KEGG   DRUG: Methotrexate
Entry
D00142                      Drug                                   

Name
Methotrexate (JP18/USP/INN);
Otrexup (TN);
Xatmep (TN)
Product
  Generic
Formula
C20H22N8O5
Exact mass
454.1713
Mol weight
454.4393
Structure
Simcomp
Class
Antineoplastic
 DG02018  Antimetabolite
  DG01978  Folic acid analog
   DG01930  Dihydrofolate reductase inhibitor
Anti-inflammatory
 DG01985  Disease modifying anti-rheumatic drugs (DMARDs)
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
  Antineoplastics, Other
   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 drugs (DMARDs)
   DG00681  Methotrexate
    D00142  Methotrexate
Drug classes [BR:br08332]
 Antineoplastic
  DG02018  Antimetabolite
   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 drugs (DMARDs)
   DG00681  Methotrexate
Other DBs
CAS: 59-05-2
PubChem: 7847210
ChEBI: 44185
ChEMBL: CHEMBL34259
DrugBank: DB00563
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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