Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C15H12FO2.Na.2H2O |
| Molecular Weight | 302.2733 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.[Na+].CC(C([O-])=O)C1=CC=C(C(F)=C1)C2=CC=CC=C2
InChI
InChIKey=GNMBMOULKUXEQF-UHFFFAOYSA-M
InChI=1S/C15H13FO2.Na.2H2O/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11;;;/h2-10H,1H3,(H,17,18);;2*1H2/q;+1;;/p-1
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C15H13FO2 |
| Molecular Weight | 244.2609 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Flurbiprofen, a propionic acid derivative, is a nonsteroidal anti-inflammatory drug that exhibits antiinflammatory, analgesic, and antipyretic activities in animal models. Flurbiprofen Tablets are indicated for relief of the signs and symptoms of rheumatoid arthritis and for relief of the signs and symptoms of osteoarthritis. It may also be used to treat pain associated with dysmenorrhea and mild to moderate pain accompanied by inflammation (e.g. bursitis, tendonitis, soft tissue trauma). Flurbiprofen may also be used topically prior to ocular surgery to prevent or reduce intraoperative miosis. Similar to other NSAIAs, the anti-inflammatory effect of flurbiprofen occurs via reversible inhibition of cyclooxygenase (COX), the enzyme responsible for the conversion of arachidonic acid to prostaglandin G2 (PGG2) and PGG2 to prostaglandin H2 (PGH2) in the prostaglandin synthesis pathway. This effectively decreases the concentration of prostaglandins involved in inflammation, pain, swelling and fever. Flurbiprofen is a non-selective COX inhibitor and inhibits the activity of both COX-1 and -2. It is also one of the most potent NSAIAs in terms of prostaglandin inhibitory activity.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20840447 | https://www.ncbi.nlm.nih.gov/pubmed/16134939
Curator's Comment: Flurbiprofen permeates into the CSF readily and thus, may have potent CNS analgesic and antipyretic action. Flurbiprofen selectively inhibits beta-amyloid(1)(-)(42) (Abeta42) secretion, the most toxic component of the senile plaques present in the brain of Alzheimer patients.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL221 |
0.11 µM [IC50] | ||
Target ID: CHEMBL230 |
6.46 µM [IC50] | ||
Target ID: CHEMBL221 |
0.2 µM [IC50] | ||
Target ID: CHEMBL230 |
0.91 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Flurbiprofen Approved UseFlurbiprofen Tablets are indicated:
• For relief of the signs and symptoms of rheumatoid arthritis.
• For relief of the signs and symptoms of osteoarthritis. Launch Date1988 |
|||
| Primary | Flurbiprofen Approved UseFlurbiprofen Tablets are indicated:
• For relief of the signs and symptoms of rheumatoid arthritis.
• For relief of the signs and symptoms of osteoarthritis. Launch Date1988 |
|||
| Primary | LOQOA® Tape Approved UseLOQOA® Tape indicated for the treatment of osteoarthritis pain and inflammation. Launch Date2015 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
14 μg/mL |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLURBIPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
19.67 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19808137 |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLURBIPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
83 μg × h/mL |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLURBIPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
124.2 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19808137 |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLURBIPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7.5 h |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLURBIPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4.77 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19808137 |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLURBIPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes [IC50 0.615 uM] | ||||
| yes [IC50 1.8 uM] | ||||
| yes [IC50 10.6 uM] | ||||
| yes [IC50 58.4 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 3.0 |
no | |||
Page: 4.0 |
no | |||
Page: 1.0 |
yes | |||
Page: 7.0 |
yes | |||
Page: 1.0 |
yes | |||
| yes | ||||
| yes | ||||
Page: 7.0 |
yes | |||
Page: 7.0 |
yes | |||
Page: 1.0 |
yes | |||
Page: 4.0 |
yes | |||
Page: 1.0 |
yes | |||
Page: 1.0 |
yes | |||
| yes | yes (co-administration study) Comment: Coadministration study with fluconazole (inhibitor of CYP2C9) increased AUCinf by 222%-299% after different visits of patients; Pharmacogenomic study: In patients who are known or suspected to be poor CYP2C9 metabolizers based on genotype or previous history/experience with other CYP2C9 substrates (such as warfarin and phenytoin), reduce the dose of flurbiprofen to avoid abnormally high plasma levels due to reduced metabolic clearance |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Effect of multimodal analgesia using periprostatic nerve block anesthesia combined with flurbiprofen in transperineal template-guided prostate biopsy]. | 2019-06-01 |
|
| Effect of flurbiprofen axetil on postoperative delirium for elderly patients. | 2019-06 |
|
| [Effect of Flurbiprofen Axetil on Low-frequency Fluctuation Amplitude of Resting-state Functional Magnetic Resonance Imaging in Trigeminal Neuralgia]. | 2019-04-28 |
|
| [Postoperative low-dose sufentanil combined with transversus abdominis plane block promotes recovery following laparoscopic hysterectomy]. | 2019-03-30 |
|
| Intraoperative administration of intravenous flurbiprofen axetil with nalbuphine reduces postoperative pain after orbital decompression: a single-center, prospective randomized controlled trial. | 2019 |
|
| Comparison of perioperative flurbiprofen axetil or celecoxib administration for pain management after total-knee arthroplasty: A retrospective study. | 2018-09 |
|
| Flurbiprofen axetil attenuates cerebral ischemia/reperfusion injury by reducing inflammation in a rat model of transient global cerebral ischemia/reperfusion. | 2018-08-31 |
|
| Flurbiprofen axetil: Analgesic effect and adverse reaction. | 2018-05 |
|
| Effect of oxycodone hydrochloride combined with flurbiprofen axetil for intravenous patient-controlled analgesia in lower abdominal patients: A randomized trial. | 2018-02 |
|
| Population pharmacokinetic modeling of flurbiprofen, the active metabolite of flurbiprofen axetil, in Chinese patients with postoperative pain. | 2018 |
|
| Analgesic effect of different dosage of Flurbiprofen axetil in laparoscopic cholecystectomy in comparison with other analgesic drugs. | 2017-09 |
|
| Analgesic effect of flurbiprofen axetil in treatment of single hole thoracoscopic surgery for pneumothorax. | 2017-09 |
|
| Postoperative benefits of dexmedetomidine combined with flurbiprofen axetil after thyroid surgery. | 2017-09 |
|
| Aging Enables Ca2+ Overload and Apoptosis Induced by Amyloid-β Oligomers in Rat Hippocampal Neurons: Neuroprotection by Non-Steroidal Anti-Inflammatory Drugs and R-Flurbiprofen in Aging Neurons. | 2016-07-22 |
|
| The geminal dimethyl analogue of Flurbiprofen as a novel Abeta42 inhibitor and potential Alzheimer's disease modifying agent. | 2006-04-15 |
|
| Synthesis and biological activity of flurbiprofen analogues as selective inhibitors of beta-amyloid(1)(-)(42) secretion. | 2005-09-08 |
|
| Contractile effect of anaphylatoxin C5a and of a mimetic peptide on the human umbilical artery: further evidence for leukocyte-dependent vasomotion. | 2002-12 |
|
| Kinetics of allopregnanolone formation catalyzed by human 3 alpha-hydroxysteroid dehydrogenase type III (AKR1C2). | 2002-11-12 |
|
| Drug therapy of urinary urge incontinence: a systematic review. | 2002-11 |
|
| Selective inhibition of Abeta42 production by NSAID R-enantiomers. | 2002-11 |
|
| Centrally administered galanin-like peptide modifies food intake in the rat: a comparison with galanin. | 2002-11 |
|
| Activation of CYP2C9-mediated metabolism by a series of dapsone analogs: kinetics and structural requirements. | 2002-11 |
|
| NO-flurbiprofen maintains duodenal blood flow, enhances mucus secretion contributing to lower mucosal injury. | 2002-11 |
|
| A nitric oxide-donating flurbiprofen derivative reduces neuroinflammation without interacting with galantamine in the rat. | 2002-10-25 |
|
| Cyclooxygenase and 5-lipoxygenase inhibitors protect against mononuclear phagocyte neurotoxicity. | 2002-10-24 |
|
| Efficient synthesis of alpha-aryl esters by room-temperature palladium-catalyzed coupling of aryl halides with ester enolates. | 2002-10-23 |
|
| Structure-function relationship and role of tumor necrosis factor-alpha-converting enzyme in the down-regulation of L-selectin by non-steroidal anti-inflammatory drugs. | 2002-10-11 |
|
| Biochemical stabilization enhances red blood cell recovery and stability following cryopreservation. | 2002-10 |
|
| Thermodynamic study of the enantiomeric resolution of flurbiprofen by HPLC using Chiralpak AD-RH column. | 2002-10 |
|
| Prostaglandin synthesis inhibitor prevents hypotension without impairing gut perfusion during normothermic cardiopulmonary bypass. | 2002-09-26 |
|
| Mechanism of in vitro release kinetics of flurbiprofen loaded ethylcellulose micropellets. | 2002-09-17 |
|
| Rapid and simple quantitative assay method for diastereomeric flurbiprofen glucuronides in the incubation mixture. | 2002-08-25 |
|
| Metabolic profile of NO-flurbiprofen (HCT1026) in rat brain and plasma: a LC-MS study. | 2002-08-16 |
|
| Therapeutic utility of aspirin in the ApcMin/+ murine model of colon carcinogenesis. | 2002-08-09 |
|
| In vitro release studies of flurbiprofen from different topical formulations. | 2002-08 |
|
| [The effectiveness of perioperative intravenous flurbiprofen in minor ear, neck and nose surgery]. | 2002-08 |
|
| Dissection of metabolic, vascular, and nerve conduction interrelationships in experimental diabetic neuropathy by cyclooxygenase inhibition and acetyl-L-carnitine administration. | 2002-08 |
|
| Prostaglandin synthesis inhibitor affects humoral conditions and oxygen metabolism during normothermic cardiopulmonary bypass. | 2002-08 |
|
| Flurbiprofen-loaded acrylate polymer nanosuspensions for ophthalmic application. | 2002-08 |
|
| The cannabinoids R(-)-7-hydroxy-delta-6-tetra-hydrocannabinol-dimethylheptyl (HU-210), 2-O-arachidonoylglycerylether (HU-310) and arachidonyl-2-chloroethylamide (ACEA) increase isoflurane provoked sleep duration by activation of cannabinoids 1 (CB1)-receptors in mice. | 2002-07-05 |
|
| Peripheral analgesic sites of action of anti-inflammatory drugs. | 2002-07 |
|
| Prevention by parenteral aspirin of indomethacin-induced gastric lesions in rats: mediation by salicylic acid. | 2002-07 |
|
| Flurbiprofen does not change the bispectral index and 95% spectral edge frequency during total intravenous anaesthesia with propofol and fentanyl. | 2002-07 |
|
| Characterization of the bone-resorptive effect of interleukin-11 in cultured mouse calvarial bones. | 2002-07 |
|
| Lipids and nitric oxide in porcine retinal and choroidal blood vessels. | 2002-06 |
|
| In vivo activation of N-methyl-D-aspartate receptors in the rat hippocampus increases prostaglandin E(2) extracellular levels and triggers lipid peroxidation through cyclooxygenase-mediated mechanisms. | 2002-06 |
|
| ATP can enhance the proton-induced CGRP release through P2Y receptors and secondary PGE(2) release in isolated rat dura mater. | 2002-06 |
|
| Nitric oxide-releasing drugs: a novel class of effective and safe therapeutic agents. | 2002-05 |
|
| Pathogenic importance of intestinal hypermotility in NSAID-induced small intestinal damage in rats. | 2002 |
|
| The effect of nonsteroidal antiinflammatory drugs ibuprofen, flurbiprofen, and diclofenac on in vitro and in vivo growth of mouse fibrosarcoma. | 2002 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Flurbiprofen may also be used topically prior to ocular surgery to prevent or reduce intraoperative miosis. https://www.drugbank.ca/drugs/DB00712
Loqoa® is available as a patch formulation, containing 40 mg of Esflurbiprofen. The recommended dose is applied to the lesion area once daily. Do not apply more than two patches simultaneously.
Route of Administration:
Topical
In Vitro Use Guide
Curator's Comment: Inhibitory action was measured in SH-SY5Y and HEK cell lines overexpressing
either the direct substrate SPA4CT or the precursor
APP695, respectively
At 100 uM concentration Esflurbiprofen (S-Flurbiprofen) demonstrated 37% inhibition of Abeta42 in SH-SY5Y cells and 65% in HEK cells.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:34:37 GMT 2025
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on
Mon Mar 31 18:34:37 GMT 2025
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| Record UNII |
Z5B97MU9K4
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| Record Status |
Validated (UNII)
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NCI_THESAURUS |
C29577
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1584155-62-3
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DBSALT000544
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C47997
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PARENT -> SALT/SOLVATE |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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ANHYDROUS->SOLVATE |
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
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