A8236

Sigma-Aldrich

AN-9

≥95% (HPLC)

Sinónimos:
Pivanex, Pivaloyloxymethyl butyrate
Empirical Formula (Hill Notation):
C10H18O4
Número de CAS:
Peso molecular:
202.25
Número MDL:
ID de la sustancia en PubChem:
NACRES:
NA.77

Nivel de calidad

100

ensayo

≥95% (HPLC)

formulario

oil

color

colorless to slightly yellow

solubilidad

DMSO: ≥10 mg/mL

temp. de almacenamiento

−20°C

SMILES string

CCCC(=O)OCOC(=O)C(C)(C)C

InChI

1S/C10H18O4/c1-5-6-8(11)13-7-14-9(12)10(2,3)4/h5-7H2,1-4H3

InChI key

GYKLFBYWXZYSOW-UHFFFAOYSA-N

Aplicación

AN-9 is a HDAC inhibitor with antimetastatic and antiangiogenic properties. These anticancer activities are thought to occur by reducing vascularization and the expression of bFGF and HIF-1α.

Acciones bioquímicas o fisiológicas

HDAC Inhibitor tested as an anti-cancer drug; butyric acid pro-drug

RIDADR

NONH for all modes of transport

WGK Alemania

nwg

Y Zimra et al.
Journal of cancer research and clinical oncology, 123(3), 152-160 (1997-01-01)
A novel butyric acid derivative, pivaloyloxymethyl butyrate, AN-9, was previously shown to be a potent differentiating agent. AN-9 exerts a significant anticancer activity in vitro and in vivo. In all the activities examined, AN-9 was more potent than butyric acid....
E Rabizadeh et al.
Leukemia research, 31(8), 1115-1123 (2007-02-03)
Chronic myelogenous leukemia (CML) is associated with the high TK activity chimeric protein BCR-ABL, known to contribute to cell tumorogenicity, resistance to apoptosis and differentiation. STI571, the TK inhibitor, is the current treatment for CML. One possible approach to overcome...
A Nudelman et al.
Journal of medicinal chemistry, 35(4), 687-694 (1992-02-21)
The antitumor activity of novel prodrugs butyric acid was examined. The in vitro effect of the compounds on induction of cytodifferentiation and on inhibition of proliferation and clonogenicity showed that (pivaloyloxy)methyl butyrate (1a) (labeled AN-9) was the most active agent....
E Rabizadeh et al.
Israel journal of medical sciences, 32(12), 1186-1191 (1996-12-01)
Pivaloyloxymethyl butyrate (AN-9) belongs to the family of acyloxyalkyl ester prodrugs of carboxylic acids which undergo intracellular hydrolysis to yield butyric acid (BA). We have previously shown that AN-9 and BA reduce the level of c-myc and enhance c-jun transcripts...
Tony Reid et al.
Lung cancer (Amsterdam, Netherlands), 45(3), 381-386 (2004-08-11)
This multicenter phase II trial evaluated the therapeutic activity and safety profile of pivaloyloxymethyl butyrate (Pivanex, AN-9) as a single agent in refractory non-small cell lung cancer (NSCLC). Pivanex (2.34 g/m2 per day) was administered as a 6-h continuous intravenous...
Artículos
Epigenetic modifications are thought to occur through two key interconnected processes—DNA methylation and the covalent modification of histones.
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