Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H8I.Cl |
| Molecular Weight | 314.549 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cl-].[I+]1C2=CC=CC=C2C3=C1C=CC=C3
InChI
InChIKey=FCFZKAVCDNTYID-UHFFFAOYSA-M
InChI=1S/C12H8I.ClH/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11;/h1-8H;1H/q+1;/p-1
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C12H8I |
| Molecular Weight | 279.0964 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Diphenyleneiodonium chloride is an irreversible inhibitor of nitric oxide synthases, iNOS and eNOS, NADPH cytochrome P450 oxidoreductase and inhibits preferentially the plasma membrane NADH oxidase (NOX) activity. Diphenyleneiodonium chloride exhibits potent antimicrobial activity against non-tuberculous mycobacteria and possesses a potentially new mechanism of action. Besides, experiments on diabetic animal models have shown, that diphenyleneiodonium mitigates sciatic nerve damage by attenuating oxidative stress.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P16435 Gene ID: 5447.0 Gene Symbol: POR Target Organism: Homo sapiens (Human) |
2.8 mM [Ki] | ||
Target ID: CHEMBL2111350 |
|||
Target ID: Q9Y5S8 Gene ID: 27035.0 Gene Symbol: NOX1 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Enhanced NADPH oxidases and reactive oxygen species in the mechanism of methanol-initiated protein oxidation and embryopathies in vivo and in embryo culture. | 2016-03 |
|
| Cadmium induces matrix metalloproteinase-9 expression via ROS-dependent EGFR, NF-кB, and AP-1 pathways in human endothelial cells. | 2015-12-02 |
|
| Endosulfan induces COX-2 expression via NADPH oxidase and the ROS, MAPK, and Akt pathways. | 2015-11 |
|
| Structurally related ganoderic acids induce apoptosis in human cervical cancer HeLa cells: Involvement of oxidative stress and antioxidant protective system. | 2015-10-05 |
|
| Purinergic signaling via P2X7 receptor mediates IL-1β production in Kupffer cells exposed to silica nanoparticle. | 2014-07-03 |
|
| Air pollution upregulates endothelial cell procoagulant activity via ultrafine particle-induced oxidant signaling and tissue factor expression. | 2014-07 |
|
| Toll-like receptor 4-mediated ROS signaling pathway involved in Ganoderma atrum polysaccharide-induced tumor necrosis factor-α secretion during macrophage activation. | 2014-04 |
|
| Oxidative stress parameters induced by exposure to either cadmium or 17β-estradiol on Mytilus galloprovincialis hemocytes. The role of signaling molecules. | 2014-01 |
|
| Hyperosmolarity-induced up-regulation of claudin-4 mediated by NADPH oxidase-dependent H2O2 production and Sp1/c-Jun cooperation. | 2013-12 |
|
| Ethanol increases matrix metalloproteinase-12 expression via NADPH oxidase-dependent ROS production in macrophages. | 2013-11-15 |
|
| NADPH oxidase/ROS-dependent PYK2 activation is involved in TNF-α-induced matrix metalloproteinase-9 expression in rat heart-derived H9c2 cells. | 2013-10-15 |
|
| TNF-Α may mediate inflammasome activation in the absence of bacterial infection in more than one way. | 2013 |
|
| Contribution of NADPH oxidase to membrane CD38 internalization and activation in coronary arterial myocytes. | 2013 |
|
| Astaxanthin protects against MPP(+)-induced oxidative stress in PC12 cells via the HO-1/NOX2 axis. | 2012-12-29 |
|
| Manganese promotes increased formation of hydrogen peroxide by activated human macrophages and neutrophils in vitro. | 2012-08 |
|
| Intervention of human breast cell carcinogenesis chronically induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. | 2012-04 |
|
| Cyclooxygenase-2 expression is up-regulated by 2-aminobiphenyl in a ROS and MAPK-dependent signaling pathway in a bladder cancer cell line. | 2012-03-19 |
|
| Insulin increases surface expression of TRPC6 channels in podocytes: role of NADPH oxidases and reactive oxygen species. | 2012-02-01 |
|
| Curcumin regulates airway epithelial cell cytokine responses to the pollutant cadmium. | 2012-01-06 |
|
| Cadmium increases HIF-1 and VEGF expression through ROS, ERK, and AKT signaling pathways and induces malignant transformation of human bronchial epithelial cells. | 2012-01 |
|
| Time-dependent stabilization of hypoxia inducible factor-1α by different intracellular sources of reactive oxygen species. | 2012 |
|
| Cigarette smoke affects keratinocytes SRB1 expression and localization via H2O2 production and HNE protein adducts formation. | 2012 |
|
| Activation of CD40 with platelet derived CD154 promotes reactive oxygen species dependent death of human hepatocytes during hypoxia and reoxygenation. | 2012 |
|
| Arsenic-induced alteration in intracellular calcium homeostasis induces head kidney macrophage apoptosis involving the activation of calpain-2 and ERK in Clarias batrachus. | 2011-10-01 |
|
| Dual function of protein kinase C (PKC) in 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced manganese superoxide dismutase (MnSOD) expression: activation of CREB and FOXO3a by PKC-alpha phosphorylation and by PKC-mediated inactivation of Akt, respectively. | 2011-08-26 |
|
| Regulation of cyclooxygenase-2 and cytosolic phospholipase A2 gene expression by lipopolysaccharide through the RNA-binding protein HuR: involvement of NADPH oxidase, reactive oxygen species and mitogen-activated protein kinases. | 2011-08 |
|
| Signaling cascades mediate astrocyte death induced by zinc. | 2011-07-28 |
|
| The signalling axis mediating neuronal apoptosis in response to [Pt(O,O'-acac)(γ-acac)(DMS)]. | 2011-06-01 |
|
| Neuroinflammation and α-synuclein dysfunction potentiate each other, driving chronic progression of neurodegeneration in a mouse model of Parkinson's disease. | 2011-06 |
|
| Lipid raft-dependent death receptor 5 (DR5) expression and activation are critical for ursodeoxycholic acid-induced apoptosis in gastric cancer cells. | 2011-05 |
|
| Redox cycling and increased oxygen utilization contribute to diquat-induced oxidative stress and cytotoxicity in Chinese hamster ovary cells overexpressing NADPH-cytochrome P450 reductase. | 2011-04-01 |
|
| Involvement of H-Ras and reactive oxygen species in proinflammatory cytokine-induced matrix metalloproteinase-13 expression in human articular chondrocytes. | 2011-03-15 |
|
| Cellular iron depletion weakens induction of heme oxygenase-1 by cadmium. | 2011-01 |
|
| Role and mechanism of arsenic in regulating angiogenesis. | 2011 |
|
| IGF-1 induces expression of zinc-finger protein 143 in colon cancer cells through phosphatidylinositide 3-kinase and reactive oxygen species. | 2010-10-31 |
|
| Protection of podocytes from hyperhomocysteinemia-induced injury by deletion of the gp91phox gene. | 2010-04-15 |
|
| Redox signaling via lipid raft clustering in homocysteine-induced injury of podocytes. | 2010-04 |
|
| Cellular mechanisms of IL-17-induced blood-brain barrier disruption. | 2010-04 |
|
| The role of NOX enzymes in ethanol-induced oxidative stress and apoptosis in mouse embryos. | 2010-03-01 |
|
| Cellular factors involved in CXCL8 expression induced by glycated serum albumin in vascular smooth muscle cells. | 2010-03 |
|
| Contribution of reactive oxygen species to migration/invasion of human glioblastoma cells U87 via ERK-dependent COX-2/PGE(2) activation. | 2010-01 |
|
| Low concentration of arsenic could induce caspase-3 mediated head kidney macrophage apoptosis with JNK-p38 activation in Clarias batrachus. | 2009-12-15 |
|
| NADPH oxidase and lipid raft-associated redox signaling are required for PCB153-induced upregulation of cell adhesion molecules in human brain endothelial cells. | 2009-10-15 |
|
| Atorvastatin attenuates homocysteine-induced apoptosis in human umbilical vein endothelial cells via inhibiting NADPH oxidase-related oxidative stress-triggered p38MAPK signaling. | 2009-10 |
|
| A benzoxazine derivative induces vascular endothelial cell apoptosis in the presence of fibroblast growth factor-2 by elevating NADPH oxidase activity and reactive oxygen species levels. | 2009-09 |
|
| Overexpression of HO-1 protects against TNF-alpha-mediated airway inflammation by down-regulation of TNFR1-dependent oxidative stress. | 2009-08 |
|
| Resveratrol blocks interleukin-18-EMMPRIN cross-regulation and smooth muscle cell migration. | 2009-08 |
|
| NADPH oxidase and ERK1/2 are involved in cadmium induced-STAT3 activation in HepG2 cells. | 2009-06-22 |
|
| Activation of ROS/NF-kappaB and Ca2+/CaM kinase II are necessary for VCAM-1 induction in IL-1beta-treated human tracheal smooth muscle cells. | 2009-05-15 |
|
| Activation of endothelial cells after exposure to ambient ultrafine particles: the role of NADPH oxidase. | 2009-04-15 |
Patents
Sample Use Guides
Diabetic Neuropathy Rat Model: diphenyleneiodonium (DPI) chloride (1 mg/kg) was injected subcutaneously 24 hours and 30 minutes before the sciatic block
Route of Administration:
Other
Diphenyleneiodonium chloride (DPI) effectively inhibited NO production (IC50=0.03+/-0.004 microM), as evaluated by the method of Griess. Nuclear factor-kappa B (NF-kappaB) activation, as evaluated by electrophoretic mobility shift assay, was inhibited by DPI (1-10 microM) in a dose-dependent manner. IL-1-induced ROS production, as evaluated by measurement of dichlorofluorescein fluorescence, was inhibited by DPI at concentrations that also prevented NF-kappaB activation and iNOS expression.
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
7M9D81YZ2N
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| Record Status |
Validated (UNII)
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| Record Version |
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