amiodarone indications/contra

Stem definitionDrug idCAS RN
antiarrhythmics 176 1951-25-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • amiodarone
  • amidorone
  • sedacoron
  • amiodarone hydrochloride
  • amiodarone HCl
An antianginal and class III antiarrhythmic drug. It increases the duration of ventricular and atrial muscle action by inhibiting POTASSIUM CHANNELS and VOLTAGE-GATED SODIUM CHANNELS. There is a resulting decrease in heart rate and in vascular resistance.
  • Molecular weight: 645.32
  • Formula: C25H29I2NO3
  • CLOGP: 8.95
  • LIPINSKI: 2
  • HAC: 4
  • HDO: 0
  • TPSA: 42.68
  • ALOGS: -5.13
  • ROTB: 11

Drug dosage:

DoseUnitRoute
0.20 g O
0.20 g P

Approvals:

DateAgencyCompanyOrphan
Dec. 24, 1985 FDA WYETH PHARMS INC

FDA Adverse Event Reporting System

scroll-->
MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hyperthyroidism 2089.19 39.33 392 5419 2442 3377606
Drug interaction 1771.48 39.33 595 5216 46217 3333831
Torsade de pointes 1125.13 39.33 237 5574 2792 3377256
Pulmonary toxicity 1098.25 39.33 204 5607 1170 3378878
Bradycardia 1061.82 39.33 317 5494 16352 3363696
Ventricular tachycardia 994.92 39.33 242 5569 5620 3374428
Electrocardiogram QT prolonged 912.00 39.33 256 5555 10539 3369509
Atrial fibrillation 849.83 39.33 292 5519 23649 3356399
Hypothyroidism 837.20 39.33 211 5600 5678 3374370
Toxicity to various agents 827.77 39.33 343 5468 46711 3333337
Pulmonary fibrosis 816.33 39.33 195 5616 4167 3375881
Interstitial lung disease 714.28 39.33 225 5586 13791 3366257
Dyspnoea 642.00 39.33 369 5442 102565 3277483
International normalised ratio increased 508.30 39.33 176 5635 14439 3365609
Thyroiditis 485.21 39.33 88 5723 427 3379621
Hypotension 483.29 39.33 240 5571 49274 3330774
Ventricular fibrillation 468.16 39.33 125 5686 4208 3375840
Cardiac arrest 454.19 39.33 192 5619 27127 3352921
Cardiac failure 414.70 39.33 165 5646 19940 3360108
Acute kidney injury 358.70 39.33 197 5614 49486 3330562
Respiratory failure 349.17 39.33 152 5659 22989 3357059
Syncope 346.97 39.33 156 5655 25477 3354571
Asthenia 320.25 39.33 202 5609 65463 3314585
Myxoedema coma 287.68 39.33 44 5767 48 3380000
Lung disorder 281.20 39.33 100 5711 8817 3371231
Pneumonitis 267.64 39.33 88 5723 6115 3373933
Hypokalaemia 259.07 39.33 106 5705 13699 3366349
Acute respiratory distress syndrome 251.80 39.33 83 5728 5811 3374237
Pleural effusion 249.71 39.33 113 5698 18666 3361382
Dizziness 236.79 39.33 178 5633 76334 3303714

Pharmacologic Action:

scroll-->
SourceCodeDescription
ATC C01BD01 CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
ANTIARRHYTHMICS, CLASS I AND III
Antiarrhythmics, class III
FDA EPC N0000175426 Antiarrhythmic
FDA MoA N0000182141 Cytochrome P450 3A4 Inhibitors
FDA MoA N0000185503 P-Glycoprotein Inhibitors
FDA MoA N0000182138 Cytochrome P450 1A2 Inhibitors
FDA MoA N0000185504 Cytochrome P450 2C9 Inhibitors
FDA MoA N0000182137 Cytochrome P450 2D6 Inhibitors
MeSH PA D000889 Anti-Arrhythmia Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D065609 Cytochrome P-450 CYP1A2 Inhibitors
MeSH PA D065688 Cytochrome P-450 CYP2C9 Inhibitors
MeSH PA D065690 Cytochrome P-450 CYP2D6 Inhibitors
MeSH PA D065692 Cytochrome P-450 CYP3A Inhibitors
MeSH PA D065607 Cytochrome P-450 Enzyme Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
MeSH PA D026902 Potassium Channel Blockers
MeSH PA D026941 Sodium Channel Blockers
MeSH PA D014665 Vasodilator Agents
CHEBI has role CHEBI:35554 cardiovascular drug

Drug Use (View source of the data)

scroll-->
DiseaseRelationSNOMED_IDDOID
Ventricular fibrillation indication 71908006
Life-Threatening Ventricular Tachycardia indication
Prevention of Ventricular Fibrillation indication
Complete atrioventricular block contraindication 27885002
Torsades de pointes contraindication 31722008
Hyperthyroidism contraindication 34486009 DOID:7998
Extrinsic allergic alveolitis contraindication 37471005 DOID:841
Hypothyroidism contraindication 40930008 DOID:1459
Hypokalemia contraindication 43339004
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Refractive keratoplasty by laser surgery contraindication 58076004
Sinus node dysfunction contraindication 60423000
Interstitial pneumonia contraindication 64667001 DOID:3082
Optic neuritis contraindication 66760008 DOID:1210
Corneal deposit contraindication 74460005 DOID:11547
Disorder of optic nerve contraindication 77157004 DOID:1891
Pulmonary hemorrhage contraindication 78144005
Cardiogenic shock contraindication 89138009
Thyrotoxicosis contraindication 90739004 DOID:7997
Prolonged QT interval contraindication 111975006
Liver function tests abnormal contraindication 166603001
Hypomagnesemia contraindication 190855004
Second degree atrioventricular block contraindication 195042002
Disease of liver contraindication 235856003 DOID:409
Drug-induced hepatitis contraindication 235876009
Pregnancy, function contraindication 289908002
Peripheral nerve disease contraindication 302226006 DOID:574
Eosinophilic asthma contraindication 367542003 DOID:9498
Surgical procedure contraindication 387713003
Breastfeeding (mother) contraindication 413712001
Chronic lung disease contraindication 413839001
Congenital long QT syndrome contraindication 442917000
Syncope due to Bradycardia contraindication
Atrial fibrillation off-label use 49436004 DOID:0060224
Prevention of Post Cardio-Thoracic Surgery Atrial Fibrillation off-label use
Cardioversion of Atrial Fibrillation off-label use

Acid dissociation constants calculated using MoKa v3.0.0

scroll-->
Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.72 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

scroll-->
TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Potassium voltage-gated channel subfamily H member 2 Ion channel BLOCKER IC50 5 WOMBAT-PK CHEMBL
Mu-type opioid receptor GPCR Ki 5.11 DRUG MATRIX
D(1A) dopamine receptor GPCR Ki 5.34 DRUG MATRIX
D(2) dopamine receptor GPCR Ki 5.18 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 5.91 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.65 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 5.99 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 6.23 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 6.67 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 5.04 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 5.23 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 6.39 DRUG MATRIX
Histamine H2 receptor GPCR Ki 4.98 DRUG MATRIX
Muscarinic acetylcholine receptor M1 GPCR Ki 6.20 DRUG MATRIX
Muscarinic acetylcholine receptor M2 GPCR Ki 5.74 DRUG MATRIX
Muscarinic acetylcholine receptor M3 GPCR Ki 6.17 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 6.30 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 5.97 DRUG MATRIX
Beta-3 adrenergic receptor GPCR Ki 4.50 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 5.70 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 5.00 DRUG MATRIX
D(4) dopamine receptor GPCR Ki 5.21 DRUG MATRIX
Kappa-type opioid receptor GPCR Ki 5.18 DRUG MATRIX
Delta-type opioid receptor GPCR Ki 5.55 DRUG MATRIX
Endothelin-1 receptor GPCR Ki 4.79 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 6.09 DRUG MATRIX
Receptor tyrosine-protein kinase erbB-2 Kinase IC50 5.04 DRUG MATRIX
C-C chemokine receptor type 2 GPCR Ki 5.37 DRUG MATRIX
Substance-K receptor GPCR Ki 5.19 DRUG MATRIX
B2 bradykinin receptor GPCR Ki 5.11 DRUG MATRIX
Melanocortin receptor 4 GPCR Ki 4.88 DRUG MATRIX
Melanocortin receptor 5 GPCR Ki 5.05 DRUG MATRIX
Melanocortin receptor 3 GPCR Ki 4.97 DRUG MATRIX
C-C chemokine receptor type 4 GPCR Ki 4.94 DRUG MATRIX
Sodium channel protein type 5 subunit alpha Ion channel BLOCKER IC50 7.10 WOMBAT-PK
Alpha-2A adrenergic receptor GPCR IC50 6.30 WOMBAT-PK
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 7 WOMBAT-PK
Thyroid hormone receptor beta Nuclear hormone receptor IC50 6.22 WOMBAT-PK
Thyroid hormone receptor alpha Nuclear hormone receptor IC50 5.64 WOMBAT-PK
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase Enzyme Ki 7.60 WOMBAT-PK
Cytochrome P450 3A4 Enzyme Ki 6.22 WOMBAT-PK
Potassium voltage-gated channel subfamily A member 7 Ion channel IC50 6 WOMBAT-PK
Multidrug resistance protein 1 Transporter Ki 5.30 WOMBAT-PK
Beta-1 adrenergic receptor GPCR IC50 4.70 WOMBAT-PK
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Ion channel IC50 5.35 WOMBAT-PK
Voltage-dependent T-type calcium channel subunit alpha-1H Ion channel Ki 5.28 WOMBAT-PK
Cytochrome P450 2C9 Enzyme EC50 7.40 WOMBAT-PK
THAP domain-containing protein 1 Unclassified IC50 6.19 WOMBAT-PK
Squalene monooxygenase Enzyme IC50 4.92 CHEMBL
Squalene synthase Enzyme IC50 5.10 CHEMBL
Androgen receptor Transcription factor Ki 4.55 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 4.41 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor IC50 6.93 DRUG MATRIX
Cruzipain Enzyme IC50 5.40 CHEMBL
Lethal factor Enzyme IC50 5.46 CHEMBL
C-8 sterol isomerase Enzyme Ki 7.21 CHEMBL
Sodium channel protein type 5 subunit alpha Unclassified BLOCKER IC50 5.70 IUPHAR

External reference:

scroll-->
IDSource
2566 IUPHAR_LIGAND_ID
4019606 VUID
N0000147701 NUI
C0002598 UMLSCUI
D00636 KEGG_DRUG
CHEMBL633 ChEMBL_ID
DB01118 DRUGBANK_ID
4019606 VANDF
703 RXNORM
372821002 SNOMEDCT_US
69236009 SNOMEDCT_US
d00002 MMSL
N0000147701 NDFRT
N0000005761 NDFRT
004484 NDDF
976728SY6Z UNII
19774-82-4 SECONDARY_CAS_RN
CHEMBL1083993 ChEMBL_ID
2157 PUBCHEM_CID
2012 INN_ID
D000638 MESH_DESCRIPTOR_UI
CHEBI:2663 CHEBI
BBI PDB_CHEM_ID

Pharmaceutical products:

scroll-->
ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Amiodarone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-9133 TABLET 200 mg ORAL ANDA 12 sections
Amiodarone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9875 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 16 sections
Amiodarone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0185-0144 TABLET 200 mg ORAL ANDA 13 sections
Pacerone HUMAN PRESCRIPTION DRUG LABEL 1 0245-0144 TABLET 100 mg ORAL ANDA 13 sections
Pacerone HUMAN PRESCRIPTION DRUG LABEL 1 0245-0145 TABLET 400 mg ORAL ANDA 13 sections
Pacerone HUMAN PRESCRIPTION DRUG LABEL 1 0245-0147 TABLET 200 mg ORAL ANDA 13 sections
Amiodarone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-4545 TABLET 200 mg ORAL ANDA 13 sections
Amiodarone hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6556 TABLET 200 mg ORAL ANDA 13 sections
Amiodarone hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-796 TABLET 200 mg ORAL ANDA 13 sections
amiodarone hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 25021-302 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 16 sections
Amiodarone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-118 TABLET 100 mg ORAL ANDA 13 sections
Amiodarone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-139 TABLET 400 mg ORAL ANDA 13 sections
Amiodarone HCl HUMAN PRESCRIPTION DRUG LABEL 1 42494-307 TABLET 200 mg ORAL ANDA 14 sections
Amiodarone HCl HUMAN PRESCRIPTION DRUG LABEL 1 42494-308 TABLET 400 mg ORAL ANDA 14 sections
Amiodarone HCl HUMAN PRESCRIPTION DRUG LABEL 1 42494-309 TABLET 100 mg ORAL ANDA 14 sections
Nexterone HUMAN PRESCRIPTION DRUG LABEL 1 43066-150 INJECTION, SOLUTION 1.50 mg INTRAVENOUS NDA 17 sections
Nexterone HUMAN PRESCRIPTION DRUG LABEL 1 43066-360 INJECTION, SOLUTION 1.80 mg INTRAVENOUS NDA 17 sections
Amiodarone hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 49349-154 TABLET 200 mg ORAL ANDA 13 sections
Amiodarone hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-2308 TABLET 200 mg ORAL ANDA 13 sections
Amiodarone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-3015 TABLET 200 mg ORAL ANDA 12 sections
Amiodarone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-906 TABLET 200 mg ORAL ANDA 12 sections
Amiodarone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51672-4025 TABLET 200 mg ORAL ANDA 13 sections
Amiodarone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51672-4055 TABLET 100 mg ORAL ANDA 13 sections
Amiodarone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51672-4056 TABLET 300 mg ORAL ANDA 13 sections
Amiodarone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51672-4057 TABLET 400 mg ORAL ANDA 13 sections
Amiodarone HCl HUMAN PRESCRIPTION DRUG LABEL 1 51862-154 TABLET 100 mg ORAL ANDA 14 sections
Amiodarone HCl HUMAN PRESCRIPTION DRUG LABEL 1 51862-155 TABLET 200 mg ORAL ANDA 14 sections
Amiodarone HCl HUMAN PRESCRIPTION DRUG LABEL 1 51862-156 TABLET 400 mg ORAL ANDA 14 sections
Amiodarone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51862-240 TABLET 100 mg ORAL ANDA 13 sections
Amiodarone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51862-242 TABLET 400 mg ORAL ANDA 13 sections