FCCP
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 522447

CAS#: 370-86-5

Description: Carbonyl cyanide-4-(trifluoromethoxy)phenylhydrazone (FCCP) is an ionophore that is a mobile ion carrier. It referred to as an uncoupling agent because it disrupts ATP synthesis by transporting hydrogen ions through a cell membrane before they can be used to provide the energy for oxidative phosphorylation. It is a nitrile and hydrazone. FCCP was first described in 1962 by Heytler.


Price and Availability

Size
Price

10mg
USD 190
Size
Price

20mg
USD 350
Size
Price

50mg
USD 550

FCCP, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 522447
Name: FCCP
CAS#: 370-86-5
Chemical Formula: C10H5F3N4O
Exact Mass: 254.04155
Molecular Weight: 254.17
Elemental Analysis: C, 47.26; H, 1.98; F, 22.42; N, 22.04; O, 6.29


Synonym: FCCP; Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone; (4-(Trifluoromethoxy)phenyl)hydrazonopropanedinitrile; Carbonyl Cyanide p Trifluoromethoxyphenylhydrazone; Carbonyl Cyanide p-Trifluoromethoxyphenylhydrazone; Carbonyl Cyanide para Trifluoromethoxyphenylhydrazone; Carbonyl Cyanide para-Trifluoromethoxyphenylhydrazone; Cyanide p-Trifluoromethoxyphenylhydrazone, Carbonyl; Cyanide para-Trifluoromethoxyphenylhydrazone, Carbonyl; p-Trifluoromethoxyphenylhydrazone, Carbonyl Cyanide; para-Trifluoromethoxyphenylhydrazone, Carbonyl Cyanide.

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


Technical Data

Appearance:
Solid powder

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).

Harmonized System Code:
293490


References

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.