U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C15H13FO2
Molecular Weight 244.2615
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLURBIPROFEN

SMILES

CC(c1ccc(-c2ccccc2)c(c1)F)C(=O)O

InChI

InChIKey=SYTBZMRGLBWNTM-UHFFFAOYSA-N
InChI=1S/C15H13FO2/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)

HIDE SMILES / InChI
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.

CNS Activity

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Flurbiprofen

Approved Use

Flurbiprofen Tablets are indicated: • For relief of the signs and symptoms of rheumatoid arthritis. • For relief of the signs and symptoms of osteoarthritis.

Launch Date

594259200000
Primary
Flurbiprofen

Approved Use

Flurbiprofen Tablets are indicated: • For relief of the signs and symptoms of rheumatoid arthritis. • For relief of the signs and symptoms of osteoarthritis.

Launch Date

594259200000
Primary
LOQOA® Tape

Approved Use

LOQOA® Tape indicated for the treatment of osteoarthritis pain and inflammation.

Launch Date

1443398400000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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

Overview

CYP3A4CYP2C9CYP2D6hERG


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 0.615 uM]
yes [IC50 1.8 uM]
yes [IC50 10.6 uM]
yes [IC50 58.4 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
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

PubMed

TitleDatePubMed
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
[A simple method for determination of flurbiprofen in human plasma by gas chromatography-mass spectrometry].
2002 Apr
Affinity capillary electrophoresis using a low-concentration additive with the consideration of relative mobilities.
2002 Apr 15
In vitro release studies of flurbiprofen from different topical formulations.
2002 Aug
[The effectiveness of perioperative intravenous flurbiprofen in minor ear, neck and nose surgery].
2002 Aug
Dissection of metabolic, vascular, and nerve conduction interrelationships in experimental diabetic neuropathy by cyclooxygenase inhibition and acetyl-L-carnitine administration.
2002 Aug
Prostaglandin synthesis inhibitor affects humoral conditions and oxygen metabolism during normothermic cardiopulmonary bypass.
2002 Aug
Flurbiprofen-loaded acrylate polymer nanosuspensions for ophthalmic application.
2002 Aug
Metabolic profile of NO-flurbiprofen (HCT1026) in rat brain and plasma: a LC-MS study.
2002 Aug 16
Rapid and simple quantitative assay method for diastereomeric flurbiprofen glucuronides in the incubation mixture.
2002 Aug 25
Therapeutic utility of aspirin in the ApcMin/+ murine model of colon carcinogenesis.
2002 Aug 9
Contractile effect of anaphylatoxin C5a and of a mimetic peptide on the human umbilical artery: further evidence for leukocyte-dependent vasomotion.
2002 Dec
Peripheral analgesic sites of action of anti-inflammatory drugs.
2002 Jul
Prevention by parenteral aspirin of indomethacin-induced gastric lesions in rats: mediation by salicylic acid.
2002 Jul
Flurbiprofen does not change the bispectral index and 95% spectral edge frequency during total intravenous anaesthesia with propofol and fentanyl.
2002 Jul
Characterization of the bone-resorptive effect of interleukin-11 in cultured mouse calvarial bones.
2002 Jul
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 Jul 5
Lipids and nitric oxide in porcine retinal and choroidal blood vessels.
2002 Jun
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 Jun
ATP can enhance the proton-induced CGRP release through P2Y receptors and secondary PGE(2) release in isolated rat dura mater.
2002 Jun
Nitric oxide-releasing drugs: a novel class of effective and safe therapeutic agents.
2002 May
Demonstration of dose response of flurbiprofen lozenges with the sore throat pain model.
2002 May
Mechanism of in vitro release kinetics of flurbiprofen loaded ethylcellulose micropellets.
2002 May-Jun
Drug therapy of urinary urge incontinence: a systematic review.
2002 Nov
Selective inhibition of Abeta42 production by NSAID R-enantiomers.
2002 Nov
Centrally administered galanin-like peptide modifies food intake in the rat: a comparison with galanin.
2002 Nov
Activation of CYP2C9-mediated metabolism by a series of dapsone analogs: kinetics and structural requirements.
2002 Nov
NO-flurbiprofen maintains duodenal blood flow, enhances mucus secretion contributing to lower mucosal injury.
2002 Nov
Kinetics of allopregnanolone formation catalyzed by human 3 alpha-hydroxysteroid dehydrogenase type III (AKR1C2).
2002 Nov 12
Biochemical stabilization enhances red blood cell recovery and stability following cryopreservation.
2002 Oct
Thermodynamic study of the enantiomeric resolution of flurbiprofen by HPLC using Chiralpak AD-RH column.
2002 Oct
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 Oct 11
Efficient synthesis of alpha-aryl esters by room-temperature palladium-catalyzed coupling of aryl halides with ester enolates.
2002 Oct 23
A nitric oxide-donating flurbiprofen derivative reduces neuroinflammation without interacting with galantamine in the rat.
2002 Oct 25
Cyclooxygenase and 5-lipoxygenase inhibitors protect against mononuclear phagocyte neurotoxicity.
2002 Sep-Oct
Prostaglandin synthesis inhibitor prevents hypotension without impairing gut perfusion during normothermic cardiopulmonary bypass.
2002 Sep-Oct
Analgesic effect of different dosage of Flurbiprofen axetil in laparoscopic cholecystectomy in comparison with other analgesic drugs.
2017 Sep
Analgesic effect of flurbiprofen axetil in treatment of single hole thoracoscopic surgery for pneumothorax.
2017 Sep
Postoperative benefits of dexmedetomidine combined with flurbiprofen axetil after thyroid surgery.
2017 Sep
Population pharmacokinetic modeling of flurbiprofen, the active metabolite of flurbiprofen axetil, in Chinese patients with postoperative pain.
2018
Flurbiprofen axetil attenuates cerebral ischemia/reperfusion injury by reducing inflammation in a rat model of transient global cerebral ischemia/reperfusion.
2018 Aug 31
Effect of oxycodone hydrochloride combined with flurbiprofen axetil for intravenous patient-controlled analgesia in lower abdominal patients: A randomized trial.
2018 Feb
Flurbiprofen axetil: Analgesic effect and adverse reaction.
2018 May
Comparison of perioperative flurbiprofen axetil or celecoxib administration for pain management after total-knee arthroplasty: A retrospective study.
2018 Sep
Intraoperative administration of intravenous flurbiprofen axetil with nalbuphine reduces postoperative pain after orbital decompression: a single-center, prospective randomized controlled trial.
2019
[Effect of Flurbiprofen Axetil on Low-frequency Fluctuation Amplitude of Resting-state Functional Magnetic Resonance Imaging in Trigeminal Neuralgia].
2019 Apr 28
Effect of flurbiprofen axetil on postoperative delirium for elderly patients.
2019 Jun
[Effect of multimodal analgesia using periprostatic nerve block anesthesia combined with flurbiprofen in transperineal template-guided prostate biopsy].
2019 Jun 1
[Postoperative low-dose sufentanil combined with transversus abdominis plane block promotes recovery following laparoscopic hysterectomy].
2019 Mar 30
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
For relief of the signs and symptoms of rheumatoid arthritis or osteoarthritis, the recommended starting
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment:: Inhibitory action was measured in SH-SY5Y and HEK cell lines overexpressing
Flurbiprofen was a potent inhibitor of the COX-1-catalysed cyclooxygenation
Name Type Language
FLURBIPROFEN
EP   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
FLURBIPROFEN [INN]
Common Name English
BTS 18,322
Code English
FLURBIPROFEN [USP MONOGRAPH]
Common Name English
FLURBIPROFEN [MART.]
Common Name English
FLURBIPROFEN [USAN]
Common Name English
FLURBIPROFEN [ORANGE BOOK]
Common Name English
(+/-)-2-(2-FLUORO-4-BIPHENYLYL)PROPIONIC ACID
Systematic Name English
FLURBIPROFEN [MI]
Common Name English
FLURBIPROFEN [VANDF]
Common Name English
(1,1'-BIPHENYL)-4-ACETIC ACID, 2-FLUORO-.ALPHA.-METHYL-, (+/-)-
Systematic Name English
NSC-757037
Code English
FLURBIPROFEN [EP MONOGRAPH]
Common Name English
BTS-18322
Code English
FLURBIPROFEN [WHO-DD]
Common Name English
U-27,182
Code English
FLURBIPROFEN [JAN]
Common Name English
(+/-)-2-FLUORO-.ALPHA.-METHYL-4-BIPHENYLACETIC ACID
Systematic Name English
ANSAID
Brand Name English
FLURBIPROFEN [USP-RS]
Common Name English
U-27182
Code English
Classification Tree Code System Code
WHO-VATC QM01AE09
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
WHO-VATC QR02AX01
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
NCI_THESAURUS C29577
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
WHO-ATC M01AE09
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
NDF-RT N0000175721
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
NCI_THESAURUS C1323
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
WHO-VATC QS01BC04
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
NDF-RT N0000000160
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
WHO-ATC M02AA19
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
WHO-ATC S01BC04
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
NDF-RT N0000175722
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
WHO-VATC QM02AA19
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
WHO-ATC R02AX01
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
LIVERTOX 428
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
225-827-6
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY
DRUG BANK
DB00712
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY
CAS
5104-49-4
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY
USP_CATALOG
1285750
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY USP-RS
RXCUI
4502
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY RxNorm
IUPHAR
4194
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY
EVMPD
SUB07745MIG
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY
INN
3220
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY
MERCK INDEX
M5499
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY Merck Index
PUBCHEM
3394
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY
EPA CompTox
5104-49-4
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY
NCI_THESAURUS
C508
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY
LACTMED
Flurbiprofen
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY
MESH
D005480
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY
FDA UNII
5GRO578KLP
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY
DRUG CENTRAL
1219
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY
WIKIPEDIA
FLURBIPROFEN
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY
ChEMBL
CHEMBL563
Created by admin on Fri Jun 25 21:00:21 UTC 2021 , Edited by admin on Fri Jun 25 21:00:21 UTC 2021
PRIMARY