FComEx: Aminopterin (PC000440)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:45 UTC

Update date

2017-01-19 02:36:24 UTC

FoodComEx ID

PC000440

FoodDB Record

FDB022702

Chemical Information

Name

Aminopterin

Description

Aminopterin Syndrome Sine Aminopterin (ASSA, OMIM 600325) is an embryopathy caused by maternal treatment with the olic acid antagonist aminopterin has been recognized since 1952 when aminopterin was used as an abortifacient. The characteristic phenotype of the children who survived infancy after having been exposed to aminopterin or its methyl derivative, methotrexate, in early pregnancy included a very unusual facies, skull anomalies, and skeletal defects.(OMIM); Aminopterin is an antimetabolite drug used in treatment of cancer and autoimmune diseases. It acts by inhibiting the metabolism of folic acid. - Wikipedia. The effects of the drug on intracellular metabolic processes, due to the inhibitory action on the enzyme dihydrofolate reductase, show that the result of this inhibition is more complex and is not limited to blockade of the reduction of folic acid alone. Although rescue methods are important in prevention of lethal effects of methotrexate, some metabolic pathways are insufficiently rescued, resulting in toxic reactions following methotrexate administration.(PMID 6398629) [HMDB]

CAS Number

54-62-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
4-Amino-4-deoxypteroylglutamate	hmdb
4-Amino-PGA	hmdb
4-Aminofolate	hmdb
4-Aminofolic acid	hmdb
4-Aminopteroylglutamate	hmdb
4-Aminopteroylglutamic acid	hmdb
Aminopterin	hmdb
Aminopterine	hmdb
APGA	hmdb
L-N-[p-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]-Glutamic acid	hmdb
Pteramina	hmdb

Chemical Formula

C19H20N8O5

IUPAC name

2-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

InChI Identifier

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)

InChI Key

TVZGACDUOSZQKY-UHFFFAOYSA-N

Isomeric SMILES

NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)C=N2)C(N)=N1

Average Molecular Weight

440.4127

Monoisotopic Molecular Weight

440.15566579

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as folic acids. These are heterocyclic compounds based on the 4-[(pteridin-6-ylmethyl)amino]benzoic acid skeleton conjugated with one or more L-glutamate units.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Folic acids

Alternative Parents