sotalol Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
aromatic ring -CH(-OH)-CH2-NH-R 2464 3930-20-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • sotalol
  • DL-Sotalol
  • sotalol hydrochloride
  • sotylize
  • sotalol HCl
An adrenergic beta-antagonist that is used in the treatment of life-threatening arrhythmias.
  • Molecular weight: 272.36
  • Formula: C12H20N2O3S
  • CLOGP: 0.23
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 3
  • TPSA: 78.43
  • ALOGS: -2.54
  • ROTB: 5

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.16 g O
0.16 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 137 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 85 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 19.57 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 95 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.30 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.62 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 6.30 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Oct. 30, 1992 FDA COVIS PHARMA SARL

FDA Adverse Event Reporting System (Female)

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
Torsade de pointes 371.43 13.63 138 14410 12867 53321651
Atrial fibrillation 340.75 13.63 265 14283 111387 53223131
Electrocardiogram QT prolonged 242.67 13.63 165 14383 56238 53278280
Bradycardia 133.44 13.63 128 14420 70928 53263590
Drug interaction 115.61 13.63 211 14337 219118 53115400
International normalised ratio increased 115.08 13.63 99 14449 47662 53286856
Hyponatraemia 89.30 13.63 128 14420 108479 53226039
Ventricular tachycardia 83.56 13.63 55 14493 17707 53316811
Arrhythmia 80.08 13.63 72 14476 36707 53297811
Ventricular fibrillation 63.68 13.63 40 14508 11885 53322633
Atrial tachycardia 57.06 13.63 22 14526 2262 53332256
Hyperkalaemia 53.69 13.63 70 14478 54186 53280332
Hypotension 52.22 13.63 170 14378 253906 53080612
Atrial flutter 48.29 13.63 31 14517 9560 53324958
Syncope 46.96 13.63 98 14450 111895 53222623
Rheumatoid arthritis 46.57 13.63 14 14534 314517 53020001
Urinary incontinence 45.85 13.63 49 14499 30772 53303746
Erythromelalgia 45.17 13.63 10 14538 138 53334380
Sinus bradycardia 40.80 13.63 33 14515 14568 53319950
Ischaemic stroke 40.69 13.63 36 14512 17957 53316561
Cardio-respiratory arrest 39.35 13.63 63 14485 58695 53275823
Palpitations 37.69 13.63 85 14463 102263 53232255
Long QT syndrome 36.86 13.63 18 14530 3278 53331240
Cerebral haematoma 35.76 13.63 18 14530 3496 53331022
Hepatocellular injury 34.94 13.63 42 14506 29944 53304574
Cardiac arrest 34.71 13.63 78 14470 93589 53240929
Gastrointestinal haemorrhage 34.48 13.63 71 14477 80259 53254259
Bundle branch block left 33.67 13.63 22 14526 6991 53327527
Atrioventricular block 33.31 13.63 22 14526 7118 53327400
Pain 31.84 13.63 71 14477 588327 52746191
Localised oedema 31.37 13.63 19 14529 5290 53329228
Subdural haematoma 29.97 13.63 27 14521 13786 53320732
Cardiac disorder 29.60 13.63 49 14499 46917 53287601
Asthenia 29.53 13.63 177 14371 343413 52991105
Acute kidney injury 29.43 13.63 142 14406 253726 53080792
Haematoma 27.92 13.63 40 14508 33804 53300714
Presyncope 27.79 13.63 35 14513 26159 53308359
Loss of consciousness 27.65 13.63 81 14467 114131 53220387
Malaise 27.46 13.63 179 14369 357438 52977080
Organising pneumonia 26.67 13.63 17 14531 5179 53329339
Ventricular arrhythmia 26.66 13.63 15 14533 3645 53330873
Cardiac failure congestive 26.62 13.63 70 14478 92687 53241831
Apallic syndrome 26.35 13.63 9 14539 654 53333864
Inappropriate antidiuretic hormone secretion 26.26 13.63 26 14522 14925 53319593
Off label use 23.89 13.63 59 14489 472153 52862365
Melaena 23.40 13.63 34 14514 29095 53305423
Nasal mucosal erosion 22.72 13.63 5 14543 67 53334451
Blood pressure increased 21.93 13.63 86 14462 140393 53194125
Cardioactive drug level decreased 20.80 13.63 5 14543 101 53334417
Joint swelling 20.79 13.63 20 14528 234618 53099900
Livedo reticularis 20.54 13.63 11 14537 2426 53332092
Fall 20.36 13.63 167 14381 358273 52976245
Cardiac ablation 20.31 13.63 9 14539 1315 53333203
Contraindicated product administered 20.11 13.63 6 14542 135623 53198895
Arthropathy 19.66 13.63 7 14541 141446 53193072
Systemic lupus erythematosus 19.62 13.63 5 14543 125409 53209109
Hypoglycaemia 18.44 13.63 46 14502 58967 53275551
Electrocardiogram QRS complex prolonged 18.24 13.63 14 14534 5728 53328790
Noninfective gingivitis 18.14 13.63 8 14540 1156 53333362
Ventricular extrasystoles 18.07 13.63 19 14529 11705 53322813
Acute pulmonary oedema 17.64 13.63 16 14532 8239 53326279
Product use issue 17.62 13.63 8 14540 139576 53194942
Extrasystoles 17.30 13.63 13 14535 5153 53329365
Muscle haemorrhage 17.07 13.63 11 14537 3412 53331106
Transient ischaemic attack 17.02 13.63 33 14515 35692 53298826
Sinus node dysfunction 16.93 13.63 12 14536 4349 53330169
Cerebrovascular accident 16.91 13.63 65 14483 105109 53229409
Supraventricular extrasystoles 16.84 13.63 12 14536 4388 53330130
Dizziness 16.80 13.63 165 14383 372094 52962424
Blood loss anaemia 16.73 13.63 16 14532 8807 53325711
Atrioventricular block first degree 16.65 13.63 14 14534 6521 53327997
Hypokalaemia 16.64 13.63 61 14487 96456 53238062
Drug intolerance 16.53 13.63 19 14529 205474 53129044
Electrocardiogram T wave amplitude increased 16.25 13.63 3 14545 15 53334503
Haemodialysis 15.86 13.63 16 14532 9388 53325130
Arthralgia 15.84 13.63 64 14484 439719 52894799
Renal failure 15.72 13.63 69 14479 118383 53216135
Wound 15.63 13.63 3 14545 91554 53242964
Medication error 15.42 13.63 32 14516 36333 53298185
Optic nerve infarction 15.39 13.63 3 14545 21 53334497
Cerebral congestion 15.27 13.63 3 14545 22 53334496
Heart rate irregular 15.23 13.63 23 14525 20361 53314157
Supraventricular tachycardia 14.97 13.63 19 14529 14306 53320212
Left ventricular failure 14.78 13.63 12 14536 5321 53329197
Cardioversion 14.70 13.63 7 14541 1206 53333312
Subarachnoid haemorrhage 14.41 13.63 17 14531 11876 53322642
Hypersensitivity 14.37 13.63 22 14526 210643 53123875
Resting tremor 14.26 13.63 6 14542 773 53333745
Occupational exposure to product 14.20 13.63 8 14540 1947 53332571
Endodontic procedure 14.15 13.63 9 14539 2730 53331788
Normocytic anaemia 14.05 13.63 7 14541 1330 53333188
Haemorrhagic stroke 13.98 13.63 12 14536 5746 53328772
Vertigo 13.77 13.63 40 14508 56041 53278477
Infection 13.77 13.63 16 14532 172189 53162329

FDA Adverse Event Reporting System (Male)

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
Atrial fibrillation 283.97 12.99 298 13755 116406 32383067
Ventricular tachycardia 147.35 12.99 107 13946 25449 32474024
Bradycardia 142.82 12.99 165 13888 71397 32428076
Torsade de pointes 110.38 12.99 57 13996 7358 32492115
Electrocardiogram QT prolonged 110.12 12.99 109 13944 39532 32459941
Cardiogenic shock 87.35 12.99 72 13981 20590 32478883
Atrial flutter 86.17 12.99 63 13990 15120 32484353
Arrhythmia 71.31 12.99 82 13971 35221 32464252
Ventricular arrhythmia 50.67 12.99 30 14023 5049 32494424
International normalised ratio increased 48.92 12.99 81 13972 48954 32450519
Palpitations 47.99 12.99 68 13985 35901 32463572
Drug interaction 44.31 12.99 199 13854 217986 32281487
Hypotension 43.05 12.99 196 13857 215914 32283559
Atrial thrombosis 37.64 12.99 18 14035 1969 32497504
Antiacetylcholine receptor antibody positive 37.62 12.99 8 14045 54 32499419
Cardiac ablation 37.06 12.99 13 14040 641 32498832
Pacemaker generated rhythm 36.32 12.99 8 14045 65 32499408
Apallic syndrome 34.09 12.99 10 14043 275 32499198
Ischaemic stroke 34.08 12.99 40 14013 17536 32481937
Staring 32.53 12.99 15 14038 1511 32497962
Petit mal epilepsy 31.16 12.99 18 14035 2894 32496579
Daydreaming 30.65 12.99 11 14042 580 32498893
Loss of consciousness 29.89 12.99 91 13962 82616 32416857
Haemoptysis 28.99 12.99 52 14001 33473 32466000
Pallor 28.67 12.99 42 14011 22839 32476634
Incontinence 26.72 12.99 21 14032 5605 32493868
Dissociation 26.13 12.99 12 14041 1198 32498275
Ventricular fibrillation 24.98 12.99 34 14019 17276 32482197
Gingival bleeding 22.77 12.99 21 14032 6960 32492513
Long QT syndrome 22.29 12.99 14 14039 2617 32496856
Drug abuse 22.08 12.99 4 14049 80239 32419234
Presyncope 22.02 12.99 32 14021 17269 32482204
Heart rate abnormal 22.01 12.99 12 14041 1725 32497748
Xanthopsia 20.35 12.99 6 14047 168 32499305
Rectal haemorrhage 18.29 12.99 46 14007 37377 32462096
Haematuria 17.25 12.99 53 14000 48308 32451165
Cardiac disorder 16.95 12.99 48 14005 41818 32457655
Sinus bradycardia 16.57 12.99 24 14029 12914 32486559
Grandiosity 16.53 12.99 6 14047 327 32499146
Acquired haemophilia 16.41 12.99 8 14045 912 32498561
Transient ischaemic attack 16.21 12.99 35 14018 25759 32473714
Cardiac failure congestive 16.11 12.99 76 13977 84776 32414697
Hyperplasia 15.86 12.99 7 14046 636 32498837
Dyspnoea 15.65 12.99 231 13822 361814 32137659
Dizziness 15.35 12.99 148 13905 209470 32290003
Brugada syndrome 15.06 12.99 7 14046 718 32498755
Pyrexia 14.63 12.99 80 13973 319888 32179585
Arrhythmia supraventricular 14.24 12.99 8 14045 1220 32498253
Pressure of speech 14.22 12.99 6 14047 489 32498984
Urine flow decreased 14.11 12.99 8 14045 1241 32498232
Venous pressure increased 13.89 12.99 3 14050 22 32499451
Coagulation factor V level decreased 13.71 12.99 5 14048 276 32499197
Food interaction 13.34 12.99 7 14046 932 32498541
Tachycardia induced cardiomyopathy 13.27 12.99 4 14049 121 32499352
Brown-Sequard syndrome 13.25 12.99 3 14050 28 32499445

Pharmacologic Action:

SourceCodeDescription
ATC C07AA07 CARDIOVASCULAR SYSTEM
BETA BLOCKING AGENTS
BETA BLOCKING AGENTS
Beta blocking agents, non-selective
ATC C07BA07 CARDIOVASCULAR SYSTEM
BETA BLOCKING AGENTS
BETA BLOCKING AGENTS AND THIAZIDES
Beta blocking agents, non-selective, and thiazides
ATC C07FX02 CARDIOVASCULAR SYSTEM
BETA BLOCKING AGENTS
BETA BLOCKING AGENTS, OTHER COMBINATIONS
Beta blocking agents, other combinations
FDA MoA N0000000161 Adrenergic beta-Antagonists
FDA PE N0000008330 Cardiac Rhythm Alteration
FDA EPC N0000175426 Antiarrhythmic
MeSH PA D018663 Adrenergic Agents
MeSH PA D018674 Adrenergic Antagonists
MeSH PA D000319 Adrenergic beta-Antagonists
MeSH PA D000889 Anti-Arrhythmia Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D013565 Sympatholytics
CHEBI has role CHEBI:35530 beta-adrenoceptor antagonists
CHEBI has role CHEBI:38070 antiarrhythmic agent
CHEBI has role CHEBI:35703 Xenobiotic
CHEBI has role CHEBI:78298 environmental contaminants

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Atrial fibrillation indication 49436004 DOID:0060224
Life-Threatening Ventricular Tachycardia indication
Bronchospasm contraindication 4386001
Complete atrioventricular block contraindication 27885002
Torsades de pointes contraindication 31722008
Sick sinus syndrome contraindication 36083008 DOID:13884
Anaphylaxis contraindication 39579001
Hypokalemia contraindication 43339004
Low blood pressure contraindication 45007003
Sinus bradycardia contraindication 49710005
Diabetes mellitus contraindication 73211009 DOID:9351
Cardiogenic shock contraindication 89138009
Prolonged QT interval contraindication 111975006
Hypomagnesemia contraindication 190855004
Second degree atrioventricular block contraindication 195042002
Decompensated cardiac failure contraindication 195111005
Asthma contraindication 195967001 DOID:2841
Impaired renal function disorder contraindication 197663003
Pregnancy, function contraindication 289908002
Congenital long QT syndrome contraindication 442917000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.95 acidic
pKa2 9.22 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
5MG/ML (5MG/ML) SOTYLIZE ARBOR PHARMS LLC N205108 Oct. 22, 2014 RX SOLUTION ORAL 10206895 April 1, 2034 INDICATED FOR THE TREATMENT OF VENTRICULAR ARRHYTHMIAS, SUCH AS SUSTAINED VENTRICULAR TACHYCARDIA, THAT IN THE JUDGEMENT OF THE PHYSICIAN ARE LIFE-THREATENING
5MG/ML (5MG/ML) SOTYLIZE ARBOR PHARMS LLC N205108 Oct. 22, 2014 RX SOLUTION ORAL 10206895 April 1, 2034 SOTYLIZE IS INDICATED FOR THE MAINTENANCE OF NORMAL SINUS RHYTHM [DELAY IN TIME TO RECURRENCE OF ATRIAL FIBRILLATION/ATRIAL FLUTTER (AFIB/AFL)] IN PATIENTS WITH SYMPTOMATIC AFIB/AFL WHO ARE CURRENTLY IN SINUS RHYTHM
5MG/ML (5MG/ML) SOTYLIZE ARBOR PHARMS LLC N205108 Oct. 22, 2014 RX SOLUTION ORAL 9724297 Aug. 31, 2035 SOTYLIZE IS INDICATED FOR THE MAINTENANCE OF NORMAL SINUS RHYTHM [DELAY IN TIME TO RECURRENCE OF ATRIAL FIBRILLATION/ATRIAL FLUTTER (AFIB/AFL)] IN PATIENTS WITH SYMPTOMATIC AFIB/AFL WHO ARE CURRENTLY IN SINUS RHYTHM
150MG/10ML (15MG/ML) SOTALOL HYDROCHLORIDE ALTATHERA PHARMS LLC N022306 July 2, 2009 RX SOLUTION INTRAVENOUS 10512620 Aug. 18, 2038 DOSING REGIMEN FOR INTRAVENOUS SOTALOL FOR ADMINISTRATION IN A FACILITY THAT CAN PROVIDE CONTINUOUS ELECTROCARDIOGRAPHIC MONITORING AND CARDIAC RESUSCITATION.
150MG/10ML (15MG/ML) SOTALOL HYDROCHLORIDE ALTATHERA PHARMS LLC N022306 July 2, 2009 RX SOLUTION INTRAVENOUS 10799138 April 5, 2039 USE FOR LOADING DOSE IN PATIENTS WITH SYMPTOMATIC AFIB/AFL WHO ARE CURRENTLY IN SINUS RHYTHM OR FOR THE TREATMENT OF LIFE-THREATENING VENTRICULAR TACHYCARDIA

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Beta-1 adrenergic receptor GPCR ANTAGONIST Ki 6.10 WOMBAT-PK CHEMBL
Beta-2 adrenergic receptor GPCR ANTAGONIST Ki 6.90 WOMBAT-PK CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel BLOCKER Ki 4 WOMBAT-PK CHEMBL
Beta-2 adrenergic receptor GPCR Kd 6.24 CHEMBL
Beta-2 adrenergic receptor GPCR IC50 5.30 CHEMBL

External reference:

IDSource
4020814 VUID
N0000148334 NUI
D01026 KEGG_DRUG
959-24-0 SECONDARY_CAS_RN
4020779 VANDF
4020814 VANDF
C0037707 UMLSCUI
CHEBI:63622 CHEBI
CHEMBL471 ChEMBL_ID
CHEMBL1700 ChEMBL_ID
DB00489 DRUGBANK_ID
D013015 MESH_DESCRIPTOR_UI
5253 PUBCHEM_CID
7297 IUPHAR_LIGAND_ID
2350 INN_ID
A6D97U294I UNII
1593726 RXNORM
230116 MMSL
31427 MMSL
5503 MMSL
d00371 MMSL
003453 NDDF
004111 NDDF
125691000 SNOMEDCT_US
372911006 SNOMEDCT_US
96301002 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Sotalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-1060 TABLET 120 mg ORAL ANDA 25 sections
Sotalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-1061 TABLET 80 mg ORAL ANDA 25 sections
Sotalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-1062 TABLET 160 mg ORAL ANDA 25 sections
Sotalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-1063 TABLET 240 mg ORAL ANDA 25 sections
Sorine HUMAN PRESCRIPTION DRUG LABEL 1 0245-0012 TABLET 80 mg ORAL ANDA 28 sections
Sorine HUMAN PRESCRIPTION DRUG LABEL 1 0245-0013 TABLET 120 mg ORAL ANDA 28 sections
Sorine HUMAN PRESCRIPTION DRUG LABEL 1 0245-0014 TABLET 160 mg ORAL ANDA 28 sections
Sorine HUMAN PRESCRIPTION DRUG LABEL 1 0245-0015 TABLET 240 mg ORAL ANDA 28 sections
Sotalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-5552 TABLET 80 mg ORAL ANDA 24 sections
Sotalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-7143 TABLET 80 mg ORAL ANDA 25 sections
Sotalol HUMAN PRESCRIPTION DRUG LABEL 1 10135-661 TABLET 80 mg ORAL ANDA 24 sections
Sotalol HUMAN PRESCRIPTION DRUG LABEL 1 10135-662 TABLET 120 mg ORAL ANDA 24 sections
Sotalol HUMAN PRESCRIPTION DRUG LABEL 1 10135-663 TABLET 160 mg ORAL ANDA 24 sections
Sotalol HydrochlorideAF HUMAN PRESCRIPTION DRUG LABEL 1 10135-715 TABLET 80 mg ORAL ANDA 24 sections
Sotalol HydrochlorideAF HUMAN PRESCRIPTION DRUG LABEL 1 10135-716 TABLET 120 mg ORAL ANDA 24 sections
Sotalol HydrochlorideAF HUMAN PRESCRIPTION DRUG LABEL 1 10135-717 TABLET 160 mg ORAL ANDA 24 sections
sotalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-397 TABLET 80 mg ORAL ANDA 19 sections
SOTYLIZE HUMAN PRESCRIPTION DRUG LABEL 1 24338-530 SOLUTION 5 mg ORAL NDA 29 sections
Sotalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42806-121 TABLET 80 mg ORAL ANDA 14 sections
Sotalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42806-122 TABLET 120 mg ORAL ANDA 14 sections
Sotalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42806-123 TABLET 160 mg ORAL ANDA 14 sections
Sotalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43353-616 TABLET 80 mg ORAL ANDA 25 sections
Sotalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-1299 TABLET 80 mg ORAL ANDA 25 sections
Sotalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50268-724 TABLET 80 mg ORAL ANDA 25 sections
Sotalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50268-725 TABLET 120 mg ORAL ANDA 25 sections
Sotalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53217-011 TABLET 80 mg ORAL ANDA 21 sections
sotalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-4435 TABLET 80 mg ORAL ANDA 19 sections
sotalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-5549 TABLET 160 mg ORAL ANDA 19 sections
sotalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-5614 TABLET 120 mg ORAL ANDA 19 sections
Sotalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55154-8179 TABLET 80 mg ORAL ANDA 25 sections