Responsive image

Common name


Methotrexate

IUPAC name


(2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid

SMILES


CN(CC1=CN=C2N=C(N)N=C(N)C2=N1)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C(O)=O

Compound class


Antineoplastic Agents; Antirheumatic Agents; Dermatologic Agents; Immunosuppressive Agents; Enzyme Inhibitors; Antimetabolites; Folic Acid Antagonists; Nucleic Acid Synthesis Inhibitors; Antimetabolites, Antineoplastic; Abortifacient Agents, Nonsteroidal; Abortifacient Agents; Antineoplastic and Immunomodulating Agents; Folic Acid Analogues;

Therapeutic area


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.

Common name


Methotrexate

IUPAC name


(2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid

SMILES


CN(CC1=CN=C2N=C(N)N=C(N)C2=N1)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C(O)=O

INCHI


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

FORMULA


C20H22N8O5

Responsive image

Common name


Methotrexate

IUPAC name


(2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid

Molecular weight


454.439

clogP


-0.664

clogS


-3.232

HBond Acceptor


10

HBond Donor


7

Total Polar
Surface Area


210.54

Number of Rings


3

Rotatable Bond


9

Drug ID Common name Structure CAS SMILE Frequency
FDBF00003 formamide Responsive image C(=O)N 0.1240
FDBF00004 acetic acid Responsive image CC(=O)O 0.0687
FDBF00005 benzene Responsive image c1ccccc1 0.2824
FDBF00047 propionic acid Responsive image CCC(=O)O 0.0395
FDBF00048 benzamide Responsive image O=C(N)c1ccccc1 0.0117
FDBF00049 N-methylaniline Responsive image CNc1ccccc1 0.0076
FDBF00050 4-(methylamino)benzamide Responsive image CNc1ccc(cc1)C(=O)N 0.0014
FDBF00066 N-methylmethanamine Responsive image N(C)C 0.0914
FDBF00642 N,N-dimethylaniline Responsive image CN(C)c1ccccc1 0.0045
FDBF01279 4-(dimethylamino)benzamide Responsive image CN(c1ccc(cc1)C(=O)N)C 0.0003
10 , 2