Synonym
Pivanex, AN9, pivaloyloxymethyl butyrate, Titan.
IUPAC/Chemical Name
(pivaloyloxy)methyl butyrate
InChi Key
GYKLFBYWXZYSOW-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H18O4/c1-5-6-8(11)13-7-14-9(12)10(2,3)4/h5-7H2,1-4H3
SMILES Code
CCCC(OCOC(C(C)(C)C)=O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>5 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
202.25
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Rabizadeh E, Shaklai M, Eisenbach L, Nudelman A, Rephaeli A. Esterase inhibitors diminish the modulation of gene expression by butyric acid derivative, pivaloyloxymethyl butyrate (AN-9). Isr J Med Sci. 1996 Dec;32(12):1186-91. PubMed PMID: 9007151.
2: Zimra Y, Wasserman L, Maron L, Shaklai M, Nudelman A, Rephaeli A. Butyric acid and pivaloyloxymethyl butyrate, AN-9, a novel butyric acid derivative, induce apoptosis in HL-60 cells. J Cancer Res Clin Oncol. 1997;123(3):152-60. PubMed PMID: 9119880.
3: Cutts SM, Rephaeli A, Nudelman A, Hmelnitsky I, Phillips DR. Molecular basis for the synergistic interaction of adriamycin with the formaldehyde-releasing prodrug pivaloyloxymethyl butyrate (AN-9). Cancer Res. 2001 Nov 15;61(22):8194-202. PubMed PMID: 11719450.
4: Hobdy E, Murren J. AN-9 (Titan). Curr Opin Investig Drugs. 2004 Jun;5(6):628-34. Review. PubMed PMID: 15242252.
5: Reid T, Valone F, Lipera W, Irwin D, Paroly W, Natale R, Sreedharan S, Keer H, Lum B, Scappaticci F, Bhatnagar A. Phase II trial of the histone deacetylase inhibitor pivaloyloxymethyl butyrate (Pivanex, AN-9) in advanced non-small cell lung cancer. Lung Cancer. 2004 Sep;45(3):381-6. PubMed PMID: 15301879.
6: Blank-Porat D, Gruss-Fischer T, Tarasenko N, Malik Z, Nudelman A, Rephaeli A. The anticancer prodrugs of butyric acid AN-7 and AN-9, possess antiangiogenic properties. Cancer Lett. 2007 Oct 18;256(1):39-48. Epub 2007 Jul 3. PubMed PMID: 17611019.
7: Tarasenko N, Nudelman A, Tarasenko I, Entin-Meer M, Hass-Kogan D, Inbal A, Rephaeli A. Histone deacetylase inhibitors: the anticancer, antimetastatic and antiangiogenic activities of AN-7 are superior to those of the clinically tested AN-9 (Pivanex). Clin Exp Metastasis. 2008;25(7):703-16. doi: 10.1007/s10585-008-9179-x. Epub 2008 May 28. PubMed PMID: 18506586.
