Identification

Name
Flurbiprofen
Accession Number
DB00712  (APRD00753)
Type
Small Molecule
Groups
Approved, Investigational
Description

Flurbiprofen, a propionic acid derivative, is a nonsteroidal anti-inflammatory agent (NSAIA) with antipyretic and analgesic activity. Oral formulations of flurbiprofen may be used for the symptomatic treatment of rheumatoid arthritis, osteoarthritis and anklylosing spondylitis. Flurbiprofen may also be used topically prior to ocular surgery to prevent or reduce intraoperative miosis. Flurbiprofen is structurally and pharmacologically related to fenoprofen, ibuprofen, and ketoprofen.

Structure
Thumb
Synonyms
  • (+-)-2-Fluoro-alpha-methyl-4-biphenylacetic acid
  • 2-(2-Fluorobiphenyl-4-yl)propanoic acid
  • 2-Fluoro-alpha-methyl-(1,1'-biphenyl)-4-acetic acid
  • 3-Fluoro-4-phenylhydratropic acid
  • FLP
  • Flurbiprofen
  • Flurbiprofene
  • Flurbiprofeno
  • Flurbiprofenum
  • S-flurbiprofen
External IDs
BTS 18 322 / FP 70 / FP 83 / U 27182
Product Ingredients
IngredientUNIICASInChI Key
Flurbiprofen SodiumZ5B97MU9K4Not AvailableAUAGTGKMTMVIKN-UHFFFAOYSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AnsaidTablet, film coated50 mg/1OralPharmacia & Upjohn Inc1988-10-312009-01-12Us
AnsaidTablet, film coated100 mg/1OralPhysicians Total Care, Inc.1988-10-312008-08-31Us
AnsaidTablet, film coated100 mg/1OralPharmacia & Upjohn Inc1988-10-312009-01-12Us
Ansaid Tablets 100 mgTablet100 mgOralPfizer1985-12-312013-07-25Canada
Ansaid Tablets 50 mgTablet50 mgOralPfizer1985-12-312013-07-25Canada
FlurbiprofenTablet50 mg/1OralCaraco Pharmaceutical Laboratories, Ltd.2007-08-09Not applicableUs
FlurbiprofenTablet100 mg/1OralCaraco Pharmaceutical Laboratories, Ltd.2007-08-09Not applicableUs
Flurbiprofen-100 Tab 100mgTablet100 mgOralPro Doc Limitee1992-12-312009-07-23Canada
Flurbiprofen-50 Tab 50mgTablet50 mgOralPro Doc Limitee1992-12-312009-07-23Canada
FrobenTablet50 mgOralAbbott1997-02-062008-06-06Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-flurbiprofen Fc Tablets 100mgTablet100 mgOralApotex Corporation1991-12-31Not applicableCanada
Apo-flurbiprofen Fc Tablets 50mgTablet50 mgOralApotex Corporation1991-12-31Not applicableCanada
FlurbiprofenTablet, film coated100 mg/1OralMylan Pharmaceuticals1994-06-20Not applicableUs
FlurbiprofenTablet, film coated100 mg/1OralPhysicians Total Care, Inc.1997-02-24Not applicableUs
FlurbiprofenTablet, film coated100 mg/1OralNucare Pharmaceuticals,inc.1995-06-02Not applicableUs
FlurbiprofenTablet, film coated100 mg/1Oralbryant ranch prepack1995-06-022014-02-01Us63629 125020180913 8702 18sey6z
FlurbiprofenTablet, film coated100 mg/1OralTeva Pharmaceuticals USA, Inc.1995-06-02Not applicableUs00093 0711 01 nlmimage10 7e2b3f69
FlurbiprofenTablet, film coated50 mg/1OralMylan Pharmaceuticals1994-06-20Not applicableUs00378 0076 01 nlmimage10 634631a1
FlurbiprofenTablet, film coated100 mg/1OralGreenstone, Llc1988-10-312009-01-12Us
FlurbiprofenTablet, film coated100 mg/1OralPd Rx Pharmaceuticals, Inc.1994-06-20Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Antiphlamine Pain RelievingPatch33 mg/51TopicalHanul Trading Co., Ltd.2015-09-01Not applicableUs
International/Other Brands
Acustop Cataplasma (Sang-A) / Adofeed (Lead Chemical) / Ansaid (Pfizer) / Antadys (Theramex) / Cebutid (Almirall) / Flurofen (Abbott Laboratories Ltd.) / Ocuflur (Allergan) / Stayban (Tokuhon) / Strefen (Reckitt Benckiser) / Strepfen (Reckitt Benckiser) / Strepsils (Reckitt Benckiser) / Strepsils Intensive (Reckitt Benckiser) / TransAct (Reckitt Benckiser) / Urbifen (General Pharma) / Zepolas (Mikasa Seiyaku)
Categories
UNII
5GRO578KLP
CAS number
5104-49-4
Weight
Average: 244.2609
Monoisotopic: 244.089957865
Chemical Formula
C15H13FO2
InChI Key
SYTBZMRGLBWNTM-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-(3-fluoro-4-phenylphenyl)propanoic acid
SMILES
CC(C(O)=O)C1=CC(F)=C(C=C1)C1=CC=CC=C1

Pharmacology

Indication

Flurbiprofen tablets are indicated for the acute or long-term symptomatic treatment of rheumatoid arthritis, osteorarthritis and anklosing spondylitis. 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). Topical ophthalmic formulations may be used pre-operatively to prevent intraoperative miosis.

Associated Conditions
Pharmacodynamics

Flurbiprofen, a nonsteroidal anti-inflammatory agent (NSAIA) of the propionic acid class, is structually and pharmacologically related to fenoprofen, ibuprofen, and ketoprofen, and has similar pharmacological actions to other prototypica NSAIAs. Flurbiprofen exhibits antiinflammatory, analgesic, and antipyretic activities. The commercially available flurbiprofen is a racemic mixture of (+)S- and (-) R-enantiomers. The S-enantiomer appears to possess most of the anti-inflammatory, while both enantiomers may possess analgesic activity.

Mechanism of action

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.

TargetActionsOrganism
UProstaglandin G/H synthase 1
inhibitor
Human
AProstaglandin G/H synthase 2
inhibitor
Human
Absorption

Fluribiprofen is rapidly and almost completely absorbed following oral administration. Peak plasma concentrations are reached 0.5 - 4 hours after oral administration.

Volume of distribution
  • 14 L [Normal Healthy Adults]
  • 12 L [Geriatric Arthritis Patients]
  • 10 L [End Stage Renal Disease Patients]
  • 14 L [Alcoholic Cirrhosis Patients]
  • 0.12 L/kg
Protein binding

> 99% bound, primarily to albumin. Binds to a different primary binding site on albumin than anticoagulants, sulfonamides and phenytoin.

Metabolism

Hepatic. Cytochrome P450 2C9 plays an important role in the metabolism of flurbiprofen to its major metabolite, 4’-hydroxy-flurbiprofen. The 4’-hydroxy-flurbiprofen metabolite showed little anti-inflammatory activity in animal models of inflammation.

Route of elimination

Flurbiprofen is poorly excreted into human milk. Following dosing with flurbiprofen, less than 3% of flurbiprofen is excreted unchanged in the urine, with about 70% of the dose eliminated in the urine as parent drug and metabolites. Renal elimination is a significant pathway of elimination of flurbiprofen metabolites.

Half life

R-flurbiprofen, 4.7 hours; S-flurbiprofen, 5.7 hours

Clearance
Not Available
Toxicity

LD50=10 mg/kg (orally in dogs).

Selective COX-2 inhibitors have been associated with increased risk of serious cardiovascular events (e.g. myocardial infarction, stroke) in some patients. Current data is insufficient to assess the cardiovascular risk of flurbiprofen. Flurbiprofen may increase blood pressure and/or cause fluid retention and edema. Use caution in patients with fluid retention or heart failure. Risk of GI toxicity including bleeding, ulceration and perforation. Risk of direct renal injury, including renal papillary necrosis. Anaphylactoid and serious skin reactions (e.g. exfoliative dermatitis, Stevens-Johnson syndrome, toxic epidermal necrolysis) may occur. Common adverse events include abdominal pain, constipation, diarrhea, dyspepsia, flatulence, GI bleeding, GI perforation, nausea, peptic ulcer, vomiting, renal function abnormalities, anemia, dizziness, edema, liver function test abnormalities, headache, prolonged bleeding time, pruritus, rash, tinnitus. Although rarely documented in the case of flurbiprofen, oral propionic acid derivatives have been associated with a relatively high frequency of allergic reactions.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Flurbiprofen Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C9CYP2C9*2Not Available430C>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*3Not Available1075A>CEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*4Not Available1076T>CEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*5Not Available1080C>GEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*8Not Available449G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*11Not Available1003C>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*12Not Available1465C>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*13Not Available269T>CEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*14Not Available374G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*16Not Available895A>GEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*18Not Available1075A>C / 1190A>C  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*26Not Available389C>GEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*28Not Available641A>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*30Not Available1429G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*33Not Available395G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*6Not Available818delAEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*15Not Available485C>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*25Not Available353_362delAGAAATGGAAEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*35Not Available374G>T / 430C>TEffect InferredPoor drug metabolizer.Details

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of gastrointestinal bleeding can be increased when Flurbiprofen is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of gastrointestinal bleeding can be increased when Flurbiprofen is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of gastrointestinal bleeding can be increased when Flurbiprofen is combined with 4-hydroxycoumarin.
AbacavirThe metabolism of Abacavir can be decreased when combined with Flurbiprofen.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Flurbiprofen is combined with Abciximab.
AcarboseFlurbiprofen may decrease the excretion rate of Acarbose which could result in a higher serum level.
AcebutololFlurbiprofen may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Acemetacin.
AcenocoumarolThe risk or severity of gastrointestinal bleeding can be increased when Flurbiprofen is combined with Acenocoumarol.
Food Interactions
  • Avoid alcohol.
  • Take with food to reduce gastric irritation.

References

Synthesis Reference

Yutaka Mizushima, Hiroyuki Okamoto, Shigetoshi Sugio, Kazumasa Yokoyama, Tadakazu Suyama, Masao Tohno, Makoto Okumura, Yoshiaki Konishi, Kiyonoshin Ichikawa, Katsuhiro Uchida, "Flurbiprofen derivative ophthalmic preparation." U.S. Patent US5171566, issued January, 1984.

US5171566
General References
  1. Geerts H: Drug evaluation: (R)-flurbiprofen--an enantiomer of flurbiprofen for the treatment of Alzheimer's disease. IDrugs. 2007 Feb;10(2):121-33. [PubMed:17285465]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  3. Calapai G, Imbesi S, Cafeo V, Ventura Spagnolo E, Minciullo PL, Caputi AP, Gangemi S, Milone L: Fatal hypersensitivity reaction to an oral spray of flurbiprofen: a case report. J Clin Pharm Ther. 2013 Aug;38(4):337-8. doi: 10.1111/jcpt.12073. Epub 2013 May 13. [PubMed:23668805]
  4. Mironov GG, Logie J, Okhonin V, Renaud JB, Mayer PM, Berezovski MV: Comparative study of three methods for affinity measurements: capillary electrophoresis coupled with UV detection and mass spectrometry, and direct infusion mass spectrometry. J Am Soc Mass Spectrom. 2012 Jul;23(7):1232-40. doi: 10.1007/s13361-012-0386-y. Epub 2012 Apr 28. [PubMed:22544663]
External Links
Human Metabolome Database
HMDB0014850
KEGG Drug
D00330
PubChem Compound
3394
PubChem Substance
46505550
ChemSpider
3277
BindingDB
50074922
ChEBI
5130
ChEMBL
CHEMBL563
Therapeutic Targets Database
DAP000621
PharmGKB
PA449683
IUPHAR
4194
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Flurbiprofen
ATC Codes
M02AA19 — FlurbiprofenM01AE09 — FlurbiprofenR02AX01 — FlurbiprofenS01BC04 — Flurbiprofen
AHFS Codes
  • 52:08.20 — Nonsteroidal Anti-inflammatory Agents
  • 28:08.04.92 — Other Nonsteroidal Antiimflammatory Agents
FDA label
Download (234 KB)
MSDS
Download (75 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentSurgery, Oral1
0Not Yet RecruitingDiagnosticPeri-implant Mucositis1
1CompletedNot AvailableDrug-drug Interaction Study1
1CompletedNot AvailableHealthy Volunteers1
1CompletedBasic ScienceDrug Interactions1
1CompletedBasic ScienceHealthy Volunteers / Human Immunodeficiency Virus (HIV) Infections1
1CompletedBasic ScienceRheumatoid Arthritis2
1CompletedDiagnosticDrug Interactions1
1CompletedDiagnosticHealthy Volunteers1
1CompletedHealth Services ResearchHealthy Volunteers1
1CompletedOtherHealthy Volunteers / Rheumatoid Arthritis1
1CompletedTreatmentAnemias / Healthy Volunteers1
1CompletedTreatmentType 2 Diabetes Mellitus1
1, 2CompletedDiagnosticHealthy Volunteers1
2CompletedTreatmentAcute Sore Throat Pain1
2CompletedTreatmentPain1
2CompletedTreatmentPeriodontitis1
3CompletedTreatmentAcute Pharyngitis / Throat Pain1
3CompletedTreatmentPharyngitis2
4CompletedTreatmentPancreatic Stone Disease1
4CompletedTreatmentPostoperative Shivering1
4RecruitingTreatmentAcute Low Back Pain1
4RecruitingTreatmentComplications / Pain1
Not AvailableCompletedNot AvailableAcute Gouty Arthritis / Arthritis / Headaches / Migraines / Muscle Spasms / Radicular syndrome / Synovitis / Tendonitis1
Not AvailableCompletedTreatmentPostoperative Sedation, Abdominal Surgery1
Not AvailableRecruitingNot AvailableDepression1
Not AvailableRecruitingTreatmentPostoperative Sedation,Gastrectomy, Enhanced Recovery After Surgery1

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
  • Caraco pharmaceutical laboratories ltd
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mylan pharmaceuticals inc
  • Pliva inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Theragen inc
  • Bausch and lomb inc
  • Allergan pharmaceutical
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Allergan Inc.
  • Amerisource Health Services Corp.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Bausch & Lomb Inc.
  • Caraco Pharmaceutical Labs
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Greenstone LLC
  • H.J. Harkins Co. Inc.
  • Ivax Pharmaceuticals
  • Lake Erie Medical and Surgical Supply
  • Major Pharmaceuticals
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Novopharm Ltd.
  • Nucare Pharmaceuticals Inc.
  • Pacific Pharma Lp
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacia Inc.
  • Physicians Total Care Inc.
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
Dosage forms
FormRouteStrength
Tablet, film coatedOral50 mg/1
PatchTopical33 mg/51
TabletOral100 mg
TabletOral50 mg
TabletOral100 mg/1
TabletOral50 mg/1
Tablet, film coatedOral100 mg/1
Solution / dropsOphthalmic0.242 mg/1mL
Solution / dropsOphthalmic0.3 mg/1mL
Capsule, extended releaseOral200 mg
LiquidOphthalmic0.03 %
Prices
Unit descriptionCostUnit
Ocufen 0.03% Solution 2.5ml Bottle22.7USD bottle
Flurbiprofen powder20.9USD g
Flurbiprofen Sodium 0.03% Solution 2.5ml Bottle15.99USD bottle
Ocufen 0.03% eye drops10.63USD ml
Flurbiprofen 0.03% eye drop4.37USD ml
Ansaid 100 mg tablet2.1USD tablet
Flurbiprofen 100 mg tablet1.08USD tablet
Flurbiprofen 50 mg tablet0.8USD tablet
Ansaid 50 mg Tablet0.58USD tablet
Apo-Flurbiprofen 100 mg Tablet0.37USD tablet
Novo-Flurprofen 100 mg Tablet0.37USD tablet
Nu-Flurbiprofen 100 mg Tablet0.37USD tablet
Apo-Flurbiprofen 50 mg Tablet0.27USD tablet
Novo-Flurprofen 50 mg Tablet0.27USD tablet
Nu-Flurbiprofen 50 mg Tablet0.27USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)110-111 °CAdams, S.S., Bernard, J., Nicholson, J.S. and Blancafort, A.R.; U.S. Patent 3,755,427; Aug. 28, 1973; assigned to The Boots Company Ltd.
water solubility8 mg/L (at 22 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP4.16HANSCH,C ET AL. (1995)
logS-4.49ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0249 mg/mLALOGPS
logP3.57ALOGPS
logP3.94ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.42ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity67.29 m3·mol-1ChemAxon
Polarizability25.23 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9824
Caco-2 permeable+0.8866
P-glycoprotein substrateNon-substrate0.76
P-glycoprotein inhibitor INon-inhibitor0.9061
P-glycoprotein inhibitor IINon-inhibitor0.9739
Renal organic cation transporterNon-inhibitor0.912
CYP450 2C9 substrateNon-substrate0.7247
CYP450 2D6 substrateNon-substrate0.9249
CYP450 3A4 substrateNon-substrate0.7205
CYP450 1A2 substrateInhibitor0.8663
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.9546
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9674
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8752
Ames testNon AMES toxic0.9659
CarcinogenicityNon-carcinogens0.5554
BiodegradationNot ready biodegradable0.9861
Rat acute toxicity3.1121 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9849
hERG inhibition (predictor II)Non-inhibitor0.9116
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (126 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-002b-0900000000-1791423706be24cc354b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-002b-0900000000-1c9889f5fc33443c7b3b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-2900000000-d74a9b309815da3ba05d
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Biphenyls and derivatives
Direct Parent
Biphenyls and derivatives
Alternative Parents
Phenylpropanoic acids / Monocyclic monoterpenoids / Aromatic monoterpenoids / Fluorobenzenes / Aryl fluorides / Monocarboxylic acids and derivatives / Carboxylic acids / Organofluorides / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Biphenyl / 2-phenylpropanoic-acid / P-cymene / Aromatic monoterpenoid / Monocyclic monoterpenoid / Monoterpenoid / Fluorobenzene / Halobenzene / Aryl halide / Aryl fluoride
show 11 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
fluorobiphenyl (CHEBI:5130)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Rieke CJ, Mulichak AM, Garavito RM, Smith WL: The role of arginine 120 of human prostaglandin endoperoxide H synthase-2 in the interaction with fatty acid substrates and inhibitors. J Biol Chem. 1999 Jun 11;274(24):17109-14. [PubMed:10358065]
  2. Hewett SJ, Uliasz TF, Vidwans AS, Hewett JA: Cyclooxygenase-2 contributes to N-methyl-D-aspartate-mediated neuronal cell death in primary cortical cell culture. J Pharmacol Exp Ther. 2000 May;293(2):417-25. [PubMed:10773011]
  3. Kurahashi K, Shirahase H, Nakamura S, Tarumi T, Koshino Y, Wang AM, Nishihashi T, Shimizu Y: Nicotine-induced contraction in the rat coronary artery: possible involvement of the endothelium, reactive oxygen species and COX-1 metabolites. J Cardiovasc Pharmacol. 2001 Oct;38 Suppl 1:S21-5. [PubMed:11811354]
  4. Klegeris A, McGeer PL: Cyclooxygenase and 5-lipoxygenase inhibitors protect against mononuclear phagocyte neurotoxicity. Neurobiol Aging. 2002 Sep-Oct;23(5):787-94. [PubMed:12392782]
  5. Droge MJ, van Sorge AA, van Haeringen NJ, Quax WJ, Zaagsma J: Alternative splicing of cyclooxygenase-1 mRNA in the human iris. Ophthalmic Res. 2003 May-Jun;35(3):160-3. [PubMed:12711844]
  6. Basselin M, Villacreses NE, Lee HJ, Bell JM, Rapoport SI: Flurbiprofen, a cyclooxygenase inhibitor, reduces the brain arachidonic acid signal in response to the cholinergic muscarinic agonist, arecoline, in awake rats. Neurochem Res. 2007 Nov;32(11):1857-67. Epub 2007 Jun 12. [PubMed:17562170]
  7. Nivsarkar M, Banerjee A, Padh H: Cyclooxygenase inhibitors: a novel direction for Alzheimer's management. Pharmacol Rep. 2008 Sep-Oct;60(5):692-8. [PubMed:19066416]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Bayly CI, Black WC, Leger S, Ouimet N, Ouellet M, Percival MD: Structure-based design of COX-2 selectivity into flurbiprofen. Bioorg Med Chem Lett. 1999 Feb 8;9(3):307-12. [PubMed:10091674]
  2. van Haeringen NJ, van Sorge AA, Carballosa Core-Bodelier VM: Constitutive cyclooxygenase-1 and induced cyclooxygenase-2 in isolated human iris inhibited by S(+) flurbiprofen. J Ocul Pharmacol Ther. 2000 Aug;16(4):353-61. [PubMed:10977131]
  3. Smith T, McCracken J, Shin YK, DeWitt D: Arachidonic acid and nonsteroidal anti-inflammatory drugs induce conformational changes in the human prostaglandin endoperoxide H2 synthase-2 (cyclooxygenase-2). J Biol Chem. 2000 Dec 22;275(51):40407-15. [PubMed:11006278]
  4. Hinz B, Brune K, Rau T, Pahl A: Flurbiprofen enantiomers inhibit inducible nitric oxide synthase expression in RAW 264.7 macrophages. Pharm Res. 2001 Feb;18(2):151-6. [PubMed:11405284]
  5. Hewett SJ, Uliasz TF, Vidwans AS, Hewett JA: Cyclooxygenase-2 contributes to N-methyl-D-aspartate-mediated neuronal cell death in primary cortical cell culture. J Pharmacol Exp Ther. 2000 May;293(2):417-25. [PubMed:10773011]
  6. Basselin M, Villacreses NE, Lee HJ, Bell JM, Rapoport SI: Flurbiprofen, a cyclooxygenase inhibitor, reduces the brain arachidonic acid signal in response to the cholinergic muscarinic agonist, arecoline, in awake rats. Neurochem Res. 2007 Nov;32(11):1857-67. Epub 2007 Jun 12. [PubMed:17562170]
  7. Nivsarkar M, Banerjee A, Padh H: Cyclooxygenase inhibitors: a novel direction for Alzheimer's management. Pharmacol Rep. 2008 Sep-Oct;60(5):692-8. [PubMed:19066416]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. [PubMed:20167001]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  4. Lin Y, Lu P, Tang C, Mei Q, Sandig G, Rodrigues AD, Rushmore TH, Shou M: Substrate inhibition kinetics for cytochrome P450-catalyzed reactions. Drug Metab Dispos. 2001 Apr;29(4 Pt 1):368-74. [PubMed:11259318]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A3
Uniprot ID
P35503
Uniprot Name
UDP-glucuronosyltransferase 1-3
Molecular Weight
60337.835 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as...
Gene Name
UGT2B4
Uniprot ID
P06133
Uniprot Name
UDP-glucuronosyltransferase 2B4
Molecular Weight
60512.035 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Other/unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Aarons L, Khan AZ, Grennan DM, Alam-Siddiqi M: The binding of flurbiprofen to plasma proteins. J Pharm Pharmacol. 1985 Sep;37(9):644-6. [PubMed:2867185]
  2. Takla PG, Schulman SG, Perrin JH: Measurement of flurbiprofen-human serum albumin interaction by fluorimetry. J Pharm Biomed Anal. 1985;3(1):41-50. [PubMed:16867708]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
May be an organic anion pump relevant to cellular detoxification.
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
Multidrug resistance-associated protein 4
Molecular Weight
149525.33 Da
References
  1. Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [PubMed:12835412]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. [PubMed:10991954]
  2. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [PubMed:10220563]

Drug created on June 13, 2005 07:24 / Updated on October 16, 2018 08:30