Chemical Component Summary

NameAminopterin
SynonymsN-(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid
Identifiers(2S)-2-[[4-[[2,4-bis(azanyl)pteridin-6-yl]methylamino]phenyl]carbonylamino]pentanedioic acid
FormulaC19 H20 N8 O5
Molecular Weight440.413
TypeNON-POLYMER
Isomeric SMILESc1cc(ccc1C(=O)N[C@@H](CCC(=O)O)C(=O)O)NCc2cnc3c(n2)c(nc(n3)N)N
InChIInChI=1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27)/t12-/m0/s1
InChIKeyTVZGACDUOSZQKY-LBPRGKRZSA-N

Chemical Details

Formal Charge0
Atom Count52
Chiral Atom Count1
Bond Count54
Aromatic Bond Count17

Drug Info: DrugBank

DrugBank IDDB08878 
NameAminopterin
Groups
  • investigational
  • withdrawn
DescriptionAminopterin is an amino derivative of folic acid, which was once used as an antineoplastic agent in the treatment of pediatric leukemia. In the 1950's its production was discontinued in favor of methotrexate, which is less potent but less toxic. Off label, aminopterin has also been used in the treatment of psoriasis. Clinicians need to be aware of the characteristic teratologic effects of aminopterin and methotrexate.
Synonyms
  • 4-aminopteroylglutamic acid
  • Minopterin
  • Aminopterin
  • 4-amino-4-deoxypteroylglutamate
  • Aminopteridine
IndicationPrior to its withdrawal, aminopterin was initially used in the treatment of childhood leukemia; specifically to induce remissions. Later, aminopterin was used off-label in the United States to treat psoriasis, yielding dramatic lesion clearing. Aminopterin was later supplanted by methotrexate for treating cancer because of its better therapeutic index. Aminopterin (as well as methotrexate) has also been explored for use as an abortifacient. However, their association with severe congenital malformations and teratogenic effects have become known as fetal aminopterin syndrome.
Categories
  • Enzyme Inhibitors
  • Folic Acid Antagonists
  • Heterocyclic Compounds, Fused-Ring
  • Pteridines
  • Pterins
CAS number54-62-6

Drug Targets

NameTarget SequencePharmacological ActionActions
Dihydrofolate reductaseMVGSLNCIVAVSQNMGIGKNGDLPWPPLRNEFRYFQRMTTTSSVEGKQNL...unknowninhibitor
Proton-coupled folate transporterMEGSASPPEKPRARPAAAVLCRGPVEPLVFLANFALVLQGPLTTQYLWHR...unknown
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 CHEMBL376180
PubChem 169371
ChEMBL CHEMBL376180
ChEBI CHEBI:22526