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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
Structure of METHOTREXATE

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

HIDE SMILES / InChI

Molecular Formula C20H22N8O5
Molecular Weight 454.4393
Charge 0
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
Brain damage after intrathecal methotrexate.
1975 Aug
[Disseminated necrotizing leukoencephalopathy following intrathecal methotrexate in childhood leukemia (author's transl)].
1976 Jan
Toxicity profile of methotrexate in rheumatoid arthritis. A preliminary survey.
1999
Combination therapy in early rheumatoid arthritis: a randomised, controlled, double blind 52 week clinical trial of sulphasalazine and methotrexate compared with the single components.
1999 Apr
Management of separation pain after single-dose methotrexate therapy for ectopic pregnancy.
1999 Apr
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
Developmental delay in fetal aminopterin/methotrexate syndrome.
1999 Jul
Subacute encephalopathy after combination chemotherapy including moderate-dose methotrexate in a patient with gastric cancer.
1999 Mar
Porphyria cutanea tarda affecting a rheumatoid arthritis patient treated with methotrexate: association or coincidence?
1999 May
Low-dose oral pulse methotrexate as monotherapy in elderly patients with bullous pemphigoid.
1999 May
Serosal complications of single-agent low-dose methotrexate used in gestational trophoblastic diseases: first reported case of methotrexate-induced peritonitis.
1999 Nov
Angio-neurotic oedema associated with methotrexate treatment in rheumatoid arthritis.
1999 Sep
Intrathecal methotrexate-induced megaloblastic anemia in patients with acute leukemia.
1999 Sep
Carboxypeptidase G2 rescue in delayed methotrexate elimination in renal failure.
2000 Apr
[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
Manic episode in an ifosfamide-treated patient.
2000 Jan-Feb
Impotence in a patient with rheumatoid arthritis treated with methotrexate.
2000 Jul
Veno-occlusive disease of the liver associated with thiopurines in a child with acute lymphoblastic leukemia.
2000 Jul-Aug
White matter changes on MRI during treatment in children with acute lymphoblastic leukemia: correlation with neuropsychological findings.
2000 Nov
Acute neurotoxicity in children with B-lineage acute lymphoblastic leukemia (B-ALL) treated with intermediate risk protocols.
2000 Nov
Expression and characterization of recombinant human-derived Pneumocystis carinii dihydrofolate reductase.
2000 Nov
Methotrexate treatment protocols and the central nervous system: significant cure with significant neurotoxicity.
2000 Sep
[Conservative therapy in endocrine orbitopathy: "State of the art"].
2001
Randomized, double-blind, crossover, placebo-controlled trial of intravenous ondansetron for the prevention of intrathecal chemotherapy-induced vomiting in children.
2001 Dec
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
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
[Fatal outcome of a multisystemic sarcoidosis in a 54-year-old patient].
2001 Jul
Successful rescue with leucovorin and thymidine in a patient with high-dose methotrexate induced acute renal failure.
2001 Jun
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
Mutation of Trp1254 in the multispecific organic anion transporter, multidrug resistance protein 2 (MRP2) (ABCC2), alters substrate specificity and results in loss of methotrexate transport activity.
2001 Oct 12
Methylation-dependent silencing of the reduced folate carrier gene in inherently methotrexate-resistant human breast cancer cells.
2001 Oct 26
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-induced systemic vasculitis.
2002 Feb
Methotrexate-related nonnecrotizing multifocal axonopathy detected by beta-amyloid precursor protein immunohistochemistry.
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
[A case of subacute transient cerebral dysfunction in a osteosarcoma patient following high-dose methotrexate].
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
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 Fri Dec 16 16:53:08 UTC 2022
Edited
by admin
on Fri Dec 16 16:53:08 UTC 2022
Record UNII
YL5FZ2Y5U1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHOTREXATE
EP   HSDB   INN   MART.   MI   USAN   USP   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
METHOTREXATE [WHO-IP]
Common Name English
METHOTREXATE [USP-RS]
Common Name English
METHYLAMINOPTERIN
Common Name English
METHOTREXATE [EP MONOGRAPH]
Common Name English
Methotrexate [WHO-DD]
Common Name English
methotrexate [INN]
Common Name English
METHOTREXATUM [WHO-IP LATIN]
Common Name English
METHOTREXATE [IARC]
Common Name English
METHOTREXATE [USAN]
Common Name English
METHOTREXATE [ORANGE BOOK]
Common Name English
AMETHOPTERIN
Common Name English
XATMEP
Brand Name English
METHOTREXATE [MART.]
Common Name English
ADX-2191
Code English
METHOTREXATE [MI]
Common Name English
REDITREX
Brand Name English
R-9985
Code English
CL-14377
Code English
METHOTREXATE [USP MONOGRAPH]
Common Name English
METHOTREXATE [INCI]
Common Name English
METHOTREXATE [HSDB]
Common Name English
MTX
Common Name English
RASUVO
Brand Name English
METHOTREXATE [USP IMPURITY]
Common Name English
CL 14377
Code English
NSC-740
Code English
METHOTREXATE [JAN]
Common Name English
(2S)-2-((4-(((2,4-DIAMINOPTERIDIN-6-YL)METHYL)(METHYL)AMINO)BENZOYL)AMINO)PENTANEDIOIC ACID
Systematic Name English
METHOTREXATE [VANDF]
Common Name English
JYLAMVO
Brand Name English
Classification Tree Code System Code
IARC Methotrexate
FDA ORPHAN DRUG 469315
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
LIVERTOX NBK548219
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
FDA ORPHAN DRUG 440314
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
FDA ORPHAN DRUG 679019
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
WHO-VATC QL01BA01
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
FDA ORPHAN DRUG 479515
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
WHO-ESSENTIAL MEDICINES LIST 8.2
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
NCI_THESAURUS C511
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
FDA ORPHAN DRUG 76693
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
FDA ORPHAN DRUG 754320
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
FDA ORPHAN DRUG 829121
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
WHO-ATC L01BA01
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
NDF-RT N0000175584
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
NCI_THESAURUS C2153
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
EU-Orphan Drug EU/3/07/495
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
FDA ORPHAN DRUG 286409
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
FDA ORPHAN DRUG 479615
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
WHO-VATC QL04AX03
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
NDF-RT N0000000111
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
WHO-ATC L04AX03
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
FDA ORPHAN DRUG 43389
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
WHO-ESSENTIAL MEDICINES LIST 2.4
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
FDA ORPHAN DRUG 630518
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
Code System Code Type Description
ChEMBL
CHEMBL34259
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
FDA UNII
YL5FZ2Y5U1
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
RS_ITEM_NUM
1414003
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
RXCUI
6851
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY RxNorm
MERCK INDEX
M7327
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY Merck Index
PUBCHEM
126941
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
CHEBI
50681
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
DRUG BANK
DB00563
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
DRUG CENTRAL
1751
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
ECHA (EC/EINECS)
200-413-8
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
HSDB
3123
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
CAS
59-05-2
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
IUPHAR
4815
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
METHOTREXATE
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
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.
EPA CompTox
DTXSID4020822
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
CHEBI
44185
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
INN
926
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
WIKIPEDIA
METHOTREXATE
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
UCSF-FDA TRANSPORTAL
Methotrexate
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
LACTMED
Methotrexate
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
DAILYMED
YL5FZ2Y5U1
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
MESH
D008727
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
NCI_THESAURUS
C642
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
EVMPD
SUB08856MIG
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
NSC
740
Created by admin on Fri Dec 16 16:53:08 UTC 2022 , Edited by admin on Fri Dec 16 16:53:08 UTC 2022
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
TRANSPORTER -> SUBSTRATE
SOLVATE->ANHYDROUS
DERIVATIVE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TARGET -> INHIBITOR
RACEMATE -> ENANTIOMER
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE INACTIVE -> PARENT
URINE
METABOLITE TOXIC -> PARENT
7-OH-MTX levels were correlated with nephrotoxicity in adolescents.
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
If present, methotrexate dimethylamide and Methotrexate related compound I may not be completely resolved by the method. These peaks are integrated together to determine conformance (NMT 0.2%)
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.8
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC Elimination
PHARMACOKINETIC
Population
PHARMACOKINETIC
Elimination
PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC Steady state
PHARMACOKINETIC
Initial
PHARMACOKINETIC