A8236
AN-9
≥95% (HPLC)
Synonym(s):
Pivaloyloxymethyl butyrate, Pivanex
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About This Item
Empirical Formula (Hill Notation):
C10H18O4
CAS Number:
Molecular Weight:
202.25
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Assay
≥95% (HPLC)
form
oil
color
colorless to slightly yellow
solubility
DMSO: ≥10 mg/mL
storage temp.
−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
Application
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.
Biochem/physiol Actions
HDAC Inhibitor tested as an anti-cancer drug; butyric acid pro-drug
Storage Class Code
12 - Non Combustible Liquids
WGK
nwg
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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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
T Kasukabe et al.
British journal of cancer, 75(6), 850-854 (1997-01-01)
A derivative of butyric acid, pivalyloxymethyl butyrate (AN-9), inhibited the proliferation and induced apoptosis of mouse monocytic leukaemia Mm-A cells, although sodium butyrate, but not AN-9, induced differentiation of the cells. AN-9 and DNA-specific antineoplastic agents synergistically inhibited the growth
L L Siu et al.
Investigational new drugs, 16(2), 113-119 (1998-12-16)
The anti-proliferative effects of pivaloyloxymethyl butyrate (AN-9), a butyric acid (BA) derivative with potent tumor-differentiating properties both in vitro and in vivo, was evaluated against colorectal, breast, lung, ovarian, renal cell, bladder, and other types of tumor colony-forming units in
Suzanne M Cutts et al.
Molecular cancer therapeutics, 2(7), 661-670 (2003-07-29)
The anticancer anthracycline compound Adriamycin is a known topoisomerase II inhibitor but is also capable of exerting other cellular consequences. After intercalation, Adriamycin can form covalent adducts with DNA, and the magnitude of these adducts appears to be limited by
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