Drug Information

Drug General Information
Drug ID
D0D2RN
Former ID
DAP001346
Drug Name
Aminopterin
Synonyms
APGA; Aminopteridine; Aminopterine; Aminopterinum; Aminotrexate; Pteramina; Pteramina [Czech]; A 1784; A-7170;A-Ninopterin; ENT-26079; Kyselina 4-aminolistova; Kyselina 4-aminolistova [Czech]; Kyselina 4-aminopteroylglutamova; Kyselina 4-aminopteroylglutamova [Czech]; L-Glutamic acid, N-[4-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]; N-(1-((2,4-Diamino-6-pteridinylmethyl)amino)benzoyl)glutaminsaeure; N-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)carbonyl]glutamic acid; N-(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid; N-(4-(((2,4-Diamino-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acid; Kyselina N-(p-((2,4-diamino-6-pteridinyl)methyl)benzoyl)-L(+)-glutamova; Kyselina N-(p-((2,4-diamino-6-pteridinyl)methyl)benzoyl)-L(+)-glutamova [Czech]; Kyselina N-(p-((2,4-diamino-6-pteridinylmethyl)amino)benzoyl)-L(+)-glutamova; Kyselina N-(p-((2,4-diamino-6-pteridinylmethyl)amino)benzoyl)-L(+)-glutamova [Czech]; N-(4-(((2,4-Diamino-6-pteridyl)-methyl)amino)benzoyl)-L-glutamic acid; (2R)-2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid; (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid; 2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid; 4'-Amino-folsaeure; 4'-Desoxy-4'-aminofolsaeure; 4-Amino pteroylglutamic acid; 4-Amino-4-deoxypteroylglutamate; 4-Amino-4-desoxy-pteroylglutaminsaeure; 4-Amino-PGA; 4-Aminofolic acid; 4-Aminopteroyl-<R>glutamic acid; 4-Aminopteroyl-L-glutamic acid; 4-Aminopteroyl-glutamic acid; 4-Aminopteroylglutamic acid
Drug Type
Small molecular drug
Indication Leukemia [ICD9: 208.9; ICD10:C90-C95] Withdrawn from market [550114]
Therapeutic Class
Anticancer Agents
Company
Lederle Laboratories
Structure
Download
2D MOL

3D MOL
Formula
C19H20N8O5
Canonical SMILES
C1=CC(=CC=C1C(=O)NC(CCC(=O)O)C(=O)O)NCC2=CN=C3C(=N2)C(=<br />NC(=N3)N)N
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)
InChIKey
TVZGACDUOSZQKY-UHFFFAOYSA-N
CAS Number
CAS 54-62-6
PubChem Compound ID
2154
PubChem Substance ID
67626, 4426032, 8151464, 11342170, 11362353, 11364803, 11367365, 11369927, 11372291, 11374552, 11378094, 11484442, 11487755, 11488709, 11491201, 11492732, 11495688, 15477678, 17404598, 24278186, 24846313, 24890768, 24890950, 26612022, 26680752, 26747419, 26747420, 26747421, 26753506, 29221333, 47365846, 47662940, 47960398, 48415548, 50105754, 50105755, 51072235, 53777140, 57264276, 57321174, 75359474, 85083722, 85083723, 85154883, 85230896, 90341578, 92124292, 92303442, 103171176, 103855303
ChEBI ID
ChEBI:22526
SuperDrug ATC ID
L01BA01
SuperDrug CAS ID
cas=000059052
Target and Pathway
Target(s) Dihydrofolate reductase Target Info Inhibitor [535644], [535830]
PathWhiz Pathway Folate Metabolism
Pterine Biosynthesis
Reactome E2F mediated regulation of DNA replication
Tetrahydrobiopterin (BH4) synthesis, recycling, salvage and regulation
Metabolism of folate and pterines
G1/S-Specific Transcription
References
Ref 550114Drug information of Aminopterin, Health Canada, 2007.
Ref 535644Loss of folylpoly-gamma-glutamate synthetase activity is a dominant mechanism of resistance to polyglutamylation-dependent novel antifolates in multiple human leukemia sublines. Int J Cancer. 2003 Feb 20;103(5):587-99.
Ref 535830vestigial suppressor genes and resistance to aminopterin in Drosophila melanogaster. Heredity. 1992 Nov;69 ( Pt 5):473-7.

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