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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL34259
CHEMBL34259
Compound Name METHOTREXATE
ChEMBL Synonyms METHOTREXATE SODIUM | Amethopterin | ABITREXATE | MAXTREX | Trexall | OTREXUP | MEXATE | METOJECT | METHYLAMINOPTERIN | Abitrexate | XATMEP | MEXATE-AQ PRESERVED | methotrexate | OTREXUP PFS | EMTEXATE HIGH-POT | METHOTREXATE LPF | FOLEX | METHOTREXATE SODIUM PRESERVATIVE FREE | MEXATE-AQ | METHOTREXATE PRESERVATIVE FREE | RHEUMATREX | RASUVO | Folex | ZLATAL | EBETREX | FOLEX PFS | Mexate-AQ | EMTEXATE PF | CL 14377 | TREXALL
Max Phase 4 (Approved)
Trade Names MAXTREX | METOJECT | MEXATE | OTREXUP | Trexall | ABITREXATE | METHOTREXATE LPF | METHOTREXATE SODIUM | XATMEP | MEXATE-AQ PRESERVED | EMTEXATE HIGH-POT | OTREXUP PFS | methotrexate | METHOTREXATE SODIUM PRESERVATIVE FREE | Folex | RASUVO | RHEUMATREX | METHOTREXATE PRESERVATIVE FREE | MEXATE-AQ | EBETREX | ZLATAL | FOLEX PFS | EMTEXATE PF | TREXALL | Amethopterin | FOLEX
Molecular Formula C20H22N8O5

Additional synonyms for CHEMBL34259 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CN(Cc1cnc2nc(N)nc(N)c2n1)c3ccc(cc3)C(=O)N[C@@H](CCC(=O)O)C(= ...
Download SMILES
Standard InChI InChI=1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20( ...
Download InChI
Standard InChI Key FBOZXECLQNJBKD-ZDUSSCGKSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • GSK Malaria Screening
  • HeCaToS Compounds
  • Orange Book
  • PubChem BioAssays
  • Sanger Institute Genomics of Drug Sensitivity in Cancer
  • Scientific Literature
  • St Jude Leishmania Screening
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL34259

Molecule Features

CHEMBL34259 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Dihydrofolate reductase inhibitor Dihydrofolate reductase DailyMed DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
AsthmaD001249EFO:0000270asthma3ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000707squamous cell carcinoma3ClinicalTrials
EpendymomaD004806EFO:1000028ependymoma2ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0006859head and neck malignant neoplasia3ClinicalTrials
Immune System DiseasesD007154EFO:0000540immune system disease4ATC
ClinicalTrials
Primary MyelofibrosisD055728EFO:0002430primary myelofibrosis2ClinicalTrials
Anemia, Sickle CellD000755Orphanet:232Sickle cell anemia2ClinicalTrials
Arthritis, PsoriaticD015535EFO:0003778psoriatic arthritis3ClinicalTrials
Cardiovascular DiseasesD002318EFO:0000319cardiovascular disease3ClinicalTrials
Crohn DiseaseD003424EFO:0000384Crohn's disease3ClinicalTrials
Hematologic NeoplasmsD019337EFO:0001642lymphoid neoplasm2ClinicalTrials
Hydatidiform MoleD006828EFO:1000298Hydatidiform Mole3ClinicalTrials
InflammationD007249MP:0001845inflammation1ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia3ClinicalTrials
LymphomaD008223EFO:0000574lymphoma3ClinicalTrials
Multiple SclerosisD009103EFO:0003885multiple sclerosis0ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
Retinal DiseasesD012164EFO:0003839retinopathy2ClinicalTrials
Burkitt LymphomaD002051EFO:0000309Burkitts lymphoma2ClinicalTrials
LeukemiaD007938EFO:0000565leukemia3ClinicalTrials
Leukemia, Biphenotypic, AcuteD015456EFO:0000094B-cell acute lymphoblastic leukemia2ClinicalTrials
Leukemia, Biphenotypic, AcuteD015456EFO:0000209T-cell acute lymphoblastic leukemia2ClinicalTrials
Leukemia, Myelomonocytic, ChronicD015477EFO:1001779chronic myelomonocytic leukemia3ClinicalTrials
Lupus Erythematosus, SystemicD008180EFO:0002690systemic lupus erythematosus3ClinicalTrials
Lymphoma, AIDS-RelatedD016483EFO:1001365Lymphoma, AIDS-Related2ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma3ClinicalTrials
MesotheliomaD008654EFO:0000588mesothelioma2ClinicalTrials
PolymyositisD017285EFO:0003063polymyositis3ClinicalTrials
Alopecia AreataD000506EFO:0004192alopecia areata3ClinicalTrials
Anemia, AplasticD000741HP:0001915aplastic anemia2ClinicalTrials
Colitis, UlcerativeD003093EFO:0000729ulcerative colitis2ClinicalTrials
Coronary Artery DiseaseD003324EFO:0000378coronary artery disease2ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia2ClinicalTrials
Liver Cirrhosis, BiliaryD008105EFO:1001486primary biliary cirrhosis3ClinicalTrials
Lymphoma, Mantle-CellD020522EFO:1001469Mantle cell lymphoma2ClinicalTrials
MalariaD008288EFO:0001068malaria1ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma2ClinicalTrials
Myasthenia GravisD009157EFO:0004991Myasthenia gravis2ClinicalTrials
Neurofibromatosis 1D009456Orphanet:636Neurofibromatosis type 12ClinicalTrials
OsteosarcomaD012516EFO:0000637osteosarcoma3ClinicalTrials
Uveitis, PosteriorD015866EFO:1001119posterior uveitis1ClinicalTrials
Breast NeoplasmsD001943EFO:0003869breast neoplasm3ClinicalTrials
Choroid Plexus NeoplasmsD016545EFO:0007206choroid plexus cancer3ClinicalTrials
Constriction, PathologicD003251EFO:0006818stricture2ClinicalTrials
Gestational Trophoblastic DiseaseD031901Orphanet:59305Gestational trophoblastic neoplasm3ClinicalTrials
Graft vs Host DiseaseD006086EFO:0004599acute graft vs. host disease3ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma3ClinicalTrials
Leukemia, LymphoidD007945EFO:0004289lymphoid leukemia2ClinicalTrials
Lymphoma, Large-Cell, AnaplasticD017728EFO:0003032anaplastic large cell lymphoma3ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome3ClinicalTrials
Neuroectodermal Tumors, PrimitiveD018242EFO:0005235primitive neuroectodermal tumor3ClinicalTrials
OsteoarthritisD010003EFO:0002506osteoarthritis3ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia3ClinicalTrials
Scleroderma, SystemicD012595EFO:0000717systemic scleroderma1ClinicalTrials
UveitisD014605EFO:1001231uveitis3ClinicalTrials
Arthritis, JuvenileD001171EFO:0002609chronic childhood arthritis3ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000181head and neck squamous cell carcinoma3ClinicalTrials
Colorectal NeoplasmsD015179EFO:0005842colorectal cancer2ClinicalTrials
Dermatitis, AtopicD003876EFO:0000274atopic eczema3ClinicalTrials
DermatomyositisD003882EFO:0000398dermatomyositis3ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer3ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection1ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0004284upper aerodigestive tract neoplasm3ClinicalTrials
Hearing Loss, SensorineuralD006319EFO:1001176sensorineural hearing loss3ClinicalTrials
Leukemia, Promyelocytic, AcuteD015473EFO:0000224acute promyelocytic leukemia3ClinicalTrials
Lymphohistiocytosis, HemophagocyticD051359Orphanet:158038Primary hemophagocytic lymphohistiocytosis2ClinicalTrials
Lymphoma, Large B-Cell, DiffuseD016403EFO:0000403diffuse large B-cell lymphoma3ClinicalTrials
MedulloblastomaD008527EFO:0002939medulloblastoma3ClinicalTrials
MelanomaD008545EFO:0000389cutaneous melanoma1ClinicalTrials
Myocardial InfarctionD009203EFO:0000612myocardial infarction2ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ClinicalTrials
Pemphigoid, BullousD010391EFO:0007187bullous pemphigoid3ClinicalTrials
PregnancyD011247EFO:0002950pregnancy3ClinicalTrials
SarcomaD012509EFO:0000691sarcoma3ClinicalTrials
Spondylitis, AnkylosingD013167EFO:0003898ankylosing spondylitis3ClinicalTrials
Brain NeoplasmsD001932EFO:0003833brain neoplasm1ClinicalTrials
Carcinoma, Merkel CellD015266EFO:1001471Merkel cell skin cancer2ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma2ClinicalTrials
DermatomyositisD003882EFO:0000557juvenile dermatomyositis3ClinicalTrials
Fanconi AnemiaD005199Orphanet:84Fanconi anemia1ClinicalTrials
Leukemia, Myelomonocytic, JuvenileD054429EFO:1000309Juvenile Myelomonocytic Leukemia1ClinicalTrials
Lymphoma, FollicularD008224EFO:0000096neoplasm of mature B-cells3ClinicalTrials
Lymphoma, T-Cell, PeripheralD016411EFO:0000211unspecified peripheral T-cell lymphoma2ClinicalTrials
MesotheliomaD008654EFO:0000770malignant pleural mesothelioma2ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma2ClinicalTrials
Precursor T-Cell Lymphoblastic Leukemia-LymphomaD054218EFO:1001830precursor T-cell lymphoblastic leukemia-lymphoma1ClinicalTrials
Urethral NeoplasmsD014523EFO:0003846urethral neoplasm3ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001061cervical carcinoma3ClinicalTrials
Arthritis, RheumatoidD001172EFO:0000685rheumatoid arthritis3ClinicalTrials
Carcinoma, Renal CellD002292EFO:0002890renal carcinoma2ClinicalTrials
Giant Cell ArteritisD013700EFO:1001209temporal arteritis3ClinicalTrials
Granulomatosis with PolyangiitisD014890EFO:0005297Wegener's granulomatosis3ClinicalTrials
Histiocytosis, Langerhans-CellD006646EFO:1000318Langerhans Cell Histiocytosis2ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL PositiveD015464EFO:0000339chronic myelogenous leukemia3ClinicalTrials
Leukemia, Plasma CellD007952EFO:0006475plasma cell leukemia1ClinicalTrials
Mycosis FungoidesD009182EFO:1001051mycosis fungoides3ClinicalTrials
Myeloproliferative DisordersD009196EFO:0004251myeloproliferative disorder3ClinicalTrials
OsteopetrosisD010022Orphanet:2781Osteopetrosis2ClinicalTrials
PsoriasisD011565EFO:0000676psoriasis3ClinicalTrials
SchizophreniaD012559EFO:0000692schizophrenia2ClinicalTrials
Small Cell Lung CarcinomaD055752EFO:0000702small cell lung carcinoma3ClinicalTrials
Urinary Bladder NeoplasmsD001749EFO:0000292bladder carcinoma3ClinicalTrials
UrticariaD014581EFO:0005531urticaria3ClinicalTrials

Clinical Data

ClinicalTrials.gov METHOTREXATE
The Cochrane Collaboration METHOTREXATE

Metabolites for CHEMBL34259

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL34259. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL202 Dihydrofolate reductase Homo sapiens 1.000
CHEMBL1952 Thymidylate synthase Homo sapiens 1.000
CHEMBL5457 Dihydrofolate reductase Mycobacterium avium 1.000
CHEMBL5328 Thymidylate synthase Lactobacillus casei 1.000
CHEMBL3972 GAR transformylase Homo sapiens 1.000
CHEMBL3160 Thymidylate synthase Mus musculus 1.000
CHEMBL2363 Dihydrofolate reductase Rattus norvegicus 1.000
CHEMBL2425 Dihydrofolate reductase Toxoplasma gondii 1.000
CHEMBL2902 Dihydrofolate reductase Lactobacillus casei 1.000
CHEMBL1926 Dihydrofolate reductase Pneumocystis carinii 1.000
CHEMBL4564 Dihydrofolate reductase Mus musculus 1.000
CHEMBL5441 Dihydrofolate reductase Escherichia coli 1.000
CHEMBL1075051 Dihydrofolate reductase Bos taurus 1.000
CHEMBL6137 Thymidylate synthase Escherichia coli 1.000
CHEMBL325 Histone deacetylase 1 Homo sapiens 0.998
CHEMBL1892 Glutamate carboxypeptidase II Homo sapiens 0.997
CHEMBL1865 Histone deacetylase 6 Homo sapiens 0.298



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL202 Dihydrofolate reductase Homo sapiens 1.000
CHEMBL1952 Thymidylate synthase Homo sapiens 1.000
CHEMBL5457 Dihydrofolate reductase Mycobacterium avium 1.000
CHEMBL6194 Pteridine reductase 1 Leishmania major 1.000
CHEMBL5328 Thymidylate synthase Lactobacillus casei 1.000
CHEMBL2363 Dihydrofolate reductase Rattus norvegicus 1.000
CHEMBL2425 Dihydrofolate reductase Toxoplasma gondii 1.000
CHEMBL2902 Dihydrofolate reductase Lactobacillus casei 1.000
CHEMBL1926 Dihydrofolate reductase Pneumocystis carinii 1.000
CHEMBL4564 Dihydrofolate reductase Mus musculus 1.000
CHEMBL5441 Dihydrofolate reductase Escherichia coli 1.000
CHEMBL3160 Thymidylate synthase Mus musculus 1.000
CHEMBL3972 GAR transformylase Homo sapiens 1.000
CHEMBL6137 Thymidylate synthase Escherichia coli 1.000
CHEMBL325 Histone deacetylase 1 Homo sapiens 0.998
CHEMBL1892 Glutamate carboxypeptidase II Homo sapiens 0.946
CHEMBL1865 Histone deacetylase 6 Homo sapiens 0.737

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
454.5 454.1713 0.27 9 210.54 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
10 5 0 13 7 2


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
3.47 5.55 -.45 -5.1 3 33 0.29

Structural Alerts

There are 3 structural alerts for CHEMBL34259. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L04 - IMMUNOSUPPRESSANTS
L04A - IMMUNOSUPPRESSANTS
L04AX - Other immunosuppressants
L04AX03 - methotrexate

L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01B - ANTIMETABOLITES
L01BA - Folic acid analogues
L01BA01 - methotrexate

ChemSpider ChemSpider:FBOZXECLQNJBKD-ZDUSSCGKSA-N
DailyMed methotrexate methotrexate sodium
PubChem SID: 11113978 SID: 124886991 SID: 144204495 SID: 144210589 SID: 170464688 SID: 26752120 SID: 26752121 SID: 26752122 SID: 50104777 SID: 50104778 SID: 56463665 SID: 67627 SID: 90340825
Wikipedia Methotrexate

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL34259



ACToR 51865-79-3
BindingDB 66082 18050
Brenda 39751 241 138514 91627 49198 132028 3613 9550
ChEBI 44185
ChemicalBook CB2739302
DrugBank DB00563
DrugCentral 1751
eMolecules 476359
EPA CompTox Dashboard DTXSID4020822
FDA SRS YL5FZ2Y5U1
Guide to Pharmacology 4815 4674
Human Metabolome Database HMDB0014703
IBM Patent System 5C28DC0562844D29D1A597AD81043B28
KEGG Ligand C01937
LINCS LSM-5690
Mcule MCULE-6523054194
MolPort MolPort-003-665-521
Nikkaji J2.334E
PDBe MTX
PharmGKB PA450428
PubChem 126941
PubChem: Drugs of the Future 22395177
PubChem: Thomson Pharma 14808762 14760074
Selleck Abitrexate
SureChEMBL SCHEMBL3711
ZINC ZINC000001529323

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/FBOZXECLQNJBKD-ZDUSSCGKSA-N spacer
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