FIPI free base
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MedKoo CAT#: 407955

CAS#: 939055-18-2 (free base)

Description: FIPI is a potent and selective phospholipase D inhibitor. FIPI attenuate mercury-induced lipid signaling leading to protection against cytotoxicity in aortic endothelial cells. FIPI rapidly blocks in vivo PA production with subnanomolar potency. FIPI may be a potential therapeutic for autoimmunity and cancer metastasis.


Price and Availability

Size
Price

50mg
USD 450
500mg
USD 1850
5g
USD 6950
Size
Price

100mg
USD 650
1g
USD 2950
Size
Price

200mg
USD 1050
2g
USD 4850

FIPI free base, 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#: 407955
Name: FIPI free base
CAS#: 939055-18-2 (free base)
Chemical Formula: C23H24FN5O2
Exact Mass: 421.1914
Molecular Weight: 421.4764
Elemental Analysis: C, 65.54; H, 5.74; F, 4.51; N, 16.62; O, 7.59


Related CAS #: 1781834-93-2 (HCl)   939055-18-2 (free base)    

Synonym: FIPI free base, FIPI; 5-Fluoro-2-indolyl des-chlorohalopemide;

IUPAC/Chemical Name: 5-fluoro-N-(2-(4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidin-1-yl)ethyl)-1H-indole-2-carboxamide

InChi Key: LHABRXRGDLASIH-UHFFFAOYSA-N

InChi Code: InChI=1S/C23H24FN5O2/c24-16-5-6-18-15(13-16)14-20(26-18)22(30)25-9-12-28-10-7-17(8-11-28)29-21-4-2-1-3-19(21)27-23(29)31/h1-6,13-14,17,26H,7-12H2,(H,25,30)(H,27,31)

SMILES Code: O=C(C(N1)=CC2=C1C=CC(F)=C2)NCCN3CCC(N(C4=CC=CC=C4N5)C5=O)CC3


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

Shelf Life:
>3 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:
2934990300


References

1: Jablonická V, Ziegler J, Vatehová Z, Lišková D, Heilmann I, Obložinský M, Heilmann M. Inhibition of phospholipases influences the metabolism of wound-induced benzylisoquinoline alkaloids in Papaver somniferum L. J Plant Physiol. 2018 Apr;223:1-8. doi: 10.1016/j.jplph.2018.01.007. Epub 2018 Jan 31. PubMed PMID: 29433083.

2: Chakraborti S, Sarkar J, Bhuyan R, Chakraborti T. Role of catechins on ET-1-induced stimulation of PLD and NADPH oxidase activities in pulmonary smooth muscle cells: determination of the probable mechanism by molecular docking studies. Biochem Cell Biol. 2018 Aug;96(4):417-432. doi: 10.1139/bcb-2017-0179. Epub 2017 Dec 5. PubMed PMID: 29206487.

3: Ganesan R, Mahankali M, Alter G, Gomez-Cambronero J. Two sites of action for PLD2 inhibitors: The enzyme catalytic center and an allosteric, phosphoinositide biding pocket. Biochim Biophys Acta. 2015 Mar;1851(3):261-72. doi: 10.1016/j.bbalip.2014.12.007. Epub 2014 Dec 20. PubMed PMID: 25532944; PubMed Central PMCID: PMC4312721.

4: Comoglio Y, Levitz J, Kienzler MA, Lesage F, Isacoff EY, Sandoz G. Phospholipase D2 specifically regulates TREK potassium channels via direct interaction and local production of phosphatidic acid. Proc Natl Acad Sci U S A. 2014 Sep 16;111(37):13547-52. doi: 10.1073/pnas.1407160111. Epub 2014 Sep 2. PubMed PMID: 25197053; PubMed Central PMCID: PMC4169921.

5: Björnström K, Turina D, Strid T, Sundqvist T, Eintrei C. Orexin A inhibits propofol-induced neurite retraction by a phospholipase D/protein kinase Cε-dependent mechanism in neurons. PLoS One. 2014 May 14;9(5):e97129. doi: 10.1371/journal.pone.0097129. eCollection 2014. PubMed PMID: 24828410; PubMed Central PMCID: PMC4020800.

6: Shaughnessy R, Retamal C, Oyanadel C, Norambuena A, López A, Bravo-Zehnder M, Montecino FJ, Metz C, Soza A, González A. Epidermal growth factor receptor endocytic traffic perturbation by phosphatidate phosphohydrolase inhibition: new strategy against cancer. FEBS J. 2014 May;281(9):2172-89. doi: 10.1111/febs.12770. Epub 2014 Mar 19. PubMed PMID: 24597955.

7: Bates RC, Fees CP, Holland WL, Winger CC, Batbayar K, Ancar R, Bergren T, Petcoff D, Stith BJ. Activation of Src and release of intracellular calcium by phosphatidic acid during Xenopus laevis fertilization. Dev Biol. 2014 Feb 1;386(1):165-80. doi: 10.1016/j.ydbio.2013.11.006. Epub 2013 Nov 21. PubMed PMID: 24269904; PubMed Central PMCID: PMC3922219.

8: Stegner D, Thielmann I, Kraft P, Frohman MA, Stoll G, Nieswandt B. Pharmacological inhibition of phospholipase D protects mice from occlusive thrombus formation and ischemic stroke--brief report. Arterioscler Thromb Vasc Biol. 2013 Sep;33(9):2212-7. doi: 10.1161/ATVBAHA.113.302030. Epub 2013 Jul 18. PubMed PMID: 23868933.

9: Henkels KM, Boivin GP, Dudley ES, Berberich SJ, Gomez-Cambronero J. Phospholipase D (PLD) drives cell invasion, tumor growth and metastasis in a human breast cancer xenograph model. Oncogene. 2013 Dec 5;32(49):5551-62. doi: 10.1038/onc.2013.207. Epub 2013 Jun 10. PubMed PMID: 23752189; PubMed Central PMCID: PMC3966651.

10: Kim BJ, Kwon YK, Kim E, So I. Effects of histamine on cultured interstitial cells of cajal in murine small intestine. Korean J Physiol Pharmacol. 2013 Apr;17(2):149-56. doi: 10.4196/kjpp.2013.17.2.149. Epub 2013 Apr 10. PubMed PMID: 23626477; PubMed Central PMCID: PMC3634092.

11: Ye Q, Kantonen S, Gomez-Cambronero J. Serum deprivation confers the MDA-MB-231 breast cancer line with an EGFR/JAK3/PLD2 system that maximizes cancer cell invasion. J Mol Biol. 2013 Feb 22;425(4):755-66. doi: 10.1016/j.jmb.2012.11.035. Epub 2012 Dec 10. PubMed PMID: 23238254; PubMed Central PMCID: PMC3568238.

12: Olala LO, Seremwe M, Tsai YY, Bollag WB. A role for phospholipase D in angiotensin II-induced protein kinase D activation in adrenal glomerulosa cell models. Mol Cell Endocrinol. 2013 Feb 5;366(1):31-7. doi: 10.1016/j.mce.2012.11.008. Epub 2012 Nov 20. PubMed PMID: 23178798; PubMed Central PMCID: PMC3656657.

13: Elvers M, Grenegård M, Khoshjabinzadeh H, Münzer P, Borst O, Tian H, Di Paolo G, Lang F, Gawaz M, Lindahl TL, Fälker K. A novel role for phospholipase D as an endogenous negative regulator of platelet sensitivity. Cell Signal. 2012 Sep;24(9):1743-52. doi: 10.1016/j.cellsig.2012.04.018. Epub 2012 May 3. PubMed PMID: 22579635.

14: Secor JD, Kotha SR, Gurney TO, Patel RB, Kefauver NR, Gupta N, Morris AJ, Haley BE, Parinandi NL. Novel lipid-soluble thiol-redox antioxidant and heavy metal chelator, N,N'-bis(2-mercaptoethyl)isophthalamide (NBMI) and phospholipase D-specific inhibitor, 5-fluoro-2-indolyl des-chlorohalopemide (FIPI) attenuate mercury-induced lipid signaling leading to protection against cytotoxicity in aortic endothelial cells. Int J Toxicol. 2011 Dec;30(6):619-38. doi: 10.1177/1091581811422413. Epub 2011 Oct 12. PubMed PMID: 21994240; PubMed Central PMCID: PMC3503146.

15: Patel RB, Kotha SR, Sherwani SI, Sliman SM, Gurney TO, Loar B, Butler SO, Morris AJ, Marsh CB, Parinandi NL. Pulmonary fibrosis inducer, bleomycin, causes redox-sensitive activation of phospholipase D and cytotoxicity through formation of bioactive lipid signal mediator, phosphatidic acid, in lung microvascular endothelial cells. Int J Toxicol. 2011 Feb;30(1):69-90. doi: 10.1177/1091581810388850. Epub 2010 Dec 3. PubMed PMID: 21131602; PubMed Central PMCID: PMC3503147.

16: Chang LC, Huang TH, Chang CS, Tsai YR, Lin RH, Lee PW, Hsu MF, Huang LJ, Wang JP. Signaling mechanisms of inhibition of phospholipase D activation by CHS-111 in formyl peptide-stimulated neutrophils. Biochem Pharmacol. 2011 Jan 15;81(2):269-78. doi: 10.1016/j.bcp.2010.10.007. Epub 2010 Oct 20. PubMed PMID: 20965153.

17: Antonescu CN, Danuser G, Schmid SL. Phosphatidic acid plays a regulatory role in clathrin-mediated endocytosis. Mol Biol Cell. 2010 Aug 15;21(16):2944-52. doi: 10.1091/mbc.E10-05-0421. Epub 2010 Jun 23. PubMed PMID: 20573978; PubMed Central PMCID: PMC2921119.

18: Yanase Y, Carvou N, Frohman MA, Cockcroft S. Reversible bleb formation in mast cells stimulated with antigen is Ca2+/calmodulin-dependent and bleb size is regulated by ARF6. Biochem J. 2009 Dec 14;425(1):179-93. doi: 10.1042/BJ20091122. PubMed PMID: 19845506.

19: Su W, Yeku O, Olepu S, Genna A, Park JS, Ren H, Du G, Gelb MH, Morris AJ, Frohman MA. 5-Fluoro-2-indolyl des-chlorohalopemide (FIPI), a phospholipase D pharmacological inhibitor that alters cell spreading and inhibits chemotaxis. Mol Pharmacol. 2009 Mar;75(3):437-46. doi: 10.1124/mol.108.053298. Epub 2008 Dec 8. PubMed PMID: 19064628; PubMed Central PMCID: PMC2684902.