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
Doses
| Dose | Population | Adverse events |
|---|---|---|
70 mg/mL 1 times / day multiple, topical Studied dose Dose: 70 mg/mL, 1 times / day Route: topical Route: multiple Dose: 70 mg/mL, 1 times / day Sources: Page: p.6414 |
unhealthy, ADULT n = 12 Health Status: unhealthy Condition: alopecia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 12 Sources: Page: p.6414 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Molecular mechanisms of tirapazamine (SR 4233, Win 59075)-induced hepatocyte toxicity under low oxygen concentrations. | 1995 Apr |
|
| Effect of lead on nitric oxide synthase expression in coronary endothelial cells: role of superoxide. | 2001 Feb |
|
| The anti-oxidant Tempol reverses and partially prevents adrenocorticotrophic hormone-induced hypertension in the rat. | 2003 Aug |
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| Tert-butyl hydroperoxide-mediated vascular responses in DOCA-salt hypertensive rats. | 2003 Jan |
|
| Redox regulation of HIF-1alpha levels and HO-1 expression in renal medullary interstitial cells. | 2003 Jun |
|
| Role of the p53/p21 system in the response of human colon carcinoma cells to Doxorubicin. | 2004 Dec 15 |
|
| The antioxidant tempol prevents and partially reverses dexamethasone-induced hypertension in the rat. | 2004 Mar |
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| Superoxide contributes to development of salt sensitivity and hypertension induced by nitric oxide deficiency. | 2005 Oct |
|
| Contribution of reactive oxygen species to the pathogenesis of left ventricular failure in Dahl salt-sensitive hypertensive rats: effects of angiotensin II blockade. | 2006 Jun |
|
| Early renal injury induced by caffeine consumption in obese, diabetic ZSF1 rats. | 2007 |
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| Comparison of the effects of the superoxide dismutase mimetics EUK-134 and tempol on paraquat-induced nephrotoxicity. | 2007 Aug 15 |
|
| The role of reactive oxygen species in capsaicin-induced mechanical hyperalgesia and in the activities of dorsal horn neurons. | 2007 Dec 15 |
|
| 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 Mar 15 |
|
| Arsenic-stimulated liver sinusoidal capillarization in mice requires NADPH oxidase-generated superoxide. | 2008 Dec |
|
| Anesthetic preconditioning confers acute cardioprotection via up-regulation of manganese superoxide dismutase and preservation of mitochondrial respiratory enzyme activity. | 2008 Feb |
|
| Tamoxifen neuroprotection in cerebral ischemia involves attenuation of kinase activation and superoxide production and potentiation of mitochondrial superoxide dismutase. | 2008 Jan |
|
| Gene expression profiling of aging in multiple mouse strains: identification of aging biomarkers and impact of dietary antioxidants. | 2009 Aug |
|
| Resveratrol improves endothelial function: role of TNF{alpha} and vascular oxidative stress. | 2009 Aug |
|
| Persistent pain is dependent on spinal mitochondrial antioxidant levels. | 2009 Jan 7 |
|
| Superoxide signaling in pain is independent of nitric oxide signaling. | 2009 Oct 28 |
|
| Different protective actions of losartan and tempol on the renal inflammatory response to acute sodium overload. | 2010 Jul |
|
| Oxidative stress contributes to methamphetamine-induced left ventricular dysfunction. | 2010 Jul 1 |
|
| Oxidative stress is important in the pathogenesis of liver injury induced by sulindac and lipopolysaccharide cotreatment. | 2010 Jun 4 |
|
| Angiotensin II inhibits neuronal nitric oxide synthase activation through the ERK1/2-RSK signaling pathway to modulate central control of blood pressure. | 2010 Mar 5 |
|
| MnSOD protects against COX1-mediated endothelial dysfunction in chronic heart failure. | 2010 May |
|
| The induction of reactive oxygen species and loss of mitochondrial Omi/HtrA2 is associated with S-nitrosoglutathione-induced apoptosis in human endothelial cells. | 2010 May 1 |
|
| eNOS activation mediated by AMPK after stimulation of endothelial cells with histamine or thrombin is dependent on LKB1. | 2011 Feb |
|
| NADPH oxidase NOX4 supports renal tumorigenesis by promoting the expression and nuclear accumulation of HIF2α. | 2014 Jul 1 |
|
| Aldosterone induces fibrosis, oxidative stress and DNA damage in livers of male rats independent of blood pressure changes. | 2014 Nov 1 |
|
| Antioxidants and NOS inhibitors selectively targets manganese-induced cell volume via Na-K-Cl cotransporter-1 in astrocytes. | 2015 Jun 12 |
|
| The miR-322-TRAF3 circuit mediates the pro-apoptotic effect of high glucose on neural stem cells. | 2015 Mar |
|
| MAPK pathway activation by chronic lead-exposure increases vascular reactivity through oxidative stress/cyclooxygenase-2-dependent pathways. | 2015 Mar 1 |
|
| Ketoconazole induces apoptosis in rat cardiomyocytes through reactive oxygen species-mediated parkin overexpression. | 2015 Oct |
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
Fri Dec 15 15:14:44 GMT 2023
by
admin
on
Fri Dec 15 15:14:44 GMT 2023
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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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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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