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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

Molecular Formula C15H13FO2
Molecular Weight 244.2615
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Esflurbiprofen (S-enantiomer of flurbiprofen), also known as BTS-24332; SFPP; TT-063, is a cyclooxygenase (COX) inhibitor indicated for the treatment of osteoarthritis pain and inflammation. Esflurbiprofen was approved by Pharmaceuticals and Medical Devices Agency of Japan (PMDA) on Sep 28, 2015. It was developed by Taisho and marketed by Taisho and Teijin as Loqoa® in Japan. 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

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
Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries.
2001
Relative contributions of CYP2C9 and 2C19 to phenytoin 4-hydroxylation in vitro: inhibition by sulfaphenazole, omeprazole, and ticlopidine.
2001 Apr
[Convulsion following the combination of single preoperative oral administration of enoxacine and single postoperative intravenous administration of flurbiprofen axetil].
2001 Apr
Review: uveitis and immunosuppressive drugs.
2001 Apr
Early clinical trials of chemopreventive and biologic agents: Designs, populations, and endpoints.
2001 Apr
Proapoptotic anti-inflammatory drugs.
2001 Apr
Intracrevicular application of 0.3% Flurbiprofen gel and 0.3% Triclosan gel as anti inflammatory agent. A comparative clinical study.
2001 Apr-Jun
Minimal in vivo activation of CYP2C9-mediated flurbiprofen metabolism by dapsone.
2001 Aug
Flurbiprofen enantiomers inhibit inducible nitric oxide synthase expression in RAW 264.7 macrophages.
2001 Feb
Bradykinin-induced nociceptor sensitization to heat is mediated by cyclooxygenase products in isolated rat skin.
2001 Jul
Dapsone activation of CYP2C9-mediated metabolism: evidence for activation of multiple substrates and a two-site model.
2001 Jul
NO-flurbiprofen attenuates excitotoxin-induced brain inflammation, and releases nitric oxide in the brain.
2001 Jun
Peroxidase self-inactivation in prostaglandin H synthase-1 pretreated with cyclooxygenase inhibitors or substituted with mangano protoporphyrin IX.
2001 Jun 8
Perioperative intravenous flurbiprofen reduces postoperative pain after abdominal hysterectomy.
2001 Mar
Inhibition of NF-kappaB and AP-1 activation by R- and S-flurbiprofen.
2001 Mar
Selective inhibition of interleukin-4 gene expression in human T cells by aspirin.
2001 Mar 15
Structural analysis of NSAID binding by prostaglandin H2 synthase: time-dependent and time-independent inhibitors elicit identical enzyme conformations.
2001 May 1
Screening procedure for detection of non-steroidal anti-inflammatory drugs and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation.
2001 May-Jun
Nicotine-induced contraction in the rat coronary artery: possible involvement of the endothelium, reactive oxygen species and COX-1 metabolites.
2001 Oct
Measurement of ketoprofen in horse urine using gas chromatography-mass spectrometry.
2001 Oct
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
Effect of flurbiprofen on hind-limb suspension-induced bone loss.
2001 Sep
Pathogenic importance of intestinal hypermotility in NSAID-induced small intestinal damage in rats.
2002
Nitric-oxide releasing molecules: a new class of drugs with several major indications.
2002
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
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
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
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
Prediction of poly(ethylene) glycol-drug eutectic compositions using an index based on the van't Hoff equation.
2002 Mar
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
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
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
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
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 dose is 200 to 300 mg per day, divided for administration two, three, or four times a day. The largest recommended single dose in a multiple-dose daily regimen is 100 mg.
Route of Administration: Oral
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
Flurbiprofen was a potent inhibitor of the COX-1-catalysed cyclooxygenation of arachidonic acid, a concentration of 3 uM reducing the initial rate of oxygen consumption (measured between times 10 and 30 s) by about 40%. COX-2-catalysed cyclooxygenation of arachidonic acid was much less affected by flurbiprofen, whereas the COX-2- catalysed cyclooxygenation of 2-AG was greatly reduced by 3 uM flurbiprofen.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:00:21 UTC 2021
Edited
by admin
on Fri Jun 25 21:00:21 UTC 2021
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
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
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC