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Dokumenty

A1784

Sigma-Aldrich

Aminopterin

powder

Synonim(y):

(S)-2-{4-[(2,4-Diaminopteridin-6-yl)methylamino]benzamido}pentanedioic acid, 4-Amino-PGA, 4-Aminofolic acid, 4-Aminopteroyl-L-glutamic acid

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About This Item

Wzór empiryczny (zapis Hilla):
C19H20N8O5
Numer CAS:
54-62-6
Masa cząsteczkowa:
440.41
Beilstein:
69045
Numer WE:
200-209-9
Kod UNSPSC:
12352200
Identyfikator substancji w PubChem:
24278186
NACRES:
NA.77

pochodzenie biologiczne

synthetic (organic)

Poziom jakości

200

Próba

≥97% (TLC)

Postać

powder

kolor

yellow

mp

225 °C

rozpuszczalność

2 M NaOH: 50 mg/mL (Solutions may be stored for 1-2 days at 4°C.)
DMSO: soluble (Solutions may be stored for 1-2 days at 4°C.)

ε (współczynnik ekstynkcji)

24,500 at 282 nm in 0.1 M NaOH at 1 M
25,700 at 261 nm in 0.1 M NaOH at 1 M
8,100 at 373 nm in 0.1 M NaOH at 1 M

temp. przechowywania

−20°C

ciąg SMILES

Nc1nc(N)c2nc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)cnc2n1

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

Klucz InChI

TVZGACDUOSZQKY-LBPRGKRZSA-N

informacje o genach

human ... FPGS(2356)
mouse ... Fpgs(14287)

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Działania biochem./fizjol.

Folic acid antagonist. Aminopterin is actively transported into cells by the folate transporter. In the cell, it is converted to a high molecular weight polyglutamate metabolite by folylpolyglutamate synthase that, in turn, binds to dihydrofolate reductase and inhibits its activity. Aminopterin-polyglutamate is degraded intracellularly by γ-glutamyl hydrolase.

Cechy i korzyści

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Powiązanie

More potent, but more toxic, than methotrexate.
This page may contain text that has been machine translated.

Piktogramy

Skull and crossbonesHealth hazard
GHS06,GHS08

Hasło ostrzegawcze

Danger

Zwroty wskazujące rodzaj zagrożenia

H300,H315,H319,H341,H360FD

Klasyfikacja zagrożeń

Acute Tox. 1 Oral - Eye Irrit. 2 - Muta. 2 - Repr. 1B - Skin Irrit. 2

Kod klasy składowania

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable

Środki ochrony indywidualnej

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certyfikaty analizy (CoA)

Poszukaj Certyfikaty analizy (CoA), wpisując numer partii/serii produktów. Numery serii i partii można znaleźć na etykiecie produktu po słowach „seria” lub „partia”.

Masz już ten produkt?

Dokumenty związane z niedawno zakupionymi produktami zostały zamieszczone w Bibliotece dokumentów.

Odwiedź Bibliotekę dokumentów

Aleem Gangjee et al.
Journal of medicinal chemistry, 48(16), 5329-5336 (2005-08-05)
We report, for the first time, the biological activities of four-carbon-atom bridged classical antifolates on dihydrofolate reductase (DHFR), thymidylate synthase (TS), and folylpolyglutamate synthetase (FPGS) as well as antitumor activity. Extension of the bridge homologation studies of classical two-carbon bridged
A Rosowsky
Current medicinal chemistry, 6(4), 329-352 (1999-04-02)
Nonpolyglutamatable antifolates are potentially of therapeutic interest for the treatment of tumors that are inherently refractory, or have become resistant, to classical antifolates as a result of decreased expression of the enzyme folylpolyglutamate synthetase. An interesting class of water-soluble nonpolyglutamatable
M Del Campo et al.
Teratology, 60(1), 10-12 (1999-07-21)
Maternal exposures to aminopterin and methotrexate have been associated with a pattern of malformation which includes prenatal-onset growth deficiency, severe lack of ossification of the calvarium, hypoplastic supraorbital ridges, small, low-set ears, micrognathia, and limb abnormalities. We report on a
Hatem A Azim et al.
Current opinion in oncology, 24(3), 325-331 (2012-02-22)
To discuss the clinical development of new formulations of old cytotoxic agents and highlight the value of adopting this strategy. Several drugs are currently in clinical development with high potential in improving clinical outcomes compared with their older counterparts. We
Edward C Keystone et al.
The Journal of rheumatology, 38(9), 1875-1883 (2011-07-05)
To investigate the potential efficacy, safety, and tolerability of daily use of CH-1504 in patients with active rheumatoid arthritis (RA). US National Institutes of Health database no. NCT00658047. In our phase II randomized double-blind double-dummy study, patients naive to methotrexate
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