epirubicin ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antineoplastics, daunorubicin derivatives 1030 56420-45-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • epirubicin
  • epiadriamycin
  • epidoxorubicin
  • epirarubicin
  • farmarubicin
  • farmarubicine
  • pharmarubicin
  • epirubicin hydrochloride
  • epirubicin HCl
An anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA.
  • Molecular weight: 543.53
  • Formula: C27H29NO11
  • CLOGP: 0.26
  • LIPINSKI: 3
  • HAC: 12
  • HDO: 6
  • TPSA: 206.07
  • ALOGS: -2.67
  • ROTB: 5

  • Status: OFP

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

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 9.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 5.75 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 45 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 20 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.25 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 36 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Sept. 15, 1999 FDA PFIZER INC

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
Agranulocytosis 786.40 17.94 319 24172 21102 50559531
Disease recurrence 672.23 17.94 280 24211 19801 50560832
Febrile neutropenia 672.09 17.94 475 24016 97192 50483441
Bone marrow failure 487.85 17.94 247 24244 27377 50553256
Neutropenia 466.57 17.94 458 24033 147507 50433126
Leukopenia 403.71 17.94 302 24189 67226 50513407
Myelosuppression 345.78 17.94 156 24335 13361 50567272
Metastases to bone 338.44 17.94 168 24323 17827 50562806
Ejection fraction decreased 296.20 17.94 155 24336 18365 50562268
Alopecia 276.36 17.94 454 24037 244593 50336040
Cardiac dysfunction 264.34 17.94 75 24416 1626 50579007
Acute myeloid leukaemia 237.72 17.94 125 24366 14949 50565684
Metastases to liver 235.40 17.94 137 24354 19967 50560666
Malignant neoplasm progression 233.16 17.94 221 24270 67903 50512730
Palmar-plantar erythrodysaesthesia syndrome 227.52 17.94 134 24357 19964 50560669
Cardiac failure 216.28 17.94 223 24268 75817 50504816
Second primary malignancy 203.21 17.94 88 24403 6826 50573807
White blood cell count decreased 198.89 17.94 263 24228 116459 50464174
Cardiotoxicity 188.91 17.94 84 24407 6943 50573690
Metastases to lung 169.81 17.94 90 24401 10930 50569703
Death 162.99 17.94 432 24059 324947 50255686
Cardiomyopathy 145.80 17.94 92 24399 15494 50565139
Metastases to lymph nodes 142.21 17.94 69 24422 6955 50573678
Congestive cardiomyopathy 142.05 17.94 64 24427 5454 50575179
Breast cancer recurrent 133.68 17.94 55 24436 3753 50576880
Neoplasm progression 132.25 17.94 111 24380 29046 50551587
Breast cancer metastatic 104.05 17.94 64 24427 10300 50570333
Neutrophil count decreased 102.87 17.94 119 24372 45907 50534726
Drug ineffective 101.97 17.94 150 24341 819183 49761450
Metastasis 97.77 17.94 46 24445 4329 50576304
Mucosal inflammation 96.86 17.94 108 24383 40034 50540599
Pyrexia 93.22 17.94 397 24094 379806 50200827
Neuropathy peripheral 91.20 17.94 166 24325 96591 50484042
Interstitial lung disease 90.67 17.94 120 24371 53056 50527577
Polyneuropathy 90.08 17.94 62 24429 12069 50568564
Rheumatoid arthritis 84.75 17.94 3 24488 202547 50378086
Disease progression 83.50 17.94 159 24332 95707 50484926
Colony stimulating factor therapy 82.40 17.94 21 24470 297 50580336
Administration site extravasation 73.69 17.94 23 24468 698 50579935
Nail disorder 72.98 17.94 50 24441 9658 50570975
Left ventricular dysfunction 71.72 17.94 51 24440 10455 50570178
Metastases to skin 69.83 17.94 26 24465 1357 50579276
Fall 69.29 17.94 38 24453 334894 50245739
Neurotoxicity 68.64 17.94 57 24434 14683 50565950
Hepatic function abnormal 67.21 17.94 81 24410 32600 50548033
Pain 65.14 17.94 113 24378 578790 50001843
Joint swelling 65.10 17.94 19 24472 245267 50335366
Hormone receptor positive breast cancer 64.69 17.94 19 24472 467 50580166
Device related thrombosis 63.91 17.94 24 24467 1283 50579350
Paraesthesia 61.25 17.94 161 24330 120082 50460551
Abdominal discomfort 56.10 17.94 21 24470 231620 50349013
Vomiting 55.61 17.94 397 24094 460361 50120272
Pneumocystis jirovecii pneumonia 54.76 17.94 50 24441 14613 50566020
Neutropenic sepsis 54.32 17.94 49 24442 14098 50566535
Extravasation 54.01 17.94 24 24467 1978 50578655
Systemic lupus erythematosus 52.80 17.94 4 24487 140618 50440015
Chemotherapy 52.25 17.94 21 24470 1348 50579285
Lymphangiosis carcinomatosa 51.44 17.94 20 24471 1176 50579457
Febrile bone marrow aplasia 51.01 17.94 34 24457 6277 50574356
Aortitis 49.98 17.94 18 24473 854 50579779
Acute leukaemia 49.80 17.94 19 24472 1061 50579572
Weight increased 49.39 17.94 18 24473 201873 50378760
Skin toxicity 49.33 17.94 28 24463 3885 50576748
Contraindicated product administered 48.85 17.94 7 24484 148951 50431682
Hypertransaminasaemia 48.68 17.94 27 24464 3584 50577049
Blood creatine increased 48.59 17.94 30 24461 4857 50575776
Troponin I increased 48.49 17.94 22 24469 1904 50578729
Urinary tract infection 48.37 17.94 24 24467 223996 50356637
Therapeutic product effect decreased 48.03 17.94 5 24486 136045 50444588
Synovitis 48.03 17.94 3 24488 123862 50456771
Systolic dysfunction 47.42 17.94 20 24471 1452 50579181
Pruritus 46.89 17.94 41 24450 283527 50297106
Drug hypersensitivity 45.63 17.94 33 24458 250977 50329656
Miller Fisher syndrome 43.87 17.94 10 24481 85 50580548
Leukaemia cutis 43.87 17.94 10 24481 85 50580548
Subclavian vein thrombosis 43.56 17.94 20 24471 1779 50578854
Menopausal disorder 43.28 17.94 9 24482 47 50580586
Somnolence 42.97 17.94 11 24480 154974 50425659
Contusion 42.66 17.94 3 24488 112180 50468453
Swelling 42.64 17.94 22 24469 200850 50379783
Asthenia 42.60 17.94 282 24209 318760 50261873
Pleural effusion 42.40 17.94 110 24381 81344 50499289
Left ventricular dilatation 41.02 17.94 13 24478 415 50580218
White blood cell count abnormal 40.84 17.94 28 24463 5412 50575221
Neutropenic colitis 40.82 17.94 21 24470 2396 50578237
Product use issue 40.70 17.94 11 24480 149464 50431169
Acute interstitial pneumonitis 40.04 17.94 14 24477 609 50580024
Granulocytopenia 39.45 17.94 27 24464 5204 50575429
Gastrointestinal necrosis 39.39 17.94 21 24470 2577 50578056
Acute lymphocytic leukaemia 39.38 17.94 20 24471 2221 50578412
Metastases to central nervous system 39.28 17.94 37 24454 11245 50569388
Hyperpyrexia 38.93 17.94 22 24469 3027 50577606
Malignant pleural effusion 38.65 17.94 20 24471 2310 50578323
Thrombocytopenia 38.08 17.94 142 24349 127531 50453102
Haematotoxicity 37.74 17.94 31 24460 7864 50572769
Treatment failure 37.71 17.94 10 24481 137627 50443006
Anaemia 37.28 17.94 229 24262 252227 50328406
Pancytopenia 36.30 17.94 106 24385 83924 50496709
Metastases to the mediastinum 35.82 17.94 12 24479 458 50580175
Xerophthalmia 34.78 17.94 11 24480 349 50580284
Hydrothorax 34.21 17.94 13 24478 718 50579915
Deafness 34.08 17.94 40 24451 15651 50564982
Arthropathy 33.94 17.94 17 24474 157889 50422744
Metastases to soft tissue 33.88 17.94 9 24482 151 50580482
Menopause 33.02 17.94 18 24473 2309 50578324
Merycism 32.30 17.94 9 24482 182 50580451
Pericardial effusion 32.19 17.94 50 24441 25539 50555094
Hypersensitivity 32.18 17.94 34 24457 215127 50365506
Acute promyelocytic leukaemia 31.81 17.94 13 24478 871 50579762
Hypertension 30.89 17.94 34 24457 211169 50369464
Metastases to thorax 30.88 17.94 9 24482 215 50580418
Osteonecrosis of jaw 30.84 17.94 56 24435 32470 50548163
Nasopharyngitis 30.55 17.94 29 24462 192898 50387735
Musculoskeletal stiffness 30.49 17.94 12 24479 128469 50452164
Sinusitis 30.23 17.94 23 24468 170535 50410098
Nausea 30.04 17.94 493 23998 704905 49875728
Urticaria 29.30 17.94 13 24478 129548 50451085
Wound 28.39 17.94 8 24483 105786 50474847
Myeloproliferative neoplasm 28.15 17.94 10 24481 456 50580177
Tympanic membrane disorder 27.95 17.94 8 24483 179 50580454
Arthralgia 27.62 17.94 114 24377 438588 50142045
Acute pulmonary oedema 27.56 17.94 25 24466 7242 50573391
Glossodynia 27.08 17.94 11 24480 115558 50465075
Acute kidney injury 26.93 17.94 43 24448 228015 50352618
Diarrhoea 26.39 17.94 415 24076 588061 49992572
Gait apraxia 26.25 17.94 5 24486 15 50580618
Injection site phlebitis 26.21 17.94 7 24484 120 50580513
Recurrent cancer 26.07 17.94 14 24477 1743 50578890
Skin exfoliation 25.90 17.94 53 24438 33559 50547074
Neutrophilia 25.89 17.94 18 24473 3557 50577076
Cardiac failure acute 24.86 17.94 25 24466 8225 50572408
Metastases to chest wall 24.18 17.94 9 24482 469 50580164
Overdose 24.18 17.94 9 24482 99718 50480915
Rash 23.76 17.94 120 24371 437351 50143282
Gastrointestinal toxicity 23.69 17.94 19 24472 4658 50575975
SAPHO syndrome 23.60 17.94 6 24485 84 50580549
Anal erythema 23.46 17.94 7 24484 182 50580451
Administration site oedema 23.46 17.94 5 24486 30 50580603
Intercepted product administration error 23.40 17.94 6 24485 87 50580546
Drug interaction 23.22 17.94 38 24453 199583 50381050
Dandy-Walker syndrome 23.09 17.94 6 24485 92 50580541
Arachnoid cyst 22.96 17.94 7 24484 196 50580437
Confusional state 22.96 17.94 34 24457 185894 50394739
Gastrointestinal haemorrhage 22.77 17.94 4 24487 73317 50507316
Septic shock 22.68 17.94 70 24421 57105 50523528
Weight decreased 22.29 17.94 46 24445 221199 50359434
Acute respiratory distress syndrome 22.16 17.94 38 24453 21061 50559572
Feeling abnormal 22.13 17.94 17 24474 125475 50455158
Infusion site vesicles 22.01 17.94 8 24483 390 50580243
Skin hypopigmentation 21.76 17.94 9 24482 622 50580011
Pulmonary embolism 21.60 17.94 102 24389 101602 50479031
Cardiac perfusion defect 21.53 17.94 4 24487 10 50580623
Mobility decreased 21.53 17.94 6 24485 79942 50500691
Loss of personal independence in daily activities 21.37 17.94 4 24487 70046 50510587
Hepatic enzyme increased 21.33 17.94 21 24470 137359 50443274
Endocardial fibrosis 21.26 17.94 4 24487 11 50580622
Metastases to pleura 21.06 17.94 11 24480 1295 50579338
Human herpesvirus 6 infection 20.96 17.94 14 24477 2592 50578041
Psoriasis 20.92 17.94 4 24487 68996 50511637
Condition aggravated 20.72 17.94 74 24417 296984 50283649
Mitral valve incompetence 20.40 17.94 33 24458 17438 50563195
Hot flush 20.31 17.94 57 24434 44112 50536521
Inappropriate schedule of product administration 20.09 17.94 5 24486 71826 50508807
Amnestic disorder 19.86 17.94 7 24484 312 50580321
Invasive ductal breast carcinoma 19.81 17.94 19 24472 5902 50574731
Migraine 19.63 17.94 6 24485 75274 50505359
Lymphatic obstruction 19.38 17.94 4 24487 20 50580613
Metastases to meninges 19.17 17.94 12 24479 1990 50578643
Pneumonitis chemical 19.07 17.94 6 24485 187 50580446
Vena cava thrombosis 19.07 17.94 12 24479 2009 50578624
Tricuspid valve incompetence 19 17.94 27 24464 12743 50567890
Blood pressure increased 18.83 17.94 22 24469 133110 50447523
Oxygen saturation decreased 18.81 17.94 6 24485 73242 50507391
Osteoarthritis 18.75 17.94 5 24486 68601 50512032
Oral pain 18.73 17.94 39 24452 24994 50555639
Bladder irritation 18.57 17.94 6 24485 204 50580429
Body temperature abnormal 18.51 17.94 10 24481 1260 50579373
Bronchitis 18.50 17.94 14 24477 104145 50476488
Tremor 18.49 17.94 17 24474 114886 50465747
Ovarian necrosis 18.49 17.94 4 24487 26 50580607
Pseudocirrhosis 18.44 17.94 8 24483 622 50580011
Injection site pain 18.38 17.94 16 24475 111008 50469625
Myelodysplastic syndrome 18.24 17.94 29 24462 15103 50565530
Jugular vein thrombosis 18.19 17.94 13 24478 2683 50577950
Intracardiac thrombus 18.19 17.94 12 24479 2177 50578456
Retinopathy 18.12 17.94 13 24478 2699 50577934
Therapeutic product effect incomplete 17.99 17.94 11 24480 91504 50489129

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
Bone marrow failure 281.95 28.42 113 3754 27336 29543324
Myelosuppression 200.56 28.42 71 3796 12156 29558504
Anastomotic leak 125.23 28.42 26 3841 570 29570090
Neutropenia 70.14 28.42 86 3781 131625 29439035
Delayed puberty 67.89 28.42 13 3854 185 29570475
Hepatic artery stenosis 65.78 28.42 12 3855 129 29570531
Neutropenic sepsis 63.85 28.42 31 3836 11696 29558964
Body height below normal 59.51 28.42 12 3855 226 29570434
Carbohydrate antigen 15-3 increased 52.07 28.42 9 3858 69 29570591
Intestinal atresia 51.73 28.42 9 3858 72 29570588
Extravasation 44.48 28.42 14 3853 1658 29569002
Ameloblastoma 43.85 28.42 8 3859 86 29570574
Mucosal inflammation 37.74 28.42 32 3835 31563 29539097
Basal cell naevus syndrome 36.91 28.42 6 3861 30 29570630
Bladder perforation 35.79 28.42 8 3859 250 29570410
Liver abscess 35.01 28.42 14 3853 3324 29567336
Vascular pseudoaneurysm 34.50 28.42 12 3855 1937 29568723
Tumour perforation 30.31 28.42 7 3860 254 29570406
Osteopenia 28.80 28.42 13 3854 4155 29566505

FDA Adverse Event Reporting System (Geriatric)

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
Agranulocytosis 718.16 17.12 329 23865 37900 64436638
Bone marrow failure 682.45 17.12 341 23853 47611 64426927
Myelosuppression 478.57 17.12 215 23979 23615 64450923
Neutropenia 375.57 17.12 455 23739 239169 64235369
Febrile neutropenia 369.36 17.12 401 23793 187256 64287282
Leukopenia 363.61 17.12 302 23892 100940 64373598
Metastases to bone 277.63 17.12 141 24053 20294 64454244
Cardiac dysfunction 242.80 17.12 76 24118 3030 64471508
White blood cell count decreased 213.71 17.12 279 23915 157558 64316980
Acute myeloid leukaemia 190.11 17.12 122 24072 27341 64447197
Ejection fraction decreased 177.91 17.12 119 24075 28588 64445950
Metastases to liver 177.30 17.12 111 24083 23830 64450708
Palmar-plantar erythrodysaesthesia syndrome 170.32 17.12 116 24078 28703 64445835
Neoplasm progression 161.10 17.12 129 24065 40835 64433703
Metastases to lung 158.32 17.12 88 24106 15176 64459362
Second primary malignancy 155.60 17.12 81 24113 12256 64462282
Metastases to lymph nodes 150.90 17.12 71 24123 8646 64465892
Malignant neoplasm progression 139.55 17.12 191 24003 112680 64361858
Cardiotoxicity 114.16 17.12 62 24132 10212 64464326
Congestive cardiomyopathy 113.77 17.12 62 24132 10282 64464256
Cardiac failure 103.12 17.12 181 24013 132192 64342346
Cardiomyopathy 102.12 17.12 81 24113 25275 64449263
Pyrexia 100.84 17.12 445 23749 558199 63916339
Mucosal inflammation 99.45 17.12 120 24074 62464 64412074
Extravasation 87.88 17.12 36 24158 3144 64471394
Neutropenic sepsis 86.62 17.12 71 24123 23201 64451337
Anastomotic leak 85.48 17.12 26 24168 940 64473598
Breast cancer recurrent 84.42 17.12 33 24161 2550 64471988
Paraesthesia 80.03 17.12 164 24030 134358 64340180
Neuropathy peripheral 79.23 17.12 151 24043 117374 64357164
Metastases to skin 78.95 17.12 27 24167 1425 64473113
Neutrophil count decreased 76.90 17.12 118 24076 77078 64397460
Vomiting 76.27 17.12 407 23787 550710 63923828
Alopecia 74.92 17.12 181 24013 165509 64309029
Administration site extravasation 74.84 17.12 24 24170 1035 64473503
Colony stimulating factor therapy 73.00 17.12 20 24174 495 64474043
Breast cancer metastatic 70.70 17.12 40 24154 7129 64467409
Nausea 66.46 17.12 512 23682 785288 63689250
Nail disorder 66.39 17.12 41 24153 8583 64465955
Fall 66.33 17.12 37 24157 416789 64057749
Hepatic artery stenosis 63.29 17.12 14 24180 136 64474402
Interstitial lung disease 62.71 17.12 123 24071 97609 64376929
Polyneuropathy 60.38 17.12 54 24140 19840 64454698
Device related thrombosis 58.97 17.12 24 24170 2061 64472477
Hepatic function abnormal 55.37 17.12 92 24102 64221 64410317
White blood cell count abnormal 53.11 17.12 29 24165 4825 64469713
Chemotherapy 51.90 17.12 20 24174 1487 64473051
Rheumatoid arthritis 49.63 17.12 3 24191 164291 64310247
Drug interaction 49.62 17.12 38 24156 362045 64112493
Menopausal disorder 47.14 17.12 9 24185 38 64474500
Aortitis 46.62 17.12 17 24177 1084 64473454
Neutropenic colitis 46.37 17.12 26 24168 4555 64469983
Haematotoxicity 45.19 17.12 38 24156 12858 64461680
Lymphangiosis carcinomatosa 44.88 17.12 19 24175 1802 64472736
Somnolence 44.16 17.12 11 24183 203634 64270904
Febrile bone marrow aplasia 43.27 17.12 35 24159 11220 64463318
Acute promyelocytic leukaemia 42.79 17.12 17 24177 1371 64473167
Leukaemia cutis 41.93 17.12 10 24184 139 64474399
Asthenia 41.76 17.12 289 23905 427755 64046783
Metastases to the mediastinum 41.45 17.12 13 24181 521 64474017
Blood creatine increased 41.45 17.12 30 24164 8162 64466376
Pruritus 41.26 17.12 34 24160 312366 64162172
Miller Fisher syndrome 40.97 17.12 10 24184 154 64474384
Hydrothorax 40.87 17.12 16 24178 1241 64473297
Metastasis 38.64 17.12 25 24169 5670 64468868
Diarrhoea 38.60 17.12 427 23767 722277 63752261
Thrombocytopenia 38.41 17.12 176 24018 223625 64250913
Disease progression 37.77 17.12 128 24066 141552 64332986
Drug ineffective 37.63 17.12 175 24019 840072 63634466
Bladder irritation 37.57 17.12 10 24184 221 64474317
Intestinal atresia 37.56 17.12 8 24186 64 64474474
Metastases to chest wall 36.64 17.12 11 24183 380 64474158
Delayed puberty 36.50 17.12 9 24185 145 64474393
Acute interstitial pneumonitis 36.43 17.12 14 24180 1033 64473505
Hyperpyrexia 36.21 17.12 23 24171 5054 64469484
Joint swelling 35.85 17.12 18 24176 215364 64259174
Hypertransaminasaemia 35.62 17.12 26 24168 7165 64467373
Ameloblastoma 35.43 17.12 8 24186 86 64474452
Acute kidney injury 34.64 17.12 73 24121 449167 64025371
Xerophthalmia 34.51 17.12 11 24183 465 64474073
Troponin I increased 34.16 17.12 20 24174 3801 64470737
Overdose 33.86 17.12 9 24185 159557 64314981
Merycism 33.31 17.12 9 24185 211 64474327
Weight increased 32.37 17.12 20 24174 213328 64261210
Contusion 31.81 17.12 3 24191 113962 64360576
Gastrointestinal necrosis 31.64 17.12 21 24173 4971 64469567
Metastases to central nervous system 31.27 17.12 32 24162 13880 64460658
Anaemia 30.82 17.12 245 23949 378435 64096103
Urinary tract infection 30.81 17.12 25 24169 231571 64242967
Basal cell naevus syndrome 30.59 17.12 6 24188 30 64474508
Breast mass 30.46 17.12 21 24173 5289 64469249
Gastrointestinal toxicity 30.42 17.12 21 24173 5301 64469237
Tympanic membrane disorder 30.14 17.12 8 24186 175 64474363
Hepatitis B 29.59 17.12 24 24170 7721 64466817
Recurrent cancer 28.26 17.12 15 24179 2358 64472180
Metastases to soft tissue 28.18 17.12 9 24185 383 64474155
Confusional state 28.06 17.12 34 24160 261110 64213428
Hyperkalaemia 27.35 17.12 3 24191 101126 64373412
Pneumocystis jirovecii pneumonia 27.15 17.12 42 24152 27592 64446946
Granulocytopenia 27.14 17.12 26 24168 10414 64464124
Gait apraxia 26.82 17.12 5 24189 18 64474520
Pleural effusion 26.69 17.12 106 24088 126453 64348085
Synovitis 26.64 17.12 3 24191 99087 64375451
Hepatic lesion 26.48 17.12 20 24174 5804 64468734
Blood creatinine increased 26.37 17.12 9 24185 135773 64338765
Injection site phlebitis 26.25 17.12 7 24187 156 64474382
Bladder perforation 26.12 17.12 8 24186 296 64474242
Myocardial infarction 25.91 17.12 15 24179 165806 64308732
Hormone receptor positive breast cancer 25.77 17.12 8 24186 310 64474228
Osteonecrosis of jaw 25.37 17.12 50 24144 39775 64434763
Arthropathy 25.32 17.12 7 24187 120960 64353578
Malignant pleural effusion 25.13 17.12 15 24179 2952 64471586
Abdominal discomfort 25.11 17.12 19 24175 182303 64292235
Administration site oedema 24.87 17.12 5 24189 29 64474509
Neurotoxicity 24.65 17.12 40 24154 27364 64447174
Left ventricular dysfunction 24.48 17.12 31 24163 16923 64457615
Swelling 24.32 17.12 15 24179 160203 64314335
Infusion site vesicles 24.10 17.12 8 24186 385 64474153
Neutrophilia 24.02 17.12 20 24174 6674 64467864
Pseudocirrhosis 23.79 17.12 9 24185 636 64473902
Therapeutic product effect decreased 23.55 17.12 7 24187 115344 64359194
Carbohydrate antigen 15-3 increased 23.33 17.12 10 24184 977 64473561
Hypertension 22.69 17.12 39 24155 259222 64215316
Dandy-Walker syndrome 22.66 17.12 5 24189 48 64474490
Pancytopenia 22.58 17.12 110 24084 143199 64331339
Musculoskeletal stiffness 22.52 17.12 9 24185 123197 64351341
Drug hypersensitivity 22.47 17.12 34 24160 237781 64236757
Cardiac perfusion defect 22.27 17.12 4 24190 11 64474527
Acute lymphocytic leukaemia 22.09 17.12 16 24178 4355 64470183
Urticaria 22.07 17.12 14 24180 147303 64327235
SAPHO syndrome 21.92 17.12 6 24188 148 64474390
Oral pain 21.89 17.12 38 24156 27455 64447083
Pneumonia 21.86 17.12 122 24072 559454 63915084
Systolic dysfunction 21.59 17.12 14 24180 3188 64471350
Vulvovaginal dryness 21.54 17.12 11 24183 1597 64472941
Arachnoid cyst 21.50 17.12 7 24187 317 64474221
Sarcoidosis 21.30 17.12 18 24176 6128 64468410
Blood pressure increased 21.28 17.12 20 24174 172532 64302006
Toxicity to various agents 21.14 17.12 68 24126 363445 64111093
Intercepted product administration error 21.06 17.12 6 24188 172 64474366
Acute pulmonary oedema 21.05 17.12 25 24169 12784 64461754
Myeloproliferative neoplasm 20.99 17.12 9 24185 880 64473658
Feeling abnormal 20.99 17.12 12 24182 133590 64340948
Menopause 20.92 17.12 11 24183 1697 64472841
Granulocyte count decreased 20.87 17.12 10 24184 1266 64473272
Liver injury 20.81 17.12 39 24155 29893 64444645
Left ventricular dilatation 20.59 17.12 9 24185 923 64473615
Skin toxicity 20.19 17.12 18 24176 6584 64467954
Mitral valve incompetence 19.94 17.12 35 24159 25503 64449035
Gastrointestinal anastomotic leak 19.85 17.12 7 24187 405 64474133
Arterial thrombosis 19.85 17.12 12 24182 2418 64472120
Ovarian necrosis 19.78 17.12 4 24190 24 64474514
Infusion site extravasation 19.64 17.12 18 24176 6819 64467719
Contraindicated product administered 19.51 17.12 8 24186 107821 64366717
Vena cava thrombosis 19.48 17.12 12 24182 2500 64472038
Bradycardia 19.48 17.12 10 24184 118209 64356329
Systemic lupus erythematosus 19.31 17.12 3 24191 77609 64396929
Arthralgia 19.18 17.12 93 24101 442167 64032371
Body temperature abnormal 18.75 17.12 10 24184 1588 64472950
Retinopathy 18.58 17.12 13 24181 3352 64471186
Acute lung injury 18.56 17.12 12 24182 2719 64471819
Hospitalisation 18.50 17.12 3 24191 75204 64399334
Ischaemic enteritis 18.43 17.12 5 24189 119 64474419
Gastrointestinal haemorrhage 17.94 17.12 14 24180 132298 64342240
Placental disorder 17.92 17.12 8 24186 862 64473676
Amnestic disorder 17.77 17.12 7 24187 552 64473986
Hypermetabolism 17.72 17.12 6 24188 307 64474231
Dysgeusia 17.70 17.12 48 24146 46999 64427539
Nasopharyngitis 17.60 17.12 29 24165 196044 64278494
Metastases to muscle 17.48 17.12 6 24188 320 64474218
Liver abscess 17.35 17.12 15 24179 5265 64469273
Fanconi syndrome acquired 17.35 17.12 11 24183 2410 64472128
Tremor 17.33 17.12 18 24176 148212 64326326
Facial discomfort 17.16 17.12 4 24190 50 64474488

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC L01DB03 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
CYTOTOXIC ANTIBIOTICS AND RELATED SUBSTANCES
Anthracyclines and related substances
FDA CS M0028312 Anthracyclines
FDA MoA N0000000176 Topoisomerase Inhibitors
FDA EPC N0000175414 Anthracycline Topoisomerase Inhibitor
CHEBI has role CHEBI:33281 antibiotics
CHEBI has role CHEBI:35610 antineoplastic agents
CHEBI has role CHEBI:50750 inhibitors of type II topoisomerase
MeSH PA D000903 Antibiotics, Antineoplastic
MeSH PA D000970 Antineoplastic Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D059005 Topoisomerase II Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Carcinoma of breast indication 254838004 DOID:3459
Diffuse non-Hodgkin's lymphoma, large cell off-label use 109969005
Hodgkin's disease off-label use 118599009
Osteosarcoma of bone off-label use 307576001 DOID:3376
Malignant tumor of stomach off-label use 363349007 DOID:10534
Metastatic Breast Carcinoma off-label use
Myocardial infarction contraindication 22298006 DOID:5844
Conduction disorder of the heart contraindication 44808001
Chronic heart failure contraindication 48447003
Hepatic failure contraindication 59927004
Stomatitis contraindication 61170000 DOID:9637
Acute infectious disease contraindication 63171007
Cardiomyopathy contraindication 85898001 DOID:0050700
Kidney disease contraindication 90708001 DOID:557
Disease of liver contraindication 235856003 DOID:409
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Breastfeeding (mother) contraindication 413712001
Life-Threatening Cardiac Arrhythmias contraindication
Severe Bone Marrow Depression contraindication




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.85 acidic
pKa2 9.21 acidic
pKa3 9.92 acidic
pKa4 11.11 acidic
pKa5 8.6 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Tyrosine-protein kinase Fyn Kinase IC50 5.29 DRUG MATRIX
5-hydroxytryptamine receptor 4 GPCR Ki 5.88 DRUG MATRIX
NS3 Enzyme IC50 6.12 CHEMBL
Genome polyprotein Unclassified IC50 6.12 CHEMBL

External reference:

IDSource
4021192 VUID
N0000148638 NUI
D02214 KEGG_DRUG
56390-09-1 SECONDARY_CAS_RN
4021192 VANDF
4021193 VANDF
C0014582 UMLSCUI
CHEBI:47898 CHEBI
DM6 PDB_CHEM_ID
CHEMBL417 ChEMBL_ID
CHEMBL1200981 ChEMBL_ID
D015251 MESH_DESCRIPTOR_UI
DB00445 DRUGBANK_ID
5171 INN_ID
3Z8479ZZ5X UNII
41867 PUBCHEM_CID
203213 RXNORM
8302 MMSL
90558 MMSL
d04454 MMSL
003716 NDDF
003717 NDDF
116108007 SNOMEDCT_US
349848009 SNOMEDCT_US
417916005 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Ellence HUMAN PRESCRIPTION DRUG LABEL 1 0009-5091 INJECTION, SOLUTION 2 mg INTRAVENOUS NDA 32 sections
Ellence HUMAN PRESCRIPTION DRUG LABEL 1 0009-5093 INJECTION, SOLUTION 2 mg INTRAVENOUS NDA 32 sections
Epirubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9202 INJECTION 2 mg INTRAVENOUS ANDA 26 sections
Epirubicin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9203 INJECTION 2 mg INTRAVENOUS ANDA 26 sections
EPIRUBICIN HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 59923-701 INJECTION 2 mg INTRAVENOUS ANDA 26 sections