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

Stem definitionDrug idCAS RN
nucleosides antiviral or antineoplastic agents, cytarabine or azacitidine derivatives 770 147-94-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cytarabine hydrochloride
  • cytarabine
  • arabinocytosine
  • Arabinoside C
  • aracytidine
  • cyclocide
  • cytarabin
  • cytarabinoside
  • cytosine beta-D-arabinofuranoside
  • cytarabine liposome
  • cytarabine HCl
A pyrimidine nucleoside analog that is used mainly in the treatment of leukemia, especially acute non-lymphoblastic leukemia. Cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. Its actions are specific for the S phase of the cell cycle. It also has antiviral and immunosuppressant properties. (From Martindale, The Extra Pharmacopoeia, 30th ed, p472)
  • Molecular weight: 243.22
  • Formula: C9H13N3O5
  • CLOGP: -2.20
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 4
  • TPSA: 128.61
  • ALOGS: -0.74
  • ROTB: 2

  • 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) 11 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 11.10 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 20 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.67 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 41.67 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.87 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.17 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 17, 1969 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 3463.17 63.34 784 5105 10098 2342098
Neutropenia 1071.51 63.34 364 5525 21184 2331012
Febrile bone marrow aplasia 971.04 63.34 179 5710 678 2351518
Sepsis 960.36 63.34 323 5566 18165 2334031
Pyrexia 952.98 63.34 429 5460 53279 2298917
Thrombocytopenia 836.46 63.34 294 5595 18837 2333359
Septic shock 732.66 63.34 210 5679 6844 2345352
Pancytopenia 725.87 63.34 233 5656 11219 2340977
Bone marrow failure 679.67 63.34 189 5700 5497 2346699
Mucosal inflammation 644.31 63.34 178 5711 5046 2347150
Pneumonia 553.61 63.34 289 5600 49007 2303189
Acute myeloid leukaemia 514.13 63.34 130 5759 2580 2349616
Venoocclusive liver disease 493.29 63.34 96 5793 512 2351684
Multiple organ dysfunction syndrome 465.05 63.34 151 5738 7490 2344706
Haematotoxicity 464.02 63.34 102 5787 1065 2351131
Hypotension 441.60 63.34 217 5672 32219 2319977
Colitis 416.74 63.34 127 5762 5099 2347097
Posterior reversible encephalopathy syndrome 411.70 63.34 107 5782 2373 2349823
Respiratory failure 391.31 63.34 154 5735 13374 2338822
Product use in unapproved indication 364.69 63.34 139 5750 11061 2341135
Pleural effusion 344.95 63.34 135 5754 11533 2340663
Platelet count decreased 338.01 63.34 145 5744 15668 2336528
Blood culture positive 328.74 63.34 71 5818 676 2351520
Alanine aminotransferase increased 307.49 63.34 131 5758 13901 2338295
Neutropenic colitis 302.48 63.34 57 5832 247 2351949
Acute lymphocytic leukaemia recurrent 292.84 63.34 53 5836 174 2352022
Bronchopulmonary aspergillosis 281.33 63.34 66 5823 938 2351258
Acute kidney injury 280.73 63.34 153 5736 27969 2324227
Vomiting 280.59 63.34 216 5673 71386 2280810
Hypofibrinogenaemia 280.30 63.34 48 5841 102 2352094
Neurotoxicity 277.91 63.34 76 5813 2054 2350142
Myelodysplastic syndrome 277.55 63.34 79 5810 2481 2349715
Neoplasm recurrence 277.45 63.34 56 5833 369 2351827
Tumour lysis syndrome 271.66 63.34 65 5824 1010 2351186
Bacteraemia 269.45 63.34 71 5818 1659 2350537
Seizure 260.55 63.34 139 5750 24327 2327869
Acute myeloid leukaemia recurrent 251.64 63.34 46 5843 162 2352034
Diarrhoea 239.01 63.34 210 5679 83354 2268842
Nausea 238.66 63.34 239 5650 111950 2240246
Hypoxia 230.52 63.34 85 5804 6142 2346054
Tachycardia 229.14 63.34 112 5777 16297 2335899
Hypokalaemia 221.79 63.34 96 5793 10558 2341638
Blood bilirubin increased 220.34 63.34 79 5810 5266 2346930
Haemophagocytic lymphohistiocytosis 216.49 63.34 57 5832 1326 2350870
Neutrophil count decreased 215.25 63.34 82 5807 6485 2345711
Off label use 214.33 63.34 187 5702 73411 2278785
Neutropenic sepsis 209.38 63.34 56 5833 1386 2350810
Acute respiratory distress syndrome 207.82 63.34 67 5822 3225 2348971
Bacterial infection 202.81 63.34 60 5829 2161 2350035
Aplasia 201.40 63.34 44 5845 443 2351753
Disease progression 198.49 63.34 103 5786 16992 2335204
Abdominal pain 194.56 63.34 130 5759 34244 2317952
Hyperbilirubinaemia 191.50 63.34 53 5836 1496 2350700
Venoocclusive disease 190.99 63.34 38 5851 230 2351966
Clostridium difficile colitis 189.11 63.34 56 5833 2023 2350173
Infection 187.69 63.34 101 5788 17928 2334268
Enterococcal infection 187.59 63.34 45 5844 706 2351490
Cytomegalovirus infection 186.81 63.34 59 5830 2654 2349542
Hypoalbuminaemia 182.99 63.34 50 5839 1344 2350852
Encephalopathy 182.65 63.34 66 5823 4495 2347701
Respiratory distress 182.39 63.34 68 5821 5061 2347135
Pulmonary oedema 182.02 63.34 75 5814 7288 2344908
Aspartate aminotransferase increased 181.72 63.34 88 5801 12524 2339672
Fungaemia 180.22 63.34 36 5853 223 2351973
Second primary malignancy 179.41 63.34 46 5843 960 2351236
Anaemia 176.49 63.34 123 5766 34669 2317527
Leukaemia recurrent 175.18 63.34 35 5854 217 2351979
Ascites 172.78 63.34 67 5822 5553 2346643
Renal failure 171.69 63.34 94 5795 17255 2334941
Pulmonary haemorrhage 170.42 63.34 46 5843 1179 2351017
Leukopenia 167.85 63.34 78 5811 10118 2342078
Graft versus host disease 162.00 63.34 42 5847 917 2351279
Myelopathy 160.67 63.34 35 5854 347 2351849
Staphylococcal sepsis 157.63 63.34 42 5847 1023 2351173
Aspergillus infection 156.99 63.34 41 5848 922 2351274
Device related infection 156.54 63.34 54 5835 3205 2348991
Hepatocellular injury 148.68 63.34 55 5834 4000 2348196
White blood cell count decreased 148.65 63.34 87 5802 18121 2334075
Fungal infection 145.71 63.34 57 5832 4832 2347364
Enterococcal bacteraemia 141.40 63.34 27 5862 127 2352069
Cytopenia 140.87 63.34 38 5851 971 2351225
Leukoencephalopathy 139.49 63.34 36 5853 771 2351425
Haemoglobin decreased 133.24 63.34 81 5808 18070 2334126
Disseminated intravascular coagulation 132.30 63.34 48 5841 3302 2348894
Headache 131.06 63.34 149 5740 80030 2272166
Disease recurrence 130.91 63.34 48 5841 3403 2348793
Staphylococcal infection 130.72 63.34 54 5835 5272 2346924
Mucormycosis 130.62 63.34 30 5859 385 2351811
Ejection fraction decreased 129.06 63.34 45 5844 2756 2349440
Mental status changes 128.27 63.34 54 5835 5528 2346668
Hypertriglyceridaemia 126.28 63.34 34 5855 862 2351334
Stomatitis 125.62 63.34 63 5826 9647 2342549
Hepatotoxicity 123.15 63.34 46 5843 3435 2348761
Neuropathy peripheral 118.71 63.34 64 5825 11368 2340828
Escherichia bacteraemia 113.61 63.34 26 5863 328 2351868
Neutropenic infection 112.19 63.34 23 5866 165 2352031
Decreased appetite 112.12 63.34 87 5802 28804 2323392
Clostridium test positive 111.81 63.34 25 5864 282 2351914
Rhinovirus infection 111.48 63.34 25 5864 286 2351910
Acute lymphocytic leukaemia 110.26 63.34 27 5862 463 2351733
Fluid overload 110.03 63.34 40 5849 2766 2349430
Cerebral haemorrhage 109.21 63.34 48 5841 5456 2346740
Left ventricular dysfunction 106.65 63.34 32 5857 1208 2350988
Cardiotoxicity 106.47 63.34 32 5857 1215 2350981
Hemiparesis 105.52 63.34 41 5848 3409 2348787
Cardiac failure 104.50 63.34 60 5829 12034 2340162
Malignant neoplasm progression 104.34 63.34 60 5829 12068 2340128
Candida infection 101.74 63.34 38 5851 2835 2349361
Unresponsive to stimuli 101.54 63.34 44 5845 4832 2347364
Palmar-plantar erythrodysaesthesia syndrome 101.06 63.34 42 5847 4159 2348037
Pseudomonas infection 99.89 63.34 30 5859 1136 2351060
Acute respiratory failure 99.68 63.34 38 5851 3000 2349196
Cystitis haemorrhagic 98.47 63.34 26 5863 610 2351586
Hyperglycaemia 98.20 63.34 43 5846 4842 2347354
Herpes simplex 98.13 63.34 29 5860 1038 2351158
Transaminases increased 97.50 63.34 42 5847 4545 2347651
Human herpesvirus 6 infection 96.07 63.34 23 5866 357 2351839
Cardiac arrest 95.30 63.34 61 5828 14869 2337327
Staphylococcal bacteraemia 94.79 63.34 25 5864 584 2351612
Neoplasm progression 93.54 63.34 41 5848 4627 2347569
Muscular weakness 92.95 63.34 60 5829 14837 2337359
Enterobacter infection 92.64 63.34 21 5868 253 2351943
Hypertension 92.47 63.34 76 5813 27285 2324911
Progressive multifocal leukoencephalopathy 92.22 63.34 33 5856 2179 2350017
Enterocolitis 91.31 63.34 26 5863 814 2351382
Hepatomegaly 90.83 63.34 31 5858 1778 2350418
Chills 90.59 63.34 60 5829 15492 2336704
Drug interaction 90.28 63.34 77 5812 29086 2323110
Hepatic failure 88.84 63.34 42 5847 5647 2346549
Diffuse large B-cell lymphoma recurrent 88.83 63.34 17 5872 81 2352115
Cellulitis 88.54 63.34 49 5840 9152 2343044
Atelectasis 88.32 63.34 31 5858 1934 2350262
Lung infiltration 87.73 63.34 32 5857 2232 2349964
Pneumonia fungal 85.38 63.34 21 5868 367 2351829
Pyomyositis 84.62 63.34 15 5874 42 2352154
Appendicitis 82.52 63.34 26 5863 1157 2351039
Aphasia 81.94 63.34 38 5851 4890 2347306
Dyspnoea 81.89 63.34 117 5772 78616 2273580
Sinusitis fungal 81.39 63.34 16 5873 90 2352106
Stem cell transplant 80.65 63.34 20 5869 362 2351834
Toxicity to various agents 80.63 63.34 76 5813 32678 2319518
Pseudomonas test positive 80.42 63.34 17 5872 144 2352052
Drug resistance 79.58 63.34 31 5858 2593 2349603
Hodgkin's disease refractory 78.84 63.34 12 5877 6 2352190
Ileus 77.89 63.34 29 5860 2143 2350053
Pancreatitis 77.66 63.34 43 5846 8036 2344160
Human bocavirus infection 77.58 63.34 12 5877 8 2352188
Escherichia sepsis 77.43 63.34 21 5868 547 2351649
Secondary immunodeficiency 77.29 63.34 15 5874 78 2352118
Tachypnoea 77.16 63.34 29 5860 2200 2349996
Systemic mycosis 76.61 63.34 16 5873 127 2352069
Hyponatraemia 76.60 63.34 51 5838 13274 2338922
Pericardial effusion 76.41 63.34 34 5855 3975 2348221
Gastrointestinal haemorrhage 74.89 63.34 49 5840 12386 2339810
Lung consolidation 74.15 63.34 20 5869 510 2351686
Systemic candida 73.04 63.34 18 5871 317 2351879
Pneumocystis jirovecii pneumonia 73.01 63.34 28 5861 2245 2349951
Haemorrhage intracranial 72.89 63.34 29 5860 2565 2349631
Haemodialysis 71.91 63.34 27 5862 2042 2350154
Death 71.71 63.34 112 5777 81356 2270840
Bacterial sepsis 71.03 63.34 19 5870 469 2351727
Toxic epidermal necrolysis 70.81 63.34 30 5859 3114 2349082
Streptococcal sepsis 69.31 63.34 16 5873 210 2351986
General physical health deterioration 69.18 63.34 49 5840 14090 2338106
Gamma-glutamyltransferase increased 68.70 63.34 35 5854 5527 2346669
Hypophosphataemia 68.38 63.34 22 5867 1048 2351148
Enteritis 68.06 63.34 22 5867 1064 2351132
Antithrombin III 67.93 63.34 10 5879 2 2352194
Malignant transformation 67.85 63.34 12 5877 33 2352163
Asthenia 67.72 63.34 82 5807 46844 2305352
C-reactive protein increased 67.64 63.34 36 5853 6219 2345977
Peripheral motor neuropathy 67.27 63.34 16 5873 241 2351955
Cough 66.90 63.34 69 5820 33048 2319148
Systemic inflammatory response syndrome 66.48 63.34 20 5869 761 2351435
Coagulopathy 66.32 63.34 28 5861 2881 2349315
Capillary leak syndrome 65.94 63.34 17 5872 362 2351834
Venous thrombosis 65.50 63.34 20 5869 801 2351395
Pseudomonal sepsis 65.29 63.34 16 5873 275 2351921
Perineal necrosis 65.05 63.34 10 5879 6 2352190
Fusarium infection 64.85 63.34 13 5876 82 2352114
Acute graft versus host disease in skin 64.74 63.34 17 5872 390 2351806
Enterococcus test positive 64.69 63.34 14 5875 134 2352062
Streptococcal bacteraemia 64.04 63.34 14 5875 141 2352055
Cardiomyopathy 63.93 63.34 27 5862 2780 2349416

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 4782.91 51.34 1194 6911 9906 1728770
Neutropenia 1549.18 51.34 566 7539 17694 1720982
Pyrexia 1228.63 51.34 631 7474 45769 1692907
Sepsis 1166.59 51.34 469 7636 18969 1719707
Pancytopenia 921.76 51.34 342 7763 11015 1727661
Thrombocytopenia 913.67 51.34 405 7700 20844 1717832
Septic shock 856.49 51.34 297 7808 7812 1730864
Mucosal inflammation 824.04 51.34 246 7859 3923 1734753
Bone marrow failure 820.33 51.34 258 7847 4942 1733734
Venoocclusive liver disease 780.78 51.34 174 7931 759 1737917
Febrile bone marrow aplasia 780.21 51.34 172 7933 706 1737970
Haematotoxicity 748.93 51.34 169 7936 789 1737887
Acute myeloid leukaemia 704.20 51.34 203 7902 2838 1735838
Product use in unapproved indication 680.95 51.34 261 7844 9161 1729515
Multiple organ dysfunction syndrome 614.34 51.34 241 7864 9001 1729675
Pneumonia 603.17 51.34 399 7706 45783 1692893
Respiratory failure 572.21 51.34 261 7844 14244 1724432
Myelodysplastic syndrome 563.35 51.34 174 7931 3115 1735561
Off label use 499.58 51.34 332 7773 38239 1700437
Acute kidney injury 474.66 51.34 310 7795 34634 1704042
Hypotension 467.14 51.34 289 7816 29365 1709311
Colitis 447.54 51.34 155 7950 4025 1734651
Bronchopulmonary aspergillosis 445.87 51.34 123 7982 1443 1737233
Hyperbilirubinaemia 399.85 51.34 123 7982 2164 1736512
Fungal infection 375.80 51.34 117 7988 2145 1736531
Aspergillus infection 364.00 51.34 102 8003 1271 1737405
Platelet count decreased 346.14 51.34 194 7911 16329 1722347
Tumour lysis syndrome 343.81 51.34 103 8002 1648 1737028
Bacteraemia 336.59 51.34 103 8002 1777 1736899
Leukoencephalopathy 328.48 51.34 84 8021 716 1737960
Anaemia 324.53 51.34 230 7875 29227 1709449
Neutropenic sepsis 306.94 51.34 91 8014 1401 1737275
Stomatitis 299.88 51.34 124 7981 5280 1733396
Blood bilirubin increased 299.62 51.34 129 7976 6081 1732595
Aplasia 299.48 51.34 70 8035 390 1738286
Hypoxia 298.02 51.34 127 7978 5836 1732840
Alanine aminotransferase increased 295.18 51.34 158 7947 12120 1726556
Infection 294.19 51.34 158 7947 12202 1726474
Neutropenic colitis 293.15 51.34 63 8042 221 1738455
Blood culture positive 291.42 51.34 76 8029 705 1737971
Hypertriglyceridaemia 280.68 51.34 81 8024 1128 1737548
Myelopathy 280.40 51.34 63 8042 285 1738391
Acute lymphocytic leukaemia recurrent 278.14 51.34 61 8044 241 1738435
Pleural effusion 275.54 51.34 146 7959 10964 1727712
Neoplasm progression 269.67 51.34 100 8005 3167 1735509
Acute myeloid leukaemia recurrent 268.01 51.34 58 8047 212 1738464
Abdominal pain 262.57 51.34 179 7926 21311 1717365
Second primary malignancy 259.47 51.34 74 8031 985 1737691
Hypofibrinogenaemia 257.18 51.34 54 8051 164 1738512
Cytomegalovirus infection 250.45 51.34 95 8010 3206 1735470
Vomiting 248.43 51.34 219 7886 38096 1700580
Staphylococcal infection 237.58 51.34 101 8004 4606 1734070
Renal failure 233.27 51.34 162 7943 19855 1718821
Diarrhoea 228.92 51.34 244 7861 53608 1685068
Neutrophil count decreased 228.23 51.34 106 7999 5975 1732701
White blood cell count decreased 223.60 51.34 135 7970 13014 1725662
Device related infection 222.30 51.34 79 8026 2207 1736469
Posterior reversible encephalopathy syndrome 218.71 51.34 70 8035 1405 1737271
Tachycardia 210.44 51.34 128 7977 12500 1726176
Nausea 206.97 51.34 226 7879 50970 1687706
Venoocclusive disease 203.87 51.34 49 8056 313 1738363
Disease progression 201.70 51.34 140 7965 17123 1721553
Hepatotoxicity 199.26 51.34 79 8026 3005 1735671
Malignant neoplasm progression 196.98 51.34 128 7977 14030 1724646
Cytopenia 192.05 51.34 57 8048 879 1737797
Mucormycosis 191.09 51.34 54 8051 693 1737983
Aspartate aminotransferase increased 189.43 51.34 113 7992 10643 1728033
Leukopenia 189.29 51.34 104 8001 8376 1730300
Acute respiratory distress syndrome 185.14 51.34 78 8027 3473 1735203
Cytomegalovirus chorioretinitis 184.73 51.34 46 8059 347 1738329
Candida infection 180.30 51.34 65 8040 1893 1736783
Drug ineffective 171.50 51.34 229 7876 63572 1675104
Escherichia sepsis 166.38 51.34 47 8058 602 1738074
Respiratory distress 166.24 51.34 81 8024 5076 1733600
Leukaemia recurrent 165.94 51.34 40 8065 259 1738417
Pulmonary oedema 158.69 51.34 85 8020 6501 1732175
Clostridium difficile colitis 158.06 51.34 56 8049 1548 1737128
Neurotoxicity 152.54 51.34 58 8047 1966 1736710
Nervous system disorder 152.02 51.34 61 8044 2393 1736283
Haemophagocytic lymphohistiocytosis 151.60 51.34 53 8052 1407 1737269
Seizure 146.52 51.34 124 7981 20317 1718359
Neuropathy peripheral 144.36 51.34 90 8015 9163 1729513
Osteonecrosis 142.17 51.34 67 8038 3895 1734781
Acute lymphocytic leukaemia 141.04 51.34 40 8065 520 1738156
Enterococcal infection 138.64 51.34 44 8061 857 1737819
Bacterial infection 137.93 51.34 53 8052 1849 1736827
Staphylococcal bacteraemia 135.85 51.34 42 8063 748 1737928
Malignant transformation 133.92 51.34 26 8079 45 1738631
Graft versus host disease 133.44 51.34 49 8056 1504 1737172
Pulmonary haemorrhage 132.77 51.34 50 8055 1649 1737027
Encephalopathy 131.78 51.34 66 8039 4386 1734290
Bacterial sepsis 130.32 51.34 39 8066 619 1738057
Gamma-glutamyltransferase increased 129.00 51.34 68 8037 5030 1733646
Hypokalaemia 128.08 51.34 73 8032 6301 1732375
Pneumonia fungal 127.86 51.34 36 8069 455 1738221
Escherichia infection 126.40 51.34 42 8063 951 1737725
Diffuse large B-cell lymphoma 125.00 51.34 43 8062 1086 1737590
Chills 122.94 51.34 89 8016 11598 1727078
Disseminated intravascular coagulation 120.15 51.34 58 8047 3556 1735120
Transaminases increased 118.67 51.34 59 8046 3858 1734818
Chloroma 118.51 51.34 25 8080 78 1738598
Disease recurrence 115.76 51.34 51 8054 2531 1736145
Systemic candida 114.27 51.34 31 8074 338 1738338
Diffuse large B-cell lymphoma recurrent 112.33 51.34 25 8080 107 1738569
Toxicity to various agents 109.28 51.34 124 7981 29017 1709659
Ascites 106.93 51.34 62 8043 5524 1733152
Atrial fibrillation 106.81 51.34 91 8014 15020 1723656
Hepatic failure 106.36 51.34 63 8042 5840 1732836
Atelectasis 105.84 51.34 44 8061 1890 1736786
Parainfluenzae virus infection 105.23 51.34 26 8079 189 1738487
Lung infiltration 104.45 51.34 45 8060 2114 1736562
Agranulocytosis 102.84 51.34 52 8053 3524 1735152
Staphylococcal sepsis 102.77 51.34 38 8067 1189 1737487
Clostridium difficile infection 102.48 51.34 42 8063 1739 1736937
Pancreatitis 102.30 51.34 66 8039 7121 1731555
Mental status changes 102.11 51.34 62 8043 6013 1732663
Oedema 101.85 51.34 65 8040 6883 1731793
Headache 100.64 51.34 129 7976 34247 1704429
Coagulopathy 99.65 51.34 47 8058 2734 1735942
Escherichia bacteraemia 99.47 51.34 27 8078 295 1738381
Viral haemorrhagic cystitis 98.95 51.34 21 8084 68 1738608
Epstein-Barr virus infection 98.50 51.34 36 8069 1089 1737587
Neoplasm recurrence 97.00 51.34 28 8077 389 1738287
Muscular weakness 96.42 51.34 73 8032 10176 1728500
Hypertension 96.33 51.34 96 8009 19352 1719324
Cystitis haemorrhagic 96.19 51.34 31 8074 635 1738041
Klebsiella infection 93.95 51.34 32 8073 783 1737893
Cerebral haemorrhage 92.69 51.34 59 8046 6218 1732458
Acute promyelocytic leukaemia 91.03 51.34 22 8083 144 1738532
Systemic mycosis 89.88 51.34 22 8083 153 1738523
Pneumonia cytomegaloviral 89.81 51.34 26 8079 365 1738311
Cardiac failure 89.24 51.34 76 8029 12526 1726150
Cytogenetic abnormality 88.44 51.34 23 8082 210 1738466
Condition aggravated 87.84 51.34 95 8010 21055 1717621
Sinusitis 86.98 51.34 53 8052 5170 1733506
Dyspnoea 86.86 51.34 150 7955 51909 1686767
Cardiotoxicity 85.72 51.34 30 8075 798 1737878
Stem cell transplant 85.26 51.34 26 8079 441 1738235
Cholestasis 84.58 51.34 46 8059 3619 1735057
Fluid overload 83.82 51.34 38 8067 2017 1736659
Cellulitis 81.36 51.34 55 8050 6413 1732263
Therapy non-responder 80.54 51.34 54 8051 6212 1732464
Cytokine release syndrome 80.51 51.34 26 8079 536 1738140
Pericardial effusion 79.48 51.34 43 8062 3347 1735329
Hypoalbuminaemia 79.15 51.34 33 8072 1427 1737249
Tachypnoea 78.83 51.34 38 8067 2320 1736356
Blood creatinine increased 78.72 51.34 74 8031 13872 1724804
Retinal haemorrhage 78.13 51.34 31 8074 1178 1737498
Lymphopenia 77.91 51.34 36 8069 1997 1736679
Hepatomegaly 77.83 51.34 34 8071 1651 1737025
Ejection fraction decreased 77.54 51.34 37 8068 2208 1736468
Decreased appetite 76.82 51.34 94 8011 23777 1714899
Stenotrophomonas infection 76.67 51.34 20 8085 185 1738491
Sinus tachycardia 76.26 51.34 38 8067 2494 1736182
Cough 75.81 51.34 84 8021 19113 1719563
Drug resistance 75.81 51.34 41 8064 3189 1735487
Blindness 75.57 51.34 39 8066 2757 1735919
Dysphagia 75.42 51.34 63 8042 10105 1728571
Fusarium infection 74.85 51.34 18 8087 115 1738561
Epistaxis 73.35 51.34 57 8048 8249 1730427
Haemoglobin decreased 73.00 51.34 78 8027 17036 1721640
Palmar-plantar erythrodysaesthesia syndrome 72.65 51.34 41 8064 3466 1735210
Progressive multifocal leukoencephalopathy 72.24 51.34 32 8073 1607 1737069
Pneumocystis jirovecii pneumonia 71.44 51.34 36 8069 2420 1736256
Glioma 70.88 51.34 16 8089 74 1738602
Metabolic acidosis 70.49 51.34 47 8058 5355 1733321
Cardio-respiratory arrest 69.79 51.34 58 8047 9235 1729441
Encephalitis 69.45 51.34 28 8077 1110 1737566
Pseudomonas test positive 69.35 51.34 17 8088 119 1738557
General physical health deterioration 69.08 51.34 67 8038 13051 1725625
Autoimmune lymphoproliferative syndrome 68.98 51.34 12 8093 6 1738670
Shock 68.70 51.34 42 8063 4119 1734557
Capillary leak syndrome 68.61 51.34 20 8085 288 1738388
Burkitt's lymphoma 67.70 51.34 17 8088 133 1738543
Hyperglycaemia 67.54 51.34 45 8060 5120 1733556
Facial paralysis 67.46 51.34 32 8073 1884 1736792
Confusional state 67.16 51.34 83 8022 21195 1717481
Blood HIV RNULL increased 66.44 51.34 18 8087 195 1738481
Post transplant lymphoproliferative disorder 65.65 51.34 24 8081 726 1737950
Treatment failure 64.04 51.34 41 8064 4360 1734316
Gastrointestinal wall thickening 62.86 51.34 16 8089 133 1738543
Systemic inflammatory response syndrome 62.84 51.34 24 8081 822 1737854
Enterobacter infection 62.08 51.34 18 8087 254 1738422
Haemodynamic instability 61.82 51.34 27 8078 1310 1737366
Asthenia 61.80 51.34 103 8002 34567 1704109
Cardiac arrest 61.66 51.34 69 8036 15861 1722815
Enterocolitis 61.37 51.34 24 8081 877 1737799
Hepatosplenic candidiasis 61.36 51.34 12 8093 22 1738654
Paraplegia 61.33 51.34 21 8084 522 1738154
Hyponatraemia 61.08 51.34 53 8052 8947 1729729
Left ventricular dysfunction 61.06 51.34 26 8079 1185 1737491
Dialysis 60.58 51.34 32 8073 2372 1736304
Hepatitis B 60.57 51.34 27 8078 1376 1737300
Skin toxicity 59.31 51.34 21 8084 578 1738098
Lung consolidation 58.94 51.34 21 8084 589 1738087
Intracranial pressure increased 58.23 51.34 22 8083 731 1737945
Paraesthesia 58.07 51.34 55 8050 10396 1728280
Hypogammaglobulinaemia 57.99 51.34 21 8084 618 1738058
Respiratory tract infection fungal 57.24 51.34 14 8091 97 1738579
Pneumonia klebsiella 57.01 51.34 18 8087 344 1738332
Oxygen saturation decreased 56.84 51.34 42 8063 5633 1733043
Adenovirus infection 56.67 51.34 19 8086 442 1738234
Dehydration 55.89 51.34 69 8036 17589 1721087
Acute graft versus host disease 55.71 51.34 22 8083 825 1737851
Klebsiella sepsis 55.70 51.34 16 8089 218 1738458
Dysarthria 55.11 51.34 40 8065 5219 1733457
Ileus 54.48 51.34 30 8075 2416 1736260
Intussusception 54.41 51.34 14 8091 122 1738554
Geotrichum infection 54.36 51.34 11 8094 26 1738650
Guillain-Barre syndrome 54.11 51.34 22 8083 891 1737785
Basal cell carcinoma 54.06 51.34 30 8075 2453 1736223
Therapeutic product effect incomplete 53.85 51.34 40 8065 5408 1733268
Haemorrhage intracranial 53.58 51.34 33 8072 3277 1735399
Appendicitis 52.48 51.34 23 8082 1125 1737551
Trichosporon infection 51.96 51.34 13 8092 100 1738576
Brain oedema 51.87 51.34 28 8077 2168 1736508
Pseudomonal sepsis 51.86 51.34 17 8088 368 1738308
Hepatocellular injury 51.76 51.34 32 8073 3199 1735477
Skin lesion 51.63 51.34 31 8074 2941 1735735
Hemiparesis 51.37 51.34 30 8075 2704 1735972

Pharmacologic Action:

SourceCodeDescription
ATC L01BC01 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ANTIMETABOLITES
Pyrimidine analogues
ATC L01XY01 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
OTHER ANTINEOPLASTIC AGENTS
Combinations of antineoplastic agents
FDA MoA N0000000233 Nucleic Acid Synthesis Inhibitors
FDA EPC N0000175595 Nucleoside Metabolic Inhibitor
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:35705 immunosuppressive agent
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000963 Antimetabolites
MeSH PA D000964 Antimetabolites, Antineoplastic
MeSH PA D000970 Antineoplastic Agents
MeSH PA D000998 Antiviral Agents
MeSH PA D007155 Immunologic Factors
MeSH PA D007166 Immunosuppressive Agents
MeSH PA D009676 Noxae

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Acute lymphoid leukemia indication 91857003 DOID:9952
Acute myeloid leukemia, disease indication 91861009
Acute promyelocytic leukemia, FAB M3 indication 110004001
Lymphomatous meningitis indication 426128009
Meningeal Leukemia indication
Allogeneic bone marrow transplantation off-label use 58390007
Chronic myeloid leukemia off-label use 92818009 DOID:8552
Diffuse non-Hodgkin's lymphoma, large cell off-label use 109969005
Myelodysplastic syndrome off-label use 109995007
Burkitt's lymphoma off-label use 118617000
Progressive Diffuse Large B-Cell Lymphoma off-label use
Adjunct for CNS Disease Prevention in Non-Hodgkin's Lymphoma off-label use
Necrotizing enterocolitis in fetus OR newborn contraindication 2707005
Mycosis contraindication 3218000 DOID:1564
Pulmonary edema contraindication 19242006 DOID:11396
Viral disease contraindication 34014006 DOID:934
Hyperuricemia contraindication 35885006 DOID:1920
Gastrointestinal ulcer contraindication 40845000
Stomatitis contraindication 61170000 DOID:9637
Diarrhea contraindication 62315008
Adult respiratory distress syndrome contraindication 67782005 DOID:11394
Leukopenia contraindication 84828003 DOID:615
Cardiomyopathy contraindication 85898001 DOID:0050700
Bacterial infectious disease contraindication 87628006
Kidney disease contraindication 90708001 DOID:557
Infectious disease of central nervous system contraindication 128117002
Acute pancreatitis contraindication 197456007 DOID:2913
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Peripheral nerve disease contraindication 302226006
Bone marrow depression contraindication 307762000
Coma contraindication 371632003
Breastfeeding (mother) contraindication 413712001
Acute cerebellar syndrome contraindication 417017003
Granulocytopenic disorder contraindication 417672002
Vomiting contraindication 422400008
Protozoal Infection contraindication
Intestinal Ischemic Necrosis contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.91 acidic
pKa2 12.58 acidic
pKa3 12.97 acidic
pKa4 4.04 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
100MG VYXEOS CELATOR PHARMS N209401 Aug. 3, 2017 RX POWDER INTRAVENOUS 8431806 April 22, 2025 FOR THE TREATMENT OF ADULTS WITH NEWLY-DIAGNOSED THERAPY-RELATED ACUTE MYELOID LEUKEMIA (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC)
100MG VYXEOS CELATOR PHARMS N209401 Aug. 3, 2017 RX POWDER INTRAVENOUS 7850990 Jan. 23, 2027 FOR THE TREATMENT OF ADULTS WITH NEWLY-DIAGNOSED THERAPY-RELATED ACUTE MYELOID LEUKEMIA (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC)
100MG VYXEOS CELATOR PHARMS N209401 Aug. 3, 2017 RX POWDER INTRAVENOUS 8022279 Sept. 14, 2027 FOR THE TREATMENT OF ADULTS WITH NEWLY-DIAGNOSED THERAPY-RELATED ACUTE MYELOID LEUKEMIA (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC)
100MG VYXEOS CELATOR PHARMS N209401 Aug. 3, 2017 RX POWDER INTRAVENOUS 8092828 April 1, 2029 FOR THE TREATMENT OF ADULTS WITH NEWLY-DIAGNOSED THERAPY-RELATED ACUTE MYELOID LEUKEMIA (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC)
100MG VYXEOS CELATOR PHARMS N209401 Aug. 3, 2017 RX POWDER INTRAVENOUS 10166184 Oct. 15, 2032 METHOD OF RECONSTITUTING A LYOPHILIZED LIPOSOMAL COMPOSITION FOR ADMINISTERING CYTARABINE AND DAUNORUBICIN TO TREAT ADULTS WITH NEWLY-DIAGNOSED THERAPY-RELATED ACUTE MYELOID LEUKEMIA (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC)
100MG VYXEOS CELATOR PHARMS N209401 Aug. 3, 2017 RX POWDER INTRAVENOUS 10028912 Sept. 29, 2034 METHOD OF ADMINISTERING A RECONSTITUTED LIPOSOMAL COMPOSITION CONTAINING CYTARABINE AND DAUNORUBICIN TO TREAT ADULTS WITH NEWLY-DIAGNOSED THERAPY-RELATED ACUTE MYELOID LEUKEMIA (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC)
100MG VYXEOS CELATOR PHARMS N209401 Aug. 3, 2017 RX POWDER INTRAVENOUS 10028912 Sept. 29, 2034 METHOD OF RECONSTITUTING A LYOPHILIZED LIPOSOMAL COMPOSITION FOR ADMINISTERING CYTARABINE AND DAUNORUBICIN TO TREAT ADULTS WITH NEWLY-DIAGNOSED THERAPY-RELATED ACUTE MYELOID LEUKEMIA (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC)

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
100MG VYXEOS CELATOR PHARMS N209401 Aug. 3, 2017 RX POWDER INTRAVENOUS Aug. 3, 2020 NEW PRODUCT

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
DNA polymerase (alpha/delta/epsilon) Enzyme INHIBITOR CHEMBL CHEMBL
Prostatic acid phosphatase Enzyme GI50 7 WOMBAT-PK
DNA polymerase beta Enzyme WOMBAT-PK
Enoyl-[acyl-carrier-protein] reductase [NADH] Enzyme IC50 4.23 CHEMBL

External reference:

IDSource
D003561 MESH_DESCRIPTOR_UI
4018080 VUID
N0000146419 NUI
C0010711 UMLSCUI
D00168 KEGG_DRUG
04079A1RDZ UNII
1709 INN_ID
69-74-9 SECONDARY_CAS_RN
89265009 SNOMEDCT_US
4018080 VANDF
002649 NDDF
372 MMSL
3041 RXNORM
387511003 SNOMEDCT_US
4526 MMSL
d00201 MMSL
6253 PUBCHEM_CID
CHEBI:28680 CHEBI
CHEMBL803 ChEMBL_ID
DB00987 DRUGBANK_ID
CHEMBL596186 ChEMBL_ID
AR3 PDB_CHEM_ID
4827 IUPHAR_LIGAND_ID
CHEMBL1256472 ChEMBL_ID
CHEMBL2092816 ChEMBL_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
CYTARABINE HUMAN PRESCRIPTION DRUG LABEL 1 61703-303 INJECTION, SOLUTION 20 mg INTRAVENOUS ANDA 14 sections
Cytarabine HUMAN PRESCRIPTION DRUG LABEL 1 61703-304 INJECTION, SOLUTION 20 mg INTRAVENOUS ANDA 14 sections
Cytarabine HUMAN PRESCRIPTION DRUG LABEL 1 61703-305 INJECTION, SOLUTION 20 mg INTRAVENOUS ANDA 14 sections
Cytarabine HUMAN PRESCRIPTION DRUG LABEL 1 61703-319 INJECTION, SOLUTION 100 mg INTRAVENOUS ANDA 16 sections
Cytarabine HUMAN PRESCRIPTION DRUG LABEL 1 63323-120 INJECTION, SOLUTION 100 mg INTRAVENOUS ANDA 14 sections
Cytarabine HUMAN PRESCRIPTION DRUG LABEL 1 67457-452 INJECTION 2 g INTRATHECAL ANDA 14 sections
Cytarabine HUMAN PRESCRIPTION DRUG LABEL 1 67457-454 INJECTION 20 mg INTRAVENOUS ANDA 14 sections
cytarabine HUMAN PRESCRIPTION DRUG LABEL 1 67457-455 INJECTION 100 mg INTRAVENOUS ANDA 14 sections
Cytarabine HUMAN PRESCRIPTION DRUG LABEL 1 68083-337 INJECTION, SOLUTION 100 mg INTRAVENOUS ANDA 13 sections
Cytarabine HUMAN PRESCRIPTION DRUG LABEL 1 68083-343 INJECTION, SOLUTION 20 mg INTRAVENOUS ANDA 12 sections
VYXEOS HUMAN PRESCRIPTION DRUG LABEL 2 68727-745 INJECTION, POWDER, LYOPHILIZED, FOR SUSPENSION 100 mg INTRAVENOUS NDA 17 sections
Cytarabine HUMAN PRESCRIPTION DRUG LABEL 1 71288-109 INJECTION, SOLUTION 2 g INTRAVENOUS ANDA 14 sections