KEGG   DRUG: Methotrexate
Entry
D00142                      Drug                                   
Name
Methotrexate (JP18/USP/INN);
Otrexup (TN);
Xatmep (TN)
Product
JYLAMVO (SHORLA ONCOLOGY), OTREXUP (Antares Pharma), OTREXUP (Otter Pharmaceuticals), XATMEP (Azurity Pharmaceuticals)
  Generic
METHOTREXATE (Accord Healthcare), METHOTREXATE (Hikma Pharmaceuticals USA), METHOTREXATE (Hikma Pharmaceuticals USA), METHOTREXATE (Hikma Pharmaceuticals USA)
Formula
C20H22N8O5
Exact mass
454.1713
Mol weight
454.44
Structure
Simcomp
Class
Antineoplastic
 DG02018  Antimetabolite
  DG01978  Folic acid analog
   DG01930  Dihydrofolate reductase inhibitor
Anti-inflammatory
 DG01985  Disease modifying anti-rheumatic drug (DMARD)
Remark
Same as: C01937
Therapeutic category: 3999 4222
ATC code: L01BA01 L04AX03
Chemical structure group: DG00681
Product (DG00681): D00142<JP/US> D02115<US>
Efficacy
Antineoplastic, Antimetabolite
  Disease
Rheumatoid arthritis [DS:H00630]
Juvenile idiopathic arthritis [DS:H01672]
Psoriasis [DS:H01656]
Lymphoblastic leukemia [DS:H00001 H00002]
Target
DHFR [HSA:1719 200895] [KO:K00287]
  Pathway
hsa00670  One carbon pool by folate
hsa00790  Folate biosynthesis
Interaction
Structure map
map07041  Antineoplastics - antimetabolic agents
map07046  Immunosuppressive agents
map07050  Antirheumatics - DMARDs and biological agents
Other map
map01523  Antifolate resistance
map04976  Bile secretion
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 L ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
  L01 ANTINEOPLASTIC AGENTS
   L01B ANTIMETABOLITES
    L01BA Folic acid analogues
     L01BA01 Methotrexate
      D00142  Methotrexate (JP18/USP/INN) <JP/US>
  L04 IMMUNOSUPPRESSANTS
   L04A IMMUNOSUPPRESSANTS
    L04AX Other immunosuppressants
     L04AX03 Methotrexate
      D00142  Methotrexate (JP18/USP/INN) <JP/US>
USP drug classification [BR:br08302]
 Antineoplastics
  Antimetabolites
   Methotrexate
    D00142  Methotrexate (JP18/USP/INN)
 Immunological Agents
  Immunosuppressants
   Antimetabolites, Antiproliferative
    Methotrexate
     D00142  Methotrexate (JP18/USP/INN)
Therapeutic category of drugs in Japan [BR:br08301]
 3  Agents affecting metabolism
  39  Other agents affecting metabolism
   399  Miscellaneous
    3999  Others
     D00142  Methotrexate (JP18/USP/INN)
 4  Agents affecting cellular function
  42  Antineoplastics
   422  Antimetabolites
    4222  Methotrexates
     D00142  Methotrexate (JP18/USP/INN)
Drug groups [BR:br08330]
 Antineoplastic
  DG02018  Antimetabolite
   DG01978  Folic acid analog
    DG01930  Dihydrofolate reductase inhibitor
     DG00681  Methotrexate
      D00142  Methotrexate
 Anti-inflammatory
  DG01985  Disease modifying anti-rheumatic drug (DMARD)
   DG00681  Methotrexate
    D00142  Methotrexate
Drug classes [BR:br08332]
 Antineoplastic
  DG02018  Antimetabolite
   D00142  Methotrexate
 Antirheumatic agent
  DG01985  Disease modifying anti-rheumatic drug (DMARD)
   D00142  Methotrexate
Target-based classification of drugs [BR:br08310]
 Enzymes
  Oxidoreductases (EC1)
   Dihydrofolate reductase
    DHFR
     D00142  Methotrexate (JP18/USP/INN) <JP/US>
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D00142  Methotrexate
  D00142  Methotrexate tablets
  D00142  Methotrexate capsules
  D00142  Methotrexate for injection
New drug approvals in Europe [br08329.html]
 European public assessment reports (EPAR) authorised medicine
  D00142
Drug groups [BR:br08330]
 Antineoplastic
  DG02018  Antimetabolite
   DG01978  Folic acid analog
    DG01930  Dihydrofolate reductase inhibitor
     DG00681  Methotrexate
 Anti-inflammatory
  DG01985  Disease modifying anti-rheumatic drug (DMARD)
   DG00681  Methotrexate
Other DBs
CAS: 59-05-2
PubChem: 7847210
ChEBI: 44185
PDB-CCD: MT1[PDBj] MTX[PDBj]
LigandBox: D00142
NIKKAJI: J2.334E
LinkDB
KCF data

ATOM        33
            1   C8y C     8.3300  -28.0700
            2   N5x N     8.3300  -29.4700
            3   C8y C     9.5424  -30.1700
            4   C8y C    10.7549  -29.4700
            5   C8y C    10.7549  -28.0700
            6   N5x N     9.5424  -27.3700
            7   N5x N    11.9673  -30.1700
            8   C8y C    13.1797  -29.4700
            9   C8x C    13.1797  -28.0700
            10  N5x N    11.9673  -27.3700
            11  N1a N     7.1176  -27.3700
            12  N1a N     9.5424  -31.5698
            13  C1b C    14.3773  -30.1615
            14  N1c N    15.5656  -29.4755
            15  C8y C    16.7564  -30.1631
            16  C1a C    15.5657  -28.0702
            17  C8x C    16.7564  -31.5698
            18  C8x C    17.9688  -32.2698
            19  C8y C    19.1812  -31.5698
            20  C8x C    19.1812  -30.1632
            21  C8x C    17.9688  -29.4631
            22  C5a C    20.3928  -32.2693
            23  N1b N    21.5877  -31.5793
            24  O5a O    20.3929  -33.6698
            25  C1c C    22.7754  -32.2649
            26  C1b C    23.9665  -31.5770
            27  C1b C    25.1560  -32.2638
            28  C6a C    26.3461  -31.5765
            29  O6a O    27.5362  -32.2635
            30  C6a C    22.7755  -33.6698
            31  O6a O    23.9689  -34.3588
            32  O6a O    21.5440  -34.3811
            33  O6a O    26.3462  -30.1702
BOND        35
            1     1   2 2
            2     2   3 1
            3     3   4 2
            4     4   5 1
            5     5   6 2
            6     1   6 1
            7     4   7 1
            8     7   8 2
            9     8   9 1
            10    9  10 2
            11    5  10 1
            12    1  11 1
            13    3  12 1
            14    8  13 1
            15   13  14 1
            16   14  15 1
            17   14  16 1
            18   15  17 2
            19   17  18 1
            20   18  19 2
            21   19  20 1
            22   20  21 2
            23   15  21 1
            24   19  22 1
            25   22  23 1
            26   22  24 2
            27   23  25 1
            28   25  26 1
            29   26  27 1
            30   27  28 1
            31   28  29 1
            32   25  30 1 #Up
            33   30  31 1
            34   30  32 2
            35   28  33 2

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