Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C16H16N2O4 |
| Molecular Weight | 300.3092 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=C(NCCCC2=CC=CC=C2)C=CC(=C1)[N+]([O-])=O
InChI
InChIKey=WBSMIPAMAXNXFS-UHFFFAOYSA-N
InChI=1S/C16H16N2O4/c19-16(20)14-11-13(18(21)22)8-9-15(14)17-10-4-7-12-5-2-1-3-6-12/h1-3,5-6,8-9,11,17H,4,7,10H2,(H,19,20)
5-Nitro-2-(3-phenylpropylamino)benzoic Acid (NPPB) is a potent Cl- channel blocker, identified through an optimization study of the diphenylamine-2-carboxylate core which demonstrates the basic Cl- channel blocking activity. NPPB also demonstrates suppression of prostaglandin E2 release with an IC50 of 8 μM, presumed to be a Cox (cyclooxygenase) inhibitor given its structural similarity to fenamic acid-type Cox inhibitors. It is also a GPR35 agonist. NPPB activates the GPR35-Gi/o and GPR35-G16 pathways in human embryonic kidney 293 (HEK293) cells and induces intracellular calcium mobilization in a concentration-dependent manner in HEK293 cells coexpressing human, rat or mouse GPR35 and the chimeric G protein G(qi5).
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Fundamental role of ClC-3 in volume-sensitive Cl- channel function and cell volume regulation in AGS cells. | 2003-11 |
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| Independence of apical Cl-/HCO3- exchange and anion conductance in duodenal HCO3- secretion. | 2003-11 |
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| Characterization of Cl-HCO3 exchange in basolateral membrane of rat distal colon. | 2003-10 |
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| Chloride influx aggravates Ca2+-dependent AMPA receptor-mediated motoneuron death. | 2003-06-15 |
|
| Basolateral Ca2+-dependent K+-channels play a key role in Cl- secretion induced by taurodeoxycholate from colon mucosa. | 2003-06-12 |
|
| Chlorotoxin-sensitive Ca2+-activated Cl- channel in type R2 reactive astrocytes from adult rat brain. | 2003-06 |
|
| Contribution of chloride channels to volume regulation of cortical astrocytes. | 2003-06 |
|
| Ca2+-activated Cl- channel currents in rat ventral prostate epithelial cells. | 2003-05-01 |
|
| Secretion of acid and base equivalents by intact distal airways. | 2003-05 |
|
| HCO(3)(-)-dependent soluble adenylyl cyclase activates cystic fibrosis transmembrane conductance regulator in corneal endothelium. | 2003-05 |
|
| PTH stimulates a Cl(-)-dependent and EIPA-sensitive current in chick proximal tubule cells in culture. | 2003-05 |
|
| Pharmacological investigation of the role of ion channels in salivary secretion. | 2003-04 |
|
| Amino acid-permeable anion channels in early mouse embryos and their possible effects on cleavage. | 2003-03 |
|
| Effects of ion transport and channel-blocking drugs on aqueous humor formation in isolated bovine eye. | 2003-03 |
|
| A novel chloride conductance activated by extracellular ATP in mouse parotid acinar cells. | 2003-02-15 |
|
| Preliminary pharmacological characterisation of an interleukin-13-enhanced calcium-activated chloride conductance in the human airway epithelium. | 2003-02 |
|
| Hypotonic-induced transport pathways in Xenopus laevis erythrocytes: taurine fluxes. | 2003-02 |
|
| Enhancement of aquaporin-3 by vasoactive intestinal polypeptide in a human colonic epithelial cell line. | 2003-02 |
|
| A chloride channel blocker reduces acetylcholine uptake into synaptic vesicles at the frog neuromuscular junction. | 2003-01-31 |
|
| The synthesis of NPPB and NPBB by reductive amination and the effects of these compounds on K+ channels of the alga Nitella hookeri. | 2003-01-20 |
|
| Impaired activity of volume-sensitive anion channel during lactacidosis-induced swelling in neuronally differentiated NG108-15 cells. | 2002-12-06 |
|
| Terbutaline-induced triphasic changes in volume of rat alveolar type II cells: the role of cAMP. | 2002-12 |
|
| Effects of 5-nitro-2-(3-phenylpropylamino) benzoic acid, anthracene-9-carboxylate, and zaprinast on endothelin-1-induced contractions of pregnant rat myometrium. | 2002-11-15 |
|
| Control of Cl- transport in the operculum epithelium of Fundulus heteroclitus: long- and short-term salinity adaptation. | 2002-11-13 |
|
| Factors affecting ammonium uptake by C11 clone of MDCK cells. | 2002-11 |
|
| Anion channels influence ECC by modulating L-type Ca(2+) channel in ventricular myocytes. | 2002-11 |
|
| Effects of bile acids on dog pancreatic duct epithelial cell secretion and monolayer resistance. | 2002-11 |
|
| Plasmalemmal voltage-activated K(+) currents in protoplasts from tobacco BY-2 cells: possible regulation by actin microfilaments? | 2002-10 |
|
| Study of a glucose-activated anion-selective channel in rat pancreatic beta-cells. | 2002-10 |
|
| Tyrosine kinases and amino acid efflux under hyposmotic and ischaemic conditions in the chicken retina. | 2002-10 |
|
| Receptor-mediated activation of a Cl(-) current by LPA and S1P in cultured corneal keratocytes. | 2002-10 |
|
| Cell cycle-dependent expression of volume-activated chloride currents in nasopharyngeal carcinoma cells. | 2002-10 |
|
| Regulatory volume decrease is actively modulated during the cell cycle. | 2002-10 |
|
| Inhibition of vacuolation toxin activity of Helicobacter pylori by iodine, nitrite and potentiation by sodium chloride, sterigmatocystin and fluoride. | 2002-10 |
|
| Effect of anion transport blockers on CFTR in the human sweat duct. | 2002-09-01 |
|
| Oscillatory chloride efflux at the pollen tube apex has a role in growth and cell volume regulation and is targeted by inositol 3,4,5,6-tetrakisphosphate. | 2002-09 |
|
| Pituitary adenylate cyclase-activating polypeptide induces a sustained increase in intracellular free Ca(2+) concentration and catechol amine release by activating Ca(2+) influx via receptor-stimulated Ca(2+) entry, independent of store-operated Ca(2+) channels, and voltage-dependent Ca(2+) channels in bovine adrenal medullary chromaffin cells. | 2002-09 |
|
| NSAIDs counteract H. pylori VacA toxin-induced cell vacuolation in MKN 28 gastric mucosal cells. | 2002-09 |
|
| The DC electrical-field-induced Ca(2+) response and growth stimulation of multicellular tumor spheroids are mediated by ATP release and purinergic receptor stimulation. | 2002-08-15 |
|
| Liquid secretion inhibitors reduce mucociliary transport in glandular airways. | 2002-08 |
|
| Activation of CFTR Cl(-) channel by tyrphostins via a protein tyrosine kinase-independent pathway in forskolin-stimulated renal epithelial A6 cells. | 2002-07-26 |
|
| Human trabecular meshwork cell volume regulation. | 2002-07 |
|
| Calcium and voltage-dependent alterations of cell volume in neuroblastomaxglioma hybrid NG108-15 cells. | 2002-05 |
|
| Amelioration of myocardial global ischemia/reperfusion injury with volume-regulatory chloride channel inhibitors in vivo. | 2002-04-27 |
|
| Basolateral membrane Cl(-)-, Na(+)-, and K(+)-coupled base transport mechanisms in rat MTALH. | 2002-04 |
|
| Two functionally distinct organic osmolyte pathways in Plasmodium gallinaceum-infected chicken red blood cells. | 2002-03-19 |
|
| Volume-activated chloride currents from human fibroblasts: blockade by nimodipine. | 2002-03 |
|
| Hydrogen peroxide-induced current in Xenopus oocytes: current characteristics similar to those induced by the removal of extracellular calcium. | 2002-02-15 |
|
| Swelling-activated taurine and creatine effluxes from rat cortical astrocytes are pharmacologically distinct. | 2002-01-15 |
|
| Transepithelial impedance analysis of chloride secretion. | 2002 |
Patents
Sample Use Guides
New Zealand white rabbits: 5-Nitro-2-(3-phenylpropylamino)benzoic Acid (NPPB) 1 mg/kg i.v. was administered 5 min before the onset of ischemia. This administration was
repeated every 12 h until killing (i.e. 72 h), starting at 2 h-CAR.
Route of Administration:
Intravenous
Arginine-vasopressin (AVP) stimulated prostaglandin biosynthesis and activated Cl- channels in cultured rat mesangial cells. AVP produced an 11-fold increase over basal levels in prostaglandin E2 release from cultured mesangial cells. This response was completely inhibited by 25 uM indomethacin and 82 +/- 5% inhibited by 25 uM 5-nitro-2-(3-phenylpropylamino)-benzoic acid (NPPB). The IC50 for NPPB inhibition of prostaglandin E2 release was 8 uM. Indomethacin and NPPB at 25 uM also inhibited AVP-stimulated cellular accumulation of prostaglandin E2 by 98% and 79 +/- 7% respectively.
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C058176
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m8084
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107254-86-4
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DTXSID90147978
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4549
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3A35O9G3YZ
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SUBSTANCE RECORD
