ESFLURBIPROFEN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H13FO2
Molecular Weight	244.2609
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H](C(O)=O)C1=CC=C(C(F)=C1)C2=CC=CC=C2

InChI

InChIKey=SYTBZMRGLBWNTM-JTQLQIEISA-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)/t10-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C15H13FO2
Molecular Weight	244.2609
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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-1 131 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15336599	Inhibitor 8504	0.11 µM [IC50]
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24120370 \| https://www.ncbi.nlm.nih.gov/pubmed/15336599	Inhibitor 8504	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 8504
Cyclooxygenase-1 131 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16455248 \| https://www.ncbi.nlm.nih.gov/pubmed/16134939	Inhibitor 8504	0.2 µM [IC50]
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16134939	Inhibitor 8504	0.91 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Rheumatoid arthritis 320 Sources: https://www.drugs.com/pro/flurbiprofen-tablets.html	Primary	Approved 8583	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 1988
Osteoarthritis 157 Sources: https://www.drugs.com/pro/flurbiprofen-tablets.html	Primary	Approved 8583	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 1988
Osteoarthritis 157 Sources: http://www.taisho-holdings.co.jp/en/release/2016/2016012001-e.pdf	Primary	Approved 8583	LOQOA® Tape Approved Use LOQOA® Tape indicated for the treatment of osteoarthritis pain and inflammation. Launch Date 2015

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 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 725 OAT3 747 MRP2 499 MRP4 290	CYP1A1 389 CYP2A6 626 CYP2B6 776 CYP2C19 1119 UGT1A1 479 UGT1A3 470 UGT1A4 399 UGT1A6 343 UGT1A7 249 UGT1A8 323 UGT1A9 423 UGT1A10 331 UGT2B4 278 UGT2B7 456 UGT2B15 236 UGT2B17 237

Drug as perpetrator

Target	Modality	Activity
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22072415/	yes [IC50 0.615 uM]
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22072415/	yes [IC50 1.8 uM]
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26659924/	yes [IC50 10.6 uM]
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26659924/	yes [IC50 58.4 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8937439/ Page: 3.0	no
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8937439/ Page: 3.0	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8937439/ Page: 3.0	no
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8937439/ Page: 3.0	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8937439/ Page: 3.0	no
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 4.0	no
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 1.0	yes
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15117964/ Page: 7.0	yes
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 1.0	yes
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/	yes
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/	yes
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15117964/ Page: 7.0	yes
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15117964/ Page: 7.0	yes
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 1.0	yes
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 4.0	yes
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 1.0	yes
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 1.0	yes
CYP2C9 1193	substrate 4014 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
eMolecules	538498	https://www.emolecules.com/cgi-bin/more?vid=538498
MolPort	MolPort-000-812-253	https://www.molport.com/shop/molecule-link/MolPort-000-812-253

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	31142067
Effect of flurbiprofen axetil on postoperative delirium for elderly patients.	2019-06	31007001
[Effect of Flurbiprofen Axetil on Low-frequency Fluctuation Amplitude of Resting-state Functional Magnetic Resonance Imaging in Trigeminal Neuralgia].	2019-04-28	31060679
[Postoperative low-dose sufentanil combined with transversus abdominis plane block promotes recovery following laparoscopic hysterectomy].	2019-03-30	31068298
Intraoperative administration of intravenous flurbiprofen axetil with nalbuphine reduces postoperative pain after orbital decompression: a single-center, prospective randomized controlled trial.	2019	30863138
Comparison of perioperative flurbiprofen axetil or celecoxib administration for pain management after total-knee arthroplasty: A retrospective study.	2018-09	30213008
Flurbiprofen axetil attenuates cerebral ischemia/reperfusion injury by reducing inflammation in a rat model of transient global cerebral ischemia/reperfusion.	2018-08-31	29540536
Flurbiprofen axetil: Analgesic effect and adverse reaction.	2018-05	29735468
Effect of oxycodone hydrochloride combined with flurbiprofen axetil for intravenous patient-controlled analgesia in lower abdominal patients: A randomized trial.	2018-02	29443767
Population pharmacokinetic modeling of flurbiprofen, the active metabolite of flurbiprofen axetil, in Chinese patients with postoperative pain.	2018	30555252
Analgesic effect of different dosage of Flurbiprofen axetil in laparoscopic cholecystectomy in comparison with other analgesic drugs.	2017-09	29084663
Analgesic effect of flurbiprofen axetil in treatment of single hole thoracoscopic surgery for pneumothorax.	2017-09	29084660
Postoperative benefits of dexmedetomidine combined with flurbiprofen axetil after thyroid surgery.	2017-09	28962135
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	27447424
The geminal dimethyl analogue of Flurbiprofen as a novel Abeta42 inhibitor and potential Alzheimer's disease modifying agent.	2006-04-15	16455248
Synthesis and biological activity of flurbiprofen analogues as selective inhibitors of beta-amyloid(1)(-)(42) secretion.	2005-09-08	16134939
Contractile effect of anaphylatoxin C5a and of a mimetic peptide on the human umbilical artery: further evidence for leukocyte-dependent vasomotion.	2002-12	12451314
Kinetics of allopregnanolone formation catalyzed by human 3 alpha-hydroxysteroid dehydrogenase type III (AKR1C2).	2002-11-12	12416991
Drug therapy of urinary urge incontinence: a systematic review.	2002-11	12423868
Selective inhibition of Abeta42 production by NSAID R-enantiomers.	2002-11	12421374
Centrally administered galanin-like peptide modifies food intake in the rat: a comparison with galanin.	2002-11	12421338
Activation of CYP2C9-mediated metabolism by a series of dapsone analogs: kinetics and structural requirements.	2002-11	12386124
NO-flurbiprofen maintains duodenal blood flow, enhances mucus secretion contributing to lower mucosal injury.	2002-11	12381522
A nitric oxide-donating flurbiprofen derivative reduces neuroinflammation without interacting with galantamine in the rat.	2002-10-25	12398920
Cyclooxygenase and 5-lipoxygenase inhibitors protect against mononuclear phagocyte neurotoxicity.	2002-10-24	12392782
Efficient synthesis of alpha-aryl esters by room-temperature palladium-catalyzed coupling of aryl halides with ester enolates.	2002-10-23	12381200
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	12147693
Biochemical stabilization enhances red blood cell recovery and stability following cryopreservation.	2002-10	12482381
Thermodynamic study of the enantiomeric resolution of flurbiprofen by HPLC using Chiralpak AD-RH column.	2002-10	12426948
Prostaglandin synthesis inhibitor prevents hypotension without impairing gut perfusion during normothermic cardiopulmonary bypass.	2002-09-26	12296570
Mechanism of in vitro release kinetics of flurbiprofen loaded ethylcellulose micropellets.	2002-09-17	12230246
Rapid and simple quantitative assay method for diastereomeric flurbiprofen glucuronides in the incubation mixture.	2002-08-25	12127333
Metabolic profile of NO-flurbiprofen (HCT1026) in rat brain and plasma: a LC-MS study.	2002-08-16	12127904
Therapeutic utility of aspirin in the ApcMin/+ murine model of colon carcinogenesis.	2002-08-09	12171603
In vitro release studies of flurbiprofen from different topical formulations.	2002-08	12236068
[The effectiveness of perioperative intravenous flurbiprofen in minor ear, neck and nose surgery].	2002-08	12229133
Dissection of metabolic, vascular, and nerve conduction interrelationships in experimental diabetic neuropathy by cyclooxygenase inhibition and acetyl-L-carnitine administration.	2002-08	12145179
Prostaglandin synthesis inhibitor affects humoral conditions and oxygen metabolism during normothermic cardiopulmonary bypass.	2002-08	12139494
Flurbiprofen-loaded acrylate polymer nanosuspensions for ophthalmic application.	2002-08	12102196
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	12095655
Peripheral analgesic sites of action of anti-inflammatory drugs.	2002-07	12166614
Prevention by parenteral aspirin of indomethacin-induced gastric lesions in rats: mediation by salicylic acid.	2002-07	12141814
Flurbiprofen does not change the bispectral index and 95% spectral edge frequency during total intravenous anaesthesia with propofol and fentanyl.	2002-07	12113610
Characterization of the bone-resorptive effect of interleukin-11 in cultured mouse calvarial bones.	2002-07	12110441
Lipids and nitric oxide in porcine retinal and choroidal blood vessels.	2002-06	12099547
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	12065615
ATP can enhance the proton-induced CGRP release through P2Y receptors and secondary PGE(2) release in isolated rat dura mater.	2002-06	12044622
Nitric oxide-releasing drugs: a novel class of effective and safe therapeutic agents.	2002-05	12076987
Pathogenic importance of intestinal hypermotility in NSAID-induced small intestinal damage in rats.	2002	12379813
The effect of nonsteroidal antiinflammatory drugs ibuprofen, flurbiprofen, and diclofenac on in vitro and in vivo growth of mouse fibrosarcoma.	2002	12094544

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 `Mon Mar 31 18:20:58 GMT 2025` Edited by `admin` on `Mon Mar 31 18:20:58 GMT 2025`
Record UNII	J5ZZK9P7MX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BTS 24332

Preferred Name

English

ESFLURBIPROFEN

Official Name

English

FLURBIPROFEN, (S)-

Common Name

English

BTS-24332

Code

English

esflurbiprofen [INN]

Common Name

English

ESFLURBIPROFEN [JAN]

Common Name

English

(S)-2-FLUORO-.ALPHA.-METHYL-4-BIPHENYLACETIC ACID

Systematic Name

English

Esflurbiprofen [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C257