Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H10O3 |
| Molecular Weight | 166.1739 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(O)C=CC(=C1)C(C)=O
InChI
InChIKey=DFYRUELUNQRZTB-UHFFFAOYSA-N
InChI=1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3
Apocynin, also known as acetovanillone, is a natural organic compound related to vanillin. It has been isolated from a variety of plant sources. Metabolites of apocynin are able to block the activity of NADPH oxidase, thus giving apocynin antioxidant and anti-inflammatory capabilities. Effects of apocynin on the concentration of reactive oxygen and nitrogen species in patients with asthma and chronic obstructive pulmonary disease were investigated in phase I clinical trials. In preclinical models, it was found that apocynin provides neuroprotective effects in models of stroke and Parkinson's disease.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P14598|||Q9BXI8 Gene ID: 653361.0 Gene Symbol: NCF1 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
26.7% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25682338/ |
APOCYNIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Gene therapy of endothelial nitric oxide synthase and manganese superoxide dismutase restores delayed wound healing in type 1 diabetic mice. | 2004-10-19 |
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| Mitochondrial requirement for endothelial responses to cyclic strain: implications for mechanotransduction. | 2004-09 |
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| NADPH oxidase-dependent acid production in airway epithelial cells. | 2004-08-27 |
|
| Role of NADPH oxidase-mediated superoxide production in the regulation of E-selectin expression by endothelial cells subjected to anoxia/reoxygenation. | 2004-08-01 |
|
| Functional role of NADPH oxidase in activation of platelets. | 2004-08 |
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| Cerebral vascular dysfunction mediated by superoxide in hyperhomocysteinemic mice. | 2004-08 |
|
| Apocynin prevents cyclooxygenase 2 expression in human monocytes through NADPH oxidase and glutathione redox-dependent mechanisms. | 2004-07-15 |
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| Characterization of V642I-AbetaPP-induced cytotoxicity in primary neurons. | 2004-07-01 |
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| Evidence for contribution of vascular NAD(P)H oxidase to increased oxidative stress in animal models of diabetes and obesity. | 2004-07-01 |
|
| Regulation of inducible nitric oxide synthase expression in advanced glycation end product-stimulated raw 264.7 cells: the role of heme oxygenase-1 and endogenous nitric oxide. | 2004-07 |
|
| Chronic high pressure-induced arterial oxidative stress: involvement of protein kinase C-dependent NAD(P)H oxidase and local renin-angiotensin system. | 2004-07 |
|
| Extracellular superoxide enhances 5-HT-induced murine pulmonary artery vasoconstriction. | 2004-07 |
|
| NADPH oxidase contributes to angiotensin II signaling in the nucleus tractus solitarius. | 2004-06-16 |
|
| Race-specific differences in endothelial function: predisposition of African Americans to vascular diseases. | 2004-06-01 |
|
| Angiotensin II and endothelin-1 regulate MAP kinases through different redox-dependent mechanisms in human vascular smooth muscle cells. | 2004-06 |
|
| Stable compounds of cigarette smoke induce endothelial superoxide anion production via NADPH oxidase activation. | 2004-06 |
|
| Silvestrol and episilvestrol, potential anticancer rocaglate derivatives from Aglaia silvestris. | 2004-05-14 |
|
| Insulin generates free radicals by an NAD(P)H, phosphatidylinositol 3'-kinase-dependent mechanism in human skin fibroblasts ex vivo. | 2004-05 |
|
| Azelnidipine, a newly developed long-acting calcium antagonist, inhibits tumor necrosis factor-alpha-induced interleukin-8 expression in endothelial cells through its anti-oxidative properties. | 2004-05 |
|
| Involvement of NADPH oxidase-mediated generation of reactive oxygen species in the apototic cell death by capsaicin in HepG2 human hepatoma cells. | 2004-04 |
|
| Reactive oxygen species amplify protein kinase C signaling in high glucose-induced fibronectin expression by human peritoneal mesothelial cells. | 2004-04 |
|
| Endogenous adrenomedullin protects against vascular response to injury in mice. | 2004-03-09 |
|
| Involvement of reactive oxygen species in bacterial killing within epithelial cells. | 2004-03-06 |
|
| Role of the epidermal growth factor receptor in signaling strain-dependent activation of the brain natriuretic peptide gene. | 2004-03-05 |
|
| Dietary compounds prevent oxidative damage and nitric oxide production by cells involved in demyelinating disease. | 2004-03-01 |
|
| Role of NAD(P)H oxidase on vascular alterations in angiotensin II-infused mice. | 2004-03 |
|
| Amino- and carboxyl-terminal mutants of presenilin 1 cause neuronal cell death through distinct toxic mechanisms: Study of 27 different presenilin 1 mutants. | 2004-02-01 |
|
| [Isolation and structural identification of C-glycosylflavones from Corallodiscus flabellata]. | 2004-02 |
|
| Role of oxidative stress and nitric oxide in regulation of spontaneous tone in aorta of DOCA-salt hypertensive rats. | 2004-02 |
|
| Iloprost inhibits superoxide formation and gp91phox expression induced by the thromboxane A2 analogue U46619, 8-isoprostane F2alpha, prostaglandin F2alpha, cytokines and endotoxin in the pig pulmonary artery. | 2004-02 |
|
| Tempol lowers blood pressure and sympathetic nerve activity but not vascular O2- in DOCA-salt rats. | 2004-02 |
|
| PPARgamma activation, by reducing oxidative stress, increases NO bioavailability in coronary arterioles of mice with Type 2 diabetes. | 2004-02 |
|
| NAD(P)H oxidase inhibitor prevents blood pressure elevation and cardiovascular hypertrophy in aldosterone-infused rats. | 2004-01-16 |
|
| Beta-amyloid peptides induce mitochondrial dysfunction and oxidative stress in astrocytes and death of neurons through activation of NADPH oxidase. | 2004-01-14 |
|
| Reactive oxygen species-sensitive p38 MAPK controls thrombin-induced migration of vascular smooth muscle cells. | 2004-01 |
|
| Oxidant stress leads to impaired regulation of renal cortical oxygen consumption by nitric oxide in the aging kidney. | 2004-01 |
|
| Coronary microvascular endothelial stunning after acute pressure overload in the conscious dog is caused by oxidant processes: the role of angiotensin II type 1 receptor and NAD(P)H oxidase. | 2003-12-09 |
|
| Superoxide does not mediate the acute vasoconstrictor effects of angiotensin II: a study in human and porcine arteries. | 2003-12 |
|
| Role of superoxide in modulating the renal effects of angiotensin II. | 2003-12 |
|
| Role of xanthine oxidoreductase and NAD(P)H oxidase in endothelial superoxide production in response to oscillatory shear stress. | 2003-12 |
|
| Platelets induce reactive oxygen species-dependent growth of human skin fibroblasts. | 2003-11 |
|
| Renal and vascular oxidative stress and salt-sensitivity of arterial pressure. | 2003-11 |
|
| Endothelin-1 stimulates arterial VCAM-1 expression via NADPH oxidase-derived superoxide in mineralocorticoid hypertension. | 2003-11 |
|
| Concomitant production of nitric oxide and superoxide in human macrophages. | 2003-10-17 |
|
| Simultaneous determination of 2-methoxyphenol, 2-methoxy-4-methylphenol, 2,6-dimethoxyphenol and 4'-hydroxy-3'-methoxyacetophenone in urine by capillary gas chromatography. | 2003-10-05 |
|
| Mechanisms involved in the early increase of serotonin contraction evoked by endotoxin in rat middle cerebral arteries. | 2003-10 |
|
| Angiotensin II-NAD(P)H oxidase-stimulated superoxide modifies tubulovascular nitric oxide cross-talk in renal outer medulla. | 2003-10 |
|
| Mitochondrial sources of H2O2 generation play a key role in flow-mediated dilation in human coronary resistance arteries. | 2003-09-19 |
|
| Gene transfer of human guanosine 5'-triphosphate cyclohydrolase I restores vascular tetrahydrobiopterin level and endothelial function in low renin hypertension. | 2003-09-09 |
|
| NADPH oxidase and enhanced superoxide generation in intrauterine undernourished rats: involvement of the renin-angiotensin system. | 2003-09-01 |
Sample Use Guides
In a clinical trial against chronic obstructive pulmonary disease, effects of nebulized apocynin (0.5 mg/ml, 6 ml) were assessed in exhaled breath condensate. In rat models of Parkinson's disease, apocynin was administered intraperitoneally at 10 mg/kg. In a model of rheumatoid arthritis, apocynin was administered orally.
Route of Administration:
Other
The NADPH oxidase inhibitory activity of apocynin and products of its oxidation (AOP) was assessed in an endothelial cell-based assay by measuring the generation of •O2− via cytochrome c reduction. Apocynin itself possesses minimal inhibitory activity (IC50 > 1 mM), while the extracted water-soluble phase of its metabolites exhibited an apparent IC50 value of 155 nM.
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C056165
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APOCYNIN
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SUBSTANCE RECORD
