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

Stem definitionDrug idCAS RN
uracil type antineoplastics 26 51-21-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • 5-fluorouracil
  • adrucil
  • fluoroblastin
  • fluorouracil
  • 5-FU
A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.
  • Molecular weight: 130.08
  • Formula: C4H3FN2O2
  • CLOGP: -0.58
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 58.20
  • ALOGS: -1.35
  • ROTB: 0

  • Status: OFP

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

Drug dosage:

None

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 92.25 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 12.20 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 5 % Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability) 28 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.23 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 26 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.64 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.12 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
April 25, 1962 FDA SPECTRUM PHARMS

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
Neutropenia 2889.82 45.62 897 10152 20651 2326385
Diarrhoea 2371.12 45.62 1116 9933 82448 2264588
Febrile neutropenia 1961.46 45.62 571 10478 10311 2336725
Vomiting 1414.34 45.62 752 10297 70850 2276186
Nausea 1396.85 45.62 871 10178 111318 2235718
Mucosal inflammation 1391.67 45.62 373 10676 4851 2342185
Leukopenia 1084.60 45.62 358 10691 9838 2337198
Pyrexia 1056.26 45.62 564 10485 53144 2293892
Stomatitis 1040.96 45.62 343 10706 9367 2337669
Thrombocytopenia 1031.18 45.62 406 10643 18725 2328311
Neuropathy peripheral 818.84 45.62 299 10750 11133 2335903
Disease progression 793.09 45.62 326 10723 16769 2330267
Anaemia 763.16 45.62 394 10655 34398 2312638
Dehydration 757.34 45.62 341 10708 21954 2325082
Breast cancer 674.57 45.62 247 10802 9248 2337788
General physical health deterioration 659.97 45.62 271 10778 13868 2333168
Asthenia 647.67 45.62 392 10657 46534 2300502
Malignant neoplasm progression 640.19 45.62 254 10795 11874 2335162
Abdominal pain 636.69 45.62 348 10701 34026 2313010
Decreased appetite 615.02 45.62 321 10728 28570 2318466
Death 556.01 45.62 441 10608 81027 2266009
Fatigue 529.50 45.62 436 10613 84437 2262599
Pulmonary embolism 527.03 45.62 249 10800 17834 2329202
Palmar-plantar erythrodysaesthesia syndrome 512.53 45.62 164 10885 4037 2342999
Bone marrow failure 486.83 45.62 170 10879 5516 2341520
Neurotoxicity 449.76 45.62 127 10922 2003 2345033
Interstitial lung disease 430.65 45.62 169 10880 7643 2339393
Neoplasm progression 428.29 45.62 147 10902 4521 2342515
Hypokalaemia 422.32 45.62 182 10867 10472 2336564
Metastases to liver 417.75 45.62 129 10920 2812 2344224
Dyspnoea 415.72 45.62 368 10681 78365 2268671
Acute myeloid leukaemia 410.97 45.62 125 10924 2585 2344451
Hypertension 392.86 45.62 235 10814 27126 2319910
Disease recurrence 381.23 45.62 125 10924 3326 2343710
Off label use 380.32 45.62 340 10709 73258 2273778
Neutrophil count decreased 365.14 45.62 143 10906 6424 2340612
Sepsis 363.06 45.62 195 10854 18293 2328743
Alopecia 334.00 45.62 196 10853 21805 2325231
Posterior reversible encephalopathy syndrome 323.73 45.62 102 10947 2378 2344658
Cardiomyopathy 319.40 45.62 104 10945 2703 2344333
Peripheral sensory neuropathy 308.90 45.62 81 10968 949 2346087
Ejection fraction decreased 299.44 45.62 99 10950 2702 2344334
Pancytopenia 297.69 45.62 146 10903 11306 2335730
Neutropenic sepsis 295.38 45.62 84 10965 1358 2345678
White blood cell count decreased 291.58 45.62 168 10881 18040 2328996
Metastases to bone 286.51 45.62 91 10958 2178 2344858
Constipation 285.03 45.62 176 10873 21453 2325583
Cardiotoxicity 279.76 45.62 78 10971 1169 2345867
Dermatitis acneiform 273.55 45.62 70 10979 739 2346297
Haemoglobin decreased 268.23 45.62 159 10890 17992 2329044
Deep vein thrombosis 263.78 45.62 140 10909 12792 2334244
Respiratory failure 249.52 45.62 137 10912 13391 2333645
Cardiac failure 246.84 45.62 131 10918 11963 2335073
Toxicity to various agents 245.08 45.62 188 10861 32566 2314470
Paraesthesia 241.96 45.62 160 10889 21928 2325108
Gastrointestinal toxicity 239.42 45.62 59 10990 527 2346509
Haematotoxicity 234.59 45.62 67 10982 1100 2345936
Metastases to lung 233.39 45.62 73 10976 1658 2345378
Second primary malignancy 230.58 45.62 64 10985 942 2346094
Polyneuropathy 227.92 45.62 72 10977 1691 2345345
Metastasis 226.50 45.62 62 10987 864 2346172
Hypomagnesaemia 220.53 45.62 77 10972 2487 2344549
Acute promyelocytic leukaemia 218.43 45.62 47 11002 211 2346825
Hyperammonaemia 209.52 45.62 57 10992 775 2346261
Chills 203.31 45.62 126 10923 15426 2331610
Exposure during pregnancy 200.09 45.62 150 10899 25069 2321967
Platelet count decreased 198.86 45.62 125 10924 15688 2331348
Chest pain 194.08 45.62 154 10895 27983 2319053
Septic shock 192.39 45.62 93 10956 6961 2340075
Arteriospasm coronary 191.66 45.62 51 10998 634 2346402
Renal failure 188.25 45.62 125 10924 17224 2329812
Proteinuria 183.08 45.62 69 10980 2781 2344255
Skin toxicity 179.85 45.62 50 10999 740 2346296
Malaise 175.42 45.62 197 10852 55388 2291648
Pneumonia 171.63 45.62 184 10865 49112 2297924
Multiple organ dysfunction syndrome 170.75 45.62 88 10961 7553 2339483
Ascites 168.21 45.62 79 10970 5541 2341495
Pleural effusion 166.45 45.62 100 10949 11568 2335468
Large intestine perforation 160.87 45.62 51 10998 1211 2345825
Hypotension 159.08 45.62 146 10903 32290 2314746
Ileus 155.69 45.62 57 10992 2115 2344921
Stress cardiomyopathy 149.54 45.62 50 10999 1411 2345625
Left ventricular dysfunction 149.36 45.62 48 11001 1192 2345844
Hypophagia 144.16 45.62 64 10985 3936 2343100
Device related infection 143.25 45.62 60 10989 3199 2343837
Infection 142.36 45.62 107 10942 17922 2329114
Dysarthria 139.11 45.62 72 10977 6230 2340806
Paronychia 137.81 45.62 41 11008 781 2346255
Myocarditis 137.78 45.62 45 11004 1178 2345858
Hyponatraemia 137.26 45.62 93 10956 13232 2333804
Intestinal obstruction 135.30 45.62 63 10986 4330 2342706
Metastases to lymph nodes 134.89 45.62 42 11007 938 2346098
Encephalopathy 133.05 45.62 63 10986 4498 2342538
Enteritis 130.64 45.62 42 11007 1044 2345992
Epistaxis 129.66 45.62 80 10969 9699 2337337
Acute kidney injury 119.52 45.62 117 10932 28005 2319031
Urinary tract infection 118.82 45.62 120 10929 29822 2317214
Colorectal cancer metastatic 118.64 45.62 27 11022 164 2346872
Hypertransaminasaemia 116.81 45.62 34 11015 598 2346438
Atrial fibrillation 116.02 45.62 85 10964 13683 2333353
Pain 115.41 45.62 169 10880 61688 2285348
Febrile bone marrow aplasia 114.90 45.62 36 11013 821 2346215
Hyperammonaemic encephalopathy 113.81 45.62 29 11020 300 2346736
Intestinal perforation 113.69 45.62 43 11006 1748 2345288
Abdominal pain upper 113.19 45.62 102 10947 21998 2325038
Leukoencephalopathy 112.81 45.62 35 11014 772 2346264
Disseminated intravascular coagulation 112.42 45.62 51 10998 3299 2343737
Peritonitis 111.81 45.62 47 11002 2527 2344509
Small intestinal obstruction 111.59 45.62 45 11004 2175 2344861
Gastrointestinal perforation 111.47 45.62 34 11015 707 2346329
Tachycardia 109.11 45.62 88 10961 16321 2330715
Metastases to central nervous system 106.11 45.62 43 11006 2105 2344931
Hepatic failure 100.33 45.62 56 10993 5633 2341403
Dysgeusia 99.09 45.62 64 10985 8395 2338641
Dysphagia 98.81 45.62 75 10974 12730 2334306
Syncope 98.66 45.62 84 10965 16791 2330245
Breast cancer recurrent 98.08 45.62 31 11018 728 2346308
Hypertensive crisis 96.33 45.62 42 11007 2471 2344565
Weight decreased 95.20 45.62 104 10945 28267 2318769
Hypersensitivity 94.36 45.62 95 10954 23498 2323538
Oral pain 93.21 45.62 45 11004 3352 2343684
Rash 93.13 45.62 150 10899 59408 2287628
Dermatitis 91.95 45.62 40 11009 2340 2344696
Colitis 90.95 45.62 51 10998 5175 2341861
Blood creatinine increased 90.92 45.62 66 10983 10467 2336569
Premature delivery 89.65 45.62 43 11006 3157 2343879
Myelodysplastic syndrome 89.15 45.62 40 11009 2520 2344516
Enterocutaneous fistula 88.69 45.62 22 11027 202 2346834
Tumour lysis syndrome 87.49 45.62 31 11018 1044 2345992
Congestive cardiomyopathy 86.93 45.62 30 11019 933 2346103
Neutropenic colitis 86.77 45.62 23 11026 281 2346755
Extravasation 85.46 45.62 28 11021 740 2346296
Proctalgia 85.34 45.62 27 11022 636 2346400
Myocardial ischaemia 84.09 45.62 37 11012 2225 2344811
Depressed level of consciousness 82.88 45.62 55 10994 7549 2339487
Breast cancer metastatic 82.72 45.62 36 11013 2108 2344928
Renal impairment 82.05 45.62 61 10988 10031 2337005
Cerebral infarction 81.86 45.62 45 11004 4392 2342644
Pulmonary fibrosis 81.71 45.62 38 11011 2602 2344434
Venous thrombosis 79.67 45.62 27 11022 794 2346242
Oedema peripheral 79.50 45.62 87 10962 23676 2323360
Organising pneumonia 78.11 45.62 27 11022 844 2346192
Metastases to meninges 76.38 45.62 22 11027 372 2346664
Colorectal cancer 75.10 45.62 20 11029 249 2346787
Infusion related reaction 74.73 45.62 57 10992 9739 2337297
Dysphonia 74.15 45.62 48 11001 6316 2340720
Erythema 72.09 45.62 85 10964 25074 2321962
Female genital tract fistula 71.78 45.62 22 11027 465 2346571
Hypocalcaemia 70.58 45.62 39 11010 3844 2343192
Hyperglycaemia 69.94 45.62 42 11007 4843 2342193
Dizziness 69.77 45.62 131 10918 58534 2288502
Cough 69.76 45.62 96 10953 33021 2314015
Agranulocytosis 68.91 45.62 37 11012 3445 2343591
Oesophagitis 68.75 45.62 31 11018 1975 2345061
Hepatic function abnormal 68.66 45.62 45 11004 6047 2340989
Drug intolerance 67.60 45.62 62 10987 13655 2333381
Dry skin 67.42 45.62 46 11003 6606 2340430
Laryngospasm 67.37 45.62 23 11026 692 2346344
Subclavian vein thrombosis 67.31 45.62 18 11031 228 2346808
Thrombosis 67.10 45.62 52 10997 9092 2337944
Venoocclusive liver disease 66.97 45.62 22 11027 586 2346450
Myocardial infarction 66.00 45.62 71 10978 18942 2328094
Odynophagia 64.09 45.62 24 11025 948 2346088
Gastrointestinal disorder 63.90 45.62 50 10999 8867 2338169
Pulmonary oedema 63.21 45.62 46 11003 7317 2339719
Deafness 62.87 45.62 32 11017 2669 2344367
Headache 62.80 45.62 151 10898 80028 2267008
Metastases to pleura 62.57 45.62 16 11033 168 2346868
Sinus tachycardia 62.09 45.62 34 11015 3291 2343745
Coma 61.07 45.62 49 11000 9007 2338029
Back pain 61.07 45.62 88 10961 31571 2315465
Aortic thrombosis 60.17 45.62 16 11033 198 2346838
Treatment failure 59.38 45.62 44 11005 7195 2339841
Electrocardiogram ST segment elevation 59.18 45.62 20 11029 583 2346453
Angina pectoris 58.94 45.62 35 11014 3952 2343084
Skin fissures 58.22 45.62 24 11025 1227 2345809
C-reactive protein increased 58.10 45.62 41 11008 6214 2340822
Cystitis radiation 57.04 45.62 10 11039 9 2347027
Cardiogenic shock 56.50 45.62 29 11020 2462 2344574
Oesophageal stenosis 56.49 45.62 18 11031 434 2346602
Nephropathy toxic 55.99 45.62 23 11026 1165 2345871
Hemiparesis 55.52 45.62 32 11017 3418 2343618
Aphthous ulcer 55.32 45.62 24 11025 1394 2345642
Aplasia 55.17 45.62 18 11031 469 2346567
Premature labour 55.06 45.62 27 11022 2079 2344957
Acute lymphocytic leukaemia 55.06 45.62 18 11031 472 2346564
Arrhythmia 54.81 45.62 39 11010 5989 2341047
Altered state of consciousness 54.77 45.62 33 11016 3827 2343209
Embolism 53.77 45.62 23 11026 1290 2345746
Multiple-drug resistance 53.68 45.62 15 11034 226 2346810
Liver abscess 53.27 45.62 17 11032 412 2346624
Splenomegaly 53.25 45.62 24 11025 1527 2345509
Seizure 53.12 45.62 72 10977 24394 2322642
Pneumothorax 52.68 45.62 27 11022 2285 2344751
Neutrophil count abnormal 52.58 45.62 17 11032 430 2346606
Hypoalbuminaemia 52.45 45.62 23 11026 1371 2345665
Blood phosphorus decreased 51.99 45.62 18 11031 565 2346471
Transaminases increased 51.97 45.62 34 11015 4553 2342483
Bladder tamponade 50.95 45.62 10 11039 25 2347011
Oral candidiasis 50.80 45.62 25 11024 1940 2345096
Haemorrhage 50.73 45.62 48 11001 10991 2336045
Drug ineffective 50.40 45.62 162 10887 101462 2245574
Duodenal ulcer 50.24 45.62 21 11028 1112 2345924
Metastases to skin 49.98 45.62 14 11035 213 2346823
Jugular vein thrombosis 49.85 45.62 16 11033 395 2346641
Acute coronary syndrome 49.73 45.62 23 11026 1554 2345482
Blood alkaline phosphatase increased 49.72 45.62 38 11011 6507 2340529
Hepatic steatosis 49.58 45.62 29 11020 3184 2343852
Dysaesthesia 49.57 45.62 18 11031 651 2346385
Cachexia 49.31 45.62 19 11030 812 2346224
Oesophageal fistula 48.44 45.62 10 11039 35 2347001
Cholangitis 48.34 45.62 19 11030 857 2346179
Lymphopenia 48.34 45.62 26 11023 2428 2344608
Dihydropyrimidine dehydrogenase deficiency 48.22 45.62 10 11039 36 2347000
Oedema 48.10 45.62 45 11004 10158 2336878
Haematemesis 48.07 45.62 31 11018 4051 2342985
Lethargy 48.03 45.62 42 11007 8688 2338348
Hypophosphataemia 48.01 45.62 20 11029 1050 2345986
Gastrointestinal stoma complication 47.94 45.62 14 11035 249 2346787
Mucosal toxicity 47.89 45.62 11 11038 70 2346966
Cerebrovascular accident 47.81 45.62 62 10987 20124 2326912
Neuralgia 47.62 45.62 27 11022 2795 2344241
Hyposideraemia 47.57 45.62 9 11040 17 2347019
Blood lactate dehydrogenase increased 47.41 45.62 29 11020 3455 2343581
Aspartate aminotransferase increased 47.13 45.62 49 11000 12563 2334473
Cardiac ventricular thrombosis 46.86 45.62 11 11038 78 2346958
Acute myocardial infarction 46.63 45.62 33 11016 5022 2342014
Neoplasm malignant 46.41 45.62 33 11016 5060 2341976
Sudden death 46.11 45.62 23 11026 1837 2345199
Colon cancer metastatic 45.85 45.62 14 11035 292 2346744

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
Diarrhoea 3124.04 54.71 1404 10450 52448 1682479
Neutropenia 2721.38 54.71 947 10907 17313 1717614
Nausea 1399.44 54.71 810 11044 50386 1684541
Mucosal inflammation 1360.16 54.71 395 11459 3774 1731153
Febrile neutropenia 1343.73 54.71 496 11358 10604 1724323
Thrombocytopenia 1273.97 54.71 573 11281 20676 1714251
Neuropathy peripheral 1180.21 54.71 430 11424 8823 1726104
Stomatitis 1163.41 54.71 372 11482 5032 1729895
Vomiting 1153.14 54.71 647 11207 37668 1697259
Decreased appetite 1103.19 54.71 538 11316 23333 1711594
Dehydration 1046.72 54.71 473 11381 17185 1717742
Pyrexia 1032.97 54.71 645 11209 45755 1689172
Leukopenia 929.88 54.71 353 11501 8127 1726800
General physical health deterioration 822.69 54.71 366 11488 12752 1722175
Interstitial lung disease 814.77 54.71 333 11521 9363 1725564
Abdominal pain 793.98 54.71 417 11437 21073 1713854
Disease progression 717.97 54.71 363 11491 16900 1718027
Asthenia 701.46 54.71 455 11399 34215 1700712
Fatigue 628.87 54.71 494 11360 50287 1684640
Dermatitis acneiform 614.59 54.71 158 11696 894 1734033
Off label use 601.13 54.71 431 11423 38140 1696787
Anaemia 596.06 54.71 387 11467 29070 1705857
Palmar-plantar erythrodysaesthesia syndrome 559.76 54.71 193 11661 3314 1731613
Sepsis 524.09 54.71 307 11547 19131 1715796
Acute kidney injury 486.15 54.71 365 11489 34579 1700348
Arteriospasm coronary 473.34 54.71 118 11736 576 1734351
Pulmonary embolism 448.68 54.71 242 11612 12817 1722110
Metastases to liver 437.61 54.71 144 11710 2123 1732804
Neutrophil count decreased 436.51 54.71 187 11667 5894 1729033
Hypertension 428.38 54.71 270 11584 19178 1715749
Cardiotoxicity 419.04 54.71 111 11743 717 1734210
Malignant neoplasm progression 392.68 54.71 228 11626 13930 1720997
White blood cell count decreased 357.27 54.71 209 11645 12940 1721987
Bone marrow failure 353.70 54.71 154 11700 5046 1729881
Paraesthesia 351.27 54.71 191 11663 10260 1724667
Hypokalaemia 348.37 54.71 162 11692 6212 1728715
Hyperammonaemia 336.63 54.71 99 11755 979 1733948
Chills 333.99 54.71 192 11662 11495 1723432
Dyspnoea 332.50 54.71 350 11504 51709 1683218
Septic shock 331.58 54.71 169 11685 7940 1726987
Skin toxicity 330.42 54.71 86 11768 513 1734414
Peripheral sensory neuropathy 322.03 54.71 91 11763 770 1734157
Pneumonia 317.27 54.71 323 11531 45859 1689068
Chest pain 314.44 54.71 225 11629 19689 1715238
Constipation 309.40 54.71 200 11654 14800 1720127
Neurotoxicity 305.75 54.71 107 11747 1917 1733010
Weight decreased 298.57 54.71 230 11624 22523 1712404
Intestinal obstruction 295.57 54.71 121 11733 3386 1731541
Paronychia 294.60 54.71 78 11776 502 1734425
Proteinuria 273.79 54.71 108 11746 2736 1732191
Dysphagia 266.47 54.71 158 11696 10010 1724917
Metastases to lung 266.24 54.71 90 11764 1445 1733482
Epistaxis 265.68 54.71 147 11707 8159 1726768
Alopecia 264.43 54.71 114 11740 3639 1731288
Haemoglobin decreased 257.74 54.71 188 11666 16926 1718001
Hypotension 253.17 54.71 234 11620 29420 1705507
Renal failure 250.84 54.71 197 11657 19820 1715107
Ascites 241.60 54.71 121 11733 5465 1729462
Deep vein thrombosis 221.06 54.71 139 11715 9781 1725146
Platelet count decreased 218.61 54.71 168 11686 16355 1718572
Hypomagnesaemia 217.18 54.71 84 11770 2014 1732913
Hyperbilirubinaemia 213.63 54.71 85 11769 2202 1732725
Oesophagitis 211.95 54.71 78 11776 1623 1733304
Hyperammonaemic encephalopathy 211.40 54.71 55 11799 327 1734600
Respiratory failure 210.74 54.71 156 11698 14349 1720578
Hypophagia 210.10 54.71 95 11759 3402 1731525
Neoplasm progression 209.84 54.71 93 11761 3174 1731753
Colorectal cancer 200.36 54.71 54 11800 375 1734552
Gastrointestinal toxicity 200.00 54.71 53 11801 342 1734585
Hiccups 199.93 54.71 72 11782 1405 1733522
Device related infection 192.97 54.71 79 11775 2207 1732720
Leukoencephalopathy 191.94 54.71 60 11794 740 1734187
Peritonitis 188.95 54.71 82 11772 2657 1732270
Small intestinal obstruction 188.56 54.71 73 11781 1754 1733173
Disseminated intravascular coagulation 182.33 54.71 87 11767 3527 1731400
Ileus 174.53 54.71 75 11779 2371 1732556
Colorectal cancer metastatic 173.53 54.71 43 11811 203 1734724
Atrial fibrillation 172.65 54.71 141 11713 14970 1719957
Malaise 170.77 54.71 189 11665 29376 1705551
Pneumatosis intestinalis 167.57 54.71 49 11805 473 1734454
Enteritis 164.28 54.71 56 11798 922 1734005
Polyneuropathy 163.09 54.71 65 11789 1690 1733237
Gastrointestinal perforation 160.50 54.71 52 11802 725 1734202
Rash 157.41 54.71 207 11647 38486 1696441
Skin reaction 154.56 54.71 56 11798 1112 1733815
Neutropenic sepsis 151.77 54.71 59 11795 1433 1733494
Acute coronary syndrome 151.07 54.71 67 11787 2288 1732639
C-reactive protein increased 150.24 54.71 90 11764 5795 1729132
Hypoalbuminaemia 149.46 54.71 58 11796 1402 1733525
Pleural effusion 149.06 54.71 114 11740 10996 1723931
Infection 146.77 54.71 118 11736 12242 1722685
Hyponatraemia 144.70 54.71 103 11751 8897 1726030
Tachycardia 142.44 54.71 117 11737 12511 1722416
Blood creatinine increased 138.36 54.71 120 11734 13826 1721101
Acute respiratory distress syndrome 136.26 54.71 71 11783 3480 1731447
Portal venous gas 136.00 54.71 30 11824 74 1734853
Electrocardiogram ST segment elevation 135.62 54.71 48 11806 888 1734039
Abdominal pain upper 134.81 54.71 107 11747 10894 1724033
Left ventricular dysfunction 134.30 54.71 51 11803 1160 1733767
Renal impairment 132.45 54.71 111 11743 12203 1722724
Hepatic failure 132.10 54.71 83 11771 5820 1729107
Abdominal pain lower 127.28 54.71 49 11805 1158 1733769
Colitis 125.40 54.71 71 11783 4109 1730818
Dry skin 124.90 54.71 68 11786 3644 1731283
Necrotising fasciitis 124.21 54.71 41 11813 608 1734319
Pancytopenia 123.42 54.71 103 11751 11254 1723673
Oedema peripheral 123.30 54.71 118 11736 15432 1719495
Erythema 122.73 54.71 113 11741 14075 1720852
Bacteraemia 119.01 54.71 53 11801 1827 1733100
Acute myeloid leukaemia 117.23 54.71 61 11793 2980 1731947
Pain 116.66 54.71 148 11706 26509 1708418
Hypertransaminasaemia 115.37 54.71 37 11817 498 1734429
Dermatitis 114.13 54.71 50 11804 1656 1733271
Large intestine perforation 114.08 54.71 45 11809 1137 1733790
Dysphonia 113.75 54.71 63 11791 3492 1731435
Oesophageal fistula 113.52 54.71 25 11829 61 1734866
Jaundice 112.97 54.71 76 11778 5986 1728941
Shock 112.35 54.71 66 11788 4095 1730832
Cardiac arrest 111.62 54.71 113 11741 15817 1719110
Syncope 111.33 54.71 107 11747 14062 1720865
Odynophagia 110.35 54.71 39 11815 718 1734209
Portal hypertension 110.21 54.71 38 11816 648 1734279
Urinary tract infection 110.14 54.71 92 11762 10061 1724866
Toxicity to various agents 107.79 54.71 149 11705 28992 1705935
Acute myocardial infarction 106.19 54.71 84 11770 8503 1726424
Oral pain 105.79 54.71 45 11809 1385 1733542
Tumour lysis syndrome 103.31 54.71 47 11807 1704 1733223
Cardiac failure 102.47 54.71 97 11757 12505 1722422
Incorrect drug administration rate 102.26 54.71 30 11824 293 1734634
Dyspepsia 101.36 54.71 66 11788 4919 1730008
Hepatitis B 99.99 54.71 43 11811 1360 1733567
Colitis microscopic 98.56 54.71 30 11824 336 1734591
Encephalopathy 98.08 54.71 62 11792 4390 1730537
Venous thrombosis 97.52 54.71 35 11819 675 1734252
Cholangitis 96.60 54.71 40 11814 1149 1733778
Angina pectoris 96.11 54.71 64 11790 4954 1729973
Hypersensitivity 95.79 54.71 86 11768 10358 1724569
Hyperglycaemia 94.43 54.71 64 11790 5101 1729826
Intestinal perforation 94.08 54.71 43 11811 1576 1733351
Rectal haemorrhage 92.67 54.71 65 11789 5477 1729450
Candida infection 92.25 54.71 45 11809 1913 1733014
Haematotoxicity 90.79 54.71 36 11818 922 1734005
Conjunctivitis 90.70 54.71 42 11812 1587 1733340
Circulatory collapse 88.38 54.71 53 11801 3414 1731513
Sudden death 88.33 54.71 50 11804 2890 1732037
Altered state of consciousness 87.96 54.71 53 11801 3444 1731483
Ileal perforation 86.29 54.71 23 11831 152 1734775
Liver abscess 86.26 54.71 31 11823 600 1734327
Blood bilirubin increased 86.03 54.71 65 11789 6145 1728782
Cardiomyopathy 85.92 54.71 48 11806 2704 1732223
Pneumonitis 84.94 54.71 54 11800 3861 1731066
Multiple organ dysfunction syndrome 84.54 54.71 76 11778 9166 1725761
Abdominal distension 83.90 54.71 65 11789 6379 1728548
Proteus infection 83.74 54.71 21 11833 105 1734822
Anal fissure 83.63 54.71 26 11828 314 1734613
Cough 82.97 54.71 106 11748 19091 1715836
Blood potassium decreased 82.66 54.71 44 11810 2251 1732676
Carcinoembryonic antigen increased 82.25 54.71 23 11831 186 1734741
Klebsiella infection 82.06 54.71 32 11822 783 1734144
Cachexia 81.93 54.71 34 11820 982 1733945
Aorto-oesophageal fistula 81.30 54.71 16 11838 16 1734911
Fistula 81.23 54.71 35 11819 1112 1733815
Abscess 80.90 54.71 41 11813 1893 1733034
Intestinal ischaemia 80.76 54.71 34 11820 1019 1733908
Haematochezia 80.49 54.71 57 11797 4875 1730052
Dry mouth 80.01 54.71 52 11802 3861 1731066
Extravasation 79.58 54.71 29 11825 585 1734342
Posterior reversible encephalopathy syndrome 78.92 54.71 37 11817 1438 1733489
Dizziness 78.67 54.71 141 11713 34220 1700707
Confusional state 77.40 54.71 108 11746 21170 1713757
Aspartate aminotransferase increased 76.57 54.71 77 11777 10679 1724248
Hepatic function abnormal 76.47 54.71 64 11790 7010 1727917
Pelvic abscess 76.08 54.71 21 11833 161 1734766
Embolism 75.56 54.71 33 11821 1084 1733843
Clostridial infection 75.52 54.71 29 11825 680 1734247
Hypoxia 75.13 54.71 59 11795 5904 1729023
Gastrointestinal haemorrhage 75.00 54.71 87 11767 14180 1720747
Leukocytosis 74.82 54.71 48 11806 3485 1731442
Gastric perforation 74.38 54.71 25 11829 393 1734534
Nail disorder 74.20 54.71 25 11829 396 1734531
Stress cardiomyopathy 73.89 54.71 24 11830 337 1734590
Tumour haemorrhage 73.75 54.71 27 11827 552 1734375
Pulmonary fibrosis 73.64 54.71 42 11812 2462 1732465
Lethargy 73.56 54.71 63 11791 7121 1727806
Inflammation 73.38 54.71 47 11807 3403 1731524
Metastases to lymph nodes 73.29 54.71 30 11824 836 1734091
Alanine aminotransferase increased 73.29 54.71 80 11774 12198 1722729
Febrile bone marrow aplasia 72.89 54.71 30 11824 848 1734079
Cholecystitis acute 72.83 54.71 30 11824 850 1734077
Coagulopathy 72.14 54.71 43 11811 2738 1732189
Loss of consciousness 72.06 54.71 87 11767 14788 1720139
Lung disorder 71.83 54.71 54 11800 5065 1729862
Subclavian vein thrombosis 71.60 54.71 20 11834 161 1734766
Hepatotoxicity 70.56 54.71 44 11810 3040 1731887
Anastomotic fistula 70.12 54.71 13 11841 6 1734921
Mouth ulceration 69.91 54.71 36 11818 1719 1733208
Ventricular fibrillation 69.90 54.71 42 11812 2714 1732213
Electrolyte imbalance 69.65 54.71 34 11820 1447 1733480
Large intestinal obstruction 68.68 54.71 21 11833 239 1734688
Folliculitis 68.32 54.71 27 11827 685 1734242
Dysgeusia 68.06 54.71 52 11802 4997 1729930
Haematemesis 67.78 54.71 49 11805 4328 1730599
Hyposideraemia 67.09 54.71 13 11841 11 1734916
Metabolic acidosis 67.09 54.71 53 11801 5349 1729578
Induration 66.95 54.71 20 11834 209 1734718
Pneumonia aspiration 66.12 54.71 52 11802 5214 1729713
Supraventricular tachycardia 65.92 54.71 34 11820 1629 1733298
Subileus 65.82 54.71 24 11830 485 1734442
Hypoaesthesia 65.62 54.71 68 11786 9767 1725160
Myocardial infarction 65.36 54.71 114 11740 27060 1707867
Thrombosis 65.15 54.71 60 11794 7461 1727466
Administration site extravasation 65.00 54.71 16 11838 73 1734854
Blood alkaline phosphatase increased 64.58 54.71 51 11803 5144 1729783
Back pain 64.42 54.71 87 11767 16526 1718401
Rash pustular 64.27 54.71 30 11824 1154 1733773
Cholestasis 63.63 54.71 44 11810 3621 1731306
Endocarditis 62.93 54.71 28 11826 962 1733965
Staphylococcal infection 62.39 54.71 48 11806 4659 1730268
Enterocolitis 62.18 54.71 27 11827 874 1734053
Bacterial translocation 61.46 54.71 14 11840 42 1734885
Aortic thrombosis 61.33 54.71 18 11836 176 1734751
Adenocarcinoma of colon 60.96 54.71 22 11832 431 1734496
Blood sodium decreased 60.74 54.71 36 11818 2268 1732659
Condition aggravated 60.59 54.71 96 11758 21054 1713873
Lymphopenia 59.51 54.71 34 11820 1999 1732928
Anal haemorrhage 58.16 54.71 19 11835 272 1734655
Recall phenomenon 57.70 54.71 16 11838 125 1734802
Proctalgia 57.51 54.71 24 11830 703 1734224
Metastasis 57.47 54.71 25 11829 813 1734114
Hypocalcaemia 57.41 54.71 39 11815 3117 1731810
Small intestinal perforation 57.30 54.71 20 11834 354 1734573
Malnutrition 56.85 54.71 30 11824 1507 1733420
Chest discomfort 56.83 54.71 55 11799 7276 1727651
Haemorrhage 56.83 54.71 63 11791 9766 1725161
Prothrombin level decreased 56.41 54.71 18 11836 238 1734689
Vena cava thrombosis 56.20 54.71 18 11836 241 1734686
Rectal perforation 56.16 54.71 15 11839 100 1734827
Oesophageal stenosis 55.70 54.71 19 11835 313 1734614
Tumour necrosis 54.93 54.71 17 11837 202 1734725

Pharmacologic Action:

SourceCodeDescription
ATC L01BC02 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ANTIMETABOLITES
Pyrimidine analogues
ATC L01BC52 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ANTIMETABOLITES
Pyrimidine analogues
CHEBI has role CHEBI:132992 radiosensitizing agent
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:35705 immunosuppressive agent
MeSH PA D000963 Antimetabolites
MeSH PA D000964 Antimetabolites, Antineoplastic
MeSH PA D000970 Antineoplastic Agents
MeSH PA D007155 Immunologic Factors
MeSH PA D007166 Immunosuppressive Agents
MeSH PA D009676 Noxae
FDA MoA N0000000233 Nucleic Acid Synthesis Inhibitors
FDA EPC N0000175595 Nucleoside Metabolic Inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Actinic keratosis indication 201101007 DOID:8866
Metastasis from malignant tumor of colon indication 314998002
Malignant tumor of stomach indication 363349007 DOID:10534
Malignant tumor of colon indication 363406005 DOID:219
Superficial basal cell carcinoma indication 403914000
Adenocarcinoma of pancreas indication 700423003 DOID:4074
Metastatic Breast Carcinoma indication
Carcinoid syndrome off-label use 35868009
Actinic cheilitis off-label use 46795000
Radiation dermatitis off-label use 49084001
Neoplasm of glans penis off-label use 126898002
Carcinoma of breast off-label use 254838004 DOID:3459
Malignant tumor of head and/or neck off-label use 255056009
Malignant tumor of cervix off-label use 363354003 DOID:4362
Malignant tumor of esophagus off-label use 363402007
Malignant tumor of anus off-label use 363490009 DOID:14110
Malignant tumor of urinary bladder off-label use 399326009 DOID:11054
Leukoplakia of oral mucosa off-label use 414603003
Biliary Tract Malignancy off-label use
Metastatic Malignant Tumor of Anus off-label use
Pancreatic Neuroendocrine Tumor off-label use
Nutritional disorder contraindication 2492009 DOID:374
Acute vomiting contraindication 23971007
Stomatitis contraindication 61170000 DOID:9637
Diarrhea contraindication 62315008
Acute infectious disease contraindication 63171007
Gastrointestinal hemorrhage contraindication 74474003
Dihydrouracil dehydrogenase (NADP^+^) deficiency contraindication 77365006 DOID:14218
Leukopenia contraindication 84828003 DOID:615
Kidney disease contraindication 90708001 DOID:557
Superficial ulcer of skin contraindication 93448009
Secondary malignant neoplasm of bone marrow contraindication 94217008
Bleeding contraindication 131148009
Angina pectoris contraindication 194828000
Disease of liver contraindication 235856003 DOID:409
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Bone marrow depression contraindication 307762000
Pharyngitis contraindication 405737000 DOID:2275
Breastfeeding (mother) contraindication 413712001
Palmar-Plantar Erythrodysesthesia contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.02 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
0.5% CARAC VALEANT PHARMS NORTH N020985 Oct. 27, 2000 RX CREAM TOPICAL 6670335 June 2, 2021 TREATMENT OF ACTINIC KERATOSIS

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Thymidylate synthase Enzyme INHIBITOR WOMBAT-PK CHEMBL
ATP-binding cassette sub-family C member 11 Transporter WOMBAT-PK
Multidrug resistance-associated protein 5 Transporter WOMBAT-PK
Thymidylate synthase Enzyme IC50 7.70 CHEMBL
Uracil phosphoribosyltransferase Unclassified Ki 4.89 CHEMBL

External reference:

IDSource
D005472 MESH_DESCRIPTOR_UI
4017806 VUID
N0000146166 NUI
C0016360 UMLSCUI
D00584 KEGG_DRUG
387172005 SNOMEDCT_US
3127006 SNOMEDCT_US
6969 MMSL
4492 RXNORM
4745 MMSL
d00235 MMSL
4017806 VANDF
002646 NDDF
3385 PUBCHEM_CID
CHEBI:46345 CHEBI
CHEMBL185 ChEMBL_ID
DB00544 DRUGBANK_ID
U3P01618RT UNII
1421 INN_ID
URF PDB_CHEM_ID
4789 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Efudex HUMAN PRESCRIPTION DRUG LABEL 1 0187-3202 SOLUTION 0.50 g TOPICAL NDA 12 sections
Efudex HUMAN PRESCRIPTION DRUG LABEL 1 0187-3203 SOLUTION 1.25 g TOPICAL NDA 12 sections
Efudex HUMAN PRESCRIPTION DRUG LABEL 1 0187-3204 CREAM 2 g TOPICAL NDA 12 sections
Carac HUMAN PRESCRIPTION DRUG LABEL 1 0187-5200 CREAM 5 mg TOPICAL NDA 13 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 0378-4791 CREAM 5 mg TOPICAL NDA 12 sections
Fluorouracil Cream HUMAN PRESCRIPTION DRUG LABEL 1 0378-8078 CREAM 5 mg TOPICAL NDA 12 sections
Adrucil HUMAN PRESCRIPTION DRUG LABEL 1 0703-3015 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
Adrucil HUMAN PRESCRIPTION DRUG LABEL 1 0703-3018 INJECTION, SOLUTION 2.50 g INTRAVENOUS ANDA 17 sections
Adrucil HUMAN PRESCRIPTION DRUG LABEL 1 0703-3019 INJECTION, SOLUTION 5 g INTRAVENOUS ANDA 17 sections
Fluoroplex HUMAN PRESCRIPTION DRUG LABEL 1 16110-812 CREAM 10 mg TOPICAL NDA 14 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 16729-276 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
FLUOROURACIL HUMAN PRESCRIPTION DRUG LABEL 1 21695-829 CREAM 50 mg TOPICAL ANDA 11 sections
fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 25021-215 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
TOLAK HUMAN PRESCRIPTION DRUG LABEL 1 28105-421 CREAM 0.04 g TOPICAL NDA 17 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 50090-4264 CREAM 50 mg TOPICAL ANDA 12 sections
FLUOROURACIL HUMAN PRESCRIPTION DRUG LABEL 1 50742-423 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
FLUOROURACIL HUMAN PRESCRIPTION DRUG LABEL 1 50742-481 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
FLUOROURACIL HUMAN PRESCRIPTION DRUG LABEL 1 50742-482 INJECTION, SOLUTION 2.50 g INTRAVENOUS ANDA 17 sections
FLUOROURACIL HUMAN PRESCRIPTION DRUG LABEL 1 50742-483 INJECTION, SOLUTION 5 g INTRAVENOUS ANDA 17 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 51672-4062 SOLUTION 20 mg TOPICAL ANDA 12 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 51672-4063 SOLUTION 50 mg TOPICAL ANDA 12 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 51672-4118 CREAM 50 mg TOPICAL ANDA 12 sections
FLUOROURACIL HUMAN PRESCRIPTION DRUG LABEL 1 51862-362 CREAM 50 mg TOPICAL ANDA 12 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 52549-4118 CREAM 50 mg TOPICAL ANDA 12 sections
FLUOROURACIL HUMAN PRESCRIPTION DRUG LABEL 1 54868-6293 CREAM 50 mg TOPICAL ANDA 11 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 63323-117 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 17 sections
TOLAK HUMAN PRESCRIPTION DRUG LABEL 1 64370-421 CREAM 40 mg TOPICAL NDA 17 sections
FLUOROURACIL HUMAN PRESCRIPTION DRUG LABEL 1 66530-249 CREAM 50 mg TOPICAL ANDA 11 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 66530-258 CREAM 5 mg TOPICAL NDA authorized generic 13 sections
Fluorouracil HUMAN PRESCRIPTION DRUG LABEL 1 66758-054 INJECTION, SOLUTION 50 mg INTRAVENOUS ANDA 13 sections