Page last updated: 2024-12-07

nitroflurbiprofen

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Nitroflurbiprofen is a nonsteroidal anti-inflammatory drug (NSAID) that is a derivative of flurbiprofen. It is a potent inhibitor of cyclooxygenase (COX) enzymes, which are involved in the production of prostaglandins, inflammatory mediators that contribute to pain, swelling, and fever. Nitroflurbiprofen is studied for its potential therapeutic effects in a variety of inflammatory conditions, including rheumatoid arthritis, osteoarthritis, and inflammatory bowel disease. Its mechanism of action involves inhibiting the synthesis of prostaglandins, thereby reducing inflammation and pain. Nitroflurbiprofen has been shown to be effective in reducing pain and inflammation in clinical trials, and it is currently marketed in several countries for the treatment of these conditions. However, like other NSAIDs, nitroflurbiprofen can cause gastrointestinal side effects, including ulcers and bleeding. It is also associated with an increased risk of cardiovascular events, such as heart attack and stroke.'

nitroflurbiprofen: a cyclooxygenase inhibitor [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

nitroflurbiprofen : A carboxylic ester obtained by formal condensation of the carboxy group of flurbiprofen with the free hydroxy group of 4-(nitrooxy)butanol. It is a non-steroidal anti-inflammatory agent showing inhibitory effects against the cyclooxygenases COX1 and COX2. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID119387
CHEMBL ID1766388
CHEBI ID77428
SCHEMBL ID135465
MeSH IDM0251792

Synonyms (29)

Synonym
hct-1026
flurbiprofen nitroxybutyl ester
no-flurbiprofen
ncx-1026
nitroflurbiprofen
flurbinitroxybutylester
nitroxybutyl flurbiprofen
(1,1'-biphenyl)-4-acetic acid, 2-fluoro-alpha-methyl-, 4-(nitrooxy)butyl ester
4-(nitrooxy)butyl 2-fluoro-alpha-methyl-(1,1'-biphenyl)-4-acetate
4-nitrooxybutyl 2-(3-fluoro-4-phenylphenyl)propanoate
chebi:77428 ,
CHEMBL1766388
158836-71-6
unii-q8eri3e76f
q8eri3e76f ,
SCHEMBL135465
4-(nitrooxy)butyl 2-(2-fluorobiphenyl-4-yl)propanoate
HY-U00013
CS-6575
(1,1'-biphenyl)-4-acetic acid, 2-fluoro-.alpha.-methyl-, 4-(nitrooxy)butyl ester
flurbinitroxy butyl ester
Q27146958
4-(nitrooxy)butyl 2-(2-fluoro-[1,1'-biphenyl]-4-yl)propanoate
DTXSID30936005
4-(nitrooxy)butyl 2-(2-fluoro[1,1'-biphenyl]-4-yl)propanoate
hct 1206;no-flurbiprofen;nitroxybutyl flurbiprofen
hct 1206
MS-25722
AKOS040742307

Research Excerpts

Overview

nitrosylated flurbiprofen analog under development by NicOx for the potential treatment of urinary incontinence, Alzheimer's disease (AD) and the prevention and treatment of accelerated bone resorption associated with disorders.

ExcerptReferenceRelevance
"Nitroflurbiprofen is a nitrosylated flurbiprofen analog under development by NicOx for the potential treatment of urinary incontinence, Alzheimer's disease (AD) and the prevention and treatment of accelerated bone resorption associated with disorders such as osteoporosis, inflammatory joint disease and Paget's disease. "( Nitroflurbiprofen (NicOx).
Scatena, R, 2004
)
3.21

Actions

ExcerptReferenceRelevance
"Nitroflurbiprofen was shown to inhibit nitric oxide synthase induction caused by lipopolysaccharide administration, while flurbiprofen had no effect on nitric oxide synthase induction."( Effect of a new non-steroidal anti-inflammatory drug, nitroflurbiprofen, on the expression of inducible nitric oxide synthase in rat neutrophils.
Adami, A; Benoni, G; Cuzzolin, L; Del Soldato, P; Mariotto, S; Suzuki, H, 1995
)
1.26

Treatment

ExcerptReferenceRelevance
"Treatment with nitroflurbiprofen, an NO-releasing cyclooxygenase inhibitor, improves portal hypertension without major adverse effects in thioacetamide-induced cirrhotic rats by attenuating intrahepatic vascular resistance, endothelial dysfunction, and hepatic hyperreactivity to vasoconstrictors."( Nitroflurbiprofen, a nitric oxide-releasing cyclooxygenase inhibitor, improves cirrhotic portal hypertension in rats.
Fevery, J; Laleman, W; Nevens, F; Van der Elst, I; Van Landeghem, L; Zeegers, M, 2007
)
2.14

Dosage Studied

ExcerptRelevanceReference
" A dose-response study with flurbiprofen (single doses of 5, 10, 20, and 40 mg/kg) and equimolar doses of nitroxybutyl-flurbiprofen was performed; assessing their effect on intestinal permeability (at 18-20 hours), with 51Cr EDTA, and the number of pointed (< 5 mm) and longitudinal (> 5 mm) small intestinal ulcers at 24 hours."( Intestinal tolerability of nitroxybutyl-flurbiprofen in rats.
Bjarnason, I; Jacob, M; Macpherson, A; Mahmud, T; Price, AB; Rafi, S; Scott, D; Sherwood, R; Sigthorsson, G; Somasundaram, S; Wrigglesworth, JM, 1997
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (6)

RoleDescription
cyclooxygenase 1 inhibitorA cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
cyclooxygenase 2 inhibitorA cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
non-steroidal anti-inflammatory drugAn anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
EC 1.14.13.39 (nitric oxide synthase) inhibitorAn EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
vasodilator agentA drug used to cause dilation of the blood vessels.
geroprotectorAny compound that supports healthy aging, slows the biological aging process, or extends lifespan.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (4)

ClassDescription
organofluorine compoundAn organofluorine compound is a compound containing at least one carbon-fluorine bond.
biphenylsBenzenoid aromatic compounds containing two phenyl or substituted-phenyl groups which are joined together by a single bond.
carboxylic esterAn ester of a carboxylic acid, R(1)C(=O)OR(2), where R(1) = H or organyl and R(2) = organyl.
nitrate esterAny member of the class of nitrates resulting from the esterification of nitric acid with an alcohol.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID592852Antiamyloidogenic activity in mouse N2A cells assessed as reduction of amyloid beta (1 to 42)/(1 to 40) ratio at 1 uM treated 24 hrs before amyloid beta (1 to 42)/(1 to 40) challenge measured after 8 hrs by MALDI/TOF analysis2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
Inhibition of amyloidogenesis by nonsteroidal anti-inflammatory drugs and their hybrid nitrates.
AID592756Antiamyloidogenic activity in mouse N2A cells transfected with human APP Swedish mutant assessed as increase of amyloid beta (1 to 40) level at 100 uM after 24 hrs by ELISA2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
Inhibition of amyloidogenesis by nonsteroidal anti-inflammatory drugs and their hybrid nitrates.
AID592743Antiinflammatory activity against mouse RAW264.7 cells assessed as inhibition of LPS-induced nitrate production at 100 uM treated 30 mins before LPS challenge measured after 24 hrs by Griess reagent method relative to control2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
Inhibition of amyloidogenesis by nonsteroidal anti-inflammatory drugs and their hybrid nitrates.
AID592840Antiamyloidogenic activity in mouse N2A cells transfected with human APP Swedish mutant assessed as increase of amyloid beta (1 to 42)/(1 to 40) ratio at 100 uM after 24 hrs by ELISA2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
Inhibition of amyloidogenesis by nonsteroidal anti-inflammatory drugs and their hybrid nitrates.
AID592839Antiamyloidogenic activity in mouse N2A cells transfected with human APP Swedish mutant assessed as increase of amyloid beta (1 to 42) level at 100 uM after 24 hrs by ELISA2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
Inhibition of amyloidogenesis by nonsteroidal anti-inflammatory drugs and their hybrid nitrates.
AID592744Cytotoxicity against mouse RAW264.7 cells assessed as cell viability at 100 uM after 24 hrs by MTT assay relative to control2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
Inhibition of amyloidogenesis by nonsteroidal anti-inflammatory drugs and their hybrid nitrates.
AID592851Antiamyloidogenic activity in mouse N2A cells assessed as degradation of amyloid beta (1 to 40) level at 1 uM treated 24 hrs before amyloid beta (1 to 40) challenge measured after 8 hrs by MALDI/TOF analysis2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
Inhibition of amyloidogenesis by nonsteroidal anti-inflammatory drugs and their hybrid nitrates.
AID592850Antiamyloidogenic activity in mouse N2A cells assessed as degradation of amyloid beta (1 to 42) level at 1 uM treated 24 hrs before amyloid beta (1 to 42) challenge measured after 8 hrs by MALDI/TOF analysis2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
Inhibition of amyloidogenesis by nonsteroidal anti-inflammatory drugs and their hybrid nitrates.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (56)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's10 (17.86)18.2507
2000's38 (67.86)29.6817
2010's8 (14.29)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.61

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.61 (24.57)
Research Supply Index4.09 (2.92)
Research Growth Index4.70 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.61)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.72%)5.53%
Reviews3 (5.17%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other54 (93.10%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]