TEMPOL

Investigational

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

Structure Search

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19112152 | https://clinicaltrials.gov/ct2/show/NCT00801086 | https://clinicaltrials.gov/ct2/show/NCT01324141 | https://www.ncbi.nlm.nih.gov/pubmed/25380160 | https://www.ncbi.nlm.nih.gov/pubmed/24586264

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
Hypoxia-inducible factor 1-alpha 10 Target ID: Q16665 Gene ID: 3091.0 Gene Symbol: HIF1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26034980	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anal cancer 1 Sources: https://clinicaltrials.gov/ct2/show/NCT01324141	Secondary		Phase I 428	Unknown Approved Use Unknown
Hair loss during radiation therapy 1 Sources: https://clinicaltrials.gov/ct2/show/NCT00801086	Secondary		Phase II 1132	Unknown Approved Use Unknown

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: https://pubmed.ncbi.nlm.nih.gov/15475427 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: https://pubmed.ncbi.nlm.nih.gov/15475427 Page: p.6414	Sources: https://pubmed.ncbi.nlm.nih.gov/15475427 Page: p.6414

Sourcing

Vendor/Aggregator	ID	URL
Accela ChemBio Inc	SY002737	http://accelachem.com/cn/search.html?keyword=SY002737&attname=0
Alfa Chemistry	ACM3637103	http://www.alfa-chemistry.com/search.aspx?q=ACM3637103
BLD Pharm	BD64176	http://www.bldpharm.com/search/Search.html?keyword=BD64176
BioSynth	J-660069	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/J-660069
Chemspace	CSC000042448	https://chem-space.com/CSC000042448
Enamine	BBV-38267745	http://www.enaminestore.com/catalog/BBV-38267745
Lab Network	LN00188889	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00188889
Lab Seeker	SC-02570	http://www.labseeker.com/search.php?keywords=SC-02570&category=0
Lab Seeker	SC-52705	http://www.labseeker.com/search.php?keywords=SC-52705&category=0
LabSeeker	SC-02570	http://www.labseeker.com/search.php?keywords=SC-02570&category=0
LabSeeker	SC-52705	http://www.labseeker.com/search.php?keywords=SC-52705&category=0
MuseChem	R037184	https://www.musechem.com/product/R037184.html
TargetMol	T6699	https://www.targetmol.com/search?keyword=T6699
Tetrahedron	TS13208	http://www.thsci.com/search.do?q=TS13208
TimTec	ST50308564	http://www.echemstore.com/catalogsearch/result/?q=ST50308564
Toronto Research Chemicals	E921550	https://www.trc-canada.com/product-detail/?CatNum=E921550
Toronto Research Chemicals	H956500	https://www.trc-canada.com/product-detail/?CatNum=H956500
Toronto Research Chemicals	H972965	https://www.trc-canada.com/product-detail/?CatNum=H972965
Toronto Research Chemicals	T304225	https://www.trc-canada.com/product-detail/?CatNum=T304225
eMolecules	29548954	https://orderbb.emolecules.com/search/#?query=29548954
eMolecules	485517	https://orderbb.emolecules.com/search/#?query=485517
mcule	MCULE-4728804324	https://mcule.com/MCULE-4728804324/

PubMed

Title	Date	PubMed
Compensatory up-regulation of nitric-oxide synthase isoforms in lead-induced hypertension; reversal by a superoxide dismutase-mimetic drug.	2001 Aug	11454931
Effect of lead on nitric oxide synthase expression in coronary endothelial cells: role of superoxide.	2001 Feb	11230275
The anti-oxidant Tempol reverses and partially prevents adrenocorticotrophic hormone-induced hypertension in the rat.	2003 Aug	12872045
Role of superoxide in modulating the renal effects of angiotensin II.	2003 Dec	14597645
Tert-butyl hydroperoxide-mediated vascular responses in DOCA-salt hypertensive rats.	2003 Jan	12646410
Redox regulation of HIF-1alpha levels and HO-1 expression in renal medullary interstitial cells.	2003 Jun	12595275
Role of the p53/p21 system in the response of human colon carcinoma cells to Doxorubicin.	2004 Dec 15	15601469
Effect of tempol (4-hydroxy tempo) on gentamicin-induced nephrotoxicity in rats.	2004 Feb	14748758
Pivotal role of gp91phox-containing NADH oxidase in lipopolysaccharide-induced tumor necrosis factor-alpha expression and myocardial depression.	2005 Apr 5	15795323
Antioxidant enzymes and effects of tempol on the development of hypertension induced by nitric oxide inhibition.	2005 Jun	15925750
Differential effect of antioxidant treatment on plasma and tissue paraoxonase activity in hyperleptinemic rats.	2005 Jun	15829432
Superoxide contributes to development of salt sensitivity and hypertension induced by nitric oxide deficiency.	2005 Oct	16103275
Oxidative stress mediates the stimulation of sympathetic nerve activity in the phenol renal injury model of hypertension.	2006 Aug	16785328
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	16685210
Receptor-independent intracellular radical scavenging activity of an angiotensin II receptor blocker.	2007 Aug	17620961
NADPH oxidase mediates angiotensin II-induced endothelin-1 expression in vascular adventitial fibroblasts.	2007 Sep 1	17391658
Anesthetic preconditioning confers acute cardioprotection via up-regulation of manganese superoxide dismutase and preservation of mitochondrial respiratory enzyme activity.	2008 Feb	17693941
Zinc deficiency-induced iron accumulation, a consequence of alterations in iron regulatory protein-binding activity, iron transporters, and iron storage proteins.	2008 Feb 22	18073202
Superoxide signaling in pain is independent of nitric oxide signaling.	2009 Oct 28	19794317
Aspirin resistance with genetic dyslipidemia: contribution of vascular thromboxane generation.	2010 Aug	20530721
Oxidative stress is important in the pathogenesis of liver injury induced by sulindac and lipopolysaccharide cotreatment.	2010 Jun 4	20371263
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	20056918
Tempol protects cardiomyocytes from nucleoside reverse transcriptase inhibitor-induced mitochondrial toxicity.	2014 May	24591154

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Fri Dec 15 15:14:44 GMT 2023` Edited by `admin` on `Fri Dec 15 15:14:44 GMT 2023`
Record UNII	U78ZX2F65X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TEMPOL

Common Name

English

4-OXYPIPERIDOL

Common Name

English

4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINOOXYL

Common Name

English

4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINLYOXY

Common Name

English

4-HYDROXY-2,2,6,6-TETRAMETHYL-1-PIPERIDINYLOXY

Common Name

English

ZJ-701

Code

English

NSC-142784

Code

English

Tempol [WHO-DD]

Common Name

English

2,2,6,6-TETRAMETHYL-4-HYDROXYPIPERIDINE 1-OXIDE RADICAL

Common Name

English

4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINE-N-OXYL

Systematic Name

English

2,2,6,6-TETRAMETHYL-4-HYDROXYPIPERIDINOOXY

Common Name

English

4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDIN-1-YL)OXIDANYL

Common Name

English

1-PIPERIDINYLOXY,4-HYDROXY-2,2,6,6-TETRAMETHYL-

Common Name

English

4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINOOXY

Common Name

English

MBM-02

Code

English

2,2,6,6-TETRAMETHYL-4-HYDROXYPIPERIDINOOXY RADICAL

Common Name

English

4-HYDROXY-2,2,6,6-TETRAMETHYLPIPERIDINEY-1-OXYL

Common Name

English

TANOL

Common Name

English

SPJ-701

Code

English

4-HYDROXY-2,2,6,6-TETRAMETHYL-PIPERIDIN-1-OXYL

Common Name

English

TEMPOL [MI]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

827721