04J

Aminopterin

Created:	2011-11-23
Last modified:	2020-06-05

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Chemical Details
Formal Charge	0
Atom Count	52
Chiral Atom Count	1
Bond Count	54
Aromatic Bond Count	17

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Chemical Component Summary
Name	Aminopterin
Synonyms	N-(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid
Systematic Name (OpenEye OEToolkits)	(2S)-2-[[4-[[2,4-bis(azanyl)pteridin-6-yl]methylamino]phenyl]carbonylamino]pentanedioic acid
Formula	C₁₉ H₂₀ N₈ O₅
Molecular Weight	440.413
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=C(O)C(NC(=O)c1ccc(cc1)NCc2nc3c(nc2)nc(nc3N)N)CCC(=O)O
SMILES	CACTVS	3.370	Nc1nc(N)c2nc(CNc3ccc(cc3)C(=O)N[CH](CCC(O)=O)C(O)=O)cnc2n1
SMILES	OpenEye OEToolkits	1.7.6	c1cc(ccc1C(=O)NC(CCC(=O)O)C(=O)O)NCc2cnc3c(n2)c(nc(n3)N)N
Canonical SMILES	CACTVS	3.370	Nc1nc(N)c2nc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)cnc2n1
Canonical SMILES	OpenEye OEToolkits	1.7.6	c1cc(ccc1C(=O)N[C@@H](CCC(=O)O)C(=O)O)NCc2cnc3c(n2)c(nc(n3)N)N
InChI	InChI	1.03	InChI=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
InChIKey	InChI	1.03	TVZGACDUOSZQKY-LBPRGKRZSA-N

Drug Info: DrugBank

DrugBank ID	DB08878
Name	Aminopterin
Groups	withdrawn investigational
Description	Aminopterin 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 Pteramina 4-amino-4-deoxypteroylglutamate N-(4-(((2,4-diamino-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acid Minopterin APGA Aminopterine 4-amino-PGA 4-aminofolic acid Aminopteridine Aminopterin
Indication	Prior 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 number	54-62-6

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Dihydrofolate reductase	MVGSLNCIVAVSQNMGIGKNGDLPWPPLRNEFRYFQRMTTTSSVEGKQNL...	unknown	inhibitor
Proton-coupled folate transporter	MEGSASPPEKPRARPAAAVLCRGPVEPLVFLANFALVLQGPLTTQYLWHR...	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