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

Stem definitionDrug idCAS RN
1708 50-44-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • mercaptopurine monohydrate
  • 6-mercaptopurine monohydrate
  • 6-mercaptopurine
  • xaluprine
  • mercaptopurine
  • mercapurin
  • purimethol
  • purinethiol
  • purinethol
  • thiohypoxanthine
  • mercaptopurine hydrate
An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia.
  • Molecular weight: 152.18
  • Formula: C5H4N4S
  • CLOGP: -1.33
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 53.07
  • ALOGS: -2.32
  • ROTB: 0

  • Status: OFP

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

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 22 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 16.43 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 12 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 15 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.85 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Sept. 11, 1953 FDA STASON 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
Febrile neutropenia 628.37 14.26 407 17487 104529 53226643
Febrile bone marrow aplasia 305.34 14.26 108 17786 7081 53324091
Crohn's disease 296.59 14.26 104 17790 6646 53324526
Venoocclusive liver disease 242.03 14.26 81 17813 4491 53326681
Colitis ulcerative 191.15 14.26 107 17787 20954 53310218
Pancytopenia 144.57 14.26 165 17729 90763 53240409
Temporal lobe epilepsy 138.27 14.26 31 17863 364 53330808
Haematotoxicity 120.66 14.26 57 17837 7840 53323332
Hyperbilirubinaemia 102.48 14.26 57 17837 11012 53320160
Acute lymphocytic leukaemia recurrent 100.11 14.26 35 17859 2213 53328959
Neurotoxicity 100.02 14.26 63 17831 15286 53315886
Haemophagocytic lymphohistiocytosis 89.95 14.26 49 17845 9088 53322084
Hypertriglyceridaemia 88.70 14.26 43 17851 6261 53324911
Off label use 87.74 14.26 351 17543 471861 52859311
Pyrexia 87.50 14.26 315 17579 402878 52928294
Rhinovirus infection 78.40 14.26 34 17860 3831 53327341
Human bocavirus infection 73.07 14.26 18 17876 325 53330847
Abdominal pain 71.52 14.26 218 17676 255685 53075487
Pancreatitis 70.33 14.26 82 17812 46060 53285112
Perineal necrosis 66.33 14.26 14 17880 121 53331051
Perineal infection 64.86 14.26 14 17880 136 53331036
Neoplasm recurrence 64.61 14.26 26 17868 2428 53328744
Acute myeloid leukaemia 62.33 14.26 49 17845 16883 53314289
Bacterial infection 52.47 14.26 45 17849 17502 53313670
Secondary immunodeficiency 52.11 14.26 18 17876 1097 53330075
Enterobacter infection 51.84 14.26 21 17873 1995 53329177
Gastroenteritis norovirus 51.77 14.26 20 17874 1677 53329495
Joint swelling 50.32 14.26 9 17885 234629 53096543
Fall 50.22 14.26 29 17865 358411 52972761
Pneumatosis intestinalis 49.65 14.26 21 17873 2225 53328947
Hepatosplenic T-cell lymphoma 49.13 14.26 15 17879 616 53330556
Occupational asthma 48.39 14.26 11 17883 138 53331034
Pain 48.29 14.26 77 17817 588321 52742851
Enterovirus test positive 48.24 14.26 11 17883 140 53331032
Leukaemia recurrent 47.78 14.26 18 17876 1409 53329763
Trichodysplasia spinulosa 47.66 14.26 14 17880 503 53330669
Bone marrow failure 46.68 14.26 54 17840 30061 53301111
Antithrombin III 46.26 14.26 11 17883 170 53331002
Mucosal inflammation 44.62 14.26 63 17831 42721 53288451
Anal abscess 44.11 14.26 23 17871 3905 53327267
Neutropenia 43.81 14.26 135 17759 159050 53172122
Hypertransaminasaemia 43.63 14.26 23 17871 3993 53327179
Hepatocellular injury 43.54 14.26 52 17842 29934 53301238
Partial seizures 42.53 14.26 25 17869 5355 53325817
Rectal cancer metastatic 41.93 14.26 11 17883 258 53330914
Acute lymphocytic leukaemia 41.68 14.26 20 17874 2845 53328327
Hepatotoxicity 41.55 14.26 49 17845 27831 53303341
Anal fistula 41.51 14.26 20 17874 2871 53328301
Human rhinovirus test positive 41.16 14.26 10 17884 170 53331002
Colitis 40.13 14.26 59 17835 41493 53289679
Epstein-Barr virus infection 39.88 14.26 27 17867 7391 53323781
Intestinal stenosis 39.74 14.26 19 17875 2682 53328490
Alanine aminotransferase increased 39.60 14.26 94 17800 95001 53236171
Death 39.54 14.26 37 17857 357195 52973977
Perirectal abscess 39.20 14.26 14 17880 942 53330230
Herpes simplex 38.88 14.26 27 17867 7702 53323470
Hypoalbuminaemia 38.85 14.26 31 17863 10905 53320267
Clostridium difficile colitis 38.56 14.26 40 17854 19725 53311447
Second primary malignancy 38.44 14.26 26 17868 7106 53324066
Oesophageal dilatation 38.31 14.26 11 17883 364 53330808
Hypoglycaemia 38.28 14.26 70 17824 58943 53272229
Peripheral swelling 38.01 14.26 11 17883 206097 53125075
Human herpesvirus 6 infection 37.84 14.26 18 17876 2512 53328660
Segmental diverticular colitis 37.56 14.26 9 17885 144 53331028
Pedal pulse abnormal 36.94 14.26 9 17885 155 53331017
Abdominal discomfort 36.91 14.26 14 17880 221048 53110124
Myelopathy 36.53 14.26 18 17876 2713 53328459
Ileal stenosis 36.09 14.26 15 17879 1521 53329651
Completed suicide 35.19 14.26 3 17891 138198 53192974
Venoocclusive disease 35.01 14.26 16 17878 2039 53329133
Bile acid malabsorption 34.98 14.26 9 17885 195 53330977
Mucormycosis 34.37 14.26 17 17877 2583 53328589
Cholestasis 34.07 14.26 45 17849 28650 53302522
Device related infection 33.88 14.26 40 17854 22746 53308426
Venous thrombosis 33.71 14.26 21 17873 4993 53326179
Female sterilisation 32.97 14.26 11 17883 603 53330569
Cerebral venous sinus thrombosis 32.63 14.26 15 17879 1937 53329235
Post lumbar puncture syndrome 32.21 14.26 11 17883 648 53330524
Calcium ionised decreased 32.19 14.26 9 17885 270 53330902
Myelodysplastic syndrome 31.21 14.26 33 17861 16627 53314545
Fistula 31.20 14.26 25 17869 8845 53322327
Leukopenia 30.99 14.26 73 17821 73390 53257782
Glioma 30.64 14.26 9 17885 323 53330849
Enteritis 30.57 14.26 23 17871 7423 53323749
Pseudomonas test positive 30.28 14.26 11 17883 777 53330395
Blood culture positive 30.15 14.26 19 17875 4610 53326562
Dyspnoea 29.97 14.26 99 17795 586133 52745039
Staphylococcal sepsis 29.52 14.26 23 17871 7817 53323355
Lymphoproliferative disorder 29.42 14.26 16 17878 2956 53328216
Insomnia 29.35 14.26 13 17881 187059 53144113
Sepsis 28.73 14.26 111 17783 146318 53184854
Inflammatory bowel disease 28.43 14.26 17 17877 3756 53327416
Swelling 27.38 14.26 15 17879 191090 53140082
Vital capacity decreased 27.32 14.26 11 17883 1028 53330144
Cardiotoxicity 26.59 14.26 21 17873 7278 53323894
Feeding intolerance 26.32 14.26 9 17885 532 53330640
Porphyria non-acute 26.14 14.26 8 17886 331 53330841
Abdominal adhesions 26.13 14.26 15 17879 3075 53328097
Asthma 26.08 14.26 3 17891 108969 53222203
Acute lymphocytic leukaemia refractory 25.99 14.26 6 17888 81 53331091
Bacillus infection 25.78 14.26 9 17885 566 53330606
Neutrophil count decreased 25.46 14.26 53 17841 49045 53282127
Superior sagittal sinus thrombosis 25.37 14.26 10 17884 884 53330288
Fatigue 25.31 14.26 143 17751 730363 52600809
Arthropathy 25.25 14.26 8 17886 141445 53189727
Pancreatitis acute 25.10 14.26 37 17857 26072 53305100
Chloroma 24.66 14.26 7 17887 222 53330950
Encopresis 24.48 14.26 6 17888 106 53331066
Large intestinal stenosis 24.33 14.26 12 17882 1812 53329360
Histoplasmosis 24.24 14.26 12 17882 1826 53329346
Epstein-Barr virus associated lymphoma 23.95 14.26 8 17886 440 53330732
Blood bilirubin increased 23.95 14.26 43 17851 35687 53295485
Drug interaction 23.77 14.26 140 17754 219189 53111983
Jaundice 23.62 14.26 39 17855 30274 53300898
Lung opacity 23.51 14.26 12 17882 1949 53329223
Aborted pregnancy 23.51 14.26 5 17889 45 53331127
Synovitis 23.41 14.26 4 17890 107889 53223283
Rectal abscess 23.33 14.26 10 17884 1094 53330078
Haemolytic uraemic syndrome 23.18 14.26 13 17881 2548 53328624
Painful respiration 22.59 14.26 13 17881 2677 53328495
Lupus-like syndrome 22.34 14.26 21 17873 9191 53321981
Cytogenetic abnormality 22.33 14.26 8 17886 543 53330629
Cytomegalovirus infection 22.20 14.26 30 17864 19509 53311663
Breakthrough pain 22.18 14.26 10 17884 1235 53329937
Aplasia 21.92 14.26 15 17879 4177 53326995
Clostridium difficile infection 21.89 14.26 36 17858 27857 53303315
Leukoencephalopathy 21.82 14.26 15 17879 4209 53326963
Anaemia megaloblastic 21.52 14.26 7 17887 354 53330818
Rhinocerebral mucormycosis 21.30 14.26 6 17888 185 53330987
Influenza B virus test positive 21.21 14.26 7 17887 371 53330801
Gastrointestinal sounds abnormal 20.55 14.26 14 17880 3870 53327302
Seizure 20.55 14.26 92 17802 129417 53201755
Bacterial vulvovaginitis 20.54 14.26 8 17886 685 53330487
Coagulopathy 20.52 14.26 29 17865 19669 53311503
Small intestinal obstruction 20.52 14.26 27 17867 17120 53314052
Respiratory tract haemorrhage 19.77 14.26 7 17887 459 53330713
Overgrowth fungal 19.72 14.26 5 17889 102 53331070
Metastases to pancreas 19.71 14.26 6 17888 244 53330928
Campylobacter infection 19.69 14.26 8 17886 766 53330406
Pseudomonal sepsis 19.56 14.26 11 17883 2168 53329004
Gamma-glutamyltransferase increased 19.51 14.26 38 17856 33517 53297655
Meningitis coccidioides 19.22 14.26 4 17890 32 53331140
Stress urinary incontinence 19.15 14.26 11 17883 2256 53328916
Cerebral haemangioma 19.03 14.26 5 17889 118 53331054
Feeling abnormal 18.83 14.26 11 17883 135290 53195882
Histoplasmosis disseminated 18.81 14.26 9 17885 1272 53329900
Proctalgia 18.78 14.26 15 17879 5281 53325891
Hemiparesis 18.61 14.26 29 17865 21446 53309726
Wound 18.58 14.26 4 17890 91553 53239619
Herpes zoster meningoencephalitis 18.51 14.26 6 17888 300 53330872
Pyoderma gangrenosum 18.40 14.26 12 17882 3087 53328085
Precursor T-lymphoblastic lymphoma/leukaemia 18.34 14.26 4 17890 41 53331131
Lipase increased 18.32 14.26 19 17875 9359 53321813
Dizziness 18.19 14.26 64 17830 372195 52958977
Hyperglycaemia 18.18 14.26 41 17853 40043 53291129
Viral infection 18.09 14.26 36 17858 32259 53298913
Somnolence 17.79 14.26 18 17876 167716 53163456
Discomfort 17.76 14.26 5 17889 95467 53235705
Pericardial cyst 17.71 14.26 3 17891 6 53331166
Listeria sepsis 17.66 14.26 7 17887 628 53330544
Bone marrow disorder 17.54 14.26 10 17884 2023 53329149
Mucoepidermoid carcinoma 17.39 14.26 4 17890 53 53331119
Blood pressure abnormal 17.34 14.26 22 17872 13461 53317711
Extraskeletal ossification 17.32 14.26 4 17890 54 53331118
Musculoskeletal stiffness 17.21 14.26 10 17884 123358 53207814
Transverse sinus thrombosis 17.15 14.26 7 17887 678 53330494
Atrial fibrillation 17.13 14.26 8 17886 111644 53219528
Oesophageal mass 17.00 14.26 4 17890 59 53331113
Haematocolpos 16.93 14.26 4 17890 60 53331112
Staphylococcal bacteraemia 16.83 14.26 14 17880 5219 53325953
Anxiety 16.76 14.26 25 17869 196679 53134493
Haematochezia 16.68 14.26 41 17853 42317 53288855
Lymphoma 16.58 14.26 19 17875 10463 53320709
Functional gastrointestinal disorder 16.58 14.26 12 17882 3652 53327520
T-cell lymphoma 16.53 14.26 7 17887 744 53330428
Vulval disorder 16.50 14.26 7 17887 747 53330425
Glossitis 16.40 14.26 11 17883 2965 53328207
T-cell type acute leukaemia 16.25 14.26 4 17890 72 53331100
Acute myelomonocytic leukaemia 16.25 14.26 5 17889 211 53330961
Depersonalisation/derealisation disorder 16.21 14.26 8 17886 1209 53329963
Toe walking 16.18 14.26 3 17891 12 53331160
Self-injurious ideation 16.02 14.26 10 17884 2386 53328786
Ocular icterus 15.97 14.26 12 17882 3867 53327305
Gambling 15.91 14.26 5 17889 226 53330946
Cerebral ischaemia 15.79 14.26 15 17879 6650 53324522
Product dose omission issue 15.71 14.26 25 17869 191595 53139577
Intracardiac thrombus 15.67 14.26 10 17884 2479 53328693
Histiocytic sarcoma 15.62 14.26 4 17890 85 53331087
Quadriplegia 15.57 14.26 9 17885 1869 53329303
Hepatosplenomegaly 15.56 14.26 10 17884 2508 53328664
Vocal cord paralysis 15.52 14.26 9 17885 1880 53329292
Glioblastoma multiforme 15.49 14.26 7 17887 869 53330303
Hippocampal sclerosis 15.45 14.26 4 17890 89 53331083
Confusional state 15.31 14.26 26 17868 194195 53136977
Thrombocytopenia 15.30 14.26 89 17805 138638 53192534
Pseudopolyp 15.30 14.26 5 17889 257 53330915
Atypical haemolytic uraemic syndrome 15.17 14.26 6 17888 535 53330637
Blood immunoglobulin G decreased 15.15 14.26 9 17885 1964 53329208
Myelosuppression 15.04 14.26 20 17874 12808 53318364
Papulopustular rosacea 15.03 14.26 3 17891 19 53331153
Drug specific antibody present 15.02 14.26 11 17883 3407 53327765
Listeriosis 15.01 14.26 8 17886 1419 53329753
Potentiating drug interaction 14.99 14.26 12 17882 4241 53326931
Lennox-Gastaut syndrome 14.87 14.26 5 17889 281 53330891
Frequent bowel movements 14.69 14.26 21 17873 14391 53316781
Anogenital dysplasia 14.65 14.26 3 17891 22 53331150
Fungal infection 14.64 14.26 33 17861 32213 53298959
Malaise 14.60 14.26 66 17828 357551 52973621
Gallbladder enlargement 14.39 14.26 6 17888 613 53330559
Aspergillus infection 14.31 14.26 15 17879 7481 53323691
Choriomeningitis lymphocytic 14.31 14.26 3 17891 25 53331147

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 738.51 14.35 583 18137 118983 32375823
Hepatosplenic T-cell lymphoma 251.98 14.35 58 18662 426 32494380
Haematotoxicity 225.29 14.35 99 18621 6677 32488129
Febrile bone marrow aplasia 204.78 14.35 99 18621 8316 32486490
Venoocclusive liver disease 201.73 14.35 94 18626 7271 32487535
Crohn's disease 169.17 14.35 71 18649 4274 32490532
Hypertriglyceridaemia 141.14 14.35 78 18642 8641 32486165
Death 133.43 14.35 29 18691 382488 32112318
Colitis ulcerative 123.86 14.35 92 18628 16959 32477847
Pancytopenia 119.16 14.35 199 18521 91036 32403770
Acute lymphocytic leukaemia recurrent 118.92 14.35 50 18670 3022 32491784
Multiple-drug resistance 109.02 14.35 50 18670 3725 32491081
Bone marrow failure 106.24 14.35 108 18612 30296 32464510
Haemophagocytic lymphohistiocytosis 95.66 14.35 67 18653 11268 32483538
Colitis 92.95 14.35 106 18614 33845 32460961
Abdominal pain 84.65 14.35 232 18488 149297 32345509
Pyrexia 81.12 14.35 381 18339 319587 32175219
Hepatotoxicity 79.31 14.35 75 18645 19262 32475544
Neutropenia 73.01 14.35 213 18507 141962 32352844
Leukoencephalopathy 72.56 14.35 39 18681 4086 32490720
Pancreatitis 72.18 14.35 99 18621 38052 32456754
Osteonecrosis 71.10 14.35 66 18654 16556 32478250
Nodular regenerative hyperplasia 68.25 14.35 23 18697 748 32494058
Cytomegalovirus chorioretinitis 65.92 14.35 35 18685 3577 32491229
Mucosal inflammation 62.10 14.35 86 18634 33348 32461458
Enterovirus infection 59.01 14.35 20 18700 662 32494144
Off label use 58.94 14.35 338 18382 305982 32188824
Frequent bowel movements 57.67 14.35 46 18674 9406 32485400
Glioma 53.80 14.35 16 18704 343 32494463
Epstein-Barr virus associated lymphoproliferative disorder 51.47 14.35 24 18696 1856 32492950
Acute myeloid leukaemia 50.99 14.35 59 18661 19115 32475691
Histoplasmosis disseminated 49.17 14.35 20 18700 1110 32493696
Myocardial infarction 49.12 14.35 7 18713 125669 32369137
Myelosuppression 47.32 14.35 45 18675 11631 32483175
Epstein-Barr virus infection 46.48 14.35 36 18684 7054 32487752
Portal hypertension 43.86 14.35 28 18692 4036 32490770
Glioblastoma multiforme 43.46 14.35 17 18703 851 32493955
Cytogenetic abnormality 43.39 14.35 17 18703 855 32493951
B-cell lymphoma 42.96 14.35 29 18691 4590 32490216
Venoocclusive disease 42.87 14.35 24 18696 2722 32492084
Dyspnoea 40.75 14.35 93 18627 361952 32132854
Ileal stenosis 40.54 14.35 18 18702 1242 32493564
Second primary malignancy 38.59 14.35 32 18688 6909 32487897
Intestinal stenosis 38.30 14.35 20 18700 1975 32492831
Rhinovirus infection 38.30 14.35 24 18696 3349 32491457
Atrial fibrillation 38.23 14.35 10 18710 116694 32378112
Fall 37.12 14.35 35 18685 196166 32298640
Gastrointestinal wall thickening 36.10 14.35 16 18704 1099 32493707
Haematopoietic neoplasm 36.00 14.35 8 18712 49 32494757
Hyperbilirubinaemia 35.01 14.35 47 18673 17683 32477123
Myelodysplastic syndrome 34.90 14.35 50 18670 19988 32474818
Cardiac failure congestive 34.90 14.35 4 18716 84848 32409958
Gallbladder oedema 33.91 14.35 10 18710 208 32494598
Leukopenia 32.63 14.35 92 18628 60030 32434776
Lentigo 32.60 14.35 11 18709 359 32494447
Anal inflammation 32.57 14.35 11 18709 360 32494446
Acute monocytic leukaemia 32.40 14.35 11 18709 366 32494440
Dizziness 31.45 14.35 45 18675 209573 32285233
Diffuse large B-cell lymphoma 31.26 14.35 31 18689 8431 32486375
Intracranial pressure increased 30.91 14.35 22 18698 3791 32491015
Candida endophthalmitis 30.49 14.35 8 18712 106 32494700
Thrombocytopenia 29.92 14.35 166 18554 148133 32346673
Fistula 29.92 14.35 25 18695 5454 32489352
Cytomegalovirus infection 29.81 14.35 53 18667 25411 32469395
Drug clearance decreased 29.02 14.35 15 18705 1450 32493356
Sepsis 28.92 14.35 173 18547 158661 32336145
Hepatocellular injury 28.75 14.35 52 18668 25266 32469540
Anal fistula 28.05 14.35 22 18698 4389 32490417
Leukaemia recurrent 27.44 14.35 15 18705 1624 32493182
Stomatitis 27.38 14.35 67 18653 40162 32454644
Pancreatitis acute 27.13 14.35 53 18667 27282 32467524
Human rhinovirus test positive 26.79 14.35 8 18712 174 32494632
Alanine aminotransferase increased 26.32 14.35 102 18618 78377 32416429
Vomiting 26.29 14.35 228 18492 235329 32259477
Superior sagittal sinus thrombosis 26.13 14.35 9 18711 313 32494493
Depression 25.48 14.35 12 18708 97048 32397758
Parainfluenzae virus infection 24.96 14.35 16 18704 2321 32492485
Proctitis 24.71 14.35 16 18704 2362 32492444
Neoplasm recurrence 24.34 14.35 15 18705 2032 32492774
Small intestinal obstruction 22.66 14.35 34 18686 14162 32480644
Adrenocortical carcinoma 22.59 14.35 5 18715 30 32494776
Neutrophil count decreased 22.57 14.35 69 18651 47070 32447736
Chest pain 22.46 14.35 23 18697 124114 32370692
Renal failure 22.05 14.35 27 18693 134451 32360355
T-cell lymphoma 21.80 14.35 11 18709 1011 32493795
Bacterial infection 21.58 14.35 33 18687 13973 32480833
Steatohepatitis 21.26 14.35 8 18712 360 32494446
Asthenia 20.91 14.35 68 18652 235876 32258930
Xanthogranuloma 20.82 14.35 5 18715 45 32494761
Lymphopenia 20.80 14.35 33 18687 14423 32480383
Transaminases increased 20.68 14.35 45 18675 24983 32469823
Vascular access complication 20.64 14.35 7 18713 232 32494574
Trichodysplasia spinulosa 20.28 14.35 7 18713 245 32494561
Cardiac failure 20.24 14.35 14 18706 91659 32403147
Intestinal diaphragm disease 19.88 14.35 7 18713 260 32494546
Metapneumovirus infection 19.87 14.35 9 18711 651 32494155
Cardiac arrest 19.80 14.35 16 18704 96760 32398046
Neurotoxicity 19.78 14.35 33 18687 15037 32479769
Anal abscess 19.76 14.35 20 18700 5570 32489236
Small intestinal stenosis 19.53 14.35 8 18712 452 32494354
Dysplastic naevus syndrome 19.41 14.35 4 18716 16 32494790
Myelopathy 19.30 14.35 13 18707 2050 32492756
Proctalgia 19.04 14.35 18 18702 4616 32490190
Bifidobacterium infection 19.03 14.35 4 18716 18 32494788
Human metapneumovirus test positive 19.01 14.35 5 18715 67 32494739
Otitis media acute 18.98 14.35 8 18712 486 32494320
Coronary artery disease 18.87 14.35 3 18717 49703 32445103
Thymus enlargement 18.80 14.35 5 18715 70 32494736
Multiple lentigines syndrome 18.69 14.35 4 18716 20 32494786
Peripheral swelling 18.63 14.35 8 18712 68337 32426469
Product dose omission issue 18.55 14.35 19 18701 102556 32392250
Chronic obstructive pulmonary disease 18.38 14.35 3 18717 48750 32446056
Fungal infection 18.17 14.35 32 18688 15223 32479583
Disseminated cytomegaloviral infection 18.14 14.35 6 18714 184 32494622
Rhabdomyolysis 18.14 14.35 8 18712 67257 32427549
Completed suicide 18.06 14.35 16 18704 92501 32402305
Meningitis enterococcal 18.01 14.35 5 18715 83 32494723
Pulmonary mucormycosis 17.96 14.35 8 18712 556 32494250
Mucormycosis 17.78 14.35 19 18701 5635 32489171
Cutaneous leishmaniasis 17.49 14.35 6 18714 206 32494600
Malignant neoplasm progression 17.31 14.35 12 18708 78484 32416322
Viral myelitis 17.30 14.35 4 18716 30 32494776
Syncope 17.10 14.35 16 18704 90108 32404698
Hip deformity 17.09 14.35 5 18715 101 32494705
Gastrointestinal injury 17.06 14.35 7 18713 397 32494409
Pneumocystis jirovecii pneumonia 16.83 14.35 35 18685 18835 32475971
Secondary hypothyroidism 16.69 14.35 5 18715 110 32494696
Cytomegalovirus colitis 16.42 14.35 13 18707 2629 32492177
Colon dysplasia 16.36 14.35 5 18715 118 32494688
Rectal haemorrhage 16.28 14.35 53 18667 37370 32457436
Staphylococcal sepsis 16.19 14.35 24 18696 9889 32484917
Anorectal cellulitis 16.18 14.35 4 18716 41 32494765
Meningoradiculitis 16.18 14.35 4 18716 41 32494765
Infectious mononucleosis 16.13 14.35 7 18713 457 32494349
Herpes zoster 16.10 14.35 48 18672 32293 32462513
Escherichia infection 15.72 14.35 20 18700 7140 32487666
Abscess limb 15.51 14.35 14 18706 3384 32491422
Splenomegaly 15.50 14.35 29 18691 14448 32480358
Central nervous system leukaemia 15.46 14.35 6 18714 294 32494512
Pneumonia viral 15.24 14.35 13 18707 2917 32491889
Eye opacity 15.23 14.35 3 18717 9 32494797
Haemorrhagic diathesis 15.19 14.35 13 18707 2929 32491877
Confusional state 15.04 14.35 38 18682 143077 32351729
Autoimmune lymphoproliferative syndrome 14.85 14.35 5 18715 162 32494644
Inflammatory bowel disease 14.82 14.35 12 18708 2506 32492300
Disease progression 14.70 14.35 17 18703 86845 32407961
Haemolytic uraemic syndrome 14.67 14.35 11 18709 2053 32492753
Pancreatitis necrotising 14.56 14.35 12 18708 2568 32492238
Rectal stenosis 14.54 14.35 5 18715 173 32494633
Cytopenia 14.51 14.35 23 18697 10041 32484765
Differentiation syndrome 14.44 14.35 9 18711 1244 32493562
Gastroenteritis Escherichia coli 14.41 14.35 5 18715 178 32494628
Atypical haemolytic uraemic syndrome 14.41 14.35 5 18715 178 32494628

Pharmacologic Action:

SourceCodeDescription
ATC L01BB02 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ANTIMETABOLITES
Purine analogues
MeSH PA D000963 Antimetabolites
MeSH PA D000964 Antimetabolites, Antineoplastic
MeSH PA D000970 Antineoplastic Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D007155 Immunologic Factors
MeSH PA D007166 Immunosuppressive Agents
MeSH PA D009676 Noxae
MeSH PA D019384 Nucleic Acid Synthesis Inhibitors
CHEBI has role CHEBI:35221 antimetabolite
CHEBI has role CHEBI:35610 cytostatic
CHEBI has role CHEBI:149553 anti-coronaviral agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Acute lymphoid leukemia indication 91857003 DOID:9952
Acute promyelocytic leukemia, FAB M3 indication 110004001
Psoriasis with arthropathy off-label use 33339001
Crohn's disease off-label use 34000006
Ulcerative colitis off-label use 64766004 DOID:8577
Acute myeloid leukemia, disease off-label use 91861009
Polycythemia vera off-label use 109992005
Hyperbilirubinemia contraindication 14783006 DOID:2741
Obstruction of bile duct contraindication 30144000
Dehydration contraindication 34095006
Gastrointestinal ulcer contraindication 40845000
Leukopenia contraindication 84828003 DOID:615
Kidney disease contraindication 90708001 DOID:557
Liver function tests abnormal contraindication 166603001
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
Neutropenic disorder contraindication 303011007 DOID:1227
Bone marrow depression contraindication 307762000
Ascites contraindication 389026000
Breastfeeding (mother) contraindication 413712001
Hepatosplenic T-cell lymphoma contraindication 445406001
Chemotherapy-Induced Hyperuricemia contraindication
Thiopurine S-Methyltransferase Deficiency contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 5.99 acidic
pKa2 10.76 acidic
pKa3 3.37 Basic
pKa4 1.4 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
Amidophosphoribosyltransferase Enzyme INHIBITOR DRUGBANK CHEMBL
Multidrug resistance-associated protein 5 Transporter WOMBAT-PK
Multidrug resistance-associated protein 4 Transporter WOMBAT-PK
Prostaglandin G/H synthase 1 Enzyme IC50 4.79 DRUG MATRIX
Thiopurine S-methyltransferase Enzyme WOMBAT-PK
Purine nucleoside phosphorylase Enzyme WOMBAT-PK
Purine nucleoside phosphorylase Enzyme Kd 4.10 CHEMBL

External reference:

IDSource
4018776 VUID
N0000147079 NUI
D00161 KEGG_DRUG
4018776 VANDF
C0000618 UMLSCUI
CHEBI:50667 CHEBI
PM6 PDB_CHEM_ID
CHEMBL1425 ChEMBL_ID
CHEMBL1200751 ChEMBL_ID
DB01033 DRUGBANK_ID
D015122 MESH_DESCRIPTOR_UI
667490 PUBCHEM_CID
7226 IUPHAR_LIGAND_ID
6112-76-1 SECONDARY_CAS_RN
E7WED276I5 UNII
103 RXNORM
3886 MMSL
48948 MMSL
5052 MMSL
NOCODE MMSL
d00289 MMSL
002647 NDDF
1039008 SNOMEDCT_US
386835005 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Mercaptopurine HUMAN PRESCRIPTION DRUG LABEL 1 0054-4581 TABLET 50 mg ORAL ANDA 29 sections
Mercaptopurine HUMAN PRESCRIPTION DRUG LABEL 1 0378-3547 TABLET 50 mg ORAL ANDA 29 sections
mercaptopurine HUMAN PRESCRIPTION DRUG LABEL 1 49884-922 TABLET 50 mg ORAL ANDA 24 sections
mercaptopurine HUMAN PRESCRIPTION DRUG LABEL 1 54868-5282 TABLET 50 mg ORAL ANDA 24 sections
PURINETHOL HUMAN PRESCRIPTION DRUG LABEL 1 60763-601 TABLET 50 mg ORAL NDA 30 sections
PURIXAN HUMAN PRESCRIPTION DRUG LABEL 1 62484-0020 SUSPENSION 20 mg ORAL NDA 19 sections
Mercaptopurine HUMAN PRESCRIPTION DRUG LABEL 1 69076-913 TABLET 50 mg ORAL NDA authorized generic 31 sections