharmaceuticals
  • Spectrum Pharmaceuticals
  • Taro Pharmaceuticals USA
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Upsher Smith Laboratories
  • Vangard Labs Inc.
  • West-Ward Pharmaceuticals
  • Wockhardt Ltd.
  • Wyeth Pharmaceuticals
  • Zydus Pharmaceuticals
Dosage forms
FormRouteStrength
Injection, solutionIntravenous1.8 mg/1mL
TabletOral100 mg/1
TabletOral400 mg/1
InjectionIntravenous150 mg/3mL
InjectionIntravenous450 mg/9mL
InjectionIntravenous50 mg/1mL
InjectionIntravenous900 mg/18mL
Injection, solutionIntravenous150 mg/3mL
Injection, solutionIntravenous450 mg/9mL
Injection, solutionIntravenous50 mg/1mL
Injection, solutionIntravenous900 mg/18mL
TabletOral200 mg/1
TabletOral300 mg/1
LiquidIntravenous50 mg
SolutionIntravenous50 mg
Injection, solutionIntravenous1.5 mg/1mL
TabletOral100 mg
TabletOral200 mg
Prices
Unit descriptionCostUnit
Amiodarone hcl powder38.98USD g
Pacerone 100 mg tablet7.58USD tablet
Pacerone 400 mg tablet7.43USD tablet
Amiodarone hcl 400 mg tablet6.32USD tablet
Cordarone 200 mg tablet4.78USD tablet
Pacerone 200 mg tablet3.53USD tablet
Amiodarone hcl 200 mg tablet3.37USD tablet
Cordarone 200 mg Tablet2.32USD tablet
Apo-Amiodarone 200 mg Tablet1.3USD tablet
Mylan-Amiodarone 200 mg Tablet1.3USD tablet
Novo-Amiodarone 200 mg Tablet1.3USD tablet
Pms-Amiodarone 200 mg Tablet1.3USD tablet
Ratio-Amiodarone 200 mg Tablet1.3USD tablet
Sandoz Amiodarone 200 mg Tablet1.3USD tablet
Amiodarone 150 mg/3 ml vial0.83USD ml
Pms-Amiodarone 100 mg Tablet0.72USD tablet
Amiodarone 900 mg/18 ml vial0.59USD ml
Amiodarone 450 mg/9 ml vial0.57USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5134127No1992-07-282010-01-23Us
US6869939No2005-03-222022-05-04Us
US7635773No2009-12-222029-03-13Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)156Tondeur, R. and Binon, F.; U.S. Patent 3,248,401; April 26,1966; assigned to Societe Beige de I'Azote et des Produits Chimiques du Marly, SA, Belgium.
water solubilityLowNot Available
logP7.57AVDEEF,A (1997)
Predicted Properties
PropertyValueSource
Water Solubility0.00476 mg/mLALOGPS
logP7.24ALOGPS
logP7.64ChemAxon
logS-5.1ALOGPS
pKa (Strongest Basic)8.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area42.68 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity145.05 m3·mol-1ChemAxon
Polarizability56.78 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8615
Caco-2 permeable+0.66
P-glycoprotein substrateSubstrate0.8044
P-glycoprotein inhibitor IInhibitor0.8563
P-glycoprotein inhibitor IIInhibitor0.8388
Renal organic cation transporterInhibitor0.5099
CYP450 2C9 substrateNon-substrate0.7959
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.7188
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorInhibitor0.8948
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8615
Ames testNon AMES toxic0.5661
CarcinogenicityNon-carcinogens0.7696
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6539 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5932
hERG inhibition (predictor II)Inhibitor0.7638
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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0000009000-8cbab89986761a7a1bc9
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0pbj-9300003000-503a542bf1a7678f385e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9110000000-543b8de3c9ba390fa765
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0791000000-77d5d18989052c45b006
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a59-0980000000-a77e32d189cf8e2acdf1
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0apl-0940000000-30e016c113387b37ca7c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0000009000-e87a9a6e983c00161beb

Taxonomy

Description
This compound belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Aryl-phenylketones
Alternative Parents
Benzofurans / Phenoxy compounds / Phenol ethers / Benzoyl derivatives / 3-aroylfurans / Iodobenzenes / Alkyl aryl ethers / Aryl iodides / Heteroaromatic compounds / Trialkylamines
show 5 more
Substituents
Aryl-phenylketone / Benzofuran / Phenol ether / 3-aroylfuran / Benzoyl / Phenoxy compound / Alkyl aryl ether / Halobenzene / Iodobenzene / Benzenoid
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, organoiodine compound, 1-benzofurans, aromatic ketone (CHEBI:2663)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the ...
Gene Name
KCNH2
Uniprot ID
Q12809
Uniprot Name
Potassium voltage-gated channel subfamily H member 2
Molecular Weight
126653.52 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Wang SP, Wang JA, Luo RH, Cui WY, Wang H: Potassium channel currents in rat mesenchymal stem cells and their possible roles in cell proliferation. Clin Exp Pharmacol Physiol. 2008 Sep;35(9):1077-84. doi: 10.1111/j.1440-1681.2008.04964.x. Epub 2008 May 25. [PubMed:18505444]
  3. Varro A, Biliczki P, Iost N, Virag L, Hala O, Kovacs P, Matyus P, Papp JG: Theoretical possibilities for the development of novel antiarrhythmic drugs. Curr Med Chem. 2004 Jan;11(1):1-11. [PubMed:14754422]
  4. Waldhauser KM, Brecht K, Hebeisen S, Ha HR, Konrad D, Bur D, Krahenbuhl S: Interaction with the hERG channel and cytotoxicity of amiodarone and amiodarone analogues. Br J Pharmacol. 2008 Oct;155(4):585-95. doi: 10.1038/bjp.2008.287. Epub 2008 Jul 7. [PubMed:18604229]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. Doggrell SA, Brown L: Present and future pharmacotherapy for heart failure. Expert Opin Pharmacother. 2002 Jul;3(7):915-30. [PubMed:12083991]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Scaffold protein binding
Specific Function
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...
Gene Name
CACNA1H
Uniprot ID
O95180
Uniprot Name
Voltage-dependent T-type calcium channel subunit alpha-1H
Molecular Weight
259160.2 Da
References
  1. Cohen CJ, Spires S, Van Skiver D: Block of T-type Ca channels in guinea pig atrial cells by antiarrhythmic agents and Ca channel antagonists. J Gen Physiol. 1992 Oct;100(4):703-28. [PubMed:1281221]
  2. Lewalter T, Pittrow D, Goette A, Kirch W, Hohnloser S: [Clinical pharmacology and electrophysiological properties of dronedarone]. Dtsch Med Wochenschr. 2010 Mar;135 Suppl 2:S43-7. doi: 10.1055/s-0030-1249208. Epub 2010 Mar 10. [PubMed:20221978]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated calcium channel activity
Specific Function
The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Acts as a regulatory subunit for P/Q-t...
Gene Name
CACNA2D2
Uniprot ID
Q9NY47
Uniprot Name
Voltage-dependent calcium channel subunit alpha-2/delta-2
Molecular Weight
129816.095 Da
References
  1. Cohen CJ, Spires S, Van Skiver D: Block of T-type Ca channels in guinea pig atrial cells by antiarrhythmic agents and Ca channel antagonists. J Gen Physiol. 1992 Oct;100(4):703-28. [PubMed:1281221]
  2. Lewalter T, Pittrow D, Goette A, Kirch W, Hohnloser S: [Clinical pharmacology and electrophysiological properties of dronedarone]. Dtsch Med Wochenschr. 2010 Mar;135 Suppl 2:S43-7. doi: 10.1055/s-0030-1249208. Epub 2010 Mar 10. [PubMed:20221978]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Isoform Alpha-1: Nuclear hormone receptor that can act as a repressor or activator of transcription. High affinity receptor for thyroid hormones, including triiodothyronine and thyroxine.Isoform Al...
Gene Name
THRA
Uniprot ID
P10827
Uniprot Name
Thyroid hormone receptor alpha
Molecular Weight
54815.055 Da
References
  1. Carlsson B, Singh BN, Temciuc M, Nilsson S, Li YL, Mellin C, Malm J: Synthesis and preliminary characterization of a novel antiarrhythmic compound (KB130015) with an improved toxicity profile compared with amiodarone. J Med Chem. 2002 Jan 31;45(3):623-30. [PubMed:11806713]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor that can act as a repressor or activator of transcription. High affinity receptor for thyroid hormones, including triiodothyronine and thyroxine.
Gene Name
THRB
Uniprot ID
P10828
Uniprot Name
Thyroid hormone receptor beta
Molecular Weight
52787.16 Da
References
  1. Carlsson B, Singh BN, Temciuc M, Nilsson S, Li YL, Mellin C, Malm J: Synthesis and preliminary characterization of a novel antiarrhythmic compound (KB130015) with an improved toxicity profile compared with amiodarone. J Med Chem. 2002 Jan 31;45(3):623-30. [PubMed:11806713]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...
Gene Name
PPARG
Uniprot ID
P37231
Uniprot Name
Peroxisome proliferator-activated receptor gamma
Molecular Weight
57619.58 Da
References
  1. Szalowska E, van der Burg B, Man HY, Hendriksen PJ, Peijnenburg AA: Model steatogenic compounds (amiodarone, valproic acid, and tetracycline) alter lipid metabolism by different mechanisms in mouse liver slices. PLoS One. 2014 Jan 29;9(1):e86795. doi: 10.1371/journal.pone.0086795. eCollection 2014. [PubMed:24489787]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Elsherbiny ME, El-Kadi AO, Brocks DR: The metabolism of amiodarone by various CYP isoenzymes of human and rat, and the inhibitory influence of ketoconazole. J Pharm Pharm Sci. 2008;11(1):147-59. [PubMed:18445370]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  4. Ohyama K, Nakajima M, Nakamura S, Shimada N, Yamazaki H, Yokoi T: A significant role of human cytochrome P450 2C8 in amiodarone N-deethylation: an approach to predict the contribution with relative activity factor. Drug Metab Dispos. 2000 Nov;28(11):1303-10. [PubMed:11038157]
  5. Clin-Info. (2006). In Compendium of Pharmaceuticals and Specialties: The Canadian Drug Reference for Health Professionals (pp. L53). Canadian Pharmacists Association. [ISBN:1-894402-22-7]
  6. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  7. Electronic Medicines Compendium Amiodarone 100mg Tablets [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Ohyama K, Nakajima M, Nakamura S, Shimada N, Yamazaki H, Yokoi T: A significant role of human cytochrome P450 2C8 in amiodarone N-deethylation: an approach to predict the contribution with relative activity factor. Drug Metab Dispos. 2000 Nov;28(11):1303-10. [PubMed:11038157]
  4. Clin-Info. (2006). In Compendium of Pharmaceuticals and Specialties: The Canadian Drug Reference for Health Professionals (pp. L53). Canadian Pharmacists Association. [ISBN:1-894402-22-7]
  5. Website [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Yamreudeewong W, DeBisschop M, Martin LG, Lower DL: Potentially significant drug interactions of class III antiarrhythmic drugs. Drug Saf. 2003;26(6):421-38. [PubMed:12688833]
  4. Clin-Info. (2006). In Compendium of Pharmaceuticals and Specialties: The Canadian Drug Reference for Health Professionals (pp. L53). Canadian Pharmacists Association. [ISBN:1-894402-22-7]
  5. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Yamreudeewong W, DeBisschop M, Martin LG, Lower DL: Potentially significant drug interactions of class III antiarrhythmic drugs. Drug Saf. 2003;26(6):421-38. [PubMed:12688833]
  3. Naganuma M, Shiga T, Nishikata K, Tsuchiya T, Kasanuki H, Fujii E: Role of desethylamiodarone in the anticoagulant effect of concurrent amiodarone and warfarin therapy. J Cardiovasc Pharmacol Ther. 2001 Oct;6(4):363-7. doi: 10.1177/107424840100600405. [PubMed:11907638]
  4. Heimark LD, Wienkers L, Kunze K, Gibaldi M, Eddy AC, Trager WF, O'Reilly RA, Goulart DA: The mechanism of the interaction between amiodarone and warfarin in humans. Clin Pharmacol Ther. 1992 Apr;51(4):398-407. [PubMed:1563209]
  5. Clin-Info. (2006). In Compendium of Pharmaceuticals and Specialties: The Canadian Drug Reference for Health Professionals (pp. L53). Canadian Pharmacists Association. [ISBN:1-894402-22-7]
  6. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  7. Drug Interactions & Labeling - FDA [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Crooy P, De Neys R: Virginiamycin: nomenclature. J Antibiot (Tokyo). 1972 Jun;25(6):371-2. [PubMed:4568014]
  4. Naganuma M, Shiga T, Nishikata K, Tsuchiya T, Kasanuki H, Fujii E: Role of desethylamiodarone in the anticoagulant effect of concurrent amiodarone and warfarin therapy. J Cardiovasc Pharmacol Ther. 2001 Oct;6(4):363-7. doi: 10.1177/107424840100600405. [PubMed:11907638]
  5. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  6. Amiodarone FDA label [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Ohyama K, Nakajima M, Nakamura S, Shimada N, Yamazaki H, Yokoi T: A significant role of human cytochrome P450 2C8 in amiodarone N-deethylation: an approach to predict the contribution with relative activity factor. Drug Metab Dispos. 2000 Nov;28(11):1303-10. [PubMed:11038157]
  3. Some Common Substrates, Inhibitors and Inducers of CYP450 Isoenzymes [Link]
  4. Amiodarone FDA label [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-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 oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Elsherbiny ME, El-Kadi AO, Brocks DR: The metabolism of amiodarone by various CYP isoenzymes of human and rat, and the inhibitory influence of ketoconazole. J Pharm Pharm Sci. 2008;11(1):147-59. [PubMed:18445370]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
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 oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
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 oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Ohyama K, Nakajima M, Suzuki M, Shimada N, Yamazaki H, Yokoi T: Inhibitory effects of amiodarone and its N-deethylated metabolite on human cytochrome P450 activities: prediction of in vivo drug interactions. Br J Clin Pharmacol. 2000 Mar;49(3):244-53. [PubMed:10718780]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Schuetz EG, Beck WT, Schuetz JD: Modulators and substrates of P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in human colon carcinoma cells. Mol Pharmacol. 1996 Feb;49(2):311-8. [PubMed:8632764]
  2. Katoh M, Nakajima M, Yamazaki H, Yokoi T: Inhibitory effects of CYP3A4 substrates and their metabolites on P-glycoprotein-mediated transport. Eur J Pharm Sci. 2001 Feb;12(4):505-13. [PubMed:11231118]
  3. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. [PubMed:12235267]
  4. Tiberghien F, Loor F: Ranking of P-glycoprotein substrates and inhibitors by a calcein-AM fluorometry screening assay. Anticancer Drugs. 1996 Jul;7(5):568-78. [PubMed:8862725]
  5. Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR: Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res. 1999 Mar;16(3):408-14. [PubMed:10213372]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [PubMed:24014644]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Electronic Medicines Compendium Amiodarone 100mg Tablets [Link]

Drug created on June 13, 2005 07:24 / Updated on December 10, 2018 13:38