methotrexate (CHEBI:44185)

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CHEBI:44185 - methotrexate

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ChEBI Name	methotrexate

ChEBI ID	CHEBI:44185

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:44183, CHEBI:6837

Supplier Information	ChemicalBook:CB2739302, ChemicalBook:CB2704227, eMolecules:476359, Selleckchem:Abitrexate, ZINC000001529323

Download	Molfile XML SDF

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M END): 18 ms

reading 55 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

55 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Molfile expand

Wikipedia	License
Methotrexate, formerly known as amethopterin, is a chemotherapy agent and immune-system suppressant. It is used to treat cancer, autoimmune diseases, and ectopic pregnancies. Types of cancers it is used for include breast cancer, leukemia, lung cancer, lymphoma, gestational trophoblastic disease, and osteosarcoma. Types of autoimmune diseases it is used for include psoriasis, rheumatoid arthritis, and Crohn's disease. It can be given by mouth or by injection. Common side effects include nausea, feeling tired, fever, increased risk of infection, low white blood cell counts, and breakdown of the skin inside the mouth. Other side effects may include liver disease, lung disease, lymphoma, and severe skin rashes. People on long-term treatment should be regularly checked for side effects. It is not safe during breastfeeding. In those with kidney problems, lower doses may be needed. It acts by blocking the body's use of folic acid. Methotrexate was first made in 1947 and initially was used to treat cancer, as it was less toxic than the then-current treatments. In 1956 it provided the first cures of a metastatic cancer. It is on the World Health Organization's List of Essential Medicines. Methotrexate is available as a generic medication. In 2022, it was the 132nd most commonly prescribed medication in the United States, with more than 4 million prescriptions.
Read full article at Wikipedia

Formula

C20H22N8O5

Net Charge

Average Mass

454.43960

Monoisotopic Mass

454.17132

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

InChIKey

FBOZXECLQNJBKD-ZDUSSCGKSA-N

SMILES

CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(cc1)C(=O)N[C@@H](CCC(O)=O)C(O)=O

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	EC 1.5.1.3 (dihydrofolate reductase) inhibitor An EC 1.5.1.* (oxidoreductase acting on donor CH-NH group, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of dihydrofolate reductase (EC 1.5.1.3). immunosuppressive agent An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. DNA synthesis inhibitor Any substance that inhibits the synthesis of DNA. antimetabolite A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.

Application(s):	immunosuppressive agent An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. abortifacient A chemical substance that interrupts pregnancy after implantation. dermatologic drug A drug used to treat or prevent skin disorders or for the routine care of skin. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. antirheumatic drug A drug used to treat rheumatoid arthritis.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	methotrexate (CHEBI:44185) has functional parent L-glutamic acid (CHEBI:16015) methotrexate (CHEBI:44185) has role abortifacient (CHEBI:50691) methotrexate (CHEBI:44185) has role antimetabolite (CHEBI:35221) methotrexate (CHEBI:44185) has role antineoplastic agent (CHEBI:35610) methotrexate (CHEBI:44185) has role antirheumatic drug (CHEBI:35842) methotrexate (CHEBI:44185) has role dermatologic drug (CHEBI:50177) methotrexate (CHEBI:44185) has role DNA synthesis inhibitor (CHEBI:59517) methotrexate (CHEBI:44185) has role EC 1.5.1.3 (dihydrofolate reductase) inhibitor (CHEBI:50683) methotrexate (CHEBI:44185) has role immunosuppressive agent (CHEBI:35705) methotrexate (CHEBI:44185) is a dicarboxylic acid (CHEBI:35692) methotrexate (CHEBI:44185) is a monocarboxylic acid amide (CHEBI:29347) methotrexate (CHEBI:44185) is a pteridines (CHEBI:26373) methotrexate (CHEBI:44185) is conjugate acid of methotrexate(1−) (CHEBI:50680)

Incoming	methotrexate(1−) (CHEBI:50680) is conjugate base of methotrexate (CHEBI:44185)

IUPAC Name

N-(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)-L-glutamic acid

INNs	Sources
methotrexate	KEGG DRUG
methotrexatum	ChemIDplus
metotrexato	ChemIDplus

Synonyms	Sources
4-amino-10-methylfolic acid	ChemIDplus
4-amino-N¹⁰-methylpteroylglutamic acid	NIST Chemistry WebBook
Methotrexate	KEGG COMPOUND
METHOTREXATE	PDBeChem
MTX	ChemIDplus
N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid	NIST Chemistry WebBook

Brand Names	Sources
Emtexate	DrugBank
Ledertrexate	DrugBank
Rheumatrex	DrugBank
Trexall	DrugBank

Manual Xrefs	Databases
1751	DrugCentral
C01937	KEGG COMPOUND
D00142	KEGG DRUG
DB00563	DrugBank
LSM-5690	LINCS
Methotrexate	Wikipedia
MTX	PDBeChem
US2512572	Patent
View more database links

Registry Numbers	Types	Sources
59-05-2	CAS Registry Number	NIST Chemistry WebBook
59-05-2	CAS Registry Number	ChemIDplus
70669	Beilstein Registry Number	Beilstein

Last Modified

22 February 2017

CHEBI:44185 - methotrexate

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