Methotrexate
Highest phase reached
Approved
Drug type
Small molecule
First approval year
1953
- First approval year
- 1953
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Methotrexate
- Molecular weight
- 454.45
- Structure (SMILES)
- CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1
- ebetrex
- Ebetrex
- emtexate high pot
- Emtexate high-pot
- emtexate pf
- Emtexate pf
- jylamvo
- Jylamvo
- maxtrex
- Maxtrex
- metoject
- Metoject
- nordimet
- Nordimet
- otrexup
- Otrexup
- otrexup pfs
- Otrexup pfs
- rasuvo
- Rasuvo
- reditrex
- Reditrex
- zlatal
- Zlatal
- (r)-methotrexate
- 3g mtx
- 3g MTX
- 5g MTX
- adx 2191
- ADX-2191
- amethopterin
- Amethopterin
- cl 14377
- CL 14377
- CL-14377
- Continue IS (MTX)
- d amethopterin
- d methotrexate
- D-amethopterin
- D-methotrexate
- emt 25299
- EMT-25299
- HD- Methotrexate (MTX)
- jylamvo
- Jylamvo
- Low-dose methotrexate (MTX)
- methotrexate
- Methotrexate
- METHOTREXATE [EP MONOGRAPH]
And 52 more, listed on the interactive page.
- CAS registry numbers
- 59-05-2
- ChEMBL ID
- CHEMBL34259
- InChIKey
- FBOZXECLQNJBKD-ZDUSSCGKSA-N
- PubChem compound IDs
- 126941
- RxNorm IDs (RxCUI)
- 6851
- FDA ingredient codes (UNII)
- YL5FZ2Y5U1
- L01BA01
- L04AX03
Sources for recorded values
- Applicant
- COSETTE
- Approval date
- 11 Oct 2013
- Application number
- NDA204824
- Status
- Authorised
- Status date
- 18 Aug 2016
- Authorisation date
- 18 Aug 2016
- Approved indications
- Nordimet is indicated for the treatment of: active rheumatoid arthritis in adult patients, polyarthritic forms of severe, active juvenile idiopathic arthritis (JIA), when the response to nonsteroidal anti-inflammatory drugs (NSAIDs) has been inadequate, moderate to severe plaque psoriasis in adults who are candidates for systemic therapy, and severe psoriatic arthritis in adult patients, induction of remission in moderate steroid-dependent Crohn's disease in adult patients, in combination with corticosteroids and for maintenance of remission, as monotherapy, in patients who have responded to methotrexate.
- Product number
- EMEA/H/C/003983
- Authorisation holder
- Nordic Group B.V.
- Priority medicines scheme
- No
- Generic
- No
- Biosimilar
- No
- Generic medicines
- 0
- Biosimilar medicines
- 0
- Advanced therapy
- No
- Conditional approval
- No
- Additional monitoring
- No
- Accelerated assessment
- No
- Exceptional circumstances
- No
Therapeutic areas
- Arthritis, Juvenile Rheumatoid
- Arthritis, Psoriatic
- Arthritis, Rheumatoid
- Psoriasis
European medicines record
- Patents
- 18
- Designations
- 4
- Earliest recorded loss of exclusivity
- 28 Oct 2035
- First in class
- No
- Fast track
- No
- Breakthrough designation
- No
- Orphan designation
- No
- Priority review
- No
- Orphan exclusivity
- No
- Accelerated approval
- No
- Availability
- Prescription only
- Boxed warning
- Yes
- Pharmacology name
- methotrexate
- Type
- Synthetic organic
- Drug name stem
- -trexate
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Oral
- Parenteral
- Action
- Inhibition
- Action type
- Inhibitor
- Target
- dihydrofolate reductase
- Gene symbol
- DHFR
- Protein identifier
- P00374
- Median affinity
- 8.92
- Affinity units
- pKi
- Primary target
- Yes
- Action
- Inhibition
- Action type
- Inhibitor
- Target
- high mobility group box 1
- Gene symbol
- HMGB1
- Protein identifier
- P09429
- Median affinity
- 7.62
- Affinity units
- pKd
- Action
- Inhibition
- Action type
- Inhibitor
- Target
- Reduced folate transporter 1
- Gene symbol
- SLC19A1
- Protein identifier
- P41440
- Median affinity
- 5.33
- Affinity units
- pKi
- Mechanism
- Dihydrofolate reductase inhibitor
- Action type
- Inhibitor
- Target
- Dihydrofolate reductase
- Protein identifier
- P00374
Open Targets mechanisms
- Mechanism
- Dihydrofolate reductase inhibitor
- Action type
- Inhibitor
- Target
- Dihydrofolate reductase
DrugCentral mechanisms
- Action type
- Inhibitor
- Gene symbol
- DHFR
- Protein identifier
- P00374
- Organism
- Homo sapiens
- Target development level
- Clinical
- Condition
- Leukemia, Biphenotypic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000094
- Subject identifier
- D015456
- Condition
- Precursor Cell Lymphoblastic Leukemia-Lymphoma
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000094
- Subject identifier
- D054198
- Condition
- Leukemia, Lymphocytic, Chronic, B-Cell
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000095
- Subject identifier
- D015451
- Condition
- Lymphoma, Follicular
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000096
- Subject identifier
- D008224
- Condition
- Carcinoma, Squamous Cell
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000181
- Subject identifier
- D002294
- Condition
- Hodgkin Disease
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000183
- Subject identifier
- D006689
- Condition
- Lymphoma, B-Cell, Marginal Zone
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000191
- Subject identifier
- D018442
- Condition
- Myelodysplastic Syndromes
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000198
- Subject identifier
- D009190
- Condition
- Neoplasms, Plasma Cell
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000200
- Subject identifier
- D054219
- Condition
- Leukemia, Biphenotypic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000209
- Subject identifier
- D015456
- Condition
- Lymphoma, T-Cell, Peripheral
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000211
- Subject identifier
- D016411
- Condition
- Leukemia, Erythroblastic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000218
- Subject identifier
- D004915
- Condition
- Precursor Cell Lymphoblastic Leukemia-Lymphoma
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000220
- Subject identifier
- D054198
- Condition
- Leukemia, Monocytic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000221
- Subject identifier
- D007948
- Condition
- Leukemia, Myeloid, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000222
- Subject identifier
- D015470
- Condition
- Leukemia, Myelomonocytic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000223
- Subject identifier
- D015479
- Condition
- Leukemia, Promyelocytic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000224
- Subject identifier
- D015473
- Condition
- Immunoblastic Lymphadenopathy
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000255
- Subject identifier
- D007119
- Condition
- Dermatitis, Atopic
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000274
- Subject identifier
- D003876
- Condition
- Breast Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000305
- Subject identifier
- D001943
- Condition
- Burkitt Lymphoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000309
- Subject identifier
- D002051
- Condition
- Cardiovascular Diseases
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000319
- Subject identifier
- D002318
- Condition
- Leukemia, Myelogenous, Chronic, BCR-ABL Positive
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000339
- Subject identifier
- D015464
- Condition
- Crohn Disease
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000384
- Subject identifier
- D003424
- Condition
- Melanoma
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000389
- Subject identifier
- D008545
And 140 more, listed on the interactive page.
- Condition identifier
- EFO_0000181
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000198
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000220
- Condition identifier
- EFO_0000222
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000274
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000305
- Condition identifier
- EFO_0000319
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000384
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000398
- Condition identifier
- EFO_0000403
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000540
- Condition identifier
- EFO_0000565
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000574
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000612
- Condition identifier
- EFO_0000616
- Condition identifier
- EFO_0000637
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000658
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000676
- Condition identifier
- EFO_0000685
- Condition identifier
- EFO_0000691
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000706
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000707
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000729
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000764
- Highest recorded phase
- 1
- Condition identifier
- EFO_0001068
- Highest recorded phase
- 1
And 309 more, listed on the interactive page.
- Warning
- Black Box Warning
- Effect
- carcinogenicity
- Warning
- Black Box Warning
- Effect
- dermatological toxicity
- Warning
- Black Box Warning
- Effect
- gastrointestinal toxicity
- Warning
- Black Box Warning
- Effect
- hematological toxicity
- Warning
- Black Box Warning
- Effect
- hepatotoxicity
- Warning
- Black Box Warning
- Effect
- infectious disease
- Warning
- Black Box Warning
- Effect
- nephrotoxicity
- Warning
- Black Box Warning
- Effect
- respiratory toxicity
- Warning
- Black Box Warning
- Effect
- teratogenicity
- Warning
- Black Box Warning
- Effect
- vascular toxicity
- Warning
- Black Box Warning
- Effect
- carcinogenicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- dermatological toxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- gastrointestinal toxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- hematological toxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- hepatotoxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- infectious disease
- Country
- United States
- Warning
- Black Box Warning
- Effect
- nephrotoxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- respiratory toxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- teratogenicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- vascular toxicity
- Country
- United States
- Event
- abdominal discomfort
- Reports
- 5,008
- Reporting signal score
- 4,600.74
- Event
- alopecia
- Reports
- 6,186
- Reporting signal score
- 6,729.83
- Event
- anti-cyclic citrullinated peptide antibody positive
- Reports
- 1,369
- Reporting signal score
- 3,485.42
- Event
- arthralgia
- Reports
- 9,338
- Reporting signal score
- 5,140.75
- Event
- arthritis
- Reports
- 2,336
- Reporting signal score
- 1,887.04
- Event
- arthropathy
- Reports
- 4,034
- Reporting signal score
- 5,462.95
- Event
- c-reactive protein abnormal
- Reports
- 1,423
- Reporting signal score
- 3,363.29
- Event
- c-reactive protein increased
- Reports
- 2,380
- Reporting signal score
- 2,416.13
- Event
- condition aggravated
- Reports
- 6,558
- Reporting signal score
- 2,946.44
- Event
- drug hypersensitivity
- Reports
- 9,021
- Reporting signal score
- 5,878.69
- Event
- drug intolerance
- Reports
- 11,306
- Reporting signal score
- 18,174.7
- Event
- febrile neutropenia
- Reports
- 3,069
- Reporting signal score
- 2,206.37
- Event
- gastrointestinal disorder
- Reports
- 2,770
- Reporting signal score
- 2,425.29
- Event
- glossodynia
- Reports
- 2,133
- Reporting signal score
- 3,981.38
- Event
- hand deformity
- Reports
- 2,276
- Reporting signal score
- 5,284.82
- Event
- hepatic enzyme increased
- Reports
- 3,755
- Reporting signal score
- 3,844.21
- Event
- infection
- Reports
- 4,446
- Reporting signal score
- 3,129.14
- Event
- joint swelling
- Reports
- 7,835
- Reporting signal score
- 10,619.3
- Event
- liver function test increased
- Reports
- 1,984
- Reporting signal score
- 2,625.07
- Event
- loss of personal independence in daily activities
- Reports
- 2,177
- Reporting signal score
- 3,142.83
- Event
- musculoskeletal stiffness
- Reports
- 4,108
- Reporting signal score
- 4,102.3
- Event
- pain
- Reports
- 9,599
- Reporting signal score
- 3,982.49
- Event
- pancytopenia
- Reports
- 2,688
- Reporting signal score
- 2,031.82
- Event
- pemphigus
- Reports
- 2,608
- Reporting signal score
- 6,185.79
- Event
- peripheral swelling
- Reports
- 3,972
- Reporting signal score
- 2,368.38
And 14 more, listed on the interactive page.
- NCT00000361
- NCT00000658
- NCT00283985
- NCT00610883
- NCT00928018
- NCT01516580
- NCT04514393
- NCT05583071
- NCT05998642
- NCT00000834
- NCT00001498
- NCT00002498
- NCT00002542
- NCT00002579
- NCT00002580
- NCT00002581
- NCT00002582
- NCT00002696
- NCT00002755
- NCT00002784
- NCT00003012
- NCT00003013
- NCT00003536
- NCT00003577
- NCT00003680
And 825 more, listed on the interactive page.
- Dose
- 7.5 mg
- Route
- Intramuscularly
- How often
- Once weekly
- Hydrogen bond acceptors
- 10
- Hydrogen bond donors
- 5
- Polar surface area
- 210.54
- Calculated partition coefficient (ALogP)
- 0.27
- Calculated partition coefficient (XLogP)
- -1.8
- Prodrug
- No
- Chirality
- Single enantiomer
- Inorganic
- No
- Rule-of-five violations
- 0
- Rotatable bonds
- 9
- Heavy atoms
- 33
- Molecular formula
- C20H22N8O5
- Monoisotopic mass
- 454.17131583
- Natural product
- Yes
- 0143-9367
- 0143-9516
- 0143-9517
- 0143-9518
- 0143-9519
- 0143-9830
- 0904-7141
- 16729-277
- 50268-554
- 54436-010
- 54436-012
- 54436-015
- 54436-017
- 54436-020
- 54436-022
- 54436-025
- 68382-775
- 81927-204
- 52652-2001
- 70771-1058
- Recorded assays
- 13,674
- Active assays
- 4,907
- Confirmatory
- Other
- Screening
- Summary
- Abortifacient Agents, Nonsteroidal
- Antimetabolites, Antineoplastic
- Dermatologic Agents
- Enzyme Inhibitors
- Folic Acid Antagonists
- Immunosuppressive Agents
- Antirheumatic Agents
- Nucleic Acid Synthesis Inhibitors
These details could not be displayed.
Related records
Trials (1,425)
- "Comparing Methotrexate Usage Techniques to Prevent Proliferative Vitreoretinopaty After Retinal Detachment Vitrectomy"
- [CREMA]Combination of R-M Followed by R-A in Elderly Patients With Primary CNS Lymphoma
- 05-001: Treatment of Acute Lymphoblastic Leukemia in Children
- 2-week dc of MTX and Influenza Vaccination in RA
- 4 x Epirubicin, Cyclophosphamide, Followed by 4 x Docetaxel Versus 6 x CMF / 6 x CEF
- 4B951, Combination Chemotherapy in Treating Patients With Bladder Cancer
- 506U78 in Treating Patients With Refractory Hematologic Cancer
- A 30-month Follow-up of MERINO Participants to Evaluate Long-term Effects of Methotrexate in Erosive Hand OA.
- A Bioavailability Study of Methotrexate 25 mg Administered by Needle Injection and a Pre Filled Needle-free Device in Healthy Volunteers.
- A Canadian Study to Evaluate Early Use of Adalimumab After Methotrexate Failure in Early Rheumatoid Arthritis
- A Clinical Research on the Relation of Blood Drug Concentration and Calcium Folinate Rescued in High-dose MTX Therapy
- A Clinical Study of Tulisokibart (MK-7240) to Treat Rheumatoid Arthritis (RA) (MK-7240-014)
- A Clinical Study on the Efficacy and Safety of Methotrexate (MTX) or Thiotepa (for MTX Intolerance) or Temozolomide (TMZ) Combined With Orelabrutinib and Selinexor in Relapsed/Refractory Primary or Secondary Central Nervous System Lymphoma（SELINA）
- A Clinical Trial Evaluating Patients With Primary Vitreoretinal Lymphoma
- A Clinical Trial in Patients With Breast Cancer Susceptibility Gene (BRCA) Defective Tumours
- A Clinical Trial of Safety and Tolerance of TQH3821 Tablets in Adult Healthy Subjects
- A Clinical Trial to Evaluate Effect of IAE0972 Combined with Chemotherapy for R/M HNSCC or NPC(Note: It is Currently Phase II.).
- A Clinical Trial Using Metronomic Oral Low-dose Cyclophosphamide Alternating With Low-dose Oral Methotrexate With Continuous Celecoxib and Weekly Vinblastine in Children and Adolescents With Relapsed or Progressing soliD Tumours.
- A Comparison of Methotrexate Alone or Combined to Infliximab or to Pulse Methylprednisolone in Early Rheumatoid Arthritis: A Magnetic Resonance Imaging Study
- A Dose Range Finding Study of JNJ-38518168 in Patients With Active Rheumatoid Arthritis in Spite of Treatment With Methotrexate
Approved for (19)
- Acute lymphoblastic leukemia
- Arthritic joint disease
- B-cell acute lymphoblastic leukemia
- Breast cancer
- Breast carcinoma
- Breast neoplasm
- Cancer
- Childhood acute lymphoblastic leukemia
- Immune system disorder
- Juvenile idiopathic arthritis
- Lymphoblastic lymphoma
- Mycosis fungoides
- Neoplasm
- Non-Hodgkin lymphoma
- Palmoplantar pustulosis
- Polyarticular arthritis
- Psoriasis
- Psoriatic arthritis
- Rheumatoid arthritis
In development for (143)
- Acquired polycythemia vera Phase 2
- Acute erythroid leukemia Phase 3
- Acute graft versus host disease Phase 3
- Acute leukemia of ambiguous lineage Phase 3
- Acute megakaryoblastic leukemia Phase 3
- Acute monocytic leukemia Phase 3
- Acute myeloblastic leukemia without maturation Phase 3
- Acute myeloid leukemia Phase 3
- Acute myelomonocytic leukemia M4 Phase 3
- Acute promyelocytic leukemia Phase 3
- Adult T-cell leukemia/lymphoma Phase 2
- Alopecia areata Phase 3
- Anaplastic large cell lymphoma Phase 3
- Angioimmunoblastic T-cell lymphoma Phase 2
- Ankylosing spondylitis Phase 3
- Aplastic anemia Phase 3
- Asthma Phase 3
- Atopic eczema Phase 3
- B-cell chronic lymphocytic leukemia Phase 2
- Blast phase chronic myelogenous leukemia, BCR-ABL1 positive Phase 2
Other linked conditions (8)
- Childhood leukemia
- Common wart
- Diabetic macular edema
- Fasciitis
- Inflammatory bowel disease
- Prostate cancer
- T-cell non-Hodgkin lymphoma
- Type 1 diabetes mellitus
Targets (1)
- DHFR Dihydrofolate reductase inhibitor