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
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
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Q16665 Gene ID: 3091.0 Gene Symbol: HIF1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26034980 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Secondary | Unknown Approved UseUnknown |
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Secondary | Unknown Approved UseUnknown |
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 |
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Compensatory up-regulation of nitric-oxide synthase isoforms in lead-induced hypertension; reversal by a superoxide dismutase-mimetic drug. | 2001 Aug |
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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 |
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Excessive zinc intake elevates systemic blood pressure levels in normotensive rats--potential role of superoxide-induced oxidative stress. | 2004 Mar |
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The antioxidant tempol prevents and partially reverses dexamethasone-induced hypertension in the rat. | 2004 Mar |
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Antioxidant enzymes and effects of tempol on the development of hypertension induced by nitric oxide inhibition. | 2005 Jun |
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Alpha2-adrenoceptors enhance angiotensin II-induced renal vasoconstriction: role for NADPH oxidase and RhoA. | 2008 Mar |
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Role of Menkes ATPase in angiotensin II-induced hypertension: a key modulator for extracellular superoxide dismutase function. | 2008 Nov |
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Persistent pain is dependent on spinal mitochondrial antioxidant levels. | 2009 Jan 7 |
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Oxidative stress contributes to methamphetamine-induced left ventricular dysfunction. | 2010 Jul 1 |
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Oxidative stress is important in the pathogenesis of liver injury induced by sulindac and lipopolysaccharide cotreatment. | 2010 Jun 4 |
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NADPH oxidase NOX4 supports renal tumorigenesis by promoting the expression and nuclear accumulation of HIF2α. | 2014 Jul 1 |
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The miR-322-TRAF3 circuit mediates the pro-apoptotic effect of high glucose on neural stem cells. | 2015 Mar |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00801086
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24586264
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.
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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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m10554
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DB12449
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8014
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ACTIVE MOIETY