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 943.99 52.40 222 1726 10660 2345477
Febrile bone marrow aplasia 499.19 52.40 86 1862 771 2355366
Pyrexia 305.91 52.40 139 1809 53569 2302568
Pancytopenia 303.01 52.40 92 1856 11360 2344777
Haematotoxicity 271.26 52.40 54 1894 1113 2355024
Alanine aminotransferase increased 205.04 52.40 72 1876 13960 2342177
Neutropenia 178.41 52.40 73 1875 21475 2334662
Sepsis 175.04 52.40 69 1879 18419 2337718
Hyperbilirubinaemia 172.10 52.40 39 1909 1510 2354627
Off label use 168.67 52.40 104 1844 73494 2282643
Mucosal inflammation 150.77 52.40 45 1903 5179 2350958
Leukopenia 147.52 52.40 52 1896 10144 2345993
Pancreatitis 135.39 52.40 46 1902 8033 2348104
Haemophagocytic lymphohistiocytosis 133.15 52.40 31 1917 1352 2354785
Hepatocellular injury 130.41 52.40 38 1910 4017 2352120
Bacterial infection 128.27 52.40 33 1915 2188 2353949
Acute lymphocytic leukaemia recurrent 126.57 52.40 22 1926 205 2355932
Vomiting 123.93 52.40 85 1863 71517 2284620
Rhinovirus infection 119.65 52.40 22 1926 289 2355848
Hypertriglyceridaemia 118.32 52.40 26 1922 870 2355267
Abdominal pain 108.50 52.40 60 1888 34314 2321823
Acute myeloid leukaemia 107.84 52.40 30 1918 2680 2353457
Crohn's disease 104.06 52.40 36 1912 6619 2349518
Thrombocytopenia 103.15 52.40 48 1900 19083 2337054
Seizure 100.64 52.40 51 1897 24415 2331722
Pancreatitis acute 97.41 52.40 30 1918 3823 2352314
Epstein-Barr virus infection 96.92 52.40 23 1925 1088 2355049
Blood bilirubin increased 95.65 52.40 32 1916 5313 2350824
Neoplasm recurrence 94.62 52.40 19 1929 406 2355731
Cholestasis 94.18 52.40 29 1919 3692 2352445
Bone marrow failure 93.71 52.40 32 1916 5654 2350483
Hypoglycaemia 92.21 52.40 35 1913 8372 2347765
Clostridium difficile colitis 91.88 52.40 25 1923 2054 2354083
Hypoalbuminaemia 91.73 52.40 23 1925 1371 2354766
Neurotoxicity 91.28 52.40 25 1923 2105 2354032
Human bocavirus infection 90.87 52.40 12 1936 8 2356129
Aspartate aminotransferase increased 88.25 52.40 38 1910 12574 2343563
Tachycardia 87.88 52.40 41 1907 16368 2339769
Temporal lobe epilepsy 86.08 52.40 14 1934 83 2356054
Perineal necrosis 84.79 52.40 11 1937 5 2356132
Pneumonia 83.76 52.40 58 1890 49238 2306899
Gamma-glutamyltransferase increased 82.73 52.40 29 1919 5533 2350604
Diarrhoea 80.14 52.40 70 1878 83494 2272643
Jaundice 79.18 52.40 28 1920 5480 2350657
Venoocclusive disease 78.05 52.40 15 1933 253 2355884
Neutrophil count decreased 78.03 52.40 29 1919 6538 2349599
Enterobacter infection 77.72 52.40 15 1933 259 2355878
Perineal infection 77.52 52.40 11 1937 20 2356117
Trichodysplasia spinulosa 77.30 52.40 12 1936 50 2356087
Hepatotoxicity 75.02 52.40 24 1924 3457 2352680
Hypotension 74.16 52.40 46 1902 32390 2323747
Product use in unapproved indication 72.63 52.40 32 1916 11168 2344969
Secondary immunodeficiency 72.44 52.40 12 1936 81 2356056
Nausea 71.52 52.40 75 1873 112114 2244023
Anaemia 71.20 52.40 46 1902 34746 2321391
Platelet count decreased 70.93 52.40 35 1913 15778 2340359
Antithrombin III 70.15 52.40 9 1939 3 2356134
Second primary malignancy 68.18 52.40 17 1931 989 2355148
Blood culture positive 67.94 52.40 16 1932 731 2355406
Gastroenteritis norovirus 66.32 52.40 13 1935 244 2355893
Colitis 65.46 52.40 24 1924 5202 2350935
Partial seizures 64.76 52.40 16 1932 896 2355241
Coagulopathy 62.44 52.40 20 1928 2889 2353248
Viral infection 60.51 52.40 22 1926 4654 2351483
Lymphoproliferative disorder 60.35 52.40 14 1934 598 2355539
Pneumatosis intestinalis 59.86 52.40 13 1935 410 2355727
Pneumocystis jirovecii pneumonia 58.69 52.40 18 1930 2255 2353882
Respiratory distress 58.53 52.40 22 1926 5107 2351030
Septic shock 58.47 52.40 24 1924 7030 2349107
Acute lymphocytic leukaemia 57.96 52.40 13 1935 477 2355660
Herpes simplex 57.41 52.40 15 1933 1052 2355085
Lipase increased 57.27 52.40 16 1932 1446 2354691
Venous thrombosis 56.27 52.40 14 1934 807 2355330
Device related infection 56.23 52.40 19 1929 3240 2352897
Pleural effusion 55.81 52.40 27 1921 11641 2344496
Human herpesvirus 6 infection 55.58 52.40 12 1936 368 2355769
Encephalopathy 53.63 52.40 20 1928 4541 2351596
Multiple organ dysfunction syndrome 53.31 52.40 23 1925 7618 2348519
Pseudomonas test positive 53.06 52.40 10 1938 151 2355986
Glioma 52.44 52.40 9 1939 77 2356060

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 1233.84 50.45 314 1975 10786 1733706
Haematotoxicity 456.58 50.45 90 2199 868 1743624
Febrile bone marrow aplasia 391.15 50.45 78 2211 800 1743692
Neutropenia 375.35 50.45 143 2146 18117 1726375
Pyrexia 323.15 50.45 170 2119 46230 1698262
Hepatosplenic T-cell lymphoma 255.60 50.45 41 2248 94 1744398
Hypertriglyceridaemia 244.21 50.45 56 2233 1153 1743339
Pancytopenia 239.87 50.45 91 2198 11266 1733226
Bone marrow failure 199.26 50.45 65 2224 5135 1739357
Thrombocytopenia 173.06 50.45 87 2202 21162 1723330
Leukopenia 168.18 50.45 65 2224 8415 1736077
Haemophagocytic lymphohistiocytosis 168.04 50.45 43 2246 1417 1743075
Vomiting 159.61 50.45 101 2188 38214 1706278
Off label use 153.99 50.45 99 2190 38472 1706020
Pancreatitis 152.88 50.45 58 2231 7129 1737363
Alanine aminotransferase increased 151.37 50.45 67 2222 12211 1732281
Sepsis 144.80 50.45 75 2214 19363 1725129
Osteonecrosis 141.48 50.45 47 2242 3915 1740577
Anaemia 135.98 50.45 83 2206 29374 1715118
Venoocclusive liver disease 134.89 50.45 33 2256 900 1743592
Acute myeloid leukaemia 132.67 50.45 42 2247 2999 1741493
Mucosal inflammation 123.51 50.45 43 2246 4126 1740366
Hepatocellular injury 122.03 50.45 40 2249 3191 1741301
Acute lymphocytic leukaemia recurrent 117.40 50.45 24 2265 278 1744214
Abdominal pain 115.85 50.45 67 2222 21423 1723069
Cytomegalovirus chorioretinitis 111.10 50.45 24 2265 369 1744123
Hyperbilirubinaemia 105.60 50.45 33 2256 2254 1742238
Nausea 102.95 50.45 87 2202 51109 1693383
Portal hypertension 102.89 50.45 25 2264 661 1743831
Multiple organ dysfunction syndrome 102.82 50.45 47 2242 9195 1735297
Nodular regenerative hyperplasia 99.95 50.45 19 2270 146 1744346
Pancreatitis acute 97.80 50.45 36 2253 4051 1740441
Glioma 91.10 50.45 16 2273 74 1744418
Leukoencephalopathy 84.38 50.45 22 2267 778 1743714
Diffuse large B-cell lymphoma 81.38 50.45 23 2266 1106 1743386
Myelodysplastic syndrome 78.77 50.45 29 2260 3260 1741232
Second primary malignancy 78.26 50.45 22 2267 1037 1743455
Stomatitis 77.90 50.45 33 2256 5371 1739121
Hepatotoxicity 76.84 50.45 28 2261 3056 1741436
Diarrhoea 73.90 50.45 74 2215 53778 1690714
Colitis 72.01 50.45 29 2260 4151 1740341
Drug-induced liver injury 71.86 50.45 27 2262 3210 1741282
Septic shock 71.01 50.45 35 2254 8074 1736418
Neutrophil count decreased 70.95 50.45 32 2257 6049 1738443
Seizure 70.31 50.45 48 2241 20393 1724099
Glioblastoma multiforme 69.32 50.45 15 2274 232 1744260
Upper respiratory tract infection 69.14 50.45 28 2261 4065 1740427
Weight decreased 67.95 50.45 49 2240 22704 1721788
Ascites 67.09 50.45 30 2259 5556 1738936
Platelet count decreased 66.98 50.45 43 2246 16480 1728012
B-cell lymphoma 64.72 50.45 18 2271 815 1743677
Cytogenetic abnormality 64.55 50.45 14 2275 219 1744273
Venoocclusive disease 63.62 50.45 15 2274 347 1744145
Crohn's disease 62.75 50.45 27 2262 4560 1739932
Headache 59.92 50.45 54 2235 34322 1710170
Acute monocytic leukaemia 57.52 50.45 10 2279 43 1744449
Hepatitis 54.39 50.45 25 2264 4930 1739562
Respiratory distress 53.44 50.45 25 2264 5132 1739360
Pneumonia 53.42 50.45 58 2231 46124 1698368
Lymphopenia 52.65 50.45 19 2270 2014 1742478
Histoplasmosis disseminated 52.50 50.45 12 2277 241 1744251
Cholestasis 51.52 50.45 22 2267 3643 1740849

Pharmacologic Action:

SourceCodeDescription
ATC L01BB02 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ANTIMETABOLITES
Purine analogues
CHEBI has role CHEBI:35610 antineoplastic agent
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

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
20MG/ML PURIXAN NOVA LABS LTD N205919 April 28, 2014 RX SUSPENSION ORAL April 28, 2021 TREATMENT OF PATIENTS WITH ACUTE LYMPHOBLASTIC LEUKEMIA AS PART OF A COMBINATION REGIMEN.

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Amidophosphoribosyltransferase Enzyme INHIBITOR DRUGBANK CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 4.79 DRUG MATRIX
Purine nucleoside phosphorylase Enzyme WOMBAT-PK
Multidrug resistance-associated protein 4 Transporter WOMBAT-PK
Multidrug resistance-associated protein 5 Transporter WOMBAT-PK
Thiopurine S-methyltransferase Enzyme WOMBAT-PK
Purine nucleoside phosphorylase Unclassified Kd 4.10 CHEMBL

External reference:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Mercaptopurine HUMAN PRESCRIPTION DRUG LABEL 1 0054-4581 TABLET 50 mg ORAL ANDA 13 sections
Mercaptopurine HUMAN PRESCRIPTION DRUG LABEL 1 0378-3547 TABLET 50 mg ORAL ANDA 13 sections
mercaptopurine HUMAN PRESCRIPTION DRUG LABEL 1 49884-922 TABLET 50 mg ORAL ANDA 13 sections
mercaptopurine HUMAN PRESCRIPTION DRUG LABEL 1 54868-5282 TABLET 50 mg ORAL ANDA 13 sections
PURIXAN HUMAN PRESCRIPTION DRUG LABEL 1 62484-0020 SUSPENSION 20 mg ORAL NDA 12 sections
Mercaptopurine HUMAN PRESCRIPTION DRUG LABEL 1 69076-913 TABLET 50 mg ORAL NDA authorized generic 13 sections