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

Stem definitionDrug idCAS RN
antihyperlipidaemics, acyl CoA: cholesterol acyltransferase (ACAT) inhibitors 1125 163222-33-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • SCH58235
  • SCH-58235
  • ezetimib
  • ezetimibe
  • ezedoc
  • ezentia
  • ezetrol
  • zetia
An azetidine derivative and ANTICHOLESTEREMIC AGENT that inhibits intestinal STEROL absorption. It is used to reduce total CHOLESTEROL; LDL CHOLESTEROL, and APOLIPOPROTEINS B in the treatment of HYPERLIPIDEMIAS.
  • Molecular weight: 409.43
  • Formula: C24H21F2NO3
  • CLOGP: 3.96
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 60.77
  • ALOGS: -4.68
  • ROTB: 6

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
10 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 2 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.35 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 50 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Oct. 25, 2002 FDA MSD INTL GMBH
April 18, 2007 PMDA Schering-Plough K.K

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
Myalgia 794.77 10.38 881 62294 132610 53153281
Rhabdomyolysis 664.82 10.38 491 62684 43432 53242459
Blood creatine phosphokinase increased 309.33 10.38 264 62911 28721 53257170
Low density lipoprotein increased 217.74 10.38 118 63057 6048 53279843
Contraindicated product administered 131.87 10.38 7 63168 135622 53150269
Muscle spasms 123.87 10.38 396 62779 134399 53151492
Maternal exposure during pregnancy 117.90 10.38 21 63154 155618 53130273
Myopathy 117.32 10.38 95 63080 9597 53276294
Pemphigus 109.16 10.38 3 63172 104028 53181863
Rheumatoid arthritis 107.15 10.38 129 63046 314402 52971489
Drug ineffective 105.54 10.38 555 62620 816690 52469201
Coronary artery disease 101.75 10.38 159 63016 33278 53252613
Synovitis 100.55 10.38 7 63168 107886 53178005
Muscular weakness 97.61 10.38 302 62873 100690 53185201
Myocardial infarction 95.93 10.38 297 62878 99057 53186834
Angina pectoris 93.60 10.38 141 63034 28584 53257307
Pancreatitis acute 93.51 10.38 134 63041 25975 53259916
Liver function test abnormal 87.75 10.38 183 62992 47888 53238003
Toxicity to various agents 81.37 10.38 84 63091 219514 53066377
Infusion related reaction 80.64 10.38 42 63133 155915 53129976
Acute kidney injury 79.14 10.38 543 62632 253325 53032566
Pain in extremity 78.08 10.38 591 62584 284459 53001432
Death 69.17 10.38 206 62969 357026 52928865
Off label use 68.61 10.38 307 62868 471905 52813986
Pancreatitis 65.56 10.38 159 63016 45983 53239908
Wound 63.82 10.38 15 63160 91542 53194349
Exposure during pregnancy 62.53 10.38 35 63140 124825 53161066
Coronary artery occlusion 62.13 10.38 62 63113 8225 53277666
Treatment failure 61.46 10.38 38 63137 128365 53157526
Completed suicide 60.67 10.38 45 63130 138156 53147735
Hyper IgE syndrome 58.05 10.38 21 63154 400 53285491
Product use issue 58.05 10.38 48 63127 139536 53146355
Blood cholesterol increased 57.36 10.38 165 63010 52824 53233067
Hyperlipidaemia 56.87 10.38 91 63084 19424 53266467
Acute coronary syndrome 55.35 10.38 65 63110 10359 53275532
Pericarditis 55.05 10.38 6 63169 64400 53221491
Glossodynia 51.84 10.38 27 63148 100264 53185627
Aspartate aminotransferase increased 51.03 10.38 216 62959 83813 53202078
High density lipoprotein decreased 50.19 10.38 30 63145 1855 53284036
Systemic lupus erythematosus 49.87 10.38 45 63130 125369 53160522
Alanine aminotransferase increased 49.14 10.38 233 62942 94862 53191029
Arterial stenosis 48.65 10.38 21 63154 647 53285244
Blood glucose increased 47.86 10.38 200 62975 77161 53208730
Blood triglycerides increased 46.23 10.38 65 63110 12376 53273515
Vascular stent stenosis 45.61 10.38 19 63156 535 53285356
Intentional overdose 44.92 10.38 12 63163 67193 53218698
Drug abuse 43.23 10.38 12 63163 65514 53220377
Therapeutic product effect decreased 42.20 10.38 52 63123 125603 53160288
Flatulence 42.01 10.38 106 63069 31411 53254480
Dyslipidaemia 41.40 10.38 44 63131 6283 53279608
Joint swelling 40.01 10.38 143 63032 234495 53051396
Carotid arteriosclerosis 39.66 10.38 21 63154 1026 53284865
Polymyositis 39.15 10.38 25 63150 1739 53284152
Dizziness 39.00 10.38 638 62537 371621 52914270
Infection 38.79 10.38 92 63083 172113 53113778
Immune-mediated myositis 38.58 10.38 21 63154 1085 53284806
Cardiac failure congestive 37.99 10.38 213 62962 92544 53193347
Febrile neutropenia 36.76 10.38 42 63133 104894 53180997
Arterial occlusive disease 36.43 10.38 37 63138 5012 53280879
Restrictive pulmonary disease 34.36 10.38 22 63153 1537 53284354
Coombs positive haemolytic anaemia 34.23 10.38 14 63161 376 53285515
Sensorimotor disorder 34.13 10.38 15 63160 483 53285408
Myositis 34.05 10.38 46 63129 8437 53277454
Angina unstable 33.86 10.38 43 63132 7425 53278466
Pyrexia 33.79 10.38 310 62865 402883 52883008
Muscle rupture 33.60 10.38 25 63150 2229 53283662
Antinuclear antibody negative 33.20 10.38 12 63163 228 53285663
Muscle disorder 32.01 10.38 33 63142 4548 53281343
Crush syndrome 31.74 10.38 10 63165 122 53285769
Asthenia 31.67 10.38 577 62598 343013 52942878
Swelling 31.56 10.38 118 63057 190987 53094904
Myopathy toxic 30.16 10.38 13 63162 399 53285492
Lipids increased 29.83 10.38 18 63157 1132 53284759
Cerebrovascular accident 29.22 10.38 219 62956 104955 53180936
Chest pain 28.77 10.38 348 62827 189837 53096054
Disease progression 28.48 10.38 48 63127 101872 53184019
Neutropenia 28.48 10.38 95 63080 159090 53126801
Duodenal ulcer perforation 28.30 10.38 4 63171 35179 53250712
Hyperkalaemia 28.06 10.38 133 63042 54123 53231768
Palpitations 27.81 10.38 212 62963 102136 53183755
Herpes simplex reactivation 27.79 10.38 12 63163 370 53285521
Hypoglycaemia 27.20 10.38 140 63035 58873 53227018
Inhibitory drug interaction 26.77 10.38 22 63153 2268 53283623
Body tinea 26.60 10.38 17 63158 1184 53284707
Gangrene 25.21 10.38 30 63145 4847 53281044
Aortic stenosis 25.14 10.38 29 63146 4534 53281357
Transient ischaemic attack 24.99 10.38 96 63079 35629 53250262
Polycystic ovaries 24.81 10.38 21 63154 2255 53283636
Microscopic polyangiitis 24.76 10.38 9 63166 174 53285717
Glucose tolerance impaired 24.70 10.38 31 63144 5289 53280602
Coma acidotic 23.52 10.38 8 63167 126 53285765
Lower respiratory tract infection 23.48 10.38 45 63130 90936 53194955
Arthropathy 22.91 10.38 88 63087 141365 53144526
Gait disturbance 22.87 10.38 288 62887 158554 53127337
Device expulsion 22.60 10.38 4 63171 29809 53256082
Ischaemic cardiomyopathy 22.35 10.38 21 63154 2587 53283304
Pregnancy 22.20 10.38 5 63170 31436 53254455
Cardiac valve disease 21.48 10.38 26 63149 4276 53281615
Renovascular hypertension 21.31 10.38 5 63170 17 53285874
Coronary artery thrombosis 21.12 10.38 15 63160 1244 53284647
Depressed level of consciousness 21.06 10.38 20 63155 54408 53231483
Blood cholesterol decreased 21.01 10.38 11 63164 525 53285366
Helicobacter infection 20.96 10.38 10 63165 39059 53246832
Fall 20.64 10.38 563 62612 357877 52928014
Coronary artery stenosis 20.50 10.38 27 63148 4832 53281059
Lipids abnormal 20.42 10.38 9 63166 292 53285599
Intentional product use issue 20.38 10.38 34 63141 72460 53213431
Back pain 20.37 10.38 390 62785 233857 53052034
Copper metabolism disorder 20.19 10.38 4 63171 4 53285887
Biliary fibrosis 20.19 10.38 4 63171 4 53285887
Peripheral artery haematoma 19.86 10.38 6 63169 63 53285828
Acute myocardial infarction 19.82 10.38 85 63090 33150 53252741
Pain 19.59 10.38 539 62636 587859 52698032
Chest discomfort 19.48 10.38 192 62983 99503 53186388
Abortion spontaneous 19.42 10.38 16 63159 46619 53239272
Pancytopenia 19.35 10.38 50 63125 90878 53195013
Vascular purpura 19.31 10.38 15 63160 1426 53284465
Sleep disorder due to general medical condition, insomnia type 19.05 10.38 3 63172 24346 53261545
Spontaneous haematoma 19.05 10.38 12 63163 815 53285076
Sepsis 18.96 10.38 99 63076 146330 53139561
Gastritis haemorrhagic 18.92 10.38 15 63160 1469 53284422
Nasopharyngitis 18.71 10.38 142 63033 192153 53093738
Obstructive pancreatitis 18.64 10.38 8 63167 243 53285648
Blood glucose decreased 18.52 10.38 59 63116 19957 53265934
Foetal exposure during pregnancy 18.45 10.38 9 63166 34706 53251185
Device dislocation 18.25 10.38 3 63172 23594 53262297
Toxic epidermal necrolysis 18.20 10.38 3 63172 23547 53262344
Lipoprotein (a) increased 17.99 10.38 5 63170 38 53285853
Diabetic neuropathy 17.96 10.38 23 63152 4004 53281887
Muscle discomfort 17.79 10.38 6 63169 92 53285799
Abnormal dreams 17.77 10.38 39 63136 10562 53275329
Depression 17.74 10.38 310 62865 182742 53103149
Intestinal transit time abnormal 17.73 10.38 6 63169 93 53285798
Total cholesterol/HDL ratio decreased 17.43 10.38 4 63171 12 53285879
Alopecia 17.25 10.38 186 62989 234397 53051494
Carotid artery stenosis 17.13 10.38 26 63149 5301 53280590
Therapy cessation 16.96 10.38 72 63103 27953 53257938
Paresis 16.93 10.38 17 63158 2272 53283619
C-reactive protein abnormal 16.58 10.38 5 63170 25865 53260026
Respiratory disorder 16.43 10.38 10 63165 34087 53251804
Euglycaemic diabetic ketoacidosis 16.38 10.38 19 63156 2988 53282903
Gastric disorder 16.37 10.38 75 63100 30090 53255801
Congenital musculoskeletal anomaly 16.24 10.38 9 63166 482 53285409
Restless legs syndrome 16.15 10.38 51 63124 17172 53268719
Oedema peripheral 16.11 10.38 288 62887 170499 53115392
Low density lipoprotein decreased 16.09 10.38 7 63168 220 53285671
Gastrooesophageal reflux disease 16.05 10.38 159 63016 82504 53203387
Hyperphosphataemia 15.96 10.38 16 63159 2133 53283758
Cell death 15.82 10.38 17 63158 2458 53283433
Disease risk factor 15.72 10.38 5 63170 63 53285828
Product use in unapproved indication 15.63 10.38 74 63101 112215 53173676
Hepatic cyst 15.53 10.38 24 63151 4972 53280919
Infection susceptibility increased 15.47 10.38 17 63158 2520 53283371
Spleen congestion 15.07 10.38 6 63169 150 53285741
Hyperparathyroidism secondary 14.75 10.38 13 63162 1474 53284417
Chromaturia 14.74 10.38 47 63128 15903 53269988
Stomatitis 14.67 10.38 63 63112 98095 53187796
Anembryonic gestation 14.58 10.38 9 63166 590 53285301
Troponin increased 14.56 10.38 32 63143 8673 53277218
Glycosylated haemoglobin increased 14.29 10.38 38 63137 11617 53274274
Lactic acidosis 14.23 10.38 84 63091 37169 53248722
Psoriatic arthropathy 14.11 10.38 22 63153 48168 53237723
Ill-defined disorder 14.07 10.38 23 63152 49421 53236470
Platelet count decreased 14.03 10.38 73 63102 108026 53177865
Helicobacter gastritis 14.00 10.38 13 63162 1577 53284314
Muscle injury 13.97 10.38 9 63166 29757 53256134
Inappropriate schedule of product discontinuation 13.93 10.38 3 63172 6 53285885
C-reactive protein increased 13.93 10.38 38 63137 67848 53218043
Sedation 13.89 10.38 9 63166 29666 53256225
Gingival oedema 13.88 10.38 5 63170 94 53285797
Condition aggravated 13.88 10.38 258 62917 296876 52989015
Seizure 13.87 10.38 93 63082 129416 53156475
Blood cholesterol abnormal 13.84 10.38 16 63159 2506 53283385
Language disorder 13.78 10.38 14 63161 1897 53283994
Complex regional pain syndrome 13.74 10.38 15 63160 2208 53283683
Irritable bowel syndrome 13.67 10.38 19 63156 43613 53242278
Blood creatine phosphokinase MM increased 13.60 10.38 4 63171 38 53285853
Cataract 13.59 10.38 103 63072 49517 53236374
Hypertension 13.49 10.38 356 62819 225075 53060816
Pulmonary pain 13.36 10.38 15 63160 2277 53283614
Vitamin D deficiency 13.11 10.38 38 63137 12210 53273681
Intervertebral disc degeneration 13.09 10.38 42 63133 14256 53271635
Necrotising myositis 12.87 10.38 7 63168 361 53285530
Myoglobin blood increased 12.84 10.38 12 63163 1468 53284423
Hypocholesterolaemia 12.79 10.38 5 63170 119 53285772
Hypotrichosis 12.75 10.38 5 63170 120 53285771
Peripheral swelling 12.63 10.38 170 63005 205938 53079953
Malignant neoplasm progression 12.57 10.38 43 63132 71498 53214393
Muscle atrophy 12.49 10.38 25 63150 6349 53279542
Arteriosclerosis 12.43 10.38 33 63142 10078 53275813
Premature baby 12.38 10.38 4 63171 19797 53266094
Suicide attempt 12.36 10.38 32 63143 58136 53227755
Drug dependence 12.30 10.38 5 63170 21467 53264424
Non-high-density lipoprotein cholesterol increased 12.23 10.38 5 63170 134 53285757
Mucosal inflammation 12.08 10.38 20 63155 42764 53243127
Pancreatitis relapsing 12.07 10.38 9 63166 805 53285086
Neutrophil count decreased 12.05 10.38 25 63150 49073 53236818
Pulmonary haematoma 12.00 10.38 4 63171 59 53285832
Hypersensitivity pneumonitis 11.97 10.38 15 63160 2555 53283336
Pleural effusion 11.96 10.38 59 63116 88520 53197371
Septic shock 11.91 10.38 36 63139 62193 53223698
Impaired quality of life 11.91 10.38 21 63154 4850 53281041
Blood pressure increased 11.89 10.38 233 62942 140246 53145645
Ear haemorrhage 11.86 10.38 11 63164 1333 53284558
Pneumonia aspiration 11.71 10.38 14 63161 34287 53251604
Weight decreased 11.57 10.38 362 62813 234586 53051305
Abdominal pain upper 11.56 10.38 268 62907 166023 53119868
Discomfort 11.55 10.38 66 63109 95406 53190485
Nephropathy 11.53 10.38 22 63153 5395 53280496
Blister 11.49 10.38 51 63124 78702 53207189
Xanthelasma 11.37 10.38 4 63171 70 53285821
Acquired epidermolysis bullosa 11.32 10.38 4 63171 71 53285820
Autoimmune hepatitis 11.11 10.38 28 63147 8290 53277601
Nasal cyst 11.07 10.38 4 63171 76 53285815
Antiphospholipid syndrome 11.06 10.38 12 63163 1754 53284137
Purpura 10.98 10.38 33 63142 10820 53275071
Small intestinal haemorrhage 10.93 10.38 13 63162 2098 53283793
Renal tubular necrosis 10.88 10.38 34 63141 11385 53274506
Cerebellar syndrome 10.75 10.38 17 63158 3590 53282301
Peroneal nerve palsy 10.72 10.38 19 63156 4404 53281487
Rash 10.71 10.38 426 62749 445765 52840126
Low density lipoprotein abnormal 10.71 10.38 5 63170 186 53285705
White blood cell count decreased 10.69 10.38 95 63080 124380 53161511
Hyperleukocytosis 10.68 10.38 7 63168 509 53285382
Encephalopathy 10.59 10.38 17 63158 36791 53249100
Neoplasm progression 10.44 10.38 12 63163 29907 53255984

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
Myalgia 977.62 10.98 957 58666 80273 32373630
Rhabdomyolysis 509.79 10.98 622 59001 66643 32387260
Blood creatine phosphokinase increased 505.74 10.98 514 59109 44962 32408941
Myopathy 315.36 10.98 218 59405 11123 32442780
Low density lipoprotein increased 235.47 10.98 127 59496 4119 32449784
Myocardial infarction 132.68 10.98 518 59105 125158 32328745
Death 118.54 10.98 337 59286 382180 32071723
Coronary artery disease 117.90 10.98 273 59350 49433 32404470
Blood cholesterol increased 111.80 10.98 150 59473 17607 32436296
Angina pectoris 107.91 10.98 201 59422 31225 32422678
Muscular weakness 106.80 10.98 320 59303 67609 32386294
Drug abuse 98.05 10.98 15 59608 80228 32373675
Toxicity to various agents 95.05 10.98 112 59511 177929 32275974
Low density lipoprotein decreased 92.38 10.98 43 59580 1010 32452893
Muscle spasms 91.77 10.98 311 59312 70107 32383796
Immune-mediated myositis 89.80 10.98 49 59574 1626 32452277
Off label use 83.99 10.98 285 59338 306035 32147868
High density lipoprotein decreased 76.11 10.98 57 59566 3295 32450608
Febrile neutropenia 74.22 10.98 66 59557 119500 32334403
Venous pressure jugular increased 71.06 10.98 33 59590 771 32453132
Pancreatitis 67.92 10.98 188 59435 37963 32415940
Neutropenia 58.62 10.98 107 59516 142068 32311835
Type IIa hyperlipidaemia 57.86 10.98 20 59603 207 32453696
Myositis 57.53 10.98 86 59537 11149 32442754
Foetal exposure during pregnancy 57.19 10.98 5 59618 41296 32412607
Dizziness 56.05 10.98 609 59014 209009 32244894
Angina unstable 55.46 10.98 89 59534 12266 32441637
Blood triglycerides increased 54.59 10.98 97 59526 14522 32439381
Completed suicide 53.95 10.98 54 59569 92463 32361440
Drug interaction 51.19 10.98 618 59005 217567 32236336
Hepatic enzyme increased 48.57 10.98 164 59459 36873 32417030
Pneumonia 47.55 10.98 420 59203 354832 32099071
Necrotising myositis 47.37 10.98 22 59601 514 32453389
Pancreatitis acute 46.97 10.98 133 59490 27202 32426701
Liver function test abnormal 45.97 10.98 146 59477 31801 32422102
Suicide attempt 44.80 10.98 8 59615 38236 32415667
Asthenia 43.19 10.98 639 58984 235305 32218598
Blood cholesterol decreased 41.83 10.98 25 59598 989 32452914
Amyotrophic lateral sclerosis 38.06 10.98 24 59599 1046 32452857
Sepsis 38.02 10.98 156 59467 158678 32295225
Acute kidney injury 37.82 10.98 751 58872 292717 32161186
Malignant neoplasm progression 37.07 10.98 54 59569 78442 32375461
Pyrexia 36.96 10.98 392 59231 319576 32134327
Intentional overdose 36.92 10.98 15 59608 41586 32412317
Chest pain 36.56 10.98 368 59255 123769 32330134
Dyspnoea exertional 35.78 10.98 154 59469 38807 32415096
Acute coronary syndrome 35.72 10.98 79 59544 13862 32440041
Product use in unapproved indication 35.58 10.98 66 59557 87138 32366765
Chromaturia 34.81 10.98 80 59543 14398 32439505
Coronary artery occlusion 33.96 10.98 69 59554 11416 32442487
Pancytopenia 33.84 10.98 73 59550 91162 32362741
Erectile dysfunction 33.56 10.98 96 59527 19743 32434160
Septic shock 33.03 10.98 47 59576 68942 32384961
Pain in extremity 32.41 10.98 347 59276 118554 32335349
Erythromelalgia 31.85 10.98 9 59614 44 32453859
Cardiac failure congestive 30.74 10.98 263 59360 84589 32369314
Dissociation 30.69 10.98 22 59601 1188 32452715
Nonalcoholic fatty liver disease 30.23 10.98 14 59609 325 32453578
Cutaneous lupus erythematosus 30.10 10.98 18 59605 713 32453190
Muscle rupture 29.83 10.98 28 59595 2214 32451689
Muscle disorder 29.71 10.98 29 59594 2408 32451495
Drug dependence 29.57 10.98 4 59619 23480 32430423
Disease progression 29.39 10.98 73 59550 86789 32367114
Alanine aminotransferase increased 29.35 10.98 245 59378 78234 32375669
Hospitalisation 29.20 10.98 28 59595 48943 32404960
Glycogen storage disease type V 28.85 10.98 8 59615 36 32453867
Bone marrow failure 28.59 10.98 10 59613 30394 32423509
Ischaemic cardiomyopathy 28.40 10.98 46 59577 6388 32447515
Cytomegalovirus infection 28.40 10.98 6 59617 25458 32428445
White blood cell count decreased 28.31 10.98 80 59543 91118 32362785
Stent placement 27.80 10.98 38 59585 4537 32449366
Treatment failure 27.58 10.98 19 59604 39144 32414759
Overdose 27.31 10.98 76 59547 87001 32366902
Type V hyperlipidaemia 27.29 10.98 17 59606 725 32453178
Left ventricular dysfunction 27.20 10.98 57 59566 9638 32444265
Leukopenia 26.80 10.98 43 59580 60079 32393824
Aspartate aminotransferase increased 26.79 10.98 211 59412 66218 32387685
Mucosal inflammation 26.65 10.98 14 59609 33420 32420483
Myasthenia gravis 26.55 10.98 33 59590 3589 32450314
Ascites 26.36 10.98 21 59602 40170 32413733
Arthralgia 26.30 10.98 400 59223 148048 32305855
Muscle atrophy 26.17 10.98 47 59576 7093 32446810
Low density lipoprotein abnormal 26.17 10.98 12 59611 272 32453631
Oedema peripheral 26.16 10.98 322 59301 113769 32340134
Left atrial dilatation 26.11 10.98 24 59599 1848 32452055
Cardio-respiratory arrest 25.96 10.98 39 59584 55950 32397953
Plasma cell myeloma 25.88 10.98 41 59582 57573 32396330
Muscle injury 25.49 10.98 20 59603 1239 32452664
Haematocrit increased 25.36 10.98 23 59600 1740 32452163
Multiple organ dysfunction syndrome 24.99 10.98 57 59566 69797 32384106
Rheumatoid arthritis 24.82 10.98 27 59596 44517 32409386
Exercise lack of 24.33 10.98 9 59614 115 32453788
Phaeochromocytoma malignant 24.14 10.98 8 59615 72 32453831
Allergy to animal 23.92 10.98 11 59612 251 32453652
Infection 23.66 10.98 78 59545 84637 32369266
Dyslipidaemia 23.58 10.98 44 59579 6839 32447064
Exercise tolerance decreased 23.31 10.98 35 59588 4553 32449350
Pancreatic neoplasm 23.16 10.98 17 59606 953 32452950
Dyspnoea 22.99 10.98 845 58778 361200 32092703
Cardiac disorder 22.75 10.98 143 59480 41723 32412180
Toxic epidermal necrolysis 22.66 10.98 5 59618 20588 32433315
Food aversion 22.65 10.98 12 59611 375 32453528
Restrictive pulmonary disease 22.19 10.98 18 59605 1170 32452733
Platelet count decreased 21.87 10.98 122 59501 114469 32339434
Pemphigoid 21.83 10.98 48 59575 8388 32445515
Orthostatic hypotension 21.73 10.98 99 59524 25551 32428352
Hypercholesterolaemia 21.35 10.98 46 59577 7928 32445975
Total cholesterol/HDL ratio increased 21.28 10.98 9 59614 167 32453736
Mucosal dryness 20.89 10.98 17 59606 1110 32452793
Candida infection 20.83 10.98 3 59620 16800 32437103
Neutrophil count decreased 20.74 10.98 34 59589 47105 32406798
Acute myocardial infarction 20.52 10.98 172 59451 54977 32398926
Hypovolaemia 20.19 10.98 48 59575 8829 32445074
Faeces pale 20.16 10.98 19 59604 1510 32452393
Cardiac murmur 19.85 10.98 42 59581 7149 32446754
Tendon rupture 19.41 10.98 42 59581 7261 32446642
Myocardial ischaemia 19.32 10.98 74 59549 17685 32436218
Iron binding capacity total increased 19.30 10.98 6 59617 43 32453860
Hepatitis cholestatic 19.28 10.98 45 59578 8180 32445723
Respiratory arrest 19.09 10.98 15 59608 28893 32425010
Intentional product use issue 18.99 10.98 30 59593 42181 32411722
Self esteem decreased 18.71 10.98 12 59611 539 32453364
Laryngeal discomfort 18.60 10.98 8 59615 155 32453748
Arteriosclerosis 18.28 10.98 53 59570 10981 32442922
Ischaemic stroke 18.11 10.98 72 59551 17504 32436399
Spinal stenosis 18.02 10.98 31 59592 4523 32449380
Paraesthesia 17.93 10.98 176 59447 58768 32395135
Respiratory failure 17.89 10.98 119 59504 107063 32346840
Neck pain 17.88 10.98 86 59537 22701 32431202
Atrial fibrillation 17.86 10.98 307 59316 116397 32337506
Sedation 17.58 10.98 6 59617 18520 32435383
Thrombocytopenia 17.33 10.98 181 59442 148118 32305785
Aldolase increased 17.20 10.98 6 59617 64 32453839
Tumour lysis syndrome 17.13 10.98 3 59620 14544 32439359
Hyperlipidaemia 17.06 10.98 62 59561 14449 32439454
Coeliac disease 16.97 10.98 12 59611 634 32453269
Suspected suicide attempt 16.90 10.98 7 59616 123 32453780
Blood creatine phosphokinase decreased 16.66 10.98 11 59612 519 32453384
Lymphocyte count decreased 16.60 10.98 9 59614 21110 32432793
Back pain 16.58 10.98 291 59332 110762 32343141
ECG signs of myocardial ischaemia 16.41 10.98 8 59615 209 32453694
Haemoglobin increased 16.36 10.98 24 59599 3058 32450845
Coronary artery stenosis 16.18 10.98 47 59576 9746 32444157
Product use issue 15.85 10.98 47 59576 52730 32401173
Agitation 15.77 10.98 53 59570 57183 32396720
Delirium 15.70 10.98 36 59587 44010 32409893
Infusion related reaction 15.67 10.98 38 59585 45561 32408342
C-reactive protein increased 15.06 10.98 42 59581 48060 32405843
Pericardial haemorrhage 14.91 10.98 23 59600 3063 32450840
Muscle discomfort 14.89 10.98 5 59618 47 32453856
Polymyositis 14.87 10.98 16 59607 1490 32452413
Transaminases abnormal 14.87 10.98 8 59615 258 32453645
Fatigue 14.78 10.98 785 58838 349916 32103987
Flatulence 14.43 10.98 72 59551 19283 32434620
Stomatitis 14.24 10.98 33 59590 40196 32413707
Seizure 14.15 10.98 122 59501 103732 32350171
Drug withdrawal syndrome 14.00 10.98 10 59613 20221 32433682
Lipase increased 13.95 10.98 43 59580 9214 32444689
Pancreatic carcinoma 13.86 10.98 40 59583 8266 32445637
International normalised ratio abnormal 13.82 10.98 23 59600 3266 32450637
Peritonitis bacterial 13.82 10.98 3 59620 12493 32441410
Myoglobin urine 13.77 10.98 4 59619 22 32453881
Syncope 13.75 10.98 237 59386 89887 32364016
Thromboangiitis obliterans 13.47 10.98 4 59619 24 32453879
Dyspnoea at rest 13.46 10.98 23 59600 3336 32450567
Muscle strength abnormal 13.44 10.98 5 59618 65 32453838
Blood creatine phosphokinase 13.37 10.98 5 59618 66 32453837
Bronchopneumopathy 13.35 10.98 9 59614 440 32453463
Hypokalaemia 13.22 10.98 54 59569 55040 32398863
Gait disturbance 13.20 10.98 214 59409 80194 32373709
Pseudomonas infection 13.12 10.98 3 59620 12053 32441850
Autoimmune hepatitis 13.10 10.98 25 59598 3950 32449953
Inspiratory capacity abnormal 13.10 10.98 5 59618 70 32453833
Influenza like illness 13.10 10.98 90 59533 27050 32426853
Hepatitis E virus test positive 13.07 10.98 4 59619 27 32453876
Tumour invasion 13.06 10.98 8 59615 331 32453572
Status epilepticus 13.04 10.98 3 59620 12003 32441900
Peritonitis 13.04 10.98 13 59610 22317 32431586
Disseminated intravascular coagulation 12.96 10.98 14 59609 23162 32430741
Lower respiratory tract infection 12.95 10.98 21 59602 29222 32424681
Diaphragmatic disorder 12.82 10.98 13 59610 1130 32452773
Glycosylated haemoglobin increased 12.74 10.98 45 59578 10344 32443559
Ureteric cancer recurrent 12.71 10.98 4 59619 30 32453873
Haemorrhagic transformation stroke 12.67 10.98 14 59609 1344 32452559
Aortic embolus 12.63 10.98 3 59620 6 32453897
Pleural neoplasm 12.59 10.98 4 59619 31 32453872
Depressed level of consciousness 12.54 10.98 36 59587 40811 32413092
Neurotoxicity 12.48 10.98 6 59617 15064 32438839
Intentional product misuse 12.42 10.98 30 59593 36021 32417882
Electrocardiogram abnormal 12.39 10.98 37 59586 7793 32446110
Drug ineffective for unapproved indication 12.37 10.98 5 59618 13907 32439996
Aspergillus infection 12.36 10.98 3 59620 11571 32442332
Dyschromatopsia 12.34 10.98 8 59615 366 32453537
Autoimmune myositis 12.22 10.98 5 59618 85 32453818
Abulia 12.14 10.98 9 59614 512 32453391
Hypercapnic coma 12.09 10.98 6 59617 163 32453740
Neoplasm progression 12.00 10.98 11 59612 19647 32434256
Gamma-glutamyltransferase increased 11.98 10.98 97 59526 30685 32423218
Pulmonary embolism 11.97 10.98 97 59526 83562 32370341
Muscle fatigue 11.82 10.98 13 59610 1241 32452662
Chronic cutaneous lupus erythematosus 11.79 10.98 4 59619 39 32453864
Psychotic disorder 11.70 10.98 15 59608 23005 32430898
Vertigo 11.41 10.98 80 59543 24203 32429700
Respiratory depression 11.34 10.98 5 59618 13206 32440697
Blood glucose increased 11.22 10.98 175 59448 65066 32388837
Gastric dilatation 11.18 10.98 9 59614 579 32453324
Aggression 11.17 10.98 36 59587 39353 32414550
Coronary artery bypass 11.06 10.98 27 59596 5049 32448854
Erythrasma 11.04 10.98 4 59619 48 32453855

Pharmacologic Action:

SourceCodeDescription
ATC C10AX09 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, PLAIN
Other lipid modifying agents
ATC C10BA02 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, COMBINATIONS
Combinations of various lipid modifying agents
ATC C10BA05 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, COMBINATIONS
Combinations of various lipid modifying agents
ATC C10BA06 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, COMBINATIONS
Combinations of various lipid modifying agents
ATC C10BA10 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, COMBINATIONS
Combinations of various lipid modifying agents
ATC C10BA11 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, COMBINATIONS
Combinations of various lipid modifying agents
ATC C10BA12 CARDIOVASCULAR SYSTEM
LIPID MODIFYING AGENTS
LIPID MODIFYING AGENTS, COMBINATIONS
Combinations of various lipid modifying agents
FDA PE N0000008553 Decreased Cholesterol Absorption
MeSH PA D000924 Anticholesteremic Agents
MeSH PA D000963 Antimetabolites
MeSH PA D000960 Hypolipidemic Agents
MeSH PA D057847 Lipid Regulating Agents
FDA EPC N0000175911 Dietary Cholesterol Absorption Inhibitor
CHEBI has role CHEBI:35221 antimetabolite
CHEBI has role CHEBI:35679 hypolipidemic agent
CHEBI has role CHEBI:35821 hypocholesteremic agent

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypercholesterolemia indication 13644009
Hyperlipidemia indication 55822004 DOID:1168
Familial hypercholesterolemia - homozygous indication 238078005
Familial hypercholesterolemia - heterozygous indication 238079002
Sitosterolemia indication 238104009 DOID:0090019
Mixed hyperlipidemia indication 267434003
Alopecia areata off-label use 68225006 DOID:986
Alcoholism contraindication 7200002
Acute nephropathy contraindication 58574008
Disorder of muscle contraindication 129565002 DOID:423
Liver function tests abnormal contraindication 166603001
Acute pancreatitis contraindication 197456007 DOID:2913
Hemorrhagic cerebral infarction contraindication 230706003
Disease of liver contraindication 235856003 DOID:409
Rhabdomyolysis contraindication 240131006
Pregnancy, function contraindication 289908002
Surgical procedure contraindication 387713003
Breastfeeding (mother) contraindication 413712001
SLCO1B1 Gene Variant for OATP1B1 Transporter Affecting Hepatic Clearance contraindication
Myopathy related to SLCO1B1 Gene Variant contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.48 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
180MG;10MG NEXLIZET ESPERION THERAPS INC N211617 Feb. 26, 2020 RX TABLET ORAL 10118881 Dec. 23, 2023 USE OF NEXLIZET AS AN ADJUNCT TO DIET AND MAXIMALLY TOLERATED STATIN THERAPY TO LOWER LDL-C IN ADULTS WITH HETEROZYGOUS FAMILIAL HYPERCHOLESTEROLEMIA OR ESTABLISHED ATHEROSCLEROTIC CARDIOVASCULAR DISEASE
180MG;10MG NEXLIZET ESPERION THERAPS INC N211617 Feb. 26, 2020 RX TABLET ORAL 10941095 Dec. 23, 2023 USE OF NEXLIZET AS AN ADJUNCT TO DIET AND MAXIMALLY TOLERATED STATIN THERAPY TO LOWER LDL-C IN ADULTS WITH HETEROZYGOUS FAMILIAL HYPERCHOLESTEROLEMIA OR ESTABLISHED ATHEROSCLEROTIC CARDIOVASCULAR DISEASE
180MG;10MG NEXLIZET ESPERION THERAPS INC N211617 Feb. 26, 2020 RX TABLET ORAL 8497301 Dec. 23, 2023 USE OF NEXLIZET AS AN ADJUNCT TO DIET AND MAXIMALLY TOLERATED STATIN THERAPY TO LOWER LDL-C IN ADULTS WITH HETEROZYGOUS FAMILIAL HYPERCHOLESTEROLEMIA OR ESTABLISHED ATHEROSCLEROTIC CARDIOVASCULAR DISEASE
180MG;10MG NEXLIZET ESPERION THERAPS INC N211617 Feb. 26, 2020 RX TABLET ORAL 9000041 Dec. 23, 2023 USE OF NEXLIZET AS AN ADJUNCT TO DIET AND MAXIMALLY TOLERATED STATIN THERAPY TO LOWER LDL-C IN ADULTS WITH HETEROZYGOUS FAMILIAL HYPERCHOLESTEROLEMIA OR ESTABLISHED ATHEROSCLEROTIC CARDIOVASCULAR DISEASE
180MG;10MG NEXLIZET ESPERION THERAPS INC N211617 Feb. 26, 2020 RX TABLET ORAL 9624152 Dec. 23, 2023 USE OF NEXLIZET AS AN ADJUNCT TO DIET AND MAXIMALLY TOLERATED STATIN THERAPY FOR INHIBITING CHOLESTEROL SYNTHESIS TO LOWER LDL-C IN ADULTS WITH HETEROZYGOUS FAMILIAL HYPERCHOLESTEROLEMIA OR ESTABLISHED ATHEROSCLEROTIC CARDIOVASCULAR DISEASE
10MG ZETIA ORGANON N021445 Oct. 25, 2002 RX TABLET ORAL 7612058 Oct. 30, 2025 REDUCTION OF ELEVATED PLASMA STEROL AND/OR STANOL LEVELS IN A MAMMAL
10MG ZETIA ORGANON N021445 Oct. 25, 2002 RX TABLET ORAL 7612058 Oct. 30, 2025 TO REDUCE ELEVATED TOTAL-C, LDL-C, APO B AND NON-HDL-C IN PATIENTS WITH PRIMARY HYPERLIPIDEMIA BY ADMINISTRATION OF EZETIMIBE ALONE OR IN COMBINATION WITH A STATIN OR WITH FENOFIBRATE
10MG;EQ 10MG BASE ROSZET ALTHERA PHARMS N213072 March 23, 2021 RX TABLET ORAL 10376470 May 1, 2033 TREATMENT OF HYPERLIPIDEMIA
10MG;EQ 10MG BASE ROSZET ALTHERA PHARMS N213072 March 23, 2021 RX TABLET ORAL 9763885 May 1, 2033 TREATMENT OF HYPERLIPIDEMIA
10MG;EQ 20MG BASE ROSZET ALTHERA PHARMS N213072 March 23, 2021 RX TABLET ORAL 10376470 May 1, 2033 TREATMENT OF HYPERLIPIDEMIA
10MG;EQ 20MG BASE ROSZET ALTHERA PHARMS N213072 March 23, 2021 RX TABLET ORAL 9763885 May 1, 2033 TREATMENT OF HYPERLIPIDEMIA
10MG;EQ 40MG BASE ROSZET ALTHERA PHARMS N213072 March 23, 2021 RX TABLET ORAL 10376470 May 1, 2033 TREATMENT OF HYPERLIPIDEMIA
10MG;EQ 40MG BASE ROSZET ALTHERA PHARMS N213072 March 23, 2021 RX TABLET ORAL 9763885 May 1, 2033 TREATMENT OF HYPERLIPIDEMIA
10MG;EQ 5MG BASE ROSZET ALTHERA PHARMS N213072 March 23, 2021 RX TABLET ORAL 10376470 May 1, 2033 TREATMENT OF HYPERLIPIDEMIA
10MG;EQ 5MG BASE ROSZET ALTHERA PHARMS N213072 March 23, 2021 RX TABLET ORAL 9763885 May 1, 2033 TREATMENT OF HYPERLIPIDEMIA
180MG;10MG NEXLIZET ESPERION THERAPS INC N211617 Feb. 26, 2020 RX TABLET ORAL 10912751 March 14, 2036 A METHOD OF TREATING HETEROZYGOUS FAMILIAL HYPERCHOLESTEROLEMIA OR ESTABLISHED ATHEROSCLEROTIC CARDIOVASCULAR DISEASE BY DECREASING THE LEVEL OF LDL-C USING A FIXED DOSE COMBINATION OF 180 MG BEMPEDOIC ACID AND 10 MG EZETIMIBE

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
180MG;10MG NEXLIZET ESPERION THERAPS INC N211617 Feb. 26, 2020 RX TABLET ORAL Feb. 26, 2023 NEW PRODUCT
180MG;10MG NEXLIZET ESPERION THERAPS INC N211617 Feb. 26, 2020 RX TABLET ORAL Feb. 21, 2025 NEW CHEMICAL ENTITY

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Niemann-Pick C1-like protein 1 Membrane other ANTAGONIST Kd 6.66 IUPHAR CHEMBL
Niemann-Pick C1-like protein 1 Unclassified Ki 6.70 CHEMBL

External reference:

IDSource
4021366 VUID
N0000148785 NUI
D01966 KEGG_DRUG
4021366 VANDF
C1142985 UMLSCUI
CHEBI:49040 CHEBI
H56 PDB_CHEM_ID
CHEMBL1138 ChEMBL_ID
D000069438 MESH_DESCRIPTOR_UI
DB00973 DRUGBANK_ID
150311 PUBCHEM_CID
6816 IUPHAR_LIGAND_ID
8010 INN_ID
EOR26LQQ24 UNII
341248 RXNORM
17026 MMSL
229065 MMSL
45364 MMSL
d04824 MMSL
009817 NDDF
408041006 SNOMEDCT_US
409149001 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Ezetimibe HUMAN PRESCRIPTION DRUG LABEL 1 0591-3713 TABLET 10 mg ORAL ANDA 26 sections
Ezetimibe HUMAN PRESCRIPTION DRUG LABEL 1 0615-8300 TABLET 10 mg ORAL ANDA 27 sections
Ezetimibe HUMAN PRESCRIPTION DRUG LABEL 1 0781-5690 TABLET 10 mg ORAL ANDA 27 sections
Ezetimibe HUMAN PRESCRIPTION DRUG LABEL 1 0904-6664 TABLET 10 mg ORAL ANDA 28 sections
Ezetimibe HUMAN PRESCRIPTION DRUG LABEL 1 0904-7103 TABLET 10 mg ORAL ANDA 26 sections
ezetimibe and simvastatin HUMAN PRESCRIPTION DRUG LABEL 2 16714-778 TABLET 10 mg ORAL ANDA 28 sections
ezetimibe and simvastatin HUMAN PRESCRIPTION DRUG LABEL 2 16714-779 TABLET 10 mg ORAL ANDA 28 sections
ezetimibe and simvastatin HUMAN PRESCRIPTION DRUG LABEL 2 16714-780 TABLET 10 mg ORAL ANDA 28 sections
ezetimibe and simvastatin HUMAN PRESCRIPTION DRUG LABEL 2 16714-781 TABLET 10 mg ORAL ANDA 28 sections
Ezetimibe Human Prescription Drug Label 1 16714-813 TABLET 10 mg ORAL ANDA 28 sections
EZETIMIBE HUMAN PRESCRIPTION DRUG LABEL 1 16729-433 TABLET 10 mg ORAL ANDA 29 sections
VYTORIN HUMAN PRESCRIPTION DRUG LABEL 2 21695-325 TABLET 10 mg ORAL NDA 28 sections
VYTORIN HUMAN PRESCRIPTION DRUG LABEL 2 21695-339 TABLET 10 mg ORAL NDA 28 sections
Zetia HUMAN PRESCRIPTION DRUG LABEL 1 21695-778 TABLET 10 mg ORAL NDA 29 sections
VYTORIN HUMAN PRESCRIPTION DRUG LABEL 2 21695-827 TABLET 10 mg ORAL NDA 28 sections
Ezetimibe and Simvastatin HUMAN PRESCRIPTION DRUG LABEL 2 43598-742 TABLET 10 mg ORAL ANDA 28 sections
Ezetimibe and Simvastatin HUMAN PRESCRIPTION DRUG LABEL 2 43598-743 TABLET 10 mg ORAL ANDA 28 sections
Ezetimibe and Simvastatin HUMAN PRESCRIPTION DRUG LABEL 2 43598-744 TABLET 10 mg ORAL ANDA 28 sections
Ezetimibe and Simvastatin HUMAN PRESCRIPTION DRUG LABEL 2 43598-745 TABLET 10 mg ORAL ANDA 28 sections
Ezetimibe and Simvastatin HUMAN PRESCRIPTION DRUG LABEL 2 45963-565 TABLET 10 mg ORAL ANDA 27 sections
Ezetimibe and Simvastatin HUMAN PRESCRIPTION DRUG LABEL 2 45963-566 TABLET 10 mg ORAL ANDA 27 sections
Ezetimibe and Simvastatin HUMAN PRESCRIPTION DRUG LABEL 2 45963-567 TABLET 10 mg ORAL ANDA 27 sections
Ezetimibe and Simvastatin HUMAN PRESCRIPTION DRUG LABEL 2 45963-568 TABLET 10 mg ORAL ANDA 27 sections
Ezetimibe HUMAN PRESCRIPTION DRUG LABEL 1 50090-3087 TABLET 10 mg ORAL ANDA 26 sections
Ezetimibe Human Prescription Drug Label 1 50090-3657 TABLET 10 mg ORAL ANDA 27 sections
Ezetimibe and Simvastatin HUMAN PRESCRIPTION DRUG LABEL 2 50090-3984 TABLET 10 mg ORAL ANDA 27 sections
Ezetimibe and Simvastatin Human Prescription Drug Label 2 50090-4772 TABLET 10 mg ORAL ANDA 27 sections
Ezetimibe HUMAN PRESCRIPTION DRUG LABEL 1 50228-379 TABLET 10 mg ORAL ANDA 29 sections
Ezetimibe HUMAN PRESCRIPTION DRUG LABEL 1 50268-298 TABLET 10 mg ORAL ANDA 26 sections
Ezetimibe and Simvastatin HUMAN PRESCRIPTION DRUG LABEL 2 51407-190 TABLET 10 mg ORAL ANDA 28 sections