Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H18NO2 |
| Molecular Weight | 172.2447 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)CC(O)CC(C)(C)N1[O]
InChI
InChIKey=CSGAUKGQUCHWDP-UHFFFAOYSA-N
InChI=1S/C9H19NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11-12H,5-6H2,1-4H3
| Molecular Formula | C9H18NO2 |
| Molecular Weight | 172.2447 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Tempol is used as an industrial catalyst and chemical oxidant. However, its ability to scavenge free oxygen species has generated interest in the biochemical potential of this compound. Biologically Tempol catalyzes the disproportionation of superoxides, facilitates hydrogen peroxide metabolism, and inhibits Fenton chemistry. These properties generated investigational interest for the use of tempol to mediate radiation damage during chemotherapy. Tempol has been used in human clinical trials for mitigation of radiation damage in related to anal cancer, and brain cancer. Tempol has also been investigated in a number of animal and invitro models for conditions, such as oxidative damage, brain hemorrhage, anxiety, malaria, platelet agregation,
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Ketoconazole induces apoptosis in rat cardiomyocytes through reactive oxygen species-mediated parkin overexpression. | 2015-10 |
|
| Antioxidants and NOS inhibitors selectively targets manganese-induced cell volume via Na-K-Cl cotransporter-1 in astrocytes. | 2015-06-12 |
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| MAPK pathway activation by chronic lead-exposure increases vascular reactivity through oxidative stress/cyclooxygenase-2-dependent pathways. | 2015-03-01 |
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| The miR-322-TRAF3 circuit mediates the pro-apoptotic effect of high glucose on neural stem cells. | 2015-03 |
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| Aldosterone induces fibrosis, oxidative stress and DNA damage in livers of male rats independent of blood pressure changes. | 2014-11-01 |
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| NADPH oxidase NOX4 supports renal tumorigenesis by promoting the expression and nuclear accumulation of HIF2α. | 2014-07-01 |
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| Tempol protects cardiomyocytes from nucleoside reverse transcriptase inhibitor-induced mitochondrial toxicity. | 2014-05 |
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| Tempol attenuates renal fibrosis in mice with unilateral ureteral obstruction: the role of PI3K-Akt-FoxO3a signaling. | 2014-02 |
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| Involvement of reactive oxygen species in brominated diphenyl ether-47-induced inflammatory cytokine release from human extravillous trophoblasts in vitro. | 2014-01-15 |
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| Mercury induces proliferation and reduces cell size in vascular smooth muscle cells through MAPK, oxidative stress and cyclooxygenase-2 pathways. | 2013-04-15 |
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| Contribution of NADPH oxidase to membrane CD38 internalization and activation in coronary arterial myocytes. | 2013 |
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| Role of copper transport protein antioxidant 1 in angiotensin II-induced hypertension: a key regulator of extracellular superoxide dismutase. | 2012-08 |
|
| Oxidative stress in Fanconi anaemia: from cells and molecules towards prospects in clinical management. | 2012-01 |
|
| Arachidonic acid- and prostaglandin E2-induced cerebral vasodilation is mediated by carbon monoxide, independent of reactive oxygen species in piglets. | 2011-12 |
|
| eNOS activation mediated by AMPK after stimulation of endothelial cells with histamine or thrombin is dependent on LKB1. | 2011-02 |
|
| Oxidative stress alters renal D1 and AT1 receptor functions and increases blood pressure in old rats. | 2011-01 |
|
| Aspirin resistance with genetic dyslipidemia: contribution of vascular thromboxane generation. | 2010-08 |
|
| Oxidative stress contributes to methamphetamine-induced left ventricular dysfunction. | 2010-07-01 |
|
| Different protective actions of losartan and tempol on the renal inflammatory response to acute sodium overload. | 2010-07 |
|
| Oxidative stress is important in the pathogenesis of liver injury induced by sulindac and lipopolysaccharide cotreatment. | 2010-06-04 |
|
| The induction of reactive oxygen species and loss of mitochondrial Omi/HtrA2 is associated with S-nitrosoglutathione-induced apoptosis in human endothelial cells. | 2010-05-01 |
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| MnSOD protects against COX1-mediated endothelial dysfunction in chronic heart failure. | 2010-05 |
|
| Angiotensin II inhibits neuronal nitric oxide synthase activation through the ERK1/2-RSK signaling pathway to modulate central control of blood pressure. | 2010-03-05 |
|
| Superoxide signaling in pain is independent of nitric oxide signaling. | 2009-10-28 |
|
| Gene expression profiling of aging in multiple mouse strains: identification of aging biomarkers and impact of dietary antioxidants. | 2009-08 |
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| Resveratrol improves endothelial function: role of TNF{alpha} and vascular oxidative stress. | 2009-08 |
|
| Persistent pain is dependent on spinal mitochondrial antioxidant levels. | 2009-01-07 |
|
| Inhibition of apoptotic signaling and neointimal hyperplasia by tempol and nitric oxide synthase following vascular injury. | 2009 |
|
| Arsenic-stimulated liver sinusoidal capillarization in mice requires NADPH oxidase-generated superoxide. | 2008-12 |
|
| Role of Menkes ATPase in angiotensin II-induced hypertension: a key modulator for extracellular superoxide dismutase function. | 2008-11 |
|
| Oxidative stress in the spinal cord is an important contributor in capsaicin-induced mechanical secondary hyperalgesia in mice. | 2008-09-15 |
|
| Alpha2-adrenoceptors enhance angiotensin II-induced renal vasoconstriction: role for NADPH oxidase and RhoA. | 2008-03 |
|
| Zinc deficiency-induced iron accumulation, a consequence of alterations in iron regulatory protein-binding activity, iron transporters, and iron storage proteins. | 2008-02-22 |
|
| Anesthetic preconditioning confers acute cardioprotection via up-regulation of manganese superoxide dismutase and preservation of mitochondrial respiratory enzyme activity. | 2008-02 |
|
| Tamoxifen neuroprotection in cerebral ischemia involves attenuation of kinase activation and superoxide production and potentiation of mitochondrial superoxide dismutase. | 2008-01 |
|
| The role of reactive oxygen species in capsaicin-induced mechanical hyperalgesia and in the activities of dorsal horn neurons. | 2007-12-15 |
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| NADPH oxidase mediates angiotensin II-induced endothelin-1 expression in vascular adventitial fibroblasts. | 2007-09-01 |
|
| Comparison of the effects of the superoxide dismutase mimetics EUK-134 and tempol on paraquat-induced nephrotoxicity. | 2007-08-15 |
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| Receptor-independent intracellular radical scavenging activity of an angiotensin II receptor blocker. | 2007-08 |
|
| Differential regulation of the superoxide dismutase family in experimental aortic aneurysms and rat aortic explants. | 2007-04 |
|
| Glucose down-regulation of cGMP-dependent protein kinase I expression in vascular smooth muscle cells involves NAD(P)H oxidase-derived reactive oxygen species. | 2007-03-15 |
|
| Early renal injury induced by caffeine consumption in obese, diabetic ZSF1 rats. | 2007 |
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| Copper activates the NF-kappaB pathway in vivo. | 2006-09-22 |
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| Oxidative stress mediates the stimulation of sympathetic nerve activity in the phenol renal injury model of hypertension. | 2006-08 |
|
| Contribution of reactive oxygen species to the pathogenesis of left ventricular failure in Dahl salt-sensitive hypertensive rats: effects of angiotensin II blockade. | 2006-06 |
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| Superoxide contributes to development of salt sensitivity and hypertension induced by nitric oxide deficiency. | 2005-10 |
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| Antioxidant enzymes and effects of tempol on the development of hypertension induced by nitric oxide inhibition. | 2005-06 |
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| Differential effect of antioxidant treatment on plasma and tissue paraoxonase activity in hyperleptinemic rats. | 2005-06 |
|
| Pivotal role of gp91phox-containing NADH oxidase in lipopolysaccharide-induced tumor necrosis factor-alpha expression and myocardial depression. | 2005-04-05 |
|
| Molecular mechanisms of tirapazamine (SR 4233, Win 59075)-induced hepatocyte toxicity under low oxygen concentrations. | 1995-04 |
Sample Use Guides
In a phase II clinical trial investigating the ability of tempol to prevent hair loss due to radiation treatment; 200 mL of 7% (w/v) Tempol gel was applied daily to patients prior to radiation dose and removed immediately thereafter.
Route of Administration:
Topical
Undifferentiated HL-60 cells were maintained in RPMI 1640 media containing 10% fetal bovine serum and 25 mM HEPES at 37 deg-C in a 5% CO2 atmosphere. HL-60 cells were differentiated in a culture medium containing 1.3% DMSO for five days prior to a 3-hour incubation with Tempol. At a concentration of <0.3 mM Tempol completely abolishes O2^- detection. At 0.3 mM and higher Tempol also attenuates H2O2 levels triggered by 1 microM of fMLP. Therefore, Tempol is a potent and effective antioxidant.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:51:29 GMT 2025
by
admin
on
Mon Mar 31 17:51:29 GMT 2025
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| Record UNII |
U78ZX2F65X
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
827721
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FDA ORPHAN DRUG |
487815
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EU-Orphan Drug |
EU/3/17/1948
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C96428
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137994
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2226-96-2
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Tempol
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SUB192815
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U78ZX2F65X
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218-760-9
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100000177373
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DTXSID4041280
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142784
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m10554
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DB12449
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8014
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