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 |
|---|---|---|
| Non-CFTR chloride channels likely contribute to secretion in the murine small intestine. | 2001 |
|
| Cellular bicarbonate protects rat duodenal mucosa from acid-induced injury. | 2001 Dec |
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| Detection of Cl- flux in the apical microenvironment of cultured foetal distal lung epithelial cells. | 2001 Feb |
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| Epidermal growth factor regulates the transition from basal sodium absorption to anion secretion in cultured endometrial epithelial cells. | 2001 Feb |
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| Adrenergic receptor activated ion transport in human fetal retinal pigment epithelium. | 2001 Jan |
|
| Extracellular adenosine modulates a volume-sensitive-like chloride conductance in immortalized rabbit DC1 cells. | 2001 Jan |
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| Forskolin activation of apical Cl- channel and Na+/K+/2Cl- cotransporter via a PTK-dependent pathway in renal epithelium. | 2001 Jul 27 |
|
| Properties of synchronous and asynchronous release during pulse train depression in cultured hippocampal neurons. | 2001 Jun |
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| Characterization of apical membrane Cl-dependent Na/H exchange in crypt cells of rat distal colon. | 2001 Mar |
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| NH(2)-terminal modification of a channel-forming peptide increases capacity for epithelial anion secretion. | 2001 Mar |
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| Cl- channel inhibitors of the arylaminobenzoate type act as photosystem II herbicides: a functional and structural study. | 2001 Mar 20 |
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| Expression of chloride channel, ClC-5, and its role in receptor-mediated endocytosis of albumin in OK cells. | 2001 Mar 23 |
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| Role of Cl- current in endothelin-1-induced contraction in rabbit basilar artery. | 2001 Nov |
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| Induction of H(2)O(2) synthesis by beta-glucan elicitors in soybean is independent of cytosolic calcium transients. | 2001 Nov 16 |
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| Chloride channel inhibition does block the protection of ischemic preconditioning in myocardium. | 2001 Oct |
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| Novel effects of minocycline on Ca(2+)-dependent Cl(-) secretion in human airway epithelial Calu-3 cells. | 2001 Oct 15 |
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| Amelioration of myocardial global ischemia/reperfusion injury with volume-regulatory chloride channel inhibitors in vivo. | 2002 Apr 27 |
|
| 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 Aug 15 |
|
| ACTH-induced Cl(-) current in bovine adrenocortical cells: correlation with cortisol secretion. | 2002 Feb |
|
| Activation of CFTR Cl(-) channel by tyrphostins via a protein tyrosine kinase-independent pathway in forskolin-stimulated renal epithelial A6 cells. | 2002 Jul 26 |
|
| Effects of 5-nitro-2-(3-phenylpropylamino) benzoic acid, anthracene-9-carboxylate, and zaprinast on endothelin-1-induced contractions of pregnant rat myometrium. | 2002 Nov 15 |
|
| Inhibition of vacuolation toxin activity of Helicobacter pylori by iodine, nitrite and potentiation by sodium chloride, sterigmatocystin and fluoride. | 2002 Oct |
|
| 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 Sep |
|
| Preliminary pharmacological characterisation of an interleukin-13-enhanced calcium-activated chloride conductance in the human airway epithelium. | 2003 Feb |
|
| Hypotonic-induced transport pathways in Xenopus laevis erythrocytes: taurine fluxes. | 2003 Feb |
|
| Enhancement of aquaporin-3 by vasoactive intestinal polypeptide in a human colonic epithelial cell line. | 2003 Feb |
|
| A novel chloride conductance activated by extracellular ATP in mouse parotid acinar cells. | 2003 Feb 15 |
|
| Effects of ion transport and channel-blocking drugs on aqueous humor formation in isolated bovine eye. | 2003 Mar |
|
| Basolateral Ca2+-dependent K+-channels play a key role in Cl- secretion induced by taurodeoxycholate from colon mucosa. | 2003 Mar-Apr |
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
