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Identification
NameFlurbiprofen
Accession NumberDB00712  (APRD00753)
TypeSmall Molecule
GroupsApproved, 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
Ansaid
FLP
Flurbiprofen
Flurbiprofene
Flurbiprofeno
Flurbiprofenum
S-flurbiprofen
External Identifiers
  • BTS 18 322
  • FP 70
  • FP 83
  • U 27182
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ansaid Tablets 100 mgtablet100 mgoralPfizer Canada Inc1985-12-312013-07-25Canada
Ansaid Tablets 50 mgtablet50 mgoralPfizer Canada Inc1985-12-312013-07-25Canada
Flurbiprofen Sodiumsolution/ drops.3 mg/mLophthalmicPacific Pharma, Inc.1997-05-29Not applicableUs
Flurbiprofen Sodiumsolution/ drops.3 mg/mLophthalmicRebel Distributors Corp1997-05-29Not applicableUs
Flurbiprofen-100 Tab 100mgtablet100 mgoralPro Doc Limitee1992-12-312009-07-23Canada
Flurbiprofen-50 Tab 50mgtablet50 mgoralPro Doc Limitee1992-12-312009-07-23Canada
Frobentablet100 mgoralAbbott Laboratories, Limited1996-12-162008-06-06Canada
Frobentablet50 mgoralAbbott Laboratories, Limited1997-02-062008-06-06Canada
Froben SRcapsule (sustained-release)200 mgoralAbbott Laboratories, Limited1997-01-282008-06-06Canada
Froben Tab 100mgtablet100 mgoralOrganon Canada Ltd Ltee1986-12-311996-09-10Canada
Froben Tab 50mgtablet50 mgoralOrganon Canada Ltd Ltee1986-12-311996-09-10Canada
Froben-SR Cap 200mgcapsule (sustained-release)200 mgoralOrganon Canada Ltd Ltee1990-12-311996-09-10Canada
Novo-flurprofen SRcapsule (sustained-release)200 mgoralNovopharm LimitedNot applicableNot applicableCanada
Nu-flurbiprofen Tab 100mgtablet100 mgoralNu Pharm Inc1993-12-312012-09-04Canada
Nu-flurbiprofen Tab 50mgtablet50 mgoralNu Pharm Inc1993-12-312012-09-04Canada
Ocufensolution/ drops.3 mg/mLophthalmicAllergan, Inc.1987-01-01Not applicableUs
Ocufen Oph Soln 0.03%liquid0.03 %ophthalmicAllergan Inc1988-12-312011-08-04Canada
Ratio-flurbiprofen Tablets 100mgtablet100 mgoralRatiopharm Inc Division Of Teva Canada Limited1991-12-312006-08-04Canada
Ratio-flurbiprofen Tablets 50mgtablet50 mgoralRatiopharm Inc Division Of Teva Canada Limited1991-12-312006-08-04Canada
Teva-flurbiprofentablet100 mgoralTeva Canada Limited1994-12-31Not applicableCanada
Teva-flurbiprofentablet50 mgoralTeva Canada Limited1994-12-31Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-flurbiprofen Fc Tablets 100mgtablet100 mgoralApotex Inc1991-12-31Not applicableCanada
Apo-flurbiprofen Fc Tablets 50mgtablet50 mgoralApotex Inc1991-12-31Not applicableCanada
Flurbiprofentablet, film coated100 mg/1oralA S Medication Solutions1995-06-02Not applicableUs
Flurbiprofentablet, film coated100 mg/1oralTeva Pharmaceuticals USA Inc1995-06-02Not applicableUs
Flurbiprofentablet, film coated100 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-05-20Not applicableUs
Flurbiprofentablet, film coated100 mg/1oralbryant ranch prepack1995-06-02Not applicableUs
Flurbiprofentablet, film coated100 mg/1oralSTAT Rx USA LLC1994-06-20Not applicableUs
Flurbiprofentablet, film coated100 mg/1oralPd Rx Pharmaceuticals, Inc.2011-05-20Not applicableUs
Flurbiprofentablet, film coated100 mg/1oralMylan Pharmaceuticals Inc.1994-06-20Not applicableUs
Flurbiprofentablet, film coated100 mg/1oralPhysicians Total Care, Inc.1997-02-24Not applicableUs
Flurbiprofentablet, film coated50 mg/1oralMylan Pharmaceuticals Inc.1994-06-20Not applicableUs
Flurbiprofentablet, film coated100 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-07Not applicableUs
Flurbiprofen Sodiumsolution/ drops.3 mg/mLophthalmicBausch & Lomb Incorporated1995-01-04Not applicableUs
Flurbiprofen Sodiumsolution/ drops.242 mg/mLophthalmicRebel Distributors Corp1995-01-04Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Antiphlamine Pain Relievingpatch33 mg/51topicalHanul Trading Co., Ltd.2015-09-01Not applicableUs
International Brands
NameCompany
Acustop CataplasmaSang-A
AdofeedLead Chemical
AnsaidPfizer
AntadysTheramex
CebutidAlmirall
FlurofenAbbott Laboratories Ltd.
OcuflurAllergan
StaybanTokuhon
StrefenReckitt Benckiser
StrepfenReckitt Benckiser
StrepsilsReckitt Benckiser
Strepsils IntensiveReckitt Benckiser
TransActReckitt Benckiser
UrbifenGeneral Pharma
ZepolasMikasa Seiyaku
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Flurbiprofen Sodium
Thumb
  • InChI Key: AUAGTGKMTMVIKN-UHFFFAOYNA-M
  • Monoisotopic Mass: 266.071902508
  • Average Mass: 266.2428
DBSALT000544
Categories
UNII5GRO578KLP
CAS number5104-49-4
WeightAverage: 244.2609
Monoisotopic: 244.089957865
Chemical FormulaC15H13FO2
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentBiphenyls and derivatives
Alternative Parents
Substituents
  • Biphenyl
  • 2-phenylpropanoic-acid
  • Phenylacetate
  • Monoterpenoid
  • Monocyclic monoterpenoid
  • Aromatic monoterpenoid
  • P-cymene
  • Halobenzene
  • Fluorobenzene
  • Aryl halide
  • Aryl fluoride
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFlurbiprofen 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.
PharmacodynamicsFlurbiprofen, 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 actionSimilar 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.
Related Articles
AbsorptionFluribiprofen 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.

SubstrateEnzymesProduct
Flurbiprofen
4'-HydroxyflurbiprofenDetails
Flurbiprofen
Flurbiprofen glucuronideDetails
Route of eliminationFlurbiprofen 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 lifeR-flurbiprofen, 4.7 hours; S-flurbiprofen, 5.7 hours
ClearanceNot Available
ToxicityLD50=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
PathwayCategorySMPDB ID
Flurbiprofen Action PathwayDrug actionSMP00697
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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
Dosage forms
FormRouteStrength
Patchtopical33 mg/51
Tabletoral100 mg
Tabletoral50 mg
Tablet, film coatedoral100 mg/1
Tablet, film coatedoral50 mg/1
Solution/ dropsophthalmic.242 mg/mL
Capsule (sustained-release)oral200 mg
Solution/ dropsophthalmic.3 mg/mL
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point110-111 °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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (126 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
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
ATC CodesM01AE09M02AA19R02AX01S01BC04
AHFS Codes
  • 28:08.04.92
  • 52:08.20
PDB EntriesNot Available
FDA labelDownload (234 KB)
MSDSDownload (75 KB)
Interactions
Drug Interactions
Drug
AbciximabFlurbiprofen may increase the anticoagulant activities of Abciximab.
AcenocoumarolFlurbiprofen may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Acetylsalicylic acid.
AliskirenFlurbiprofen may decrease the antihypertensive activities of Aliskiren.
AlteplaseFlurbiprofen may increase the anticoagulant activities of Alteplase.
AmikacinFlurbiprofen may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
AmitriptylineAmitriptyline may increase the antiplatelet activities of Flurbiprofen.
AnistreplaseFlurbiprofen may increase the anticoagulant activities of Anistreplase.
ApixabanThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Apixaban.
ArbekacinFlurbiprofen may decrease the excretion rate of Arbekacin which could result in a lower serum level and potentially a reduction in efficacy.
BalsalazideFlurbiprofen may increase the nephrotoxic activities of Balsalazide.
Citric AcidFlurbiprofen may increase the anticoagulant activities of Citric Acid.
ColesevelamColesevelam can cause a decrease in the absorption of Flurbiprofen resulting in a reduced serum concentration and potentially a decrease in efficacy.
CollagenaseThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Collagenase.
CyclosporineFlurbiprofen may increase the nephrotoxic activities of Cyclosporine.
Dabigatran etexilateFlurbiprofen may increase the anticoagulant activities of Dabigatran etexilate.
DalteparinFlurbiprofen may increase the anticoagulant activities of Dalteparin.
DasatinibDasatinib may increase the anticoagulant activities of Flurbiprofen.
DeferasiroxThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Deferasirox.
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Deoxycholic Acid.
DesmopressinThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Desmopressin.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Flurbiprofen.
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Flurbiprofen.
DicoumarolFlurbiprofen may increase the anticoagulant activities of Dicoumarol.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Flurbiprofen.
DrospirenoneFlurbiprofen may increase the hyperkalemic activities of Drospirenone.
Edetic AcidFlurbiprofen may increase the anticoagulant activities of Edetic Acid.
EnoxaparinFlurbiprofen may increase the anticoagulant activities of Enoxaparin.
EplerenoneFlurbiprofen may decrease the antihypertensive activities of Eplerenone.
Ethyl biscoumacetateFlurbiprofen may increase the anticoagulant activities of Ethyl biscoumacetate.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Flurbiprofen.
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Flurbiprofen.
Fondaparinux sodiumFlurbiprofen may increase the anticoagulant activities of Fondaparinux sodium.
FramycetinFlurbiprofen may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
GentamicinFlurbiprofen may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
GlucosamineGlucosamine may increase the antiplatelet activities of Flurbiprofen.
HaloperidolThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Haloperidol.
HeparinFlurbiprofen may increase the anticoagulant activities of Heparin.
HydralazineFlurbiprofen may decrease the antihypertensive activities of Hydralazine.
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Ibritumomab.
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Flurbiprofen.
IcosapentThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Icosapent.
InfliximabThe risk or severity of adverse effects can be increased when Infliximab is combined with Flurbiprofen.
KanamycinFlurbiprofen may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Flurbiprofen.
LimaprostLimaprost may increase the antiplatelet activities of Flurbiprofen.
LithiumThe serum concentration of Lithium can be increased when it is combined with Flurbiprofen.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Flurbiprofen.
MorniflumateThe risk or severity of adverse effects can be increased when Morniflumate is combined with Flurbiprofen.
NadololFlurbiprofen may decrease the antihypertensive activities of Nadolol.
NeomycinFlurbiprofen may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
NetilmicinFlurbiprofen may decrease the excretion rate of Netilmicin which could result in a lower serum level and potentially a reduction in efficacy.
ObinutuzumabThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Obinutuzumab.
Omacetaxine mepesuccinateThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Homoharringtonine.
Omega-3 fatty acidsOmega-3 fatty acids may increase the antiplatelet activities of Flurbiprofen.
PamidronateThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Pamidronate.
ParoxetineParoxetine may increase the antiplatelet activities of Flurbiprofen.
PemetrexedThe serum concentration of Pemetrexed can be increased when it is combined with Flurbiprofen.
Pentosan PolysulfateThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Flurbiprofen.
PentoxifyllinePentoxifylline may increase the antiplatelet activities of Flurbiprofen.
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Flurbiprofen.
PhenindioneFlurbiprofen may increase the anticoagulant activities of Phenindione.
PhenprocoumonFlurbiprofen may increase the anticoagulant activities of Phenprocoumon.
PorfimerFlurbiprofen may increase the photosensitizing activities of Porfimer.
PralatrexateThe serum concentration of Pralatrexate can be increased when it is combined with Flurbiprofen.
ProbenecidThe serum concentration of Flurbiprofen can be increased when it is combined with Probenecid.
ReteplaseFlurbiprofen may increase the anticoagulant activities of Reteplase.
RibostamycinFlurbiprofen may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
RidogrelFlurbiprofen may increase the anticoagulant activities of Ridogrel.
RivaroxabanFlurbiprofen may increase the anticoagulant activities of Rivaroxaban.
SparfloxacinFlurbiprofen may increase the neuroexcitatory activities of Sparfloxacin.
SpectinomycinFlurbiprofen may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
StreptokinaseFlurbiprofen may increase the anticoagulant activities of Streptokinase.
StreptomycinFlurbiprofen may decrease the excretion rate of Streptomycin which could result in a lower serum level and potentially a reduction in efficacy.
SulodexideFlurbiprofen may increase the anticoagulant activities of Sulodexide.
TacrolimusFlurbiprofen may increase the nephrotoxic activities of Tacrolimus.
TalniflumateThe risk or severity of adverse effects can be increased when Talniflumate is combined with Flurbiprofen.
TenecteplaseFlurbiprofen may increase the anticoagulant activities of Tenecteplase.
TenofovirThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Tenofovir.
TipranavirTipranavir may increase the antiplatelet activities of Flurbiprofen.
TobramycinFlurbiprofen may decrease the excretion rate of Tobramycin which could result in a lower serum level and potentially a reduction in efficacy.
TorasemideFlurbiprofen may decrease the diuretic activities of Torasemide.
TositumomabThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Tositumomab.
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Flurbiprofen.
TriamtereneFlurbiprofen may decrease the antihypertensive activities of Triamterene.
TrichlormethiazideThe therapeutic efficacy of Trichlormethiazide can be decreased when used in combination with Flurbiprofen.
UnoprostoneThe therapeutic efficacy of Unoprostone can be decreased when used in combination with Flurbiprofen.
UrokinaseFlurbiprofen may increase the anticoagulant activities of Urokinase.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Flurbiprofen.
VancomycinThe serum concentration of Vancomycin can be increased when it is combined with Flurbiprofen.
VenlafaxineVenlafaxine may increase the antiplatelet activities of Flurbiprofen.
VerteporfinFlurbiprofen may increase the photosensitizing activities of Verteporfin.
Vitamin EVitamin E may increase the antiplatelet activities of Flurbiprofen.
WarfarinFlurbiprofen may increase the anticoagulant activities of Warfarin.
Food Interactions
  • Avoid alcohol.
  • Take with food to reduce gastric irritation.

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 gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
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 brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
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 suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol...
Gene Name:
UGT2B7
Uniprot ID:
P16662
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
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 IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naph...
Gene Name:
UGT1A1
Uniprot ID:
P22309
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 regulator of isoform 1.
Gene Name:
UGT1A3
Uniprot ID:
P35503
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 transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A9
Uniprot ID:
O60656
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 estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydr...
Gene Name:
UGT2B4
Uniprot ID:
P06133
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 colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
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
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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23