KEGG   DRUG: MethotrexateHelp
Entry
D00142                      Drug                                   

Name
Methotrexate (JP17/USP/INN);
Otrexup (TN)
Product
  Generic
Formula
C20H22N8O5
Exact mass
454.1713
Mol weight
454.4393
Structure
Mol fileKCF fileDB searchJmolKegDraw
Simcomp SIMCOMP
Class
Antineoplastic
 DG01930  Dihydrofolate reductase inhibitor, antineoplastic
 DG01978  Folic acid analogue
  DG01930  Dihydrofolate reductase inhibitor, antineoplastic
Anti-inflammatory
 DG01985  Disease modifying anti-rheumatic drugs (DMARDs)
Transporter substrate
 DG01913  BCRP substrate
Unclassified
 DG02018  Antimetabolite
  DG01978  Folic acid analogue
   DG01930  Dihydrofolate reductase inhibitor, antineoplastic
Remark
Same as: 
Therapeutic category: 
ATC code: 
Chemical group: 
Activity
Antineoplastic, Antimetabolite
Target
DHFR [HSA:1719 200895] [KO:K00287]
  Pathway
One carbon pool by folate
Folate biosynthesis
Metabolism
Transporter: SLC22A6 [HSA:9356], SLC22A8 [HSA:9376], SLCO1A2 [HSA:6579], ABCG2 [HSA:9429], ABCC2 [HSA:1244], ABCC3 [HSA:8714], ABCC4 [HSA:10257]
Interaction
Drug interaction
Structure map
Antineoplastics - antimetabolic agents
Immunosuppressive agents
Antirheumatics - DMARDs and biological agents
Other map
Antifolate resistance
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 (JP17/USP/INN)
  L04 IMMUNOSUPPRESSANTS
   L04A IMMUNOSUPPRESSANTS
    L04AX Other immunosuppressants
     L04AX03 Methotrexate
      D00142  Methotrexate (JP17/USP/INN)
USP drug classification [BR:br08302]
 Immunological Agents
  Immune Suppressants
   Methotrexate
    D00142  Methotrexate (JP17/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 (JP17/USP/INN)
 4  Agents affecting cellular function
  42  Antineoplastics
   422  Antimetabolites
    4222  Methotrexates
     D00142  Methotrexate (JP17/USP/INN)
Target-based classification of drugs [BR:br08310]
 Enzymes
  Oxidoreductases
   dihydrofolate reductase
    Methotrexate
     D00142  Methotrexate (JP17/USP/INN)
Cytochrome P450 interactions [BR:br08309]
 Transporter substrates
  ABCC2
   Methotrexate
    D00142  Methotrexate (JP17/USP/INN)
  ABCC3
   Methotrexate
    D00142  Methotrexate (JP17/USP/INN)
  ABCC4
   Methotrexate
    D00142  Methotrexate (JP17/USP/INN)
  ABCG2
   Methotrexate
    D00142  Methotrexate (JP17/USP/INN)
   Methotrexate
    D00142  Methotrexate (JP17/USP/INN)
  OAT1
   Methotrexate
    D00142  Methotrexate (JP17/USP/INN)
  OAT3
   Methotrexate
    D00142  Methotrexate (JP17/USP/INN)
  SLCO1A2
   Methotrexate
    D00142  Methotrexate (JP17/USP/INN)
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D00142  Methotrexate
  D00142  Methotrexate capsules
Antineoplastics [br08340.html]
 D00142
Antirheumatic and antigout drugs [br08366.html]
 Antirheumatic drugs
  D00142
New drug approvals in Europe [br08329.html]
 European public assessment reports (EPAR) authorised medicine
  D00142
BRITE hierarchy
Other DBs
CAS: 
59-05-2
PubChem: 
ChEBI: 
ChEMBL: 
DrugBank: 
PDB-CCD: 
LigandBox: 
NIKKAJI: 
KCF data Show

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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