Synonym
FCCP; Trifluoromethoxy carbonylcyanide phenylhydrazone
IUPAC/Chemical Name
N-(4-(trifluoromethoxy)phenyl)carbonohydrazonoyl dicyanide
InChi Key
BMZRVOVNUMQTIN-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H5F3N4O/c11-10(12,13)18-9-3-1-7(2-4-9)16-17-8(5-14)6-15/h1-4,16H
SMILES Code
N#C/C(C#N)=N/NC1=CC=C(OC(F)(F)F)C=C1
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, not in water
Shelf Life
>2 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
254.17
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: Mlejnek P, Dolezel P. Loss of mitochondrial transmembrane potential and glutathione depletion are not sufficient to account for induction of apoptosis by carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone in human leukemia K562 cells. Chem Biol Interact. 2015 Sep 5;239:100-10. doi: 10.1016/j.cbi.2015.06.033. Epub 2015 Jun 23. PubMed PMID: 26115783.
2: Cutró AC, Montich GG, Roveri OA. Effect of carbonylcyanide-4-(trifluoromethoxy)phenylhydrazone (FCCP) on the interaction of 1-anilino-8-naphthalene sulfonate (ANS) with phosphatidylcholine liposomes. J Bioenerg Biomembr. 2014 Apr;46(2):119-25. doi: 10.1007/s10863-014-9545-0. Epub 2014 Feb 26. Erratum in: J Bioenerg Biomembr. 2014 Jun;46(3):243. PubMed PMID: 24570377.
3: Han YH, Park WH. Intracellular glutathione levels are involved in carbonyl cyanide p-(trifluoromethoxy) phenylhydrazone-induced apoptosis in As4.1 juxtaglomerular cells. Int J Mol Med. 2011 Apr;27(4):575-81. doi: 10.3892/ijmm.2011.604. Epub 2011 Jan 21. PubMed PMID: 21258765.
4: Han YH, Moon HJ, You BR, Kim SZ, Kim SH, Park WH. Effects of carbonyl cyanide p-(trifluoromethoxy) phenylhydrazone on the growth inhibition in human pulmonary adenocarcinoma Calu-6 cells. Toxicology. 2009 Nov 30;265(3):101-7. doi: 10.1016/j.tox.2009.10.001. Epub 2009 Oct 9. PubMed PMID: 19819288.
5: Han YH, Kim SH, Kim SZ, Park WH. Carbonyl cyanide p-(trifluoromethoxy) phenylhydrazone (FCCP) as an O2(*-) generator induces apoptosis via the depletion of intracellular GSH contents in Calu-6 cells. Lung Cancer. 2009 Feb;63(2):201-9. doi: 10.1016/j.lungcan.2008.05.005. Epub 2008 Jun 27. PubMed PMID: 18585819.
6: Kuruvilla S, Qualls CW Jr, Tyler RD, Witherspoon SM, Benavides GR, Yoon LW, Dold K, Brown RH, Sangiah S, Morgan KT. Effects of minimally toxic levels of carbonyl cyanide P-(trifluoromethoxy) phenylhydrazone (FCCP), elucidated through differential gene expression with biochemical and morphological correlations. Toxicol Sci. 2003 Jun;73(2):348-61. Epub 2003 Apr 15. PubMed PMID: 12700400.
7: Connop BP, Thies RL, Beyreuther K, Ida N, Reiner PB. Novel effects of FCCP [carbonyl cyanide p-(trifluoromethoxy)phenylhydrazone] on amyloid precursor protein processing. J Neurochem. 1999 Apr;72(4):1457-65. PubMed PMID: 10098849.
8: Cramer WA, Horton P, Donnell JJ. Inhibition of chemical oxidation and reduction of cytochromes f and b-559 by carbonylcyanide p-trifluoromethoxy phenylhydrazone. Biochim Biophys Acta. 1974 Dec 19;368(3):361-70. PubMed PMID: 4451656.
9: Prezioso G, Palmieri F, Quagliariello E. [Effect of p-trifluoromethoxy-phenylhydrazone of carbonylcyanide on the kinetics of dicarboxylic acid uptake in rat liver mitochondria]. Boll Soc Ital Biol Sper. 1971 Oct 30;47(20):637-41. Italian. PubMed PMID: 5143112.
10: Kovác L, Hrusovská E. The effect of carbonyl cyanide p-trifluoromethoxy-phenylhydrazone on yeast cells. Folia Microbiol (Praha). 1967;12(1):56-63. PubMed PMID: 6031585.
