TMQ

TRIMETREXATE

Created: 1999-07-08
Last modified:  2011-06-04

Help

Find related ligands:

Chemical Details

Formal Charge1
Atom Count51
Chiral Atom Count0
Bond Count53
Aromatic Bond Count17
2D diagram of TMQ
Toggle HydrogenToggle Labels

Chemical Component Summary

NameTRIMETREXATE
Systematic Name (OpenEye OEToolkits)5-methyl-6-[[(3,4,5-trimethoxyphenyl)amino]methyl]quinazolin-1-ium-2,4-diamine
FormulaC19 H24 N5 O3
Molecular Weight370.426
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O(c1cc(cc(OC)c1OC)NCc2c(c3c(cc2)[nH+]c(nc3N)N)C)C
SMILESCACTVS3.341COc1cc(NCc2ccc3[nH+]c(N)nc(N)c3c2C)cc(OC)c1OC
SMILESOpenEye OEToolkits1.5.0Cc1c(ccc2c1c(nc([nH+]2)N)N)CNc3cc(c(c(c3)OC)OC)OC
Canonical SMILESCACTVS3.341 COc1cc(NCc2ccc3[nH+]c(N)nc(N)c3c2C)cc(OC)c1OC
Canonical SMILESOpenEye OEToolkits1.5.0 Cc1c(ccc2c1c(nc([nH+]2)N)N)CNc3cc(c(c(c3)OC)OC)OC
InChIInChI1.03 InChI=1S/C19H23N5O3/c1-10-11(5-6-13-16(10)18(20)24-19(21)23-13)9-22-12-7-14(25-2)17(27-4)15(8-12)26-3/h5-8,22H,9H2,1-4H3,(H4,20,21,23,24)/p+1
InChIKeyInChI1.03 NOYPYLRCIDNJJB-UHFFFAOYSA-O

Drug Info: DrugBank

DrugBank IDDB01157 
NameTrimetrexate
Groups
  • approved
  • investigational
DescriptionA nonclassical folic acid inhibitor through its inhibition of the enzyme dihydrofolate reductase. It is being tested for efficacy as an antineoplastic agent and as an antiparasitic agent against pneumocystis pneumonia in AIDS patients. Myelosuppression is its dose-limiting toxic effect.
Synonyms
  • Trimetrexatum
  • Trimetrexate
  • Trimetrexate glucuronate
  • Trimetrexato
Brand Names
  • Neutrexin
  • Neutrexin Pws IV 25mg/vial
IndicationFor use, with concurrent leucovorin administration (leucovorin protection), as an alternative therapy for the treatment of moderate-to-severe <i>Pneumocystis carinii</i> pneumonia (PCP) in immunocompromised patients, including patients with the acquired immunodeficiency syndrome (AIDS). Also used to treat several types of cancer including colon cancer.
Categories
  • Acids, Acyclic
  • Acids, Aldehydic
  • Anti-Infective Agents
  • Antimetabolites
  • Antineoplastic Agents
ATC-CodeP01AX07
CAS number52128-35-5

Drug Targets

NameTarget SequencePharmacological ActionActions
Dihydrofolate reductaseMVGSLNCIVAVSQNMGIGKNGDLPWPPLRNEFRYFQRMTTTSSVEGKQNL...unknowninhibitor
Folate transporter 1MVPSSPAVEKQVPVEPGPDPELRSWRHLVCYLCFYGFMAQIRPGESFITP...unknownsubstrate
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
PubChem 59961053, 5582
CCDC/CSD FOGWAZ, FUFQUS
COD 2011412