m
methotrexate
Chemical compound
Also known as amethopterin · 4-amino-10-methylfolic acid · 4-amino-N(10)-methylpteroylglutamic acid · MTX · N-(4-{[(2,4-diamino-6-pteridinyl)methyl]methylamino}benzoyl)-L-glutamic acid
- Formula
- C₂₀H₂₂N₈O₅
1
- C₂₀H₂₂N₈O₅
- Mass
- 454.171 Da
1
- 454.171 Da
Overview
Chemistry
All data
293 statements · 85% with external sources · numbers in brackets are citations
- Medical condition treated
- head and neck cancer
1
- spindle cell sarcoma
1
- breast cancer
1
- trophoblastic neoplasm
1
- esophageal cancer
1
- rheumatoid arthritis
1
- juvenile rheumatoid arthritis
1
- osteosarcoma
1
Show 31 moreShow less
- mycosis fungoides
2
Sources- 1.Stated in NDF-RTRetrieved 2016-12-13
- 2.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- lung benign neoplasm
1
- testicular cancer
1
- leukemia
2
Sources- 1.Stated in NDF-RTRetrieved 2016-12-13
- 2.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- stomach cancer
1
- lymphoma
2
Sources- 1.Stated in NDF-RTRetrieved 2016-12-13
- 2.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- acropustulosis
1
- polyarthritis
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- ankylosing spondylitis
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- precursor T-cell lymphoblastic leukemia
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- granulomatosis with polyangiitis
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- acute myeloid leukemia
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- precursor T-cell acute lymphoblastic leukemia
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- ectopic pregnancy
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- polymyositis
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- diffuse large B-cell lymphoma
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- T-cell lymphoma
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- polymyalgia rheumatica
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- ulcerative colitis
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- non-Hodgkin lymphoma
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- uveitis
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- bone sarcoma
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- acute promyelocytic leukemia
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- B-cell lymphoma
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- osteoarthritis susceptibility 1
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- arthritis
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- giant cell arteritis
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- systemic-onset juvenile idiopathic arthritis
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- central nervous system lymphoma
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- precursor B-cell acute lymphoblastic leukemia
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- bullous pemphigoid
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- head and neck cancer
- Canonical SMILES
- CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O
1
- CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O
- Isomeric SMILES
- CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O
1
- CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O
- Defined daily dose
- 2.5 milligram route of administration: oral administration
- Subject has role
- folic acid
1
- disease-modifying antirheumatic drug
1
- enzyme inhibitor
1
- Abortifacient Agents, Nonsteroidal
1
- antineoplastic antimetabolite
1
- dermatologic drug
1
- folic acid antagonists
1
- immunosuppressive drug
1
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- DNA polymerase inhibitors
1
- WHO essential medicines
- developmental toxicant(since 1989)
1
Sources- 1.Stated in California Proposition 65 list of chemicalsoehha.ca.gov/chemicals/methotrexateRetrieved 2020-03-18
- folic acid
- Part of
- cellular response to methotrexate subject has role: reactant
1
- methotrexate transmembrane transporter activity subject has role: cargo
1
- response to methotrexate subject has role: reactant
1
- cellular response to methotrexate subject has role: reactant
- Significant drug interaction
- nabumetone side effect: nephrotoxicity
- naproxen side effect: nephrotoxicity
- Diclofenac side effect: nephrotoxicity
- piroxicam side effect: nephrotoxicity
- (RS)-fenoprofen side effect: nephrotoxicity
- (RS)-ketoprofen side effect: nephrotoxicity
- (RS)-etodolac side effect: nephrotoxicity
- tenoxicam side effect: nephrotoxicity
Show 52 moreShow less
- (±)-flurbiprofen side effect: nephrotoxicity
- ibuprofen side effect: nephrotoxicity
- indomethacin side effect: nephrotoxicity
- sulindac side effect: nephrotoxicity
- foscarnet side effect: nephrotoxicity
- cyclosporine side effect: nephrotoxicity
- celecoxib side effect: nephrotoxicity
- meloxicam side effect: nephrotoxicity
- trimethoprim side effect: nephrotoxicity
- parecoxib side effect: nephrotoxicity
- aceclofenac side effect: nephrotoxicity
- trimethoprim side effect: bone marrow failure
- sulfamethoxazole side effect: bone marrow failure
- aspirin side effect: leukopenia
- aspirin side effect: thrombocytopenia
- aspirin side effect: anemia
- aspirin side effect: nephrotoxicity
- aspirin side effect: mouth ulcer
- nabumetone side effect: leukopenia
- nabumetone side effect: thrombocytopenia
- nabumetone side effect: anemia
- nabumetone side effect: mouth ulcer
- naproxen side effect: leukopenia
- naproxen side effect: thrombocytopenia
- naproxen side effect: anemia
- naproxen side effect: mouth ulcer
- Diclofenac side effect: leukopenia
- Diclofenac side effect: thrombocytopenia
- Diclofenac side effect: anemia
- Diclofenac side effect: mouth ulcer
- piroxicam side effect: leukopenia
- piroxicam side effect: thrombocytopenia
- piroxicam side effect: anemia
- piroxicam side effect: mouth ulcer
- (RS)-fenoprofen side effect: leukopenia
- (RS)-fenoprofen side effect: thrombocytopenia
- (RS)-fenoprofen side effect: anemia
- (RS)-fenoprofen side effect: mouth ulcer
- (RS)-ketoprofen side effect: leukopenia
- (RS)-ketoprofen side effect: thrombocytopenia
- (RS)-ketoprofen side effect: anemia
- (RS)-ketoprofen side effect: mouth ulcer
- (RS)-etodolac side effect: leukopenia
- (RS)-etodolac side effect: thrombocytopenia
- (RS)-etodolac side effect: anemia
- (RS)-etodolac side effect: mouth ulcer
- tenoxicam side effect: leukopenia
- tenoxicam side effect: thrombocytopenia
- tenoxicam side effect: anemia
- tenoxicam side effect: mouth ulcer
- (±)-flurbiprofen side effect: thrombocytopenia
- (±)-flurbiprofen side effect: leukopenia
- Legal status (medicine)
- boxed warning
1
Sources- 1.“FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.”nctr-crs.fda.gov/fdalabel/ui/spl-summaries/criteria/343802
- boxed warning
On other databases
63 identifiers linking methotrexate across the web's reference databases
- ATC codeL01BA01
- CA PROP 65 IDmethotrexate
- CAMEO Chemicals ID20602
- CAS Registry Number59-05-2
- ChEBI ID44185
- ChEMBL IDCHEMBL34259
- ChemSpider ID112728
- CosIng number95795
- DeCS ID28169
- DrugBank IDDB00563
- DrugCentral ID1751
- DSSTOX compound identifierDTXCID80822
- DSSTox substance IDDTXSID4020822
- EC number200-413-8
- ECHA Substance Infocard ID100.000.376
- Electronic Essential Medicines List medicine ID99
- Encyclopædia Britannica Online IDscience/methotrexate
- Freebase ID/m/01q2jc
- GND ID4038985-6
- Gran Enciclopèdia Catalana IDmetotrexat
- Gran Enciclopèdia Catalana ID (former scheme)0123343
- Guide to Pharmacology Ligand ID4815
- HSDB ID3123
- Human Metabolome Database IDHMDB0014703
- IEDB Epitope ID230085
- InChIInChI=1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/t13-/m0/s1
- InChIKeyFBOZXECLQNJBKD-ZDUSSCGKSA-N
- J9U entity ID987007529313305171
- KEGG IDD00142
- Library of Congress Authorities IDsh85084418
- MassBank accession IDMSBNK-Athens_Univ-AU273001
- MedlinePlus drug identifiera682019
- MeSH concept IDM0013595
- MeSH descriptor IDD008727
- MeSH tree codeD03.633.100.733.631.192.500
- Microsoft Academic ID (discontinued)2781059491
- NALT ID10468
- National Drug Code61703-350
- NDF-RT IDN0000147916
- NSC number740
- OpenAlex IDC2909950847
- OSHA Occupational Chemical Database ID874
- PatientsLikeMe treatment IDmethotrexate
- PDB ligand IDMTX
- PDB structure ID1DLS
- Probes And Drugs IDPD002823
- PubChem CID126941
- Quora topic IDMethotrexate
- Reaxys registry number70669
- Römpp online IDRD-13-01707
- RxNorm CUI6851
- SPLASHsplash10-0fai-6900000000-25b0e287457fb3845ef4
- Store medisinske leksikon IDmetotreksat
- SureChEMBL ID3711
- UK Parliament thesaurus ID11575
- UMLS CUIC0025677
- UniChem compound ID647984
- UNIIYL5FZ2Y5U1
- WikiProjectMed IDMethotrexate
- WikiSkripta article ID7572
- WordNet 3.1 Synset ID03761241-n
- Yale LUX IDconcept/0ec2699c-0443-4233-9d12-52a8c8cc355c
- ZVG number490067