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(F)=C(C=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-1 125 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15336599	Inhibitor 8146	0.11 µM [IC50]
Cyclooxygenase-2 191 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24120370 \| https://www.ncbi.nlm.nih.gov/pubmed/15336599	Inhibitor 8146	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 8146
Cyclooxygenase-1 125 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16455248 \| https://www.ncbi.nlm.nih.gov/pubmed/16134939	Inhibitor 8146	0.2 µM [IC50]
Cyclooxygenase-2 191 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16134939	Inhibitor 8146	0.91 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Rheumatoid arthritis 310 Sources: https://www.drugs.com/pro/flurbiprofen-tablets.html	Primary	Approved 8307	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 155 Sources: https://www.drugs.com/pro/flurbiprofen-tablets.html	Primary	Approved 8307	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 155 Sources: http://www.taisho-holdings.co.jp/en/release/2016/2016012001-e.pdf	Primary	Approved 8307	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 985	substrate 1168

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 584 OAT3 625 MRP2 363 MRP4 202	CYP1A1 344 CYP2A6 510 CYP2B6 648 CYP2C19 955 UGT1A1 417 UGT1A3 421 UGT1A4 345 UGT1A6 306 UGT1A7 235 UGT1A8 282 UGT1A9 378 UGT1A10 289 UGT2B4 248 UGT2B7 387 UGT2B15 202 UGT2B17 212

Drug as perpetrator

Target	Modality	Activity
OAT1 588	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/22072415/	yes [IC50 0.615 uM]
OAT3 627	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/22072415/	yes [IC50 1.8 uM]
MRP4 235	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/26659924/	yes [IC50 10.6 uM]
MRP2 452	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/26659924/	yes [IC50 58.4 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A1 344	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/8937439/ Page: 3.0	no
CYP2A6 510	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/8937439/ Page: 3.0	no
CYP2B6 648	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/8937439/ Page: 3.0	no
CYP2C19 955	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/8937439/ Page: 3.0	no
CYP2D6 1168	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/8937439/ Page: 3.0	no
UGT2B15 202	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 4.0	no
UGT1A1 417	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 1.0	yes
UGT1A10 289	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15117964/ Page: 7.0	yes
UGT1A3 421	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 1.0	yes
UGT1A4 345	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/	yes
UGT1A6 306	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/	yes
UGT1A7 235	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15117964/ Page: 7.0	yes
UGT1A8 282	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15117964/ Page: 7.0	yes
UGT1A9 378	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 1.0	yes
UGT2B17 212	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 4.0	yes
UGT2B4 248	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 1.0	yes
UGT2B7 387	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 1.0	yes
CYP2C9 985	substrate 3264 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
Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries.	2001	11296921
Review: uveitis and immunosuppressive drugs.	2001 Apr	11324985
Early clinical trials of chemopreventive and biologic agents: Designs, populations, and endpoints.	2001 Apr	11295631
Proapoptotic anti-inflammatory drugs.	2001 Apr	11295599
Using evidence from different sources: an example using paracetamol 1000 mg plus codeine 60 mg.	2001 Jan 10	11231885
Protection by aspirin of indomethacin-induced small intestinal damage in rats: mediation by salicylic acid.	2001 Jan-Dec	11595418
Bradykinin-induced nociceptor sensitization to heat is mediated by cyclooxygenase products in isolated rat skin.	2001 Jul	11553274
Dapsone activation of CYP2C9-mediated metabolism: evidence for activation of multiple substrates and a two-site model.	2001 Jul	11408370
Peroxidase self-inactivation in prostaglandin H synthase-1 pretreated with cyclooxygenase inhibitors or substituted with mangano protoporphyrin IX.	2001 Jun 8	11279106
Perioperative intravenous flurbiprofen reduces postoperative pain after abdominal hysterectomy.	2001 Mar	11305822
Inhibition of NF-kappaB and AP-1 activation by R- and S-flurbiprofen.	2001 Mar	11291649
Selective inhibition of interleukin-4 gene expression in human T cells by aspirin.	2001 Mar 15	11238116
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	11386636
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
Dominant role of an endothelium-derived hyperpolarizing factor (EDHF)-like vasodilator in the ciliary vascular bed of the bovine isolated perfused eye.	2001 Oct	11606333
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
Inhibition of bone resorption in vitro and prevention of ovariectomy-induced bone loss in vivo by flurbiprofen nitroxybutylester (HCT1026).	2001 Sep	11592384
Comparative evaluation of corneal epithelial permeability after the use of diclofenac 0.1% and flurbiprofen 0.03% after phacoemulsification.	2001 Sep	11566521
Effect of flurbiprofen on hind-limb suspension-induced bone loss.	2001 Sep	11565811
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
Affinity capillary electrophoresis using a low-concentration additive with the consideration of relative mobilities.	2002 Apr 15	11985325
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
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
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	12065615
ATP can enhance the proton-induced CGRP release through P2Y receptors and secondary PGE(2) release in isolated rat dura mater.	2002 Jun	12044622
Catalytic properties of rice alpha-oxygenase. A comparison with mammalian prostaglandin H synthases.	2002 Jun 21	11909851
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
Identification of drug-binding sites on human serum albumin using affinity capillary electrophoresis and chemically modified proteins as buffer additives.	2002 Mar	11920883
Demonstration of dose response of flurbiprofen lozenges with the sore throat pain model.	2002 May	12011823
Activation of CYP2C9-mediated metabolism by a series of dapsone analogs: kinetics and structural requirements.	2002 Nov	12386124
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
Efficient synthesis of alpha-aryl esters by room-temperature palladium-catalyzed coupling of aryl halides with ester enolates.	2002 Oct 23	12381200
Cyclooxygenase and 5-lipoxygenase inhibitors protect against mononuclear phagocyte neurotoxicity.	2002 Sep-Oct	12392782
Prostaglandin synthesis inhibitor prevents hypotension without impairing gut perfusion during normothermic cardiopulmonary bypass.	2002 Sep-Oct	12296570
Synthesis and biological activity of flurbiprofen analogues as selective inhibitors of beta-amyloid(1)(-)(42) secretion.	2005 Sep 8	16134939
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
Effect of oxycodone hydrochloride combined with flurbiprofen axetil for intravenous patient-controlled analgesia in lower abdominal patients: A randomized trial.	2018 Feb	29443767
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 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 `Fri Dec 16 19:27:14 UTC 2022` Edited by `admin` on `Fri Dec 16 19:27:14 UTC 2022`
Record UNII	J5ZZK9P7MX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ESFLURBIPROFEN

Official Name

English

FLURBIPROFEN, (S)-

Common Name

English

BTS-24332

Code

English

esflurbiprofen [INN]

Common Name

English

ESFLURBIPROFEN [JAN]

Common Name

English

BTS 24332

Code

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