EIPA

Names

[ Name ]:
EIPA

[Synonym ]:
ethylisopropylamiloride
MFCD00151710
3-amino-6-chloro-N-(diaminomethylidene)-5-[ethyl(propan-2-yl)amino]pyrazine-2-carboxamide
3-amino-6-chloro-n-(diaminomethylene)-5-[ethyl(isopropyl)amino]pyrazine-2-carboxamide
2-Pyrazinecarboxamide, 3-amino-6-chloro-N-(diaminomethylene)-5-[ethyl(1-methylethyl)amino]-
3-Amino-6-chloro-N-(diaminomethylene)-5-[ethyl(isopropyl)amino]-2-pyrazinecarboxamide
EIPA

Biological Activity

[Description]:

EIPA is a TRPP3 channel inhibitor with an IC50 of 10.5 μM. EIPA also inhibits Na+/H+-exchanger (NHE) and macropinocytosis.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel

Signaling Pathways >> Membrane Transporter/Ion Channel >> TRP Channel

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

[Target]

IC50: 10.5 μM (TRPP3 channel)[1] NHE[2] Macropinocytosis[3]

[In Vitro]

In the presence of 500 μM amiloride, 100 μM EIPA, 10 μM benzamil, and 10 μM phenamil, 45Ca2+ uptake decreases from 79±9 to 46±4 (58% remaining), 27±4 (34%), 29±5 (37%), and 38±4 (48%) pmol/oocyte/30 min (n=6, P=0.008), respectively. It is found that EIPA, benzamil, and phenamil rapidly and reversibly block Ca2+-activated TRPP3 channel activation at -50 mV, with IC50s of 143±8 (n=36), 10.5±2.2 (n=28), 1.1±0.3 (n=30), and 0.14±0.04 μM (n=25), respectively[1]. The number of autophagic vacuoles increases dramatically in the HAE and HPE groups after EIPA treatment compare with the HAN and HPN groups. EIPA regulates the initiation and maturation of the autophagy associated with amino acids in IEC-18 cells[2]. In addition, the uptake of cinnamoylphenazine (CA-PZ) and neutral red (NR) is inhibited by EIPA[3].

[Cell Assay]

The effect of EIPA alone (without alanine or proline) is also examined in both control (DMEM cultured cells) and amino acid-starved cells. The cells are incubated for 6 h in DMEM containing 5% FBS and either 0 or 0.3 mM EIPA (labelled QNN and QNE, respectively), HBSS containing either 0 or 0.3 mM EIPA (labelled HNN and HNE, respectively), HBSS with 1.0 mM alanine (labelled HAN) or 0.5 mM proline (labelled HPN), HBSS with 1.0 mM alanine and 0.3 mM EIPA (labelled HAE), and HBSS with 0.5 mM proline and 0.3 mM EIPA (labelled HPE)[2].

[References]

[1]. Dai XQ, et al. Inhibition of TRPP3 channel by amiloride and analogs. Mol Pharmacol. 2007 Dec;72(6):1576-85.

[2]. Shi H, et al. Na+/H+ Exchanger Regulates Amino Acid-Mediated Autophagy in Intestinal Epithelial Cells. Cell Physiol Biochem. 2017;42(6):2418-2429.

[3]. Zhu BY, et al. A new HDAC inhibitor cinnamoylphenazine shows antitumor activity in association with intensive macropinocytosis.

[Related Small Molecules]

capsaicin | Capsazepine | Diphenyleneiodonium chloride | HC-030031 | SKF-96365 | HC 067047 | AMG 9810 | GSK-1016790A | SAR7334 | Riluzole | Ginsenoside Rg3 | PF-4840154 | RN-1734 | Cariporide | Eleclazine hydrochloride

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
543.9±60.0 °C at 760 mmHg

[ Melting Point ]:
202-205ºC(lit.)

[ Molecular Formula ]:
C₁₁H₁₈ClN₇O

[ Molecular Weight ]:
299.760

[ Flash Point ]:
282.8±32.9 °C

[ Exact Mass ]:
299.126129

[ PSA ]:
134.01000

[ LogP ]:
4.86

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.665

[ Storage condition ]:
2-8℃

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-37/39

[ RIDADR ]:
UN 2811

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2934999090

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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