Basic information
- CAS
122110-53-6- Standard SMILES
CCCC(=O)OCOC(=O)C(C)(C)C- InChIKey
GYKLFBYWXZYSOW-UHFFFAOYSA-N- Molecular formula
- C10H18O4
- Average molar mass
- 202.25 g/mol
- Monoisotopic mass
- 202.12050905
Overview
Pivaloyloxymethyl butyrate (AN-9), an acyloxyalkyl ester prodrug of butyric acid (BA), exhibited low toxicity and significant anticancer activity in vitro and in vivo. It shows greater potency than BA at inducing malignant cell differentiation and tumor growth inhibition and has demonstrated more favorable toxicological, pharmacological, and pharmaceutical properties than BA in preclinical studies.
Names & identifiers
- Preferred name
- Pivalyloxymethyl butyrate
- IUPAC
- butanoyloxymethyl 2,2-dimethylpropanoate
- English name
- (PIVALOYLOXY)METHYL BUTYRATE
- Molecular formula
- C10H18O4
- Molecular weight
- 202.25
Names & synonyms
Pivalyloxymethyl butyrateRefChem:929363Pivanex122110-53-6AN-9(PIVALOYLOXY)METHYL BUTYRATEPivaloyloxymethyl butyrateAN 9Butanoic acid,(2,2-dimethyl-1-oxopropoxy)methyl ester37380-45-3pivaloyloxymethylbutyrateAN 9 (ion exchanger)
Show more names
Pivalic acid butyryloxymethyl esterButanoic acid pivalyloxymethyl esterButyric acid pivaloyloxymethyl esterButyric acid 1-oxo-2,2-dimethylpropoxymethyl ester
butanoyloxymethyl 2,2-dimethylpropanoateMFCD00209896UNII-55VNK5440PBRN 4861411Butanoic acid, (2,2-dimethyl-1-oxopropoxy)methyl esterAN-9;Pivalyloxymethyl butyrate((2,2-Dimethylpropanoyl)oxy)methyl butanoate55VNK5440P
Database identifiers
- CAS
122110-53-6、37380-45-3- PubChem CID
- 60748
- DTXSID
DTXSID40190818- ChEMBL
CHEMBL100014- UNII
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 52.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 7
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 203
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- FDA UNII
- 55 VNK5440P · 55VNK5440P
Chemistry & industry
Pharmacology
Mechanism of Action
Pivaloyloxymethyl butyrate is a histone deacetylase inhibitor analog of butyric acid that causes apoptosis of cancer cells through signaling cellular differentiation. It is rapidly and extensively transported intracellularly because of its high lipophilicity, where it undergoes esterase-mediated hydrolysis to form pivalic acid, formaldehyde, and BA.
Applications
UsesAN-9 is an HDAC inhibitor with antimetastic and antiangiogenic properties. Histone deacetylase inhibitors in cancer therapy. Formaldehyde-releasing prodrugs for localized anticancer chemotherapy.
Suppliers22 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
河南阿尔法化工有限公司0371-55013243 15324716602 · [email protected]
InvivoChem中国13549236410 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
北京博奥森生物技术有限公司400-901-9800 18611424007 · [email protected]
天津狄克特科技有限公司22-58627059 13920586291 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
韶关市启程生物科技有限公司
Related reactions
1 records
Compound notes
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