General
Preferred name
METHOTREXATE
Synonyms
METHOTREXATE HYDRATE ()
CL14377 ()
WR19039 ()
Amethopterin ()
NCI-C04671 ()
Rheumatrex ()
Trexall ()
MTX ()
Methotrexate (Abitrexate) ()
Abitrexate ()
Mexate ()
Folex ()
HDMTX ()
Methylaminopterin ()
Metatrexan ()
METHOTREXATE SODIUM ()
CH4474 ()
Methotrexate (disodium) ()
L-Glutamic acid, N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]- ()
Amethopterin (disodium) ()
CL14377 (disodium) ()
WR19039 (disodium) ()
Methotrexate (CL-14377) ()
Methotrexate disodium ()
NCI-C04671, Amethopterin, CL14377, WR19039, abitrexate ()
Metoject ()
CL 14377 ()
Otrexup ()
R-9985 ()
Otrexup pfs ()
ADX-2191 ()
Zlatal ()
R-methotrexate ()
TCMDC-123832 ()
Methotrexate, d- ()
Mexate-Aq ()
TCMDC-125858 ()
(r)-methotrexate ()
Emtexate High-Pot ()
Rasuvo ()
D-methotrexate ()
NSC-740 ()
Ebetrex ()
Emtexate PF ()
Methotrexate, (r)- ()
EMT-25299 ()
Maxtrex ()
D-amethopterin ()
TCMDC-125488 ()
CL-14377 ()
Methotrexatum ()
Reditrex ()
Methotrexate ()
Disodium methotrexate ()
Folex Pfs ()
Methotrexate Lpf ()
Methotrexate (as disodium) ()
Methotrexate sodium preservative free ()
Methotrexate, sodium salt ()
Mexate-Aq Preserved ()
Methotrexate disodium salt ()
ADX-2191 SODIUM ()
Xatmep ()
Methotrexate sodium salt ()
Methotrexate preservative free ()
Methotrexate (hydrate) ()
Methotrexate-d3 ()
P&D ID
PD002823
CAS
6745-93-3
7532-09-4
7413-34-5
51865-79-3
432545-63-6
102613-64-9
59-05-2
133073-73-1
Tags
drug candidate
natural product
drug
available
Approved by
PMDA
EMA
FDA
First approval
1953
Drug Status
approved
Drug indication
Proliferative vitreoretinopathy
Discovery agent
Antineoplastic
Rheumatoid arthritis
leukaemia
Prostate cancer
Solid tumour/cancer
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION Methotrexate is an antimetabolite and antifolate drug, and a disease-modifying anti-rheumatic drug (DMARD). It is on the World Health Organisations List of Essential Medicines (link to 2015 list). A 2017 a paper has reported a combination of methotrexate with leflunomide relieves the immune defects and ameliorates symptoms of rheumatoid arthritis .
DESCRIPTION Methotrexate is a folate (folic acid) analogue that is classified as an antimetabolite and antifolate drug, and a disease-modifying anti-rheumatic drug (DMARD). It is used clinically for its antiproliferative and anti-inflammatory effects. The primary action of methotrexate is inhibition of the enzyme dihydrofolate reductase (DHFR). DHFR is essential for the production of precursors that are required for de novo purine synthesis. (GtoPdb)
DESCRIPTION inhibitor of dihydrofolate reductase (Informer Set)
DESCRIPTION Disrupts protein translocation to Golgi (Tocris Bioactive Compound Library)
DESCRIPTION Folic acid antagonist (LOPAC library)
DESCRIPTION Cytotoxic agent (Tocriscreen Total)
Cell lines
593
Organisms
12
Compound Sets
38
AdooQ Bioactive Compound Library
A10021
Axon Medchem Screening Library
3319
Cayman Chemical Bioactives
13960
22378
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
CHEMBL34259
CHEMBL3244648
ChEMBL Drugs
CHEMBL34259
CHEMBL3244648
Concise Guide to Pharmacology 2017/18
4674
4815
Concise Guide to Pharmacology 2019/20
4674
4815
Concise Guide to Pharmacology 2021/22
4674
4815
Concise Guide to Pharmacology 2023/24
4674
4815
Drug Repurposing Hub
DrugBank
DB00563
DrugBank Approved Drugs
DB00563
DrugCentral
1751
DrugCentral Approved Drugs
1751
DrugMAP
DM2TEOL
DMP9UHT
DM5XH2C
DrugMAP Approved Drugs
DM2TEOL
DM5XH2C
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
EOS101066
Guide to Pharmacology
4674
4815
Informer Set
30371
LINCS compound set
10264-101
10264-999
LOPAC library
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL34259
MedChem Express Bioactive Compound Library
HY-14519
HY-14519A
NCATS Inxight Approved Drugs
YL5FZ2Y5U1
NIH Approved Oncology Drugs
67627
NIH Clinical Collections (NCC)
NIH Mechanistic Set
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
ReFrame library
Selleckchem Bioactive Compound Library
Abitrexate
methotrexate-disodium
TargetMol Bioactive Compound Library
T1485
Tocris Bioactive Compound Library
1230
Tocriscreen Total
Welcome Trust Cancer Drugs
1008
ZINC Tool Compounds
ZINC000001529323
External IDs
110
Properties
(calculated by RDKit )
Molecular Weight
454.17
Hydrogen Bond Acceptors
10
Hydrogen Bond Donors
5
Rotatable Bonds
9
Ring Count
3
Aromatic Ring Count
3
cLogP
0.27
TPSA
210.54
Fraction CSP3
0.25
Chiral centers
1.0
Largest ring
6.0
QED
0.29
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
DHFR
Dihydrofolate reductase (DHFR)
Dihydrofolate reductase
hDHFR
DHFR reductase inhibitor
ADC Cytotoxin
Antifolate
Bacterial
DNA/RNA Synthesis
ADC Cytotoxin,DHFR
Dehydrogenase,DHFR
Compound status
FDA
Pathway
DNA replication
Metabolism
Antibody-drug Conjugate/ADC Related
Anti-infection
Apoptosis
Cell Cycle/DNA Damage
MOA
dihydrofolate reductase inhibitor
Folate Antagonists
Dihydrofolate Reductase (DHFR) Inhibitors
Primary Target
Cell Cycle Inhibitors
Member status
member
Indication
gestational choriocarcinoma, hydatidiform mole, acute lymphoblastic leukemia (ALL), psoriasis, rheumatoid arthritis
Disease Area
oncology, hematologic malignancy, dermatology, rheumatology
Therapeutic Class
Anticancer Agents
Source data