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

Stem definitionDrug idCAS RN
1112 33419-42-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • etoposide
  • etosid
  • fytosid
  • toposar
  • zuyeyidal
  • VP-16
A semisynthetic derivative of PODOPHYLLOTOXIN that exhibits antitumor activity. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent entry into the mitotic phase of cell division, and lead to cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle.
  • Molecular weight: 588.56
  • Formula: C29H32O13
  • CLOGP: -0.11
  • LIPINSKI: 2
  • HAC: 13
  • HDO: 3
  • TPSA: 160.83
  • ALOGS: -2.78
  • 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) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.22 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 38 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 6.30 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 52 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.18 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.50 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.12 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 5.70 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Nov. 10, 1983 FDA

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
Febrile neutropenia 2993.99 67.56 707 5600 10175 2341603
Neutropenia 1506.25 67.56 478 5829 21070 2330708
Off label use 1083.74 67.56 527 5780 73071 2278707
Mucosal inflammation 1032.48 67.56 262 6045 4962 2346816
Pancytopenia 990.23 67.56 300 6007 11152 2340626
Thrombocytopenia 958.34 67.56 331 5976 18800 2332978
Bone marrow failure 957.11 67.56 251 6056 5435 2346343
Sepsis 810.87 67.56 290 6017 18198 2333580
Acute myeloid leukaemia 805.63 67.56 189 6118 2521 2349257
Product use in unapproved indication 727.18 67.56 236 6071 10964 2340814
Pyrexia 640.26 67.56 335 5972 53373 2298405
Ovarian failure 578.99 67.56 98 6209 170 2351608
Myelodysplastic syndrome 572.43 67.56 142 6165 2418 2349360
Anaemia 558.41 67.56 266 6041 34526 2317252
Haematotoxicity 495.63 67.56 109 6198 1058 2350720
Haemophagocytic lymphohistiocytosis 487.98 67.56 111 6196 1272 2350506
Disease progression 486.82 67.56 196 6111 16899 2334879
Malignant neoplasm progression 444.13 67.56 167 6140 11961 2339817
Posterior reversible encephalopathy syndrome 442.89 67.56 115 6192 2365 2349413
Vomiting 439.39 67.56 291 6016 71311 2280467
Multiple organ dysfunction syndrome 438.78 67.56 147 6160 7494 2344284
Pneumonia 422.49 67.56 248 6059 49048 2302730
Tumour lysis syndrome 415.66 67.56 93 6214 982 2350796
Septic shock 402.15 67.56 135 6172 6919 2344859
Leukopenia 389.94 67.56 145 6162 10051 2341727
Maternal exposure before pregnancy 363.26 67.56 80 6227 780 2350998
Neutropenic sepsis 357.60 67.56 87 6220 1355 2350423
Nausea 351.29 67.56 305 6002 111884 2239894
Second primary malignancy 323.99 67.56 75 6232 931 2350847
Venoocclusive liver disease 315.47 67.56 67 6240 541 2351237
Platelet count decreased 309.04 67.56 139 6168 15674 2336104
Acute kidney injury 278.96 67.56 156 6151 27966 2323812
Colitis 258.48 67.56 90 6217 5136 2346642
Hypokalaemia 258.01 67.56 109 6198 10545 2341233
Renal failure 257.06 67.56 126 6181 17223 2334555
Infection 252.46 67.56 126 6181 17903 2333875
Diarrhoea 250.12 67.56 222 6085 83342 2268436
Neutrophil count decreased 242.05 67.56 91 6216 6476 2345302
Drug ineffective 240.79 67.56 237 6070 101387 2250391
Drug resistance 239.65 67.56 72 6235 2552 2349226
White blood cell count decreased 239.54 67.56 122 6185 18086 2333692
Cytomegalovirus infection 237.29 67.56 72 6235 2641 2349137
Febrile bone marrow aplasia 234.49 67.56 56 6251 801 2350977
Bacteraemia 231.89 67.56 64 6243 1666 2350112
Disease recurrence 228.35 67.56 74 6233 3377 2348401
Encephalopathy 219.57 67.56 77 6230 4484 2347294
Pleural effusion 216.46 67.56 99 6208 11569 2340209
Respiratory failure 214.59 67.56 103 6204 13425 2338353
Neuropathy peripheral 212.08 67.56 97 6210 11335 2340443
Hypotension 207.80 67.56 136 6171 32300 2319478
Venoocclusive disease 206.38 67.56 41 6266 227 2351551
Ovarian germ cell teratoma 200.15 67.56 30 6277 8 2351770
Dehydration 194.87 67.56 114 6193 22181 2329597
Stomatitis 188.31 67.56 85 6222 9625 2342153
Aplasia 176.54 67.56 40 6267 447 2351331
Aspergillus infection 173.40 67.56 45 6262 918 2350860
Clostridium difficile colitis 168.25 67.56 52 6255 2027 2349751
Oesophagitis 165.84 67.56 51 6256 1955 2349823
Candida infection 159.57 67.56 54 6253 2819 2348959
Hepatosplenic T-cell lymphoma 150.40 67.56 25 6282 36 2351742
Toxicity to various agents 148.07 67.56 111 6196 32643 2319135
Teratoma 145.58 67.56 25 6282 49 2351729
Enterococcal infection 144.49 67.56 37 6270 714 2351064
Disseminated intravascular coagulation 143.91 67.56 52 6255 3298 2348480
Stem cell transplant 141.84 67.56 32 6275 350 2351428
Neoplasm progression 140.96 67.56 56 6251 4612 2347166
Bronchopulmonary aspergillosis 138.47 67.56 38 6269 966 2350812
Ascites 137.56 67.56 58 6249 5562 2346216
General physical health deterioration 135.94 67.56 77 6230 14062 2337716
Staphylococcal infection 133.81 67.56 56 6251 5270 2346508
Decreased appetite 132.96 67.56 99 6208 28792 2322986
Haemoglobin decreased 128.09 67.56 81 6226 18070 2333708
Hyponatraemia 126.56 67.56 72 6235 13253 2338525
Asthenia 124.71 67.56 117 6190 46809 2304969
Pericardial effusion 124.20 67.56 49 6258 3960 2347818
Fatigue 120.67 67.56 152 6155 84721 2267057
Fungal infection 118.12 67.56 50 6257 4839 2346939
Abdominal pain 115.69 67.56 98 6209 34276 2317502
Dyspnoea 115.07 67.56 143 6164 78590 2273188
Tachycardia 112.70 67.56 72 6235 16337 2335441
Acute respiratory distress syndrome 111.74 67.56 43 6264 3249 2348529
Pulmonary oedema 110.39 67.56 54 6253 7309 2344469
BK virus infection 110.18 67.56 25 6282 281 2351497
Renal impairment 108.00 67.56 59 6248 10033 2341745
Alveolar soft part sarcoma 107.76 67.56 16 6291 3 2351775
Nephroblastoma 106.67 67.56 17 6290 15 2351763
Cytomegalovirus viraemia 104.28 67.56 26 6281 448 2351330
Hypoxia 103.43 67.56 49 6258 6178 2345600
Alanine aminotransferase increased 102.42 67.56 64 6243 13968 2337810
Thrombotic microangiopathy 101.87 67.56 32 6275 1315 2350463
Pneumothorax 99.70 67.56 36 6271 2276 2349502
Capillary leak syndrome 99.68 67.56 24 6283 355 2351423
Human herpesvirus 6 infection 99.62 67.56 24 6283 356 2351422
Herpes zoster 98.96 67.56 55 6252 9670 2342108
Death 98.78 67.56 135 6172 81333 2270445
Acute promyelocytic leukaemia 97.89 67.56 22 6285 236 2351542
Cystitis haemorrhagic 96.70 67.56 26 6281 610 2351168
Plasma cell myeloma 96.69 67.56 51 6256 8082 2343696
Herpes simplex 96.16 67.56 29 6278 1038 2350740
Varicella zoster virus infection 95.86 67.56 23 6284 335 2351443
Teratoma benign 95.36 67.56 15 6292 11 2351767
Neutropenic colitis 94.30 67.56 22 6285 282 2351496
Bacterial infection 93.59 67.56 34 6273 2187 2349591
Amenorrhoea 93.32 67.56 34 6273 2205 2349573
Pulmonary haemorrhage 92.21 67.56 29 6278 1196 2350582
Seizure 91.08 67.56 74 6233 24392 2327386
Osteosarcoma 90.48 67.56 16 6291 40 2351738
Retinoblastoma 89.67 67.56 15 6292 23 2351755
Nephropathy toxic 88.91 67.56 28 6279 1160 2350618
Therapy non-responder 88.42 67.56 48 6259 8056 2343722
Product use issue 87.52 67.56 55 6252 12114 2339664
Respiratory distress 87.14 67.56 41 6266 5088 2346690
Deafness 87.11 67.56 34 6273 2667 2349111
Leukoencephalopathy 86.12 67.56 25 6282 782 2350996
Enterobacter infection 85.89 67.56 20 6287 254 2351524
Enterococcal sepsis 85.62 67.56 18 6289 137 2351641
Unmasking of previously unidentified disease 84.78 67.56 16 6291 64 2351714
Deep vein thrombosis 84.45 67.56 55 6252 12877 2338901
Respiratory symptom 84.27 67.56 19 6288 207 2351571
Acute lymphocytic leukaemia 83.86 67.56 22 6285 468 2351310
Hypertension 83.86 67.56 74 6233 27287 2324491
Hypomagnesaemia 81.72 67.56 32 6275 2532 2349246
Klebsiella infection 81.41 67.56 24 6283 793 2350985
Large intestinal ulcer perforation 81.03 67.56 12 6295 2 2351776
Primary hypogonadism 80.67 67.56 14 6293 30 2351748
Malignant transformation 80.36 67.56 14 6293 31 2351747
Neurotoxicity 80.13 67.56 30 6277 2100 2349678
Enteritis 78.80 67.56 25 6282 1061 2350717
Graft versus host disease 77.62 67.56 24 6283 935 2350843
Human bocavirus infection 76.75 67.56 12 6295 8 2351770
Therapeutic product effect incomplete 76.73 67.56 48 6259 10483 2341295
Fungaemia 76.42 67.56 18 6289 241 2351537
Secondary immunodeficiency 76.26 67.56 15 6292 78 2351700
Ototoxicity 75.68 67.56 18 6289 252 2351526
Ewing's sarcoma 75.66 67.56 14 6293 49 2351729
Pulmonary mycosis 75.63 67.56 16 6291 126 2351652
Cough 75.48 67.56 76 6231 33041 2318737
Cardiac failure 75.47 67.56 50 6257 12044 2339734
Epstein-Barr virus infection 74.14 67.56 24 6283 1087 2350691
Syncope 73.46 67.56 56 6251 16819 2334959
Acute lymphocytic leukaemia recurrent 73.44 67.56 17 6290 210 2351568
Treatment failure 71.06 67.56 40 6267 7199 2344579
Blood creatinine increased 69.26 67.56 45 6262 10488 2341290
Hepatotoxicity 69.06 67.56 31 6276 3450 2348328
Fungal oesophagitis 68.39 67.56 14 6293 92 2351686
Gastrointestinal fungal infection 67.92 67.56 13 6294 57 2351721
Blood bilirubin increased 67.74 67.56 35 6272 5310 2346468
Left ventricular dysfunction 67.61 67.56 23 6284 1217 2350561
Neoplasm recurrence 67.57 67.56 18 6289 407 2351371

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
Febrile neutropenia 3851.64 55.66 1035 8147 10065 1727534
Neutropenia 1974.37 55.66 699 8483 17561 1720038
Off label use 1465.28 55.66 698 8484 37873 1699726
Thrombocytopenia 1432.93 55.66 577 8605 20672 1716927
Pancytopenia 1249.44 55.66 442 8740 10915 1726684
Bone marrow failure 1042.24 55.66 319 8863 4881 1732718
Mucosal inflammation 1040.40 55.66 303 8879 3866 1733733
Sepsis 908.27 55.66 408 8774 19030 1718569
Acute myeloid leukaemia 860.90 55.66 244 8938 2797 1734802
Pyrexia 860.27 55.66 523 8659 45877 1691722
Product use in unapproved indication 845.23 55.66 316 8866 9106 1728493
Myelodysplastic syndrome 788.87 55.66 232 8950 3057 1734542
Anaemia 724.95 55.66 400 8782 29057 1708542
Pneumonia 693.08 55.66 456 8726 45726 1691873
Septic shock 665.26 55.66 255 8927 7854 1729745
Malignant neoplasm progression 596.14 55.66 277 8905 13881 1723718
Leukopenia 584.01 55.66 235 8947 8245 1729354
Venoocclusive liver disease 549.36 55.66 134 9048 799 1736800
Second primary malignancy 483.15 55.66 124 9058 935 1736664
Acute kidney injury 427.30 55.66 305 8877 34639 1702960
Respiratory failure 411.09 55.66 217 8965 14288 1723311
Vomiting 402.11 55.66 305 8877 38010 1699589
Disease progression 397.24 55.66 225 8957 17038 1720561
Stomatitis 396.72 55.66 157 9025 5247 1732352
Multiple organ dysfunction syndrome 391.95 55.66 182 9000 9060 1728539
Tumour lysis syndrome 377.89 55.66 114 9068 1637 1735962
Drug ineffective 369.42 55.66 361 8821 63440 1674159
Colitis 369.35 55.66 139 9043 4041 1733558
Neutrophil count decreased 341.92 55.66 146 9036 5935 1731664
Diarrhoea 328.76 55.66 314 8868 53538 1684061
Neutropenic sepsis 325.62 55.66 98 9084 1394 1736205
Renal failure 323.45 55.66 208 8974 19809 1717790
Nausea 305.66 55.66 295 8887 50901 1686698
White blood cell count decreased 303.81 55.66 172 9010 12977 1724622
Haemophagocytic lymphohistiocytosis 293.37 55.66 90 9092 1370 1736229
Haematotoxicity 280.17 55.66 79 9103 879 1736720
Posterior reversible encephalopathy syndrome 275.59 55.66 86 9096 1389 1736210
Hypotension 271.20 55.66 218 8964 29436 1708163
Neuropathy peripheral 263.33 55.66 139 9043 9114 1728485
Platelet count decreased 257.60 55.66 168 9014 16355 1721244
Aspergillus infection 252.10 55.66 79 9103 1294 1736305
Dyspnoea 252.00 55.66 268 8914 51791 1685808
Bronchopulmonary aspergillosis 241.88 55.66 79 9103 1487 1736112
Encephalopathy 221.09 55.66 98 9084 4354 1733245
Febrile bone marrow aplasia 219.12 55.66 64 9118 814 1736785
Pulmonary embolism 216.28 55.66 138 9044 12921 1724678
Bacteraemia 200.98 55.66 72 9110 1808 1735791
Aplasia 195.75 55.66 51 9131 409 1737190
Pleural effusion 192.89 55.66 121 9061 10989 1726610
Neurotoxicity 188.43 55.66 70 9112 1954 1735645
Cytomegalovirus infection 184.50 55.66 79 9103 3222 1734377
Lymphopenia 184.47 55.66 69 9113 1964 1735635
Stem cell transplant 175.88 55.66 47 9135 420 1737179
Hypokalaemia 173.43 55.66 93 9089 6281 1731318
Cytopenia 168.22 55.66 53 9129 883 1736716
Disease recurrence 165.05 55.66 68 9114 2514 1735085
Acute lymphocytic leukaemia 162.88 55.66 46 9136 514 1737085
Pneumonitis 162.23 55.66 76 9106 3839 1733760
Hyponatraemia 158.63 55.66 99 9083 8901 1728698
Neutropenic colitis 157.95 55.66 39 9143 245 1737354
Neoplasm progression 156.01 55.66 70 9112 3197 1734402
Staphylococcal infection 154.76 55.66 78 9104 4629 1732970
Infection 152.76 55.66 109 9073 12251 1725348
Pneumocystis jirovecii pneumonia 151.30 55.66 63 9119 2393 1735206
Hypoxia 148.32 55.66 82 9100 5881 1731718
Diffuse large B-cell lymphoma 146.62 55.66 50 9132 1079 1736520
Asthenia 145.53 55.66 166 9016 34504 1703095
Abdominal pain 143.11 55.66 132 9050 21358 1716241
Drug resistance 140.94 55.66 65 9117 3165 1734434
Cytomegalovirus chorioretinitis 140.67 55.66 38 9144 355 1737244
Candida infection 140.36 55.66 56 9126 1902 1735697
Bone marrow toxicity 139.41 55.66 37 9145 321 1737278
Haemoglobin decreased 137.60 55.66 117 9065 16997 1720602
Toxicity to various agents 136.83 55.66 148 9034 28993 1708606
Malignant transformation 136.72 55.66 27 9155 44 1737555
Hepatitis B 136.00 55.66 50 9132 1353 1736246
Enterococcal infection 133.23 55.66 44 9138 857 1736742
Venoocclusive disease 129.56 55.66 35 9147 327 1737272
Clostridium difficile colitis 129.48 55.66 50 9132 1554 1736045
Acute respiratory distress syndrome 129.03 55.66 63 9119 3488 1734111
Respiratory distress 128.46 55.66 71 9111 5086 1732513
Fungal infection 125.92 55.66 54 9128 2208 1735391
Nephropathy toxic 125.76 55.66 50 9132 1682 1735917
Cough 122.14 55.66 115 9067 19082 1718517
Device related infection 122.09 55.66 53 9129 2233 1735366
Hepatotoxicity 122.00 55.66 58 9124 3026 1734573
Cystitis haemorrhagic 120.87 55.66 38 9144 628 1736971
Neoplasm recurrence 120.12 55.66 34 9148 383 1737216
Agranulocytosis 119.70 55.66 60 9122 3516 1734083
Deep vein thrombosis 119.12 55.66 86 9096 9834 1727765
Alanine aminotransferase increased 115.50 55.66 92 9090 12186 1725413
Staphylococcal bacteraemia 110.51 55.66 37 9145 753 1736846
Renal impairment 108.90 55.66 89 9093 12225 1725374
Epstein-Barr virus infection 108.69 55.66 40 9142 1085 1736514
Decreased appetite 108.06 55.66 119 9063 23752 1713847
Disseminated intravascular coagulation 107.50 55.66 56 9126 3558 1734041
Product use issue 104.47 55.66 75 9107 8496 1729103
Chills 104.46 55.66 85 9097 11602 1725997
Chloroma 104.26 55.66 23 9159 80 1737519
Pulmonary haemorrhage 102.66 55.66 43 9139 1656 1735943
Thrombotic microangiopathy 99.67 55.66 39 9143 1256 1736343
Hypertension 98.64 55.66 103 9079 19345 1718254
Systemic candida 96.92 55.66 28 9154 341 1737258
Bacterial sepsis 96.75 55.66 32 9150 626 1736973
Retinal haemorrhage 95.13 55.66 37 9145 1172 1736427
Hodgkin's disease 95.06 55.66 33 9149 752 1736847
Treatment failure 94.50 55.66 55 9127 4346 1733253
Klebsiella infection 93.85 55.66 33 9149 782 1736817
Acute promyelocytic leukaemia 93.33 55.66 23 9159 143 1737456
Diffuse large B-cell lymphoma recurrent 93.32 55.66 22 9160 110 1737489
Lymphadenopathy 92.56 55.66 53 9129 4061 1733538
Hyperbilirubinaemia 90.40 55.66 43 9139 2244 1735355
Pulmonary fibrosis 89.68 55.66 44 9138 2460 1735139
Tachycardia 88.69 55.66 80 9102 12548 1725051
General physical health deterioration 88.01 55.66 81 9101 13037 1724562
Embolism 87.24 55.66 34 9148 1083 1736516
Systemic mycosis 87.15 55.66 22 9160 153 1737446
Osteonecrosis 86.35 55.66 50 9132 3912 1733687
Osteosarcoma 86.01 55.66 18 9164 45 1737554
Condition aggravated 84.72 55.66 99 9083 21051 1716548
Nervous system disorder 84.55 55.66 42 9140 2412 1735187
Escherichia infection 83.87 55.66 32 9150 961 1736638
Lung infiltration 83.53 55.66 40 9142 2119 1735480
Confusional state 82.58 55.66 98 9084 21180 1716419
Cardiotoxicity 82.05 55.66 30 9152 798 1736801
Progressive multifocal leukoencephalopathy 81.03 55.66 36 9146 1603 1735996
Renal tubular disorder 80.44 55.66 30 9152 845 1736754
Cardiomyopathy 80.00 55.66 42 9140 2710 1734889
C-reactive protein increased 79.83 55.66 55 9127 5830 1731769
Plasma cell myeloma 79.44 55.66 68 9114 9946 1727653
Bacterial infection 78.98 55.66 37 9145 1865 1735734
Pulmonary toxicity 77.99 55.66 29 9153 810 1736789
Pneumothorax 77.72 55.66 41 9141 2671 1734928
Seizure 77.43 55.66 93 9089 20348 1717251
Interstitial lung disease 77.23 55.66 66 9116 9630 1727969
Transaminases increased 76.37 55.66 46 9136 3871 1733728
Dehydration 76.34 55.66 86 9096 17572 1720027
Cytogenetic abnormality 76.26 55.66 21 9161 212 1737387
Ameloblastoma 75.67 55.66 13 9169 3 1737596
Pneumonia klebsiella 75.58 55.66 23 9159 339 1737260
Intestinal perforation 75.06 55.66 34 9148 1585 1736014
Bicytopenia 74.88 55.66 21 9161 228 1737371
Electrolyte imbalance 74.73 55.66 33 9149 1448 1736151
Acute graft versus host disease 74.08 55.66 28 9154 819 1736780
Human herpesvirus 6 infection 74.06 55.66 23 9159 364 1737235
Escherichia bacteraemia 73.87 55.66 22 9160 300 1737299
Cerebral infarction 73.77 55.66 50 9132 5159 1732440
Graft versus host disease 73.22 55.66 33 9149 1520 1736079
Atelectasis 72.30 55.66 35 9147 1899 1735700
Herpes zoster 72.27 55.66 47 9135 4526 1733073
Enterococcal bacteraemia 71.76 55.66 19 9163 163 1737436
Gastrointestinal haemorrhage 69.50 55.66 74 9108 14193 1723406
Hodgkin's disease refractory 68.89 55.66 12 9170 4 1737595
Hypoalbuminaemia 68.76 55.66 31 9151 1429 1736170
Dysphagia 68.59 55.66 63 9119 10105 1727494
Streptococcal infection 68.51 55.66 25 9157 661 1736938
Blood creatinine increased 67.34 55.66 72 9110 13874 1723725
Papillary thyroid cancer 65.88 55.66 18 9164 176 1737423
Therapy partial responder 65.76 55.66 20 9162 294 1737305
Cerebral haemorrhage 65.39 55.66 50 9132 6227 1731372
Fanconi syndrome 64.14 55.66 20 9162 321 1737278
Shock 63.88 55.66 42 9140 4119 1733480
Metastasis 63.64 55.66 25 9157 813 1736786
Therapy non-responder 63.28 55.66 49 9133 6217 1731382
Deafness 62.88 55.66 32 9150 1934 1735665
Therapeutic product effect incomplete 62.54 55.66 46 9136 5402 1732197
Klebsiella sepsis 62.54 55.66 18 9164 216 1737383
Haemoptysis 62.45 55.66 44 9138 4832 1732767
Pleuritic pain 62.45 55.66 21 9161 433 1737166
Hypophosphataemia 62.32 55.66 28 9154 1280 1736319
Acute lymphocytic leukaemia recurrent 62.24 55.66 19 9163 283 1737316
Adenovirus infection 62.13 55.66 21 9161 440 1737159
Pneumonia cytomegaloviral 61.45 55.66 20 9162 371 1737228
Epistaxis 61.01 55.66 54 9128 8252 1729347
Burkitt's lymphoma 60.77 55.66 16 9166 134 1737465
Non-Hodgkin's lymphoma 60.73 55.66 25 9157 920 1736679
Clostridium difficile infection 59.92 55.66 30 9152 1751 1735848
Kaposi's sarcoma 59.36 55.66 24 9158 843 1736756
Ependymoma 59.18 55.66 12 9170 24 1737575
Hypogammaglobulinaemia 59.07 55.66 22 9160 617 1736982
Respiratory disorder 58.86 55.66 36 9146 3113 1734486
Basal cell carcinoma 58.56 55.66 33 9149 2450 1735149
Staphylococcal sepsis 57.61 55.66 26 9156 1201 1736398
Ascites 57.10 55.66 44 9138 5542 1732057
Muscular weakness 56.82 55.66 57 9125 10192 1727407
Myelitis transverse 56.37 55.66 16 9166 182 1737417
Small intestinal obstruction 56.29 55.66 29 9153 1798 1735801
Metabolic acidosis 56.20 55.66 43 9139 5359 1732240
Metastases to liver 55.83 55.66 31 9151 2236 1735363
Intentional product use issue 55.77 55.66 33 9149 2686 1734913
Recurrent cancer 55.77 55.66 17 9165 252 1737347
Pulmonary alveolar haemorrhage 55.70 55.66 25 9157 1140 1736459

Pharmacologic Action:

SourceCodeDescription
ATC L01CB01 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
PLANT ALKALOIDS AND OTHER NATURAL PRODUCTS
Podophyllotoxin derivatives
FDA EPC N0000175609 Topoisomerase Inhibitor
FDA MoA N0000000176 Topoisomerase Inhibitors
MeSH PA D000970 Antineoplastic Agents
MeSH PA D000972 Antineoplastic Agents, Phytogenic
MeSH PA D004791 Enzyme Inhibitors
CHEBI has role CHEBI:35610 antineoplastic agent
MeSH PA D059005 Topoisomerase II Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Small cell carcinoma of lung indication 254632001 DOID:5409
Malignant tumor of testis indication 363449006 DOID:2998
Allogeneic bone marrow transplantation off-label use 58390007
Ewing's sarcoma off-label use 76909002 DOID:3369
Acute myeloid leukemia, disease off-label use 91861009
Kaposi's sarcoma off-label use 109385007
Diffuse non-Hodgkin's lymphoma, large cell off-label use 109969005
Multiple myeloma off-label use 109989006 DOID:9538
Hodgkin's disease off-label use 118599009
Burkitt's lymphoma off-label use 118617000
Non-small cell lung cancer off-label use 254637007 DOID:3908
Osteosarcoma of bone off-label use 307576001 DOID:3376
Malignant tumor of ovary off-label use 363443007 DOID:2394
Neuroblastoma off-label use 432328008 DOID:769
Neuroendocrine Prostate Carcinoma off-label use
Progressive Diffuse Large B-Cell Lymphoma off-label use
Testicular Germ Cell Tumor off-label use
Ovarian Germ Cell Tumor Carcinoma off-label use
Acute hemorrhage contraindication 8573003
Fibrosis of lung contraindication 51615001 DOID:3770
Metabolic acidosis contraindication 59455009
Acute infectious disease contraindication 63171007
Interstitial pneumonia contraindication 64667001
Leukopenia contraindication 84828003 DOID:615
Hypoalbuminemia contraindication 119247004
Impaired renal function disorder contraindication 197663003
Drug-induced hepatitis contraindication 235876009
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Bone marrow depression contraindication 307762000
Breastfeeding (mother) contraindication 413712001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.96 acidic
pKa2 13.08 acidic
pKa3 13.86 acidic

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
DNA topoisomerase 2-alpha Enzyme INHIBITOR IC50 7.30 IUPHAR CHEMBL
Nuclear receptor subfamily 1 group I member 2 Nuclear hormone receptor WOMBAT-PK
Canalicular multispecific organic anion transporter 2 Transporter WOMBAT-PK
Multidrug resistance-associated protein 6 Transporter WOMBAT-PK
ATP-binding cassette sub-family G member 2 Transporter WOMBAT-PK
Multidrug resistance-associated protein 1 Transporter WOMBAT-PK
Canalicular multispecific organic anion transporter 1 Transporter Km 3.21 WOMBAT-PK
Multidrug resistance protein 1 Transporter Ki 3.28 WOMBAT-PK
Arachidonate 15-lipoxygenase Enzyme IC50 5.50 DRUG MATRIX

External reference:

IDSource
D005047 MESH_DESCRIPTOR_UI
4018141 VUID
N0000146478 NUI
C0015133 UMLSCUI
D00125 KEGG_DRUG
6PLQ3CP4P3 UNII
3835 INN_ID
56928005 SNOMEDCT_US
4209 MMSL
4179 RXNORM
387316009 SNOMEDCT_US
4709 MMSL
d00230 MMSL
4018141 VANDF
002674 NDDF
CHEMBL44657 ChEMBL_ID
DB00773 DRUGBANK_ID
CHEMBL1200645 ChEMBL_ID
EVP PDB_CHEM_ID
CHEBI:4911 CHEBI
36462 PUBCHEM_CID
6815 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Etoposide HUMAN PRESCRIPTION DRUG LABEL 1 0143-9376 INJECTION 20 mg INTRAVENOUS ANDA 13 sections
Etoposide HUMAN PRESCRIPTION DRUG LABEL 1 0143-9510 INJECTION 20 mg INTRAVENOUS ANDA 13 sections
Etoposide HUMAN PRESCRIPTION DRUG LABEL 1 0143-9511 INJECTION 20 mg INTRAVENOUS ANDA 13 sections
Etoposide HUMAN PRESCRIPTION DRUG LABEL 1 0143-9512 INJECTION 20 mg INTRAVENOUS ANDA 13 sections
Etoposide HUMAN PRESCRIPTION DRUG LABEL 1 0378-3266 CAPSULE 50 mg ORAL ANDA 13 sections
Toposar HUMAN PRESCRIPTION DRUG LABEL 1 0703-5653 INJECTION, SOLUTION, CONCENTRATE 20 mg INTRAVENOUS ANDA 14 sections
Toposar HUMAN PRESCRIPTION DRUG LABEL 1 0703-5656 INJECTION, SOLUTION, CONCENTRATE 20 mg INTRAVENOUS ANDA 14 sections
Toposar HUMAN PRESCRIPTION DRUG LABEL 1 0703-5657 INJECTION, SOLUTION, CONCENTRATE 20 mg INTRAVENOUS ANDA 14 sections
Etoposide HUMAN PRESCRIPTION DRUG LABEL 1 16729-114 INJECTION 20 mg INTRAVENOUS ANDA 13 sections
Etoposide HUMAN PRESCRIPTION DRUG LABEL 1 16729-262 INJECTION 20 mg INTRAVENOUS ANDA 12 sections
Etoposide HUMAN PRESCRIPTION DRUG LABEL 1 63323-104 INJECTION, SOLUTION 20 mg INTRAVENOUS ANDA 14 sections
Etoposide HUMAN PRESCRIPTION DRUG LABEL 1 68001-265 INJECTION 20 mg INTRAVENOUS ANDA 13 sections