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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
SynonymLanguageCode
(+-)-2-Fluoro-alpha-methyl-4-biphenylacetic acidNot AvailableNot Available
2-(2-Fluorobiphenyl-4-yl)propanoic acidNot AvailableNot Available
2-Fluoro-alpha-methyl-(1,1'-biphenyl)-4-acetic acidNot AvailableNot Available
3-Fluoro-4-phenylhydratropic acidNot AvailableNot Available
AnsaidNot AvailableNot Available
FLPNot AvailableNot Available
FlurbiprofenGermanINN
FlurbiprofeneFrenchINN
FlurbiprofenoSpanishINN
FlurbiprofenumLatinINN
S-flurbiprofenNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ocufensolution/ drops.3 mg/mLophthalmicAllergan, Inc.1987-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flurbiprofen Sodiumsolution/ drops.3 mg/mLophthalmicRebel Distributors Corp1997-05-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flurbiprofen Sodiumsolution/ drops.3 mg/mLophthalmicPacific Pharma, Inc.1997-05-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Flurbiprofentablet, film coated100 mgoralTeva Pharmaceuticals USA Inc1995-06-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flurbiprofentablet, film coated50 mgoralMylan Pharmaceuticals Inc.1994-06-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flurbiprofentablet, film coated100 mgoralMylan Pharmaceuticals Inc.1994-06-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flurbiprofentablet, film coated100 mgoralSTAT Rx USA LLC1994-06-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flurbiprofen Sodiumsolution/ drops.242 mg/mLophthalmicRebel Distributors Corp1995-01-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flurbiprofen Sodiumsolution/ drops.3 mg/mLophthalmicBausch & Lomb Incorporated1995-01-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flurbiprofentablet, film coated100 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-05-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flurbiprofentablet, film coated100 mgoralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flurbiprofentablet, film coated100 mgoralPhysicians Total Care, Inc.1997-02-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flurbiprofentablet, film coated100 mgoralPd Rx Pharmaceuticals, Inc.2011-05-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flurbiprofentablet, film coated100 mgoralbryant ranch prepack1995-06-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
Acustop CataplasmaSang-A
AdofeedLead Chemical
AnsaidPfizer
AntadysTheramex
CebutidAlmirall
FlurofenAbbott Laboratories Ltd.
FrobenAbbott Laboratories Ltd.
Froben SrAbbott Laboratories Ltd.
OcuflurAllergan
StaybanTokuhon
StrefenReckitt Benckiser
StrepfenReckitt Benckiser
StrepsilsReckitt Benckiser
Strepsils IntensiveReckitt Benckiser
TransActReckitt Benckiser
UrbifenGeneral Pharma
ZepolasMikasa Seiyaku
Brand mixtures
Brand NameIngredients
FlurbirenFlurbiprofen and Hypromellose
Salts
Name/CASStructureProperties
Flurbiprofen Sodium
Thumb
  • InChI Key: AUAGTGKMTMVIKN-UHFFFAOYNA-M
  • Monoisotopic Mass: 266.071902508
  • Average Mass: 266.2428
DBSALT000544
Categories
CAS number5104-49-4
WeightAverage: 244.2609
Monoisotopic: 244.089957865
Chemical FormulaC15H13FO2
InChI KeySYTBZMRGLBWNTM-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.
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 substrateInhibitor0.8949
CYP450 2D6 substrateNon-inhibitor0.9546
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateNon-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
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
Solution/ dropsophthalmic.242 mg/mL
Solution/ dropsophthalmic.3 mg/mL
Tablet, film coatedoral100 mg
Tablet, film coatedoral50 mg
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)
Spectra1D NMR
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 Reference
  1. Geerts H: Drug evaluation:®-flurbiprofen—an enantiomer of flurbiprofen for the treatment of Alzheimer’s disease. IDrugs. 2007 Feb;10(2):121-33. Pubmed
  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
  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
  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
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
AcenocoumarolThe NSAID, flurbiprofen, may increase the anticoagulant effect of acenocoumarol.
AlendronateIncreased risk of gastric toxicity
AnisindioneThe NSAID, flurbiprofen, may increase the anticoagulant effect anisindione.
Azilsartan medoxomilIncreases toxicity of each. May deteriorate renal function, particularly in volume depleted or elderly patients. Decreases effects of azilsartan by antagonism.
ColesevelamBile acid sequestrants may decrease the absorption of Nonsteroidal Anti-Inflammatory Agents. Monitor for decreased serum concentrations/therapeutic effects of nonsteroidal anti-inflammatory agents (NSAID) if coadministered with bile acid sequestrants. Separating the administration of doses by 2 or more hours may reduce (but not eliminate) the risk of interaction. The manufacturer of colesevelam recommends that drugs should be administered at least 1 hour before or 4 hours after colesevelam.
CyclosporineMonitor for nephrotoxicity
DicoumarolThe NSAID, flurbiprofen, may increase the anticoagulant effect of dicumarol.
DifluprednateNSAIDs may slow healing.
EltrombopagIncreases levels of Flurbiprofen via metabolism decrease. UDP-glucuronosyltransferase inhibition.
Ginkgo bilobaAdditive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
MethotrexateThe NSAID, flurbiprofen, may decrease the renal excretion of methotrexate. Increased risk of methotrexate toxicity.
PralatrexateNSAIDs increase the risk of toxicity due to impairment of renal clearance of pralatrexate thus increasing exposure. Monitor for adverse effects or adjust dose of pralatrexate.
TamoxifenFlurbiprofen may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Flurbiprofen is initiated, discontinued or dose changed.
TelmisartanConcomitant use of Telmisartan and Flurbiprofen may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
TimololThe NSAID, Flurbiprofen, may antagonize the antihypertensive effect of Timolol.
TolbutamideFlurbiprofen, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Flurbiprofen is initiated, discontinued or dose changed.
TorasemideFlurbiprofen, a strong CYP2C9 inhibitor, may increase the serum concentration of Torasemide, a CYP2C9 substrate, by decreasing Torasemide metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Torasemide if Flurbiprofen is initiated, discontinued or dose changed.
TrandolaprilThe NSAID, Flurbiprofen, may reduce the antihypertensive effect of Trandolapril. Consider alternate therapy or monitor for changes in Trandolapril efficacy if Flurbiprofen is initiated, discontinued or dose changed.
TreprostinilThe prostacyclin analogue, Treprostinil, may increase the risk of bleeding when combined with the NSAID, Flurbiprofen. Monitor for increased bleeding during concomitant thearpy.
TrimethoprimThe strong CYP2C9 inhibitor, Flurbiprofen, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Flurbiprofen is initiated, discontinued or dose changed.
VoriconazoleFlurbiprofen, a strong CYP2C9 inhibitor, may increase the serum concentration of voriconazole by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of voriconazole if flurbiprofen is initiated, discontinued or dose changed.
WarfarinFlurbiprofen, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. The antiplatelet effect of flurbiprofen may also increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if flurbiprofen is initiated, discontinued or dose changed.
Food Interactions
  • Avoid alcohol.
  • Take with food to reduce gastric irritation.

Targets

1. Prostaglandin G/H synthase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 1 P23219 Details

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
  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
  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
  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
  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
  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
  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

2. Prostaglandin G/H synthase 2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 2 P35354 Details

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
  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
  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
  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
  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
  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
  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

Enzymes

1. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

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
  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
  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. Epub 2009 Nov 24. Pubmed
  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

2. UDP-glucuronosyltransferase 2B7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 2B7 P16662 Details

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

3. UDP-glucuronosyltransferase 1-1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-1 P22309 Details

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

4. UDP-glucuronosyltransferase 1-3

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-3 P35503 Details

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

5. UDP-glucuronosyltransferase 1-9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-9 O60656 Details

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

6. UDP-glucuronosyltransferase 2B4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 2B4 P06133 Details

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

Carriers

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: no

Actions: other/unknown

Components

Name UniProt ID Details
Serum albumin P02768 Details

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
  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

Transporters

1. Multidrug resistance-associated protein 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance-associated protein 4 O15439 Details

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

2. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

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
  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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11