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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H20N8O5.2Na
Molecular Weight 498.4037
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHOTREXATE SODIUM

SMILES

CN(Cc1cnc2c(c(N)[nH]c(=N)n2)n1)c3ccc(cc3)C(=O)N[C@@]([H])(CCC(=O)[O-])C(=O)[O-].[Na+].[Na+]

InChI

InChIKey=DASQOOZCTWOQPA-GXKRWWSZSA-L
InChI=1S/C20H22N8O5.2Na/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);;/q;2*+1/p-2/t13-;;/m0../s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C20H20N8O5
Molecular Weight 452.4242
Charge -2
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

CNS Activity

Curator's Comment:: modest blood-brain barrier (BBB) permeability

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.19 pM [Ki]
0.18 mM [IC50]
15.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
OTREXUP

Approved Use

Otrexup 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 Use

Neoplastic 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 Date

9.8504638E11
Primary
TREXALL

Approved Use

Neoplastic 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 Date

9.8504638E11
Primary
TREXALL

Approved Use

Neoplastic 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 Date

9.8504638E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
3533 nM × h
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

T1/2

ValueDoseCo-administeredAnalytePopulation
55 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
50%
METHOTREXATE serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
75 mg single, oral
Overdose
Dose: 75 mg
Route: oral
Route: single
Dose: 75 mg
Sources:
unknown, 10-19 years
n = 1
Health Status: unknown
Age Group: 10-19 years
Sex: M
Population Size: 1
Sources:
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea (1 patient)
Vomiting (1 patient)
Sources:
87.5 mg single, oral
Overdose
Dose: 87.5 mg
Route: oral
Route: single
Dose: 87.5 mg
Sources:
unknown, 10-19 years
n = 1
Health Status: unknown
Age Group: 10-19 years
Sex: F
Population Size: 1
Sources:
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea (1 patient)
Vomiting (1 patient)
Sources:
50 mg single, oral
Overdose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
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)
Neutropenia (grade 3, 1 patient)
Digestion impaired (grade 3, 1 patient)
Sources:
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)
Mucosal ulceration (1 patient)
Abdominal pain (1 patient)
Sources:
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)
guratimod(50 mg/day for approximately 3 years.)
Sources:
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...
Other AEs:
Mucosal ulceration (2 patients)
Sources:
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)
Nausea (1 patient)
Vomiting (1 patient)
Diarrhea (1 patient)
Abdominal pain (1 patient)
Sources:
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...
Other AEs:
Adverse event (grade 5)
Sources:
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...
Other AEs:
Adverse event (grade 5)
Sources:
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...
Other AEs:
Adverse event (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:
pregnant, adult
Other AEs: Fetal damage...
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)
Hepatic and hepatobiliary disorders (serious)
Respiratory tract disorders NEC (serious)
Skin and subcutaneous conditions NEC (serious)
Kidney disorder (serious)
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:
pregnant, adult
Health Status: pregnant
Age Group: adult
Sex: F
Sources:
Other AEs: Fetal damage...
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
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)
Respiratory tract disorders NEC (serious)
Skin and subcutaneous conditions NEC (serious)
Kidney disorder (serious)
Sources:
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
Other AEs: Bone marrow depression, Aplastic anemia...
Other AEs:
Bone marrow depression (severe|grade 5)
Aplastic anemia (severe|grade 5)
Gastrointestinal toxicity (severe|grade 5)
Sources:
AEs

AEs

AESignificanceDosePopulation
Nausea 1 patient
75 mg single, oral
Overdose
Dose: 75 mg
Route: oral
Route: single
Dose: 75 mg
Sources:
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
Dose: 75 mg
Route: oral
Route: single
Dose: 75 mg
Sources:
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
Dose: 87.5 mg
Route: oral
Route: single
Dose: 87.5 mg
Sources:
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
Dose: 87.5 mg
Route: oral
Route: single
Dose: 87.5 mg
Sources:
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)
guratimod(50 mg/day for approximately 3 years.)
Sources:
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
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
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
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
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victim
PubMed

PubMed

TitleDatePubMed
Cytogenetic studies in a patient with acute granulocytic leukemia of seven and one-half years duration.
1975 Nov
Letter: Vasculitis as a complication of high-dose methotrexate in the treatment of acute leukemia.
1976 Jun
Anterior lumbosacral radiculopathy after intrathecal methotrexate treatment.
1999 Aug
Toxic epidermal necrolysis and graft vs. host disease: a clinical spectrum but a diagnostic dilemma.
1999 Jul
Intrathecal methotrexate-induced megaloblastic anemia in patients with acute leukemia.
1999 Sep
Atypical methotrexate dermatitis and vasculitis in a patient with ankylosing spondylitis.
2000
[A case of rheumatoid arthritis associated with autoimmune hemolytic anemia due to weekly low-dose methotrexate therapy].
2000 Aug
[Carboxypeptidase-G2-rescue in a woman with methotrexate-induced renal failure].
2000 Aug 15
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
Atrial fibrillation occurring in a patient taking etanercept plus methotrexate for rheumatoid arthritis.
2000 Dec
Identification by RNA-based arbitrarily primed PCR of the involvement of cytochrome c oxidase in the development of resistance to methotrexate.
2000 Feb 28
Veno-occlusive disease of the liver associated with thiopurines in a child with acute lymphoblastic leukemia.
2000 Jul-Aug
Hepatocellular carcinoma: a rare late event in childhood acute lymphoblastic leukemia.
2000 May-Jun
Serious liver disease in a patient receiving methotrexate and leflunomide.
2000 Nov
Expression and characterization of recombinant human-derived Pneumocystis carinii dihydrofolate reductase.
2000 Nov
Design, synthesis, and X-ray crystal structure of a potent dual inhibitor of thymidylate synthase and dihydrofolate reductase as an antitumor agent.
2000 Oct 19
Methotrexate treatment protocols and the central nervous system: significant cure with significant neurotoxicity.
2000 Sep
Cutaneous ulcerations in a patient with rheumatoid arthritis receiving treatment with methotrexate.
2000 Sep
[Conservative therapy in endocrine orbitopathy: "State of the art"].
2001
Stereoselectivity of the folate transporter in rabbit small intestine: studies with amethopterin enantiomers.
2001
Hospital resources used for ectopic pregnancy treatment by laparoscopy and methotrexate.
2001 Apr-Jun
Transient posterior encephalopathy induced by chemotherapy in children.
2001 Feb
[Listeria arthritis in chronic polyarthritis during low dose prednisolone and methotrexate therapy. Case report and review of the literature].
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
Development of fulminant hepatitis B (precore variant mutant type) after the discontinuation of low-dose methotrexate therapy in a rheumatoid arthritis patient.
2001 Feb
The value of amino-terminal propeptide of type III procollagen in routine screening for methotrexate-induced liver fibrosis: a 10-year follow-up.
2001 Jan
A clinical study to determine the efficacy and safety of 1% methotrexate/Azone (MAZ) gel applied topically once daily in patients with psoriasis vulgaris.
2001 Jul
[Methotrexate, liver and rheumatoid arthritis in tropical areas].
2001 Jul-Sep
Successful rescue with leucovorin and thymidine in a patient with high-dose methotrexate induced acute renal failure.
2001 Jun
Motor nervous pathway function is impaired after treatment of childhood acute lymphoblastic leukemia: a study with motor evoked potentials.
2001 Mar
Inappropriate medical management of spinal epidural abscess.
2001 Mar
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
2001 May
[Meningeal carcinomatosis as the first manifestation of gastric adenocarcinoma].
2001 Oct 11
Methylation-dependent silencing of the reduced folate carrier gene in inherently methotrexate-resistant human breast cancer cells.
2001 Oct 26
Isolation of rat dihydrofolate reductase gene and characterization of recombinant enzyme.
2001 Sep
Neurotoxicity with leukoencephalopathy after a single intravenous high dose of methotrexate in a patient with lymphoma.
2002
Multiple anomalies in a fetus exposed to low-dose methotrexate in the first trimester.
2002 Apr
Methotrexate leukoencephalopathy presenting as Klüver-Bucy syndrome and uncinate seizures.
2002 Apr
Methotrexate-induced systemic vasculitis.
2002 Feb
High-dose cyclophosphamide followed by autologous peripheral blood progenitor cell transplantation improves the salvage treatment for persistent or sensitive relapsed malignant lymphoma.
2002 Jan
Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice.
2002 Jul
CYP3A4 induction by drugs: correlation between a pregnane X receptor reporter gene assay and CYP3A4 expression in human hepatocytes.
2002 Jul
Oral methotrexate for treatment of ectopic pregnancy.
2002 Jun
Radiation myelitis in a 5-year-old girl.
2002 Mar
Nephrotoxicity due to intermediate-dose methotrexate without rescue in an obese adolescent with acute lymphoblastic leukemia.
2002 Mar
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
Quantitative MRI assessment of leukoencephalopathy.
2002 May
CNS late-effects after ALL therapy in childhood. Part III: neuropsychological performance in long-term survivors of childhood ALL: impairments of concentration, attention, and memory.
2002 May
Comparison of abortions induced by methotrexate or mifepristone followed by misoprostol.
2002 May
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
VEGF and Ang-1 levels were significantly lower, and Ang-2 levels were significantly higher in NPs (organ-cultured nasal polyps) treated with 100-umolar Methotrexate than in nontreated NPs
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:29:47 UTC 2021
Edited
by admin
on Sat Jun 26 14:29:47 UTC 2021
Record UNII
3IG1E710ZN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHOTREXATE SODIUM
MART.   ORANGE BOOK   VANDF   WHO-DD  
Common Name English
ABITREXATE
Brand Name English
METHOTREXATE SODIUM SALT
Common Name English
METHOTREXATE (AS DISODIUM)
Common Name English
METHOTREXATE SODIUM [VANDF]
Common Name English
MEXATE
Brand Name English
TREXALL
Brand Name English
ADX-2191 SODIUM
Code English
METHOTREXATE SODIUM [WHO-DD]
Common Name English
METHOTREXATE DISODIUM
Common Name English
SODIUM L-(+)-METHOTREXATE
Common Name English
FOLEX
Brand Name English
DISODIUM METHOTREXATE
Common Name English
METHOTREXATE SODIUM [ORANGE BOOK]
Common Name English
METHOTREXATE DISODIUM SALT [MI]
Common Name English
METHOTREXATE DISODIUM SALT
MI  
Common Name English
METHOTREXATE SODIUM [MART.]
Common Name English
METHOTREXATE, SODIUM SALT
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2153
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
FDA ORPHAN DRUG 9985
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
NCI_THESAURUS C511
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
Code System Code Type Description
CAS
7413-34-5
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
PRIMARY
EVMPD
SUB03225MIG
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
PRIMARY
FDA UNII
3IG1E710ZN
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
PRIMARY
NCI_THESAURUS
C1735
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
PRIMARY
WIKIPEDIA
Methotrexate sodium
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
PRIMARY
CAS
15475-56-6
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
NON-SPECIFIC STOICHIOMETRY
RXCUI
287734
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
PRIMARY RxNorm
PUBCHEM
11329481
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
PRIMARY
DRUG BANK
DBSALT000115
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
PRIMARY
EVMPD
SUB16442MIG
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
PRIMARY
ECHA (EC/EINECS)
231-022-0
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
PRIMARY
ChEMBL
CHEMBL34259
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
PRIMARY
MERCK INDEX
M7327
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
PRIMARY Merck Index
EPA CompTox
15475-56-6
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
PRIMARY
ECHA (EC/EINECS)
239-495-5
Created by admin on Sat Jun 26 14:29:47 UTC 2021 , Edited by admin on Sat Jun 26 14:29:47 UTC 2021
ALTERNATIVE
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY