Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H22N8O5 |
| Molecular Weight | 454.4393 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(CC1=NC2=C(N)N=C(N)N=C2N=C1)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O
InChI
InChIKey=FBOZXECLQNJBKD-ZDUSSCGKSA-N
InChI=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
DescriptionSources: http://www.drugbank.ca/drugs/DB00563Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/methotrexate.html
Sources: http://www.drugbank.ca/drugs/DB00563
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/methotrexate.html
Methotrexate is an antineoplastic anti-metabolite. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (of the cell cycle), stopping normal development and division. Methotrexate inhibits folic acid reductase which is responsible for the conversion of folic acid to tetrahydrofolic acid. At two stages in the biosynthesis of purines and at one stage in the synthesis of pyrimidines, one-carbon transfer reactions occur which require specific coenzymes synthesized in the cell from tetrahydrofolic acid. Tetrahydrofolic acid itself is synthesized in the cell from folic acid with the help of an enzyme, folic acid reductase. Methotrexate looks a lot like folic acid to the enzyme, so it binds to it quite strongly and inhibits the enzyme. Thus, DNA synthesis cannot proceed because the coenzymes needed for one-carbon transfer reactions are not produced from tetrahydrofolic acid because there is no tetrahydrofolic acid. Methotrexate selectively affects the most rapidly dividing cells (neoplastic and psoriatic cells). Methotrexate is indicated in the treatment of gestational choriocarcinoma, chorioadenoma destruens and hydatidiform mole. In acute lymphocytic leukemia, methotrexate is indicated in the prophylaxis of meningeal leukemia and is used in maintenance therapy in combination with other chemotherapeutic agents. Methotrexate is also indicated in the treatment of meningeal leukemia. Methotrexate is used alone or in combination with other anticancer agents in the treatment of breast cancer, epidermoid cancers of the head and neck, advanced mycosis fungoides (cutaneous T cell lymphoma), and lung cancer, particularly squamous cell and small cell types. Methotrexate is also used in combination with other chemotherapeutic agents in the treatment of advanced stage non-Hodgkin’s lymphomas. Methotrexate is indicated in the symptomatic control of severe, recalcitrant, disabling psoriasis. Methotrexate is indicated in the management of selected adults with severe, active rheumatoid arthritis (ACR criteria), or children with active polyarticular-course juvenile rheumatoid arthritis.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL202 Sources: http://www.drugbank.ca/drugs/DB00563 |
5.19 pM [Ki] | ||
Target ID: CHEMBL3167 |
0.18 mM [IC50] | ||
Target ID: CHEMBL614580 |
15.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | OTREXUP Approved UseOtrexup is a folate analog metabolic inhibitor indicated for the:
• Management of patients with severe, active rheumatoid arthritis (RA) and polyarticular juvenile idiopathic arthritis (pJIA), who are intolerant of or had an inadequate response to first-line therapy
• Symptomatic control of severe, recalcitrant, disabling psoriasis in adults who are not adequately responsive to other forms of therapy Launch Date-5.36543986E11 |
|||
| Primary | TREXALL Approved UseNeoplastic Diseases
Methotrexate, USP is indicated in the treatment of gestational choriocarcinoma, chorioadenoma destruens and hydatidiform mole.
In acute lymphocytic leukemia, methotrexate, USP is indicated in the prophylaxis of meningeal leukemia and is used in maintenance therapy in combination with other chemotherapeutic agents. Methotrexate, USP is also indicated in the treatment of meningeal leukemia.
Methotrexate, USP is used alone or in combination with other anticancer agents in the treatment of breast cancer, epidermoid cancers of the head and neck, advanced mycosis fungoides (cutaneous T cell lymphoma), and lung cancer, particularly squamous cell and small cell types. Methotrexate, USP is also used in combination with other chemotherapeutic agents in the treatment of advanced stage non-Hodgkin's lymphomas.
Methotrexate, USP in high doses followed by leucovorin rescue in combination with other chemotherapeutic agents is effective in prolonging relapse-free survival in patients with non-metastatic osteosarcoma who have undergone surgical resection or amputation for the primary tumor.
Psoriasis
Methotrexate, USP is indicated in the symptomatic control of severe, recalcitrant, disabling psoriasis that is not adequately responsive to other forms of therapy, but only when the diagnosis has been established, as by biopsy and/or after dermatologic consultation. It is important to ensure that a psoriasis "flare" is not due to an undiagnosed concomitant disease affecting immune responses.
Rheumatoid Arthritis including Polyarticular-Course Juvenile Rheumatoid Arthritis
Methotrexate, USP is indicated in the management of selected adults with severe, active rheumatoid arthritis (ACR criteria), or children with active polyarticular-course juvenile rheumatoid arthritis, who have had an insufficient therapeutic response to, or are intolerant of, an adequate trial of first-line therapy including full dose non-steroidal anti-inflammatory agents (NSAIDs). Launch Date9.8504638E11 |
|||
| Primary | TREXALL Approved UseNeoplastic Diseases
Methotrexate, USP is indicated in the treatment of gestational choriocarcinoma, chorioadenoma destruens and hydatidiform mole.
In acute lymphocytic leukemia, methotrexate, USP is indicated in the prophylaxis of meningeal leukemia and is used in maintenance therapy in combination with other chemotherapeutic agents. Methotrexate, USP is also indicated in the treatment of meningeal leukemia.
Methotrexate, USP is used alone or in combination with other anticancer agents in the treatment of breast cancer, epidermoid cancers of the head and neck, advanced mycosis fungoides (cutaneous T cell lymphoma), and lung cancer, particularly squamous cell and small cell types. Methotrexate, USP is also used in combination with other chemotherapeutic agents in the treatment of advanced stage non-Hodgkin's lymphomas.
Methotrexate, USP in high doses followed by leucovorin rescue in combination with other chemotherapeutic agents is effective in prolonging relapse-free survival in patients with non-metastatic osteosarcoma who have undergone surgical resection or amputation for the primary tumor.
Psoriasis
Methotrexate, USP is indicated in the symptomatic control of severe, recalcitrant, disabling psoriasis that is not adequately responsive to other forms of therapy, but only when the diagnosis has been established, as by biopsy and/or after dermatologic consultation. It is important to ensure that a psoriasis "flare" is not due to an undiagnosed concomitant disease affecting immune responses.
Rheumatoid Arthritis including Polyarticular-Course Juvenile Rheumatoid Arthritis
Methotrexate, USP is indicated in the management of selected adults with severe, active rheumatoid arthritis (ACR criteria), or children with active polyarticular-course juvenile rheumatoid arthritis, who have had an insufficient therapeutic response to, or are intolerant of, an adequate trial of first-line therapy including full dose non-steroidal anti-inflammatory agents (NSAIDs). Launch Date9.8504638E11 |
|||
| Primary | TREXALL Approved UseNeoplastic Diseases
Methotrexate, USP is indicated in the treatment of gestational choriocarcinoma, chorioadenoma destruens and hydatidiform mole.
In acute lymphocytic leukemia, methotrexate, USP is indicated in the prophylaxis of meningeal leukemia and is used in maintenance therapy in combination with other chemotherapeutic agents. Methotrexate, USP is also indicated in the treatment of meningeal leukemia.
Methotrexate, USP is used alone or in combination with other anticancer agents in the treatment of breast cancer, epidermoid cancers of the head and neck, advanced mycosis fungoides (cutaneous T cell lymphoma), and lung cancer, particularly squamous cell and small cell types. Methotrexate, USP is also used in combination with other chemotherapeutic agents in the treatment of advanced stage non-Hodgkin's lymphomas.
Methotrexate, USP in high doses followed by leucovorin rescue in combination with other chemotherapeutic agents is effective in prolonging relapse-free survival in patients with non-metastatic osteosarcoma who have undergone surgical resection or amputation for the primary tumor.
Psoriasis
Methotrexate, USP is indicated in the symptomatic control of severe, recalcitrant, disabling psoriasis that is not adequately responsive to other forms of therapy, but only when the diagnosis has been established, as by biopsy and/or after dermatologic consultation. It is important to ensure that a psoriasis "flare" is not due to an undiagnosed concomitant disease affecting immune responses.
Rheumatoid Arthritis including Polyarticular-Course Juvenile Rheumatoid Arthritis
Methotrexate, USP is indicated in the management of selected adults with severe, active rheumatoid arthritis (ACR criteria), or children with active polyarticular-course juvenile rheumatoid arthritis, who have had an insufficient therapeutic response to, or are intolerant of, an adequate trial of first-line therapy including full dose non-steroidal anti-inflammatory agents (NSAIDs). Launch Date9.8504638E11 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.205 μM |
20 mg/m² single, oral dose: 20 mg/m² route of administration: Oral experiment type: SINGLE co-administered: |
METHOTREXATE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3533 nM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8485020 |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
METHOTREXATE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
55 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8485020 |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
METHOTREXATE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
3.25 h |
20 mg/m² single, oral dose: 20 mg/m² route of administration: Oral experiment type: SINGLE co-administered: |
METHOTREXATE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
50% |
METHOTREXATE serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
75 mg single, oral Overdose |
unknown, 10-19 years n = 1 Health Status: unknown Age Group: 10-19 years Sex: M Population Size: 1 Sources: |
Other AEs: Nausea, Vomiting... |
87.5 mg single, oral Overdose |
unknown, 10-19 years n = 1 Health Status: unknown Age Group: 10-19 years Sex: F Population Size: 1 Sources: |
Other AEs: Nausea, Vomiting... |
50 mg single, oral Overdose |
unknown, 40-49 years n = 1 Health Status: unknown Age Group: 40-49 years Sex: M Population Size: 1 Sources: |
|
3 g/m2 multiple, intravenous Highest studied dose Dose: 3 g/m2 Route: intravenous Route: multiple Dose: 3 g/m2 Co-administed with:: calcium folinate(oral, 50 mg at H24 and pursued this treatment every 6 h during 3 days (until day 4) for a total of 12 administrations) Sources: |
unhealthy, 41 years (range: 17–60 years) n = 103 Health Status: unhealthy Condition: aggressive lymphoma Age Group: 41 years (range: 17–60 years) Sex: M+F Population Size: 103 Sources: |
Disc. AE: Toxicity renal... AEs leading to discontinuation/dose reduction: Toxicity renal (grade 1-2, 2 patients) Sources: |
3 g/m2 multiple, intravenous Highest studied dose Dose: 3 g/m2 Route: intravenous Route: multiple Dose: 3 g/m2 Co-administed with:: (oral, 50 mg at H24 and pursued this treatment every 6 h during 3 days (until day 4) for a total of 12 administrations) Sources: |
unhealthy, 41 years (range: 17–60 years) n = 103 Health Status: unhealthy Condition: aggressive lymphoma Age Group: 41 years (range: 17–60 years) Sex: M+F Population Size: 103 Sources: |
Disc. AE: Cytolysis, Neutropenia... AEs leading to discontinuation/dose reduction: Cytolysis (grade 2-3, 2 patients) Sources: Neutropenia (grade 3, 1 patient) Digestion impaired (grade 3, 1 patient) |
50 mg 1 times / week multiple, oral Overdose Dose: 50 mg, 1 times / week Route: oral Route: multiple Dose: 50 mg, 1 times / week Sources: |
unhealthy, 50-59 years n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 50-59 years Sex: F Population Size: 1 Sources: |
Other AEs: Skin lesion, Mucosal ulceration... Other AEs: Skin lesion (1 patient) Sources: Mucosal ulceration (1 patient) Abdominal pain (1 patient) |
10 mg 1 times / week multiple, oral Recommended Dose: 10 mg, 1 times / week Route: oral Route: multiple Dose: 10 mg, 1 times / week Co-administed with:: adalimumab(40 mg per every other week; 3 years) Sources: guratimod(50 mg/day for approximately 3 years.) |
unhealthy, 54 years n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 54 years Sex: F Population Size: 1 Sources: |
Disc. AE: Lymphoproliferative disorder... AEs leading to discontinuation/dose reduction: Lymphoproliferative disorder (1 patient) Sources: |
70 mg 1 times / week multiple, oral Overdose Dose: 70 mg, 1 times / week Route: oral Route: multiple Dose: 70 mg, 1 times / week Sources: |
unhealthy, 60-79 years n = 2 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 60-79 years Sex: F Population Size: 2 Sources: |
Other AEs: Mucosal ulceration... |
17.5 mg 1 times / week multiple, oral Overdose Dose: 17.5 mg, 1 times / week Route: oral Route: multiple Dose: 17.5 mg, 1 times / week Sources: |
unhealthy, 70-79 years n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 70-79 years Sex: F Population Size: 1 Sources: |
Other AEs: Mucosal ulceration, Nausea... Other AEs: Mucosal ulceration (1 patient) Sources: Nausea (1 patient) Vomiting (1 patient) Diarrhea (1 patient) Abdominal pain (1 patient) |
10 mg 1 times / day multiple, oral Overdose Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: adult Population Size: 1 Sources: |
Other AEs: Adverse event... |
15 mg 1 times / day multiple, oral Overdose Dose: 15 mg, 1 times / day Route: oral Route: multiple Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: adult Population Size: 1 Sources: |
Other AEs: Adverse event... |
2.5 mg 2 times / day multiple, oral Overdose Dose: 2.5 mg, 2 times / day Route: oral Route: multiple Dose: 2.5 mg, 2 times / day Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: adult Population Size: 1 Sources: |
Other AEs: Adverse event... |
25 mg 1 times / week steady, oral Recommended Dose: 25 mg, 1 times / week Route: oral Route: steady Dose: 25 mg, 1 times / week Sources: |
pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: |
Other AEs: Fetal damage... Other AEs: Fetal damage (severe|grade 5) Sources: |
25 mg 1 times / week steady, oral Recommended Dose: 25 mg, 1 times / week Route: oral Route: steady Dose: 25 mg, 1 times / week Sources: |
unhealthy, adult Health Status: unhealthy Condition: Mycosis fungoides Age Group: adult Sources: |
Other AEs: Gastrointestinal disorder (NOS), Hepatic and hepatobiliary disorders... Other AEs: Gastrointestinal disorder (NOS) Sources: Hepatic and hepatobiliary disorders (serious) Respiratory tract disorders NEC (serious) Skin and subcutaneous conditions NEC (serious) Kidney disorder (serious) |
7.5 mg 1 times / week steady, subcutaneous Recommended Dose: 7.5 mg, 1 times / week Route: subcutaneous Route: steady Dose: 7.5 mg, 1 times / week Sources: |
pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: |
Other AEs: Fetal damage... Other AEs: Fetal damage (severe|grade 5) Sources: |
7.5 mg 1 times / week steady, subcutaneous Recommended Dose: 7.5 mg, 1 times / week Route: subcutaneous Route: steady Dose: 7.5 mg, 1 times / week Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Skin and subcutaneous conditions NEC... Other AEs: Skin and subcutaneous conditions NEC (severe|grade 5) Sources: |
7.5 mg 1 times / week steady, subcutaneous Recommended Dose: 7.5 mg, 1 times / week Route: subcutaneous Route: steady Dose: 7.5 mg, 1 times / week Sources: |
unhealthy, adult Health Status: unhealthy Condition: rheumatoid arthritis Age Group: adult Sources: |
Disc. AE: Interstitial pneumonitis... Other AEs: Hepatic and hepatobiliary disorders, Respiratory tract disorders NEC... AEs leading to discontinuation/dose reduction: Interstitial pneumonitis (serious) Other AEs:Hepatic and hepatobiliary disorders (serious) Sources: Respiratory tract disorders NEC (serious) Skin and subcutaneous conditions NEC (serious) Kidney disorder (serious) |
30 mg 1 times / week multiple, subcutaneous Dose: 30 mg, 1 times / week Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / week Co-administed with:: Nonsteroidal anti-inflammatory drugs Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Bone marrow depression, Aplastic anemia... Other AEs: Bone marrow depression (severe|grade 5) Sources: Aplastic anemia (severe|grade 5) Gastrointestinal toxicity (severe|grade 5) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Nausea | 1 patient | 75 mg single, oral Overdose |
unknown, 10-19 years n = 1 Health Status: unknown Age Group: 10-19 years Sex: M Population Size: 1 Sources: |
| Vomiting | 1 patient | 75 mg single, oral Overdose |
unknown, 10-19 years n = 1 Health Status: unknown Age Group: 10-19 years Sex: M Population Size: 1 Sources: |
| Nausea | 1 patient | 87.5 mg single, oral Overdose |
unknown, 10-19 years n = 1 Health Status: unknown Age Group: 10-19 years Sex: F Population Size: 1 Sources: |
| Vomiting | 1 patient | 87.5 mg single, oral Overdose |
unknown, 10-19 years n = 1 Health Status: unknown Age Group: 10-19 years Sex: F Population Size: 1 Sources: |
| Toxicity renal | grade 1-2, 2 patients Disc. AE |
3 g/m2 multiple, intravenous Highest studied dose Dose: 3 g/m2 Route: intravenous Route: multiple Dose: 3 g/m2 Co-administed with:: calcium folinate(oral, 50 mg at H24 and pursued this treatment every 6 h during 3 days (until day 4) for a total of 12 administrations) Sources: |
unhealthy, 41 years (range: 17–60 years) n = 103 Health Status: unhealthy Condition: aggressive lymphoma Age Group: 41 years (range: 17–60 years) Sex: M+F Population Size: 103 Sources: |
| Cytolysis | grade 2-3, 2 patients Disc. AE |
3 g/m2 multiple, intravenous Highest studied dose Dose: 3 g/m2 Route: intravenous Route: multiple Dose: 3 g/m2 Co-administed with:: (oral, 50 mg at H24 and pursued this treatment every 6 h during 3 days (until day 4) for a total of 12 administrations) Sources: |
unhealthy, 41 years (range: 17–60 years) n = 103 Health Status: unhealthy Condition: aggressive lymphoma Age Group: 41 years (range: 17–60 years) Sex: M+F Population Size: 103 Sources: |
| Digestion impaired | grade 3, 1 patient Disc. AE |
3 g/m2 multiple, intravenous Highest studied dose Dose: 3 g/m2 Route: intravenous Route: multiple Dose: 3 g/m2 Co-administed with:: (oral, 50 mg at H24 and pursued this treatment every 6 h during 3 days (until day 4) for a total of 12 administrations) Sources: |
unhealthy, 41 years (range: 17–60 years) n = 103 Health Status: unhealthy Condition: aggressive lymphoma Age Group: 41 years (range: 17–60 years) Sex: M+F Population Size: 103 Sources: |
| Neutropenia | grade 3, 1 patient Disc. AE |
3 g/m2 multiple, intravenous Highest studied dose Dose: 3 g/m2 Route: intravenous Route: multiple Dose: 3 g/m2 Co-administed with:: (oral, 50 mg at H24 and pursued this treatment every 6 h during 3 days (until day 4) for a total of 12 administrations) Sources: |
unhealthy, 41 years (range: 17–60 years) n = 103 Health Status: unhealthy Condition: aggressive lymphoma Age Group: 41 years (range: 17–60 years) Sex: M+F Population Size: 103 Sources: |
| Abdominal pain | 1 patient | 50 mg 1 times / week multiple, oral Overdose Dose: 50 mg, 1 times / week Route: oral Route: multiple Dose: 50 mg, 1 times / week Sources: |
unhealthy, 50-59 years n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 50-59 years Sex: F Population Size: 1 Sources: |
| Mucosal ulceration | 1 patient | 50 mg 1 times / week multiple, oral Overdose Dose: 50 mg, 1 times / week Route: oral Route: multiple Dose: 50 mg, 1 times / week Sources: |
unhealthy, 50-59 years n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 50-59 years Sex: F Population Size: 1 Sources: |
| Skin lesion | 1 patient | 50 mg 1 times / week multiple, oral Overdose Dose: 50 mg, 1 times / week Route: oral Route: multiple Dose: 50 mg, 1 times / week Sources: |
unhealthy, 50-59 years n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 50-59 years Sex: F Population Size: 1 Sources: |
| Lymphoproliferative disorder | 1 patient Disc. AE |
10 mg 1 times / week multiple, oral Recommended Dose: 10 mg, 1 times / week Route: oral Route: multiple Dose: 10 mg, 1 times / week Co-administed with:: adalimumab(40 mg per every other week; 3 years) Sources: guratimod(50 mg/day for approximately 3 years.) |
unhealthy, 54 years n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 54 years Sex: F Population Size: 1 Sources: |
| Mucosal ulceration | 2 patients | 70 mg 1 times / week multiple, oral Overdose Dose: 70 mg, 1 times / week Route: oral Route: multiple Dose: 70 mg, 1 times / week Sources: |
unhealthy, 60-79 years n = 2 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 60-79 years Sex: F Population Size: 2 Sources: |
| Abdominal pain | 1 patient | 17.5 mg 1 times / week multiple, oral Overdose Dose: 17.5 mg, 1 times / week Route: oral Route: multiple Dose: 17.5 mg, 1 times / week Sources: |
unhealthy, 70-79 years n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 70-79 years Sex: F Population Size: 1 Sources: |
| Diarrhea | 1 patient | 17.5 mg 1 times / week multiple, oral Overdose Dose: 17.5 mg, 1 times / week Route: oral Route: multiple Dose: 17.5 mg, 1 times / week Sources: |
unhealthy, 70-79 years n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 70-79 years Sex: F Population Size: 1 Sources: |
| Mucosal ulceration | 1 patient | 17.5 mg 1 times / week multiple, oral Overdose Dose: 17.5 mg, 1 times / week Route: oral Route: multiple Dose: 17.5 mg, 1 times / week Sources: |
unhealthy, 70-79 years n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 70-79 years Sex: F Population Size: 1 Sources: |
| Nausea | 1 patient | 17.5 mg 1 times / week multiple, oral Overdose Dose: 17.5 mg, 1 times / week Route: oral Route: multiple Dose: 17.5 mg, 1 times / week Sources: |
unhealthy, 70-79 years n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 70-79 years Sex: F Population Size: 1 Sources: |
| Vomiting | 1 patient | 17.5 mg 1 times / week multiple, oral Overdose Dose: 17.5 mg, 1 times / week Route: oral Route: multiple Dose: 17.5 mg, 1 times / week Sources: |
unhealthy, 70-79 years n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 70-79 years Sex: F Population Size: 1 Sources: |
| Adverse event | grade 5 | 10 mg 1 times / day multiple, oral Overdose Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: adult Population Size: 1 Sources: |
| Adverse event | grade 5 | 15 mg 1 times / day multiple, oral Overdose Dose: 15 mg, 1 times / day Route: oral Route: multiple Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: adult Population Size: 1 Sources: |
| Adverse event | grade 5 | 2.5 mg 2 times / day multiple, oral Overdose Dose: 2.5 mg, 2 times / day Route: oral Route: multiple Dose: 2.5 mg, 2 times / day Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: adult Population Size: 1 Sources: |
| Fetal damage | severe|grade 5 | 25 mg 1 times / week steady, oral Recommended Dose: 25 mg, 1 times / week Route: oral Route: steady Dose: 25 mg, 1 times / week Sources: |
pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: |
| Gastrointestinal disorder (NOS) | 25 mg 1 times / week steady, oral Recommended Dose: 25 mg, 1 times / week Route: oral Route: steady Dose: 25 mg, 1 times / week Sources: |
unhealthy, adult Health Status: unhealthy Condition: Mycosis fungoides Age Group: adult Sources: |
|
| Hepatic and hepatobiliary disorders | serious | 25 mg 1 times / week steady, oral Recommended Dose: 25 mg, 1 times / week Route: oral Route: steady Dose: 25 mg, 1 times / week Sources: |
unhealthy, adult Health Status: unhealthy Condition: Mycosis fungoides Age Group: adult Sources: |
| Kidney disorder | serious | 25 mg 1 times / week steady, oral Recommended Dose: 25 mg, 1 times / week Route: oral Route: steady Dose: 25 mg, 1 times / week Sources: |
unhealthy, adult Health Status: unhealthy Condition: Mycosis fungoides Age Group: adult Sources: |
| Respiratory tract disorders NEC | serious | 25 mg 1 times / week steady, oral Recommended Dose: 25 mg, 1 times / week Route: oral Route: steady Dose: 25 mg, 1 times / week Sources: |
unhealthy, adult Health Status: unhealthy Condition: Mycosis fungoides Age Group: adult Sources: |
| Skin and subcutaneous conditions NEC | serious | 25 mg 1 times / week steady, oral Recommended Dose: 25 mg, 1 times / week Route: oral Route: steady Dose: 25 mg, 1 times / week Sources: |
unhealthy, adult Health Status: unhealthy Condition: Mycosis fungoides Age Group: adult Sources: |
| Fetal damage | severe|grade 5 | 7.5 mg 1 times / week steady, subcutaneous Recommended Dose: 7.5 mg, 1 times / week Route: subcutaneous Route: steady Dose: 7.5 mg, 1 times / week Sources: |
pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: |
| Skin and subcutaneous conditions NEC | severe|grade 5 | 7.5 mg 1 times / week steady, subcutaneous Recommended Dose: 7.5 mg, 1 times / week Route: subcutaneous Route: steady Dose: 7.5 mg, 1 times / week Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Hepatic and hepatobiliary disorders | serious | 7.5 mg 1 times / week steady, subcutaneous Recommended Dose: 7.5 mg, 1 times / week Route: subcutaneous Route: steady Dose: 7.5 mg, 1 times / week Sources: |
unhealthy, adult Health Status: unhealthy Condition: rheumatoid arthritis Age Group: adult Sources: |
| Kidney disorder | serious | 7.5 mg 1 times / week steady, subcutaneous Recommended Dose: 7.5 mg, 1 times / week Route: subcutaneous Route: steady Dose: 7.5 mg, 1 times / week Sources: |
unhealthy, adult Health Status: unhealthy Condition: rheumatoid arthritis Age Group: adult Sources: |
| Respiratory tract disorders NEC | serious | 7.5 mg 1 times / week steady, subcutaneous Recommended Dose: 7.5 mg, 1 times / week Route: subcutaneous Route: steady Dose: 7.5 mg, 1 times / week Sources: |
unhealthy, adult Health Status: unhealthy Condition: rheumatoid arthritis Age Group: adult Sources: |
| Skin and subcutaneous conditions NEC | serious | 7.5 mg 1 times / week steady, subcutaneous Recommended Dose: 7.5 mg, 1 times / week Route: subcutaneous Route: steady Dose: 7.5 mg, 1 times / week Sources: |
unhealthy, adult Health Status: unhealthy Condition: rheumatoid arthritis Age Group: adult Sources: |
| Interstitial pneumonitis | serious Disc. AE |
7.5 mg 1 times / week steady, subcutaneous Recommended Dose: 7.5 mg, 1 times / week Route: subcutaneous Route: steady Dose: 7.5 mg, 1 times / week Sources: |
unhealthy, adult Health Status: unhealthy Condition: rheumatoid arthritis Age Group: adult Sources: |
| Aplastic anemia | severe|grade 5 | 30 mg 1 times / week multiple, subcutaneous Dose: 30 mg, 1 times / week Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / week Co-administed with:: Nonsteroidal anti-inflammatory drugs Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Bone marrow depression | severe|grade 5 | 30 mg 1 times / week multiple, subcutaneous Dose: 30 mg, 1 times / week Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / week Co-administed with:: Nonsteroidal anti-inflammatory drugs Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Gastrointestinal toxicity | severe|grade 5 | 30 mg 1 times / week multiple, subcutaneous Dose: 30 mg, 1 times / week Route: subcutaneous Route: multiple Dose: 30 mg, 1 times / week Co-administed with:: Nonsteroidal anti-inflammatory drugs Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Intracerebral calcifications appearing during the course of acute lymphocytic leukemia treated with methotrexate and X-rays. | 1975 Feb |
|
| Cerebral calcifications associated with intrathecal methotrexate therapy in acute lymphocytic leukemia. | 1976 Apr |
|
| Toxicity profile of methotrexate in rheumatoid arthritis. A preliminary survey. | 1999 |
|
| Inhibitory effects of combinations of HER-2/neu antibody and chemotherapeutic agents used for treatment of human breast cancers. | 1999 Apr 1 |
|
| Leukoencephalopathy complicating an Ommaya reservoir and chemotherapy. | 1999 Feb |
|
| Acute dysarthria induced by low dose methotrexate therapy in a patient with erythrodermic cutaneous T-cell lymphoma: an unusual manifestation of neurotoxicity. | 1999 Jan |
|
| Toxic epidermal necrolysis and graft vs. host disease: a clinical spectrum but a diagnostic dilemma. | 1999 Jul |
|
| Subacute encephalopathy after combination chemotherapy including moderate-dose methotrexate in a patient with gastric cancer. | 1999 Mar |
|
| Delayed methotrexate clearance in a patient with sickle cell anemia and osteosarcoma. | 1999 Mar-Apr |
|
| Nonmetastatic osteosarcoma of the extremity: results of a neoadjuvant chemotherapy protocol (IOR/OS-3) with high-dose methotrexate, intraarterial or intravenous cisplatin, doxorubicin, and salvage chemotherapy based on histologic tumor response. | 1999 Nov-Dec |
|
| Antifungal activities of antineoplastic agents: Saccharomyces cerevisiae as a model system to study drug action. | 1999 Oct |
|
| Intrathecal methotrexate-induced megaloblastic anemia in patients with acute leukemia. | 1999 Sep |
|
| Atypical methotrexate dermatitis and vasculitis in a patient with ankylosing spondylitis. | 2000 |
|
| Influence of cyclosporin A on radiological progression in early rheumatoid arthritis patients: a 42-month prospective study. | 2000 |
|
| Carboxypeptidase G2 rescue in delayed methotrexate elimination in renal failure. | 2000 Apr |
|
| Methotrexate, uracil and tegafur, and leucovorin chemotherapy for patients with breast cancer in progression after high-dose chemotherapy with peripheral blood progenitor cell transplant: a phase II study. | 2000 Dec |
|
| Adjuvant doxorubicin and cyclophosphamide versus cyclophosphamide, methotrexate, and 5-fluorouracil chemotherapy in premenopausal women with axillary lymph node positive breast carcinoma. | 2000 Dec 15 |
|
| Manic episode in an ifosfamide-treated patient. | 2000 Jan-Feb |
|
| Veno-occlusive disease of the liver associated with thiopurines in a child with acute lymphoblastic leukemia. | 2000 Jul-Aug |
|
| Cerebral vasculopathy and multiple infarctions in a woman with carcinomatous meningitis while on treatment with intrathecal methotrexate. | 2000 May |
|
| Hepatocellular carcinoma: a rare late event in childhood acute lymphoblastic leukemia. | 2000 May-Jun |
|
| Cutaneous ulcerations in a patient with rheumatoid arthritis receiving treatment with methotrexate. | 2000 Sep |
|
| Role of non-alcoholic steatohepatitis in methotrexate-induced liver injury. | 2001 Dec |
|
| Transient posterior encephalopathy induced by chemotherapy in children. | 2001 Feb |
|
| A comparison of methods of loco-regional chemotherapy combined with systemic chemotherapy as neo-adjuvant treatment of osteosarcoma of the extremity. | 2001 Feb |
|
| Neoadjuvant chemotherapy for high grade osteosarcoma of the extremities: long-term results for patients treated according to the Rizzoli IOR/OS-3b protocol. | 2001 Feb |
|
| [Methotrexate, liver and rheumatoid arthritis in tropical areas]. | 2001 Jul-Sep |
|
| Motor nervous pathway function is impaired after treatment of childhood acute lymphoblastic leukemia: a study with motor evoked potentials. | 2001 Mar |
|
| Neoadjuvant chemotherapy for osteosarcoma of the extremity: long-term results of the Rizzoli's 4th protocol. | 2001 Nov |
|
| Tamoxifen-based treatment induces clinically meaningful responses in multiple myeloma patients with relapsing disease after autotransplantation. | 2001 Nov-Dec |
|
| Multiple anomalies in a fetus exposed to low-dose methotrexate in the first trimester. | 2002 Apr |
|
| CYP3A4 induction by drugs: correlation between a pregnane X receptor reporter gene assay and CYP3A4 expression in human hepatocytes. | 2002 Jul |
|
| The MRP4/ABCC4 gene encodes a novel apical organic anion transporter in human kidney proximal tubules: putative efflux pump for urinary cAMP and cGMP. | 2002 Mar |
Patents
Sample Use Guides
Usual Adult Dose for Acute Lymphoblastic Leukemia
Induction: 3.3 mg/m2/day orally or IM (in combination with prednisone 60 mg/m2) daily
Usual Adult Dose for Psoriasis
Single Dose: 7.5 mg/week orally, IM, or IV until adequate response is achieved
Divided Dose: 2.5 mg orally, IM, or IV every 12 hours for 3 doses once a week
Maximum weekly dose: 20 mg
Route of Administration:
Other
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
IARC | Methotrexate | ||
|
FDA ORPHAN DRUG |
469315
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
LIVERTOX |
NBK548219
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
FDA ORPHAN DRUG |
440314
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
FDA ORPHAN DRUG |
679019
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
WHO-VATC |
QL01BA01
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
FDA ORPHAN DRUG |
479515
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
WHO-ESSENTIAL MEDICINES LIST |
8.2
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
NCI_THESAURUS |
C511
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
FDA ORPHAN DRUG |
76693
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
FDA ORPHAN DRUG |
754320
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
FDA ORPHAN DRUG |
829121
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
WHO-ATC |
L01BA01
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
NDF-RT |
N0000175584
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
NCI_THESAURUS |
C2153
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
EU-Orphan Drug |
EU/3/07/495
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
FDA ORPHAN DRUG |
286409
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
FDA ORPHAN DRUG |
479615
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
WHO-VATC |
QL04AX03
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
NDF-RT |
N0000000111
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
WHO-ATC |
L04AX03
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
FDA ORPHAN DRUG |
43389
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
WHO-ESSENTIAL MEDICINES LIST |
2.4
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
||
|
FDA ORPHAN DRUG |
630518
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
CHEMBL34259
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
YL5FZ2Y5U1
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
1414003
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
6851
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | RxNorm | ||
|
m7327
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | Merck Index | ||
|
126941
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
50681
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
DB00563
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
1751
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
100000090250
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
200-413-8
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
3123
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
59-05-2
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
4815
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
METHOTREXATE
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | Description: A yellow to orange, crystalline powder. Solubility: Practically insoluble in water, ethanol (~750 g/l) TS, dichloroethane R, and ether R; very soluble in diluted solutions of alkali hydroxides and carbonates. Category: Cytotoxic drug.Storage: Methotrexate should be kept in a tightly closed container, protected from light. Additional information: Methotrexate is gradually affected by light. CAUTION: Methotrexate must be handled with care, avoiding contact with the skin and inhalation of airborne particles. Definition: Methotrexate contains not less than 96.0% and not more than 102.0% of C20H22N8O5, calculated with reference to the anhydrous substance. | ||
|
DTXSID4020822
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
44185
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
926
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
METHOTREXATE
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
Methotrexate
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
Methotrexate
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
YL5FZ2Y5U1
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
D008727
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
C642
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
SUB08856MIG
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY | |||
|
740
Created by
admin on Sat Dec 16 20:08:03 UTC 2023 , Edited by admin on Sat Dec 16 20:08:03 UTC 2023
|
PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE INACTIVE (PARENT)
SALT/SOLVATE (PARENT)
