FLURBIPROFEN

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 Search

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	( + / - )

Description
Sources: http://adisinsight.springer.com/drugs/800006253 | http://www.taisho-holdings.co.jp/en/release/2016/2016012001-e.pdf | https://www.ncbi.nlm.nih.gov/pubmed/16134939https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018766s015lbl.pdf | https://www.drugbank.ca/drugs/DB00712

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cyclooxygenase-1 125 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15336599	Inhibitor 8228	0.11 µM [IC50]
Cyclooxygenase-2 192 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24120370 \| https://www.ncbi.nlm.nih.gov/pubmed/15336599	Inhibitor 8228	6.46 µM [IC50]
Cyclooxygenase 89 Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26315084 \| https://www.selleckchem.com/products/flurbiprofen-axetil.html \| https://www.ncbi.nlm.nih.gov/pubmed/29540536	Inhibitor 8228
Cyclooxygenase-1 125 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16455248 \| https://www.ncbi.nlm.nih.gov/pubmed/16134939	Inhibitor 8228	0.2 µM [IC50]
Cyclooxygenase-2 192 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16134939	Inhibitor 8228	0.91 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Rheumatoid arthritis 313 Sources: https://www.drugs.com/pro/flurbiprofen-tablets.html	Primary	Approved 8360	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
Osteoarthritis 157 Sources: https://www.drugs.com/pro/flurbiprofen-tablets.html	Primary	Approved 8360	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
Osteoarthritis 157 Sources: http://www.taisho-holdings.co.jp/en/release/2016/2016012001-e.pdf	Primary	Approved 8360	LOQOA® Tape Approved Use LOQOA® Tape indicated for the treatment of osteoarthritis pain and inflammation. Launch Date 1.44339842E12

C_max

Value	Dose	Co-administered	Analyte	Population
14 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018766s015lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018766s015lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
7.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018766s015lbl.pdf	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
	substrate 1010	substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 595 OAT3 636 MRP2 367 MRP4 203	CYP1A1 348 CYP2A6 523 CYP2B6 660 CYP2C19 985 UGT1A1 418 UGT1A3 422 UGT1A4 347 UGT1A6 307 UGT1A7 236 UGT1A8 283 UGT1A9 380 UGT1A10 290 UGT2B4 249 UGT2B7 389 UGT2B15 203 UGT2B17 213

Drug as perpetrator

Target	Modality	Activity
OAT1 599	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/22072415/	yes [IC50 0.615 uM]
OAT3 638	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/22072415/	yes [IC50 1.8 uM]
MRP4 237	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/26659924/	yes [IC50 10.6 uM]
MRP2 459	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/26659924/	yes [IC50 58.4 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A1 348	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/8937439/ Page: 3.0	no
CYP2A6 523	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/8937439/ Page: 3.0	no
CYP2B6 660	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/8937439/ Page: 3.0	no
CYP2C19 985	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/8937439/ Page: 3.0	no
CYP2D6 1193	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/8937439/ Page: 3.0	no
UGT2B15 203	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 4.0	no
UGT1A1 418	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 1.0	yes
UGT1A10 290	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15117964/ Page: 7.0	yes
UGT1A3 422	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 1.0	yes
UGT1A4 347	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/	yes
UGT1A6 307	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/	yes
UGT1A7 236	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15117964/ Page: 7.0	yes
UGT1A8 283	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15117964/ Page: 7.0	yes
UGT1A9 380	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 1.0	yes
UGT2B17 213	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 4.0	yes
UGT2B4 249	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 1.0	yes
UGT2B7 389	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 1.0	yes
CYP2C9 1010	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/books/NBK537365/	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 Sources: https://www.ncbi.nlm.nih.gov/books/NBK537365/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5130	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5130
ChemicalBook	CB7465967	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7465967
MolPort	MolPort-000-812-253	https://www.molport.com/shop/molecule-link/MolPort-000-812-253
eMolecules	538498	https://www.emolecules.com/cgi-bin/more?vid=538498

PubMed

Title	Date	PubMed
Estimation of acute flurbiprofen and ketoprofen toxicity in rat gastric mucosa at therapy-relevant doses.	2001 Dec	11822786
Protection by aspirin of indomethacin-induced small intestinal damage in rats: mediation by salicylic acid.	2001 Jan-Dec	11595418
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
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	11746392
Prostaglandin synthesis inhibitor improves hypotension during normothermic cardiopulmonary bypass.	2001 Nov-Dec	11730209
The effect of flurbiprofen and tiaprofenic acid on serum cytokine levels of patients with osteoarthrosis.	2001 Oct	11728078
Measurement of ketoprofen in horse urine using gas chromatography-mass spectrometry.	2001 Oct	11696081
Nonsteroid anti-inflammatory drugs inhibit both the activity and the inflammation-induced expression of acid-sensing ion channels in nociceptors.	2001 Oct 15	11588175
Inhibition of human brain tumor cell growth by the anti-inflammatory drug, flurbiprofen.	2001 Oct 18	11687965
Interactive roles of superoxide and inducible nitric oxide synthase in rat intestinal injury provoked by non-steroidal anti-inflammatory drugs.	2001 Oct 19	11698048
Synthesis and receptor docking studies of N-substituted indole-2-carboxylic acid esters as a search for COX-2 selective enzyme inhibitors.	2001 Sep	11672885
The effect of nonsteroidal antiinflammatory drugs ibuprofen, flurbiprofen, and diclofenac on in vitro and in vivo growth of mouse fibrosarcoma.	2002	12094544
Polymorphic variants (CYP2C93 and CYP2C95) and the F114L active site mutation of CYP2C9: effect on atypical kinetic metabolism profiles.	2002 Apr	11901091
In vitro release studies of flurbiprofen from different topical formulations.	2002 Aug	12236068
Dissection of metabolic, vascular, and nerve conduction interrelationships in experimental diabetic neuropathy by cyclooxygenase inhibition and acetyl-L-carnitine administration.	2002 Aug	12145179
Flurbiprofen-loaded acrylate polymer nanosuspensions for ophthalmic application.	2002 Aug	12102196
Rapid and simple quantitative assay method for diastereomeric flurbiprofen glucuronides in the incubation mixture.	2002 Aug 25	12127333
Contractile effect of anaphylatoxin C5a and of a mimetic peptide on the human umbilical artery: further evidence for leukocyte-dependent vasomotion.	2002 Dec	12451314
Beneficial effects of NO-releasing derivative of flurbiprofen (HCT-1026) in rat model of vascular injury and restenosis.	2002 Feb 1	11834526
Characterization of the bone-resorptive effect of interleukin-11 in cultured mouse calvarial bones.	2002 Jul	12110441
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	12095655
Lipids and nitric oxide in porcine retinal and choroidal blood vessels.	2002 Jun	12099547
Prediction of poly(ethylene) glycol-drug eutectic compositions using an index based on the van't Hoff equation.	2002 Mar	11934239
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	11926713
Nitric oxide-releasing drugs: a novel class of effective and safe therapeutic agents.	2002 May	12076987
Drug therapy of urinary urge incontinence: a systematic review.	2002 Nov	12423868
Selective inhibition of Abeta42 production by NSAID R-enantiomers.	2002 Nov	12421374
Centrally administered galanin-like peptide modifies food intake in the rat: a comparison with galanin.	2002 Nov	12421338
Activation of CYP2C9-mediated metabolism by a series of dapsone analogs: kinetics and structural requirements.	2002 Nov	12386124
Biochemical stabilization enhances red blood cell recovery and stability following cryopreservation.	2002 Oct	12482381
Thermodynamic study of the enantiomeric resolution of flurbiprofen by HPLC using Chiralpak AD-RH column.	2002 Oct	12426948
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	12147693
A nitric oxide-donating flurbiprofen derivative reduces neuroinflammation without interacting with galantamine in the rat.	2002 Oct 25	12398920
Cyclooxygenase and 5-lipoxygenase inhibitors protect against mononuclear phagocyte neurotoxicity.	2002 Sep-Oct	12392782
Synthesis and biological activity of flurbiprofen analogues as selective inhibitors of beta-amyloid(1)(-)(42) secretion.	2005 Sep 8	16134939
The geminal dimethyl analogue of Flurbiprofen as a novel Abeta42 inhibitor and potential Alzheimer's disease modifying agent.	2006 Apr 15	16455248
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	27447424
Analgesic effect of different dosage of Flurbiprofen axetil in laparoscopic cholecystectomy in comparison with other analgesic drugs.	2017 Sep	29084663
Analgesic effect of flurbiprofen axetil in treatment of single hole thoracoscopic surgery for pneumothorax.	2017 Sep	29084660
Postoperative benefits of dexmedetomidine combined with flurbiprofen axetil after thyroid surgery.	2017 Sep	28962135
Population pharmacokinetic modeling of flurbiprofen, the active metabolite of flurbiprofen axetil, in Chinese patients with postoperative pain.	2018	30555252
Flurbiprofen axetil attenuates cerebral ischemia/reperfusion injury by reducing inflammation in a rat model of transient global cerebral ischemia/reperfusion.	2018 Aug 31	29540536
Effect of oxycodone hydrochloride combined with flurbiprofen axetil for intravenous patient-controlled analgesia in lower abdominal patients: A randomized trial.	2018 Feb	29443767
Flurbiprofen axetil: Analgesic effect and adverse reaction.	2018 May	29735468
Comparison of perioperative flurbiprofen axetil or celecoxib administration for pain management after total-knee arthroplasty: A retrospective study.	2018 Sep	30213008
Intraoperative administration of intravenous flurbiprofen axetil with nalbuphine reduces postoperative pain after orbital decompression: a single-center, prospective randomized controlled trial.	2019	30863138
[Effect of Flurbiprofen Axetil on Low-frequency Fluctuation Amplitude of Resting-state Functional Magnetic Resonance Imaging in Trigeminal Neuralgia].	2019 Apr 28	31060679
Effect of flurbiprofen axetil on postoperative delirium for elderly patients.	2019 Jun	31007001
[Effect of multimodal analgesia using periprostatic nerve block anesthesia combined with flurbiprofen in transperineal template-guided prostate biopsy].	2019 Jun 1	31142067
[Postoperative low-dose sufentanil combined with transversus abdominis plane block promotes recovery following laparoscopic hysterectomy].	2019 Mar 30	31068298

Patents

Sample Use Guides

In Vivo Use Guide

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

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

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Name

Type

Language

FLURBIPROFEN

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