MTX

METHOTREXATE

Created: 1999-07-08
Last modified:  2024-09-27

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Chemical Details

Formal Charge0
Atom Count55
Chiral Atom Count1
Bond Count57
Aromatic Bond Count17
2D diagram of MTX
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Chemical Component Summary

NameMETHOTREXATE
Systematic Name (OpenEye OEToolkits)(2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]phenyl]carbonylamino]pentanedioic acid
FormulaC20 H22 N8 O5
Molecular Weight454.439
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C(O)C(NC(=O)c1ccc(cc1)N(C)Cc2nc3c(nc2)nc(nc3N)N)CCC(=O)O
SMILESCACTVS3.341CN(Cc1cnc2nc(N)nc(N)c2n1)c3ccc(cc3)C(=O)N[CH](CCC(O)=O)C(O)=O
SMILESOpenEye OEToolkits1.5.0CN(Cc1cnc2c(n1)c(nc(n2)N)N)c3ccc(cc3)C(=O)NC(CCC(=O)O)C(=O)O
Canonical SMILESCACTVS3.341 CN(Cc1cnc2nc(N)nc(N)c2n1)c3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O
Canonical SMILESOpenEye OEToolkits1.5.0 CN(Cc1cnc2c(n1)c(nc(n2)N)N)c3ccc(cc3)C(=O)N[C@@H](CCC(=O)O)C(=O)O
InChIInChI1.03 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
InChIKeyInChI1.03 FBOZXECLQNJBKD-ZDUSSCGKSA-N

Drug Info: DrugBank

DrugBank IDDB00563 
NameMethotrexate
Groups approved
DescriptionMethotrexate is a folate derivative that inhibits several enzymes responsible for nucleotide synthesis.[A180322] This inhibition leads to suppression of inflammation as well as prevention of cell division.[A180322] Because of these effects, methotrexate is often used to treat inflammation caused by arthritis or to control cell division in neoplastic diseases such as breast cancer and non-Hodgkin's lymphoma.[A180322,L7144,L7147,L7150,L7180] Due to the toxic effects of methotrexate, it is indicated for treatment of some forms of arthritis and severe psoriasis only if first line treatment has failed or patients are intolerant of those treatments.[L7180] Methotrexate was granted FDA approval on 7 December 1953.[L7198]
Synonyms
  • 4-amino-N(10)-methylpteroylglutamic acid
  • Méthotrexate
  • Methotrexatum
  • Metotrexato
  • Amethopterin
Brand Names
  • Methotrexate-pws Im IV Iar Int Ivr 20mg/vial
  • Auro-methotrexate
  • Methotrexate-liq Im IV Iar Int Ivr 25mg/ml
  • Methotrexate Dbl Inj 25mg/ml
  • Methotrexate PF/sa Injection
IndicationMethotrexate oral solution is indicated for pediatric acute lymphoblastic leukemia and pediatric polyarticular juvenile idiopathic arthritis.[L7144] Methotrexate injections for subcutaneous use are indicated for severe active rheumatoid arthritis, polyarticular juvenile idiopathic arthritis and severe, recalcitrant, disabling psoriasis.[L7147,L7150,L10457] It has also been approved by the EMA for the treatment of adult patients requiring systemic therapy for moderate-to-severe plaque psoriasis.[L48796] Other formulations are indicated to treat gestational choriocarcinoma, chorioadenoma destruens, hydatiform mole, breast cancer, epidermoid cancer of the head and neck, advanced mycosis fungoides, lung cancer, and advanced non-Hodgkin's lymphoma.[L7180] It is also used in the maintenance of acute lymphocytic leukemia.[L7180] Methotrexate is also given before treatment with leucovorin to prolong relapse-free survival following surgical removal of a tumour in non-metastatic osteosarcoma.[L7180]
Categories
  • Abortifacient Agents
  • Abortifacient Agents, Nonsteroidal
  • Agents Causing Muscle Toxicity
  • Antimetabolites
  • Antineoplastic Agents
ATC-Code
  • L04AX03
  • L01BA01
CAS number59-05-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Thymidylate synthaseMPVAGSELPRRPLPPAAQERDAEPRPPHGELQYLGQIQHILRCGVRKDDR...unknowninhibitor
Bifunctional purine biosynthesis protein PURHMAPGQLALFSVSDKTGLVEFARNLTALGLNLVASGGTAKALRDAGLAVRD...unknowninhibitor
Dihydrofolate reductaseMVGSLNCIVAVSQNMGIGKNGDLPWPPLRNEFRYFQRMTTTSSVEGKQNL...unknowninhibitor
Dihydrofolate reductaseMVGSLNCIVAVSQNMGIGKNGDLPWPPLRNEFRYFQRMTTTSSVEGKQNL...unknownsubstrate
Aldehyde oxidaseMDRASELLFYVNGRKVIEKNVDPETMLLPYLRKKLRLTGTKYGCGGGGCG...unknownsubstrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL34259
PubChem 126941
ChEMBL CHEMBL34259
ChEBI CHEBI:44185