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

Details

Stereochemistry RACEMIC
Molecular Formula C15H13FO2
Molecular Weight 244.2609
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLURBIPROFEN

SMILES

CC(C(O)=O)C1=CC(F)=C(C=C1)C2=CC=CC=C2

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

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

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

5.9425921E11
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

5.9425921E11
Primary
LOQOA® Tape

Approved Use

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

Launch Date

1.44339842E12
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
Estimation of acute flurbiprofen and ketoprofen toxicity in rat gastric mucosa at therapy-relevant doses.
2001 Dec
Protection by aspirin of indomethacin-induced small intestinal damage in rats: mediation by salicylic acid.
2001 Jan-Dec
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Differential effects of the nonsteroidal antiinflammatory drug flurbiprofen and its nitric oxide-releasing derivative, nitroflurbiprofen, on prostaglandin E(2), interleukin-1beta, and nitric oxide synthesis by activated microglia.
2001 Nov 15
Prostaglandin synthesis inhibitor improves hypotension during normothermic cardiopulmonary bypass.
2001 Nov-Dec
The effect of flurbiprofen and tiaprofenic acid on serum cytokine levels of patients with osteoarthrosis.
2001 Oct
Measurement of ketoprofen in horse urine using gas chromatography-mass spectrometry.
2001 Oct
Nonsteroid anti-inflammatory drugs inhibit both the activity and the inflammation-induced expression of acid-sensing ion channels in nociceptors.
2001 Oct 15
Inhibition of human brain tumor cell growth by the anti-inflammatory drug, flurbiprofen.
2001 Oct 18
Interactive roles of superoxide and inducible nitric oxide synthase in rat intestinal injury provoked by non-steroidal anti-inflammatory drugs.
2001 Oct 19
Synthesis and receptor docking studies of N-substituted indole-2-carboxylic acid esters as a search for COX-2 selective enzyme inhibitors.
2001 Sep
The effect of nonsteroidal antiinflammatory drugs ibuprofen, flurbiprofen, and diclofenac on in vitro and in vivo growth of mouse fibrosarcoma.
2002
Polymorphic variants (CYP2C9*3 and CYP2C9*5) and the F114L active site mutation of CYP2C9: effect on atypical kinetic metabolism profiles.
2002 Apr
In vitro release studies of flurbiprofen from different topical formulations.
2002 Aug
Dissection of metabolic, vascular, and nerve conduction interrelationships in experimental diabetic neuropathy by cyclooxygenase inhibition and acetyl-L-carnitine administration.
2002 Aug
Flurbiprofen-loaded acrylate polymer nanosuspensions for ophthalmic application.
2002 Aug
Rapid and simple quantitative assay method for diastereomeric flurbiprofen glucuronides in the incubation mixture.
2002 Aug 25
Contractile effect of anaphylatoxin C5a and of a mimetic peptide on the human umbilical artery: further evidence for leukocyte-dependent vasomotion.
2002 Dec
Beneficial effects of NO-releasing derivative of flurbiprofen (HCT-1026) in rat model of vascular injury and restenosis.
2002 Feb 1
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
Prediction of poly(ethylene) glycol-drug eutectic compositions using an index based on the van't Hoff equation.
2002 Mar
Multidose flurbiprofen 8.75 mg lozenges in the treatment of sore throat: a randomised, double-blind, placebo-controlled study in UK general practice centres.
2002 Mar
Nitric oxide-releasing drugs: a novel class of effective and safe therapeutic agents.
2002 May
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
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
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
Synthesis and biological activity of flurbiprofen analogues as selective inhibitors of beta-amyloid(1)(-)(42) secretion.
2005 Sep 8
The geminal dimethyl analogue of Flurbiprofen as a novel Abeta42 inhibitor and potential Alzheimer's disease modifying agent.
2006 Apr 15
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 Jul 22
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
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 Wed Jul 05 22:51:11 UTC 2023
Edited
by admin
on Wed Jul 05 22:51:11 UTC 2023
Record UNII
5GRO578KLP
Record Status Validated (UNII)
Record Version
  • Download
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
Flurbiprofen [WHO-DD]
Common Name English
NSC-757037
Code English
FLURBIPROFEN [EP MONOGRAPH]
Common Name English
BTS-18322
Code 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 Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
WHO-VATC QR02AX01
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
NCI_THESAURUS C29577
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
WHO-ATC M01AE09
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
NDF-RT N0000175721
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
NCI_THESAURUS C1323
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
WHO-VATC QS01BC04
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
NDF-RT N0000000160
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
WHO-ATC M02AA19
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
WHO-ATC S01BC04
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
NDF-RT N0000175722
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
WHO-VATC QM02AA19
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
WHO-ATC R02AX01
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
LIVERTOX NBK548121
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
225-827-6
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
CHEBI
42446
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
DRUG BANK
DB00712
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
CAS
5104-49-4
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
RXCUI
4502
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY RxNorm
NSC
757037
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
IUPHAR
4194
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
EVMPD
SUB07745MIG
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
CHEBI
5130
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
RS_ITEM_NUM
1285750
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
INN
3220
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
SMS_ID
100000092659
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
MERCK INDEX
M5499
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY Merck Index
PUBCHEM
3394
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
EPA CompTox
DTXSID0037231
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
NCI_THESAURUS
C508
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
LACTMED
Flurbiprofen
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
MESH
D005480
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
FDA UNII
5GRO578KLP
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
DRUG CENTRAL
1219
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
WIKIPEDIA
FLURBIPROFEN
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
ChEMBL
CHEMBL563
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
DAILYMED
5GRO578KLP
Created by admin on Wed Jul 05 22:51:11 UTC 2023 , Edited by admin on Wed Jul 05 22:51:11 UTC 2023
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
METABOLIC ENZYME -> SUBSTRATE
DERIVATIVE -> PARENT
TRANSPORTER -> INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
METABOLIC ENZYME -> INDUCER
Related Record Type Details
METABOLITE -> PARENT
PLASMA; URINE
METABOLITE -> PARENT
MAJOR
PLASMA; URINE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC