Identification

Name
Antrafenine
Accession Number
DB01419
Type
Small Molecule
Groups
Approved
Description

Antrafenine is a piperazine derivative drug that acts as an analgesic and anti-inflammatory drug with similar efficacy to naproxen. It is not widely used as it has largely been replaced by newer drugs.

Structure
Thumb
Synonyms
Not Available
International/Other Brands
Stakane
Categories
UNII
21FS93Y6OE
CAS number
55300-29-3
Weight
Average: 588.5435
Monoisotopic: 588.195995326
Chemical Formula
C30H26F6N4O2
InChI Key
NWGGKKGAFZIVBJ-UHFFFAOYSA-N
InChI
InChI=1S/C30H26F6N4O2/c31-29(32,33)20-4-3-5-22(18-20)40-14-12-39(13-15-40)16-17-42-28(41)24-6-1-2-7-25(24)38-26-10-11-37-27-19-21(30(34,35)36)8-9-23(26)27/h1-11,18-19H,12-17H2,(H,37,38)
IUPAC Name
2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl 2-{[7-(trifluoromethyl)quinolin-4-yl]amino}benzoate
SMILES
FC(F)(F)C1=CC(=CC=C1)N1CCN(CCOC(=O)C2=CC=CC=C2NC2=C3C=CC(=CC3=NC=C2)C(F)(F)F)CC1

Pharmacology

Indication

Antrafenine is used as an anti-inflammatory and analgesic agent for the relief of mild to moderate pain.

Pharmacodynamics

Its mode of action is not fully understood; however, its ability to inhibit prostaglandin synthesis may be involved in the anti-inflammatory effect.

Mechanism of action

Antrafenine is believed to be associated with the inhibition of cyclooxygenase activity. Two unique cyclooxygenases have been described in mammals. The constitutive cyclooxygenase, COX-1, synthesizes prostaglandins necessary for normal gastrointestinal and renal function. The inducible cyclooxygenase, COX-2, generates prostaglandins involved in inflammation. Inhibition of COX-1 is thought to be associated with gastrointestinal and renal toxicity while inhibition of COX-2 provides anti-inflammatory activity.

TargetActionsOrganism
UProstaglandin G/H synthase 1
inhibitor
Human
UProstaglandin G/H synthase 2
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Antrafenine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when 16-Bromoepiandrosterone is combined with Antrafenine.Investigational
19-norandrostenedioneThe risk or severity of adverse effects can be increased when 19-norandrostenedione is combined with Antrafenine.Experimental, Illicit
5-androstenedioneThe risk or severity of adverse effects can be increased when 5-androstenedione is combined with Antrafenine.Experimental, Illicit
AcenocoumarolAntrafenine may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
AlaproclateAlaproclate may increase the antiplatelet activities of Antrafenine.Experimental
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Antrafenine.Approved
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Antrafenine.Experimental, Investigational
AmcinonideThe risk or severity of adverse effects can be increased when Amcinonide is combined with Antrafenine.Approved
AndrostenedioneThe risk or severity of adverse effects can be increased when Androstenedione is combined with Antrafenine.Experimental, Illicit
AnecortaveThe risk or severity of adverse effects can be increased when Anecortave is combined with Antrafenine.Investigational
anecortave acetateThe risk or severity of adverse effects can be increased when anecortave acetate is combined with Antrafenine.Investigational
AtamestaneThe risk or severity of adverse effects can be increased when Atamestane is combined with Antrafenine.Investigational
BazedoxifeneAntrafenine may increase the thrombogenic activities of Bazedoxifene.Approved, Investigational
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Antrafenine.Approved, Investigational
BetamethasoneThe risk or severity of adverse effects can be increased when Betamethasone is combined with Antrafenine.Approved, Vet Approved
BudesonideThe risk or severity of adverse effects can be increased when Budesonide is combined with Antrafenine.Approved
ChlorotrianiseneAntrafenine may increase the thrombogenic activities of Chlorotrianisene.Investigational, Withdrawn
CiclesonideThe risk or severity of adverse effects can be increased when Ciclesonide is combined with Antrafenine.Approved, Investigational
CitalopramCitalopram may increase the antiplatelet activities of Antrafenine.Approved
ClobetasolThe risk or severity of adverse effects can be increased when Clobetasol is combined with Antrafenine.Approved, Investigational
Clobetasol propionateThe risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Antrafenine.Approved
ClobetasoneThe risk or severity of adverse effects can be increased when Clobetasone is combined with Antrafenine.Approved
ClocortoloneThe risk or severity of adverse effects can be increased when Clocortolone is combined with Antrafenine.Approved
ClorindioneAntrafenine may increase the anticoagulant activities of Clorindione.Experimental
Conjugated estrogensAntrafenine may increase the thrombogenic activities of Conjugated estrogens.Approved
Cortexolone 17α-propionateThe risk or severity of adverse effects can be increased when Cortexolone 17α-propionate is combined with Antrafenine.Investigational
CorticosteroneThe risk or severity of adverse effects can be increased when Corticosterone is combined with Antrafenine.Experimental
Cortisone acetateThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Antrafenine.Approved, Investigational
DaidzeinAntrafenine may increase the thrombogenic activities of Daidzein.Experimental
DapoxetineDapoxetine may increase the antiplatelet activities of Antrafenine.Investigational
DeflazacortThe risk or severity of adverse effects can be increased when Deflazacort is combined with Antrafenine.Approved, Investigational
DesonideThe risk or severity of adverse effects can be increased when Desonide is combined with Antrafenine.Approved, Investigational
DesoximetasoneThe risk or severity of adverse effects can be increased when Desoximetasone is combined with Antrafenine.Approved
Desoxycorticosterone acetateThe risk or severity of adverse effects can be increased when Desoxycorticosterone acetate is combined with Antrafenine.Approved
Desoxycorticosterone PivalateThe risk or severity of adverse effects can be increased when Desoxycorticosterone Pivalate is combined with Antrafenine.Experimental, Vet Approved
DesvenlafaxineDesvenlafaxine may increase the antiplatelet activities of Antrafenine.Approved, Investigational
DexamethasoneThe risk or severity of adverse effects can be increased when Dexamethasone is combined with Antrafenine.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe risk or severity of adverse effects can be increased when Dexamethasone isonicotinate is combined with Antrafenine.Vet Approved
DicoumarolAntrafenine may increase the anticoagulant activities of Dicoumarol.Approved
DienestrolAntrafenine may increase the thrombogenic activities of Dienestrol.Approved, Investigational
DiethylstilbestrolAntrafenine may increase the thrombogenic activities of Diethylstilbestrol.Approved, Investigational
DiflorasoneThe risk or severity of adverse effects can be increased when Diflorasone is combined with Antrafenine.Approved
DifluocortoloneThe risk or severity of adverse effects can be increased when Difluocortolone is combined with Antrafenine.Approved, Investigational, Withdrawn
DifluprednateThe risk or severity of adverse effects can be increased when Difluprednate is combined with Antrafenine.Approved
DiphenadioneAntrafenine may increase the anticoagulant activities of Diphenadione.Experimental
DuloxetineDuloxetine may increase the antiplatelet activities of Antrafenine.Approved
EpimestrolAntrafenine may increase the thrombogenic activities of Epimestrol.Experimental
EquileninThe risk or severity of adverse effects can be increased when Equilenin is combined with Antrafenine.Experimental
EquilinThe risk or severity of adverse effects can be increased when Equilin is combined with Antrafenine.Approved
EquolAntrafenine may increase the thrombogenic activities of Equol.Investigational
EscitalopramEscitalopram may increase the antiplatelet activities of Antrafenine.Approved, Investigational
EstradiolAntrafenine may increase the thrombogenic activities of Estradiol.Approved, Investigational, Vet Approved
Estradiol acetateAntrafenine may increase the thrombogenic activities of Estradiol acetate.Approved, Investigational, Vet Approved
Estradiol cypionateAntrafenine may increase the thrombogenic activities of Estradiol cypionate.Approved, Investigational, Vet Approved
Estradiol valerateAntrafenine may increase the thrombogenic activities of Estradiol valerate.Approved, Investigational, Vet Approved
EstriolAntrafenine may increase the thrombogenic activities of Estriol.Approved, Investigational, Vet Approved
Estrogens, esterifiedAntrafenine may increase the thrombogenic activities of Estrogens, esterified.Approved
EstroneAntrafenine may increase the thrombogenic activities of Estrone.Approved
Estrone sulfateThe risk or severity of adverse effects can be increased when Estrone sulfate is combined with Antrafenine.Approved
Ethinyl EstradiolAntrafenine may increase the thrombogenic activities of Ethinyl Estradiol.Approved
Ethyl biscoumacetateAntrafenine may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtoperidoneEtoperidone may increase the antiplatelet activities of Antrafenine.Withdrawn
FluasteroneThe risk or severity of adverse effects can be increased when Fluasterone is combined with Antrafenine.Investigational
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Antrafenine.Approved, Investigational
FluindioneAntrafenine may increase the anticoagulant activities of Fluindione.Approved, Investigational
FlumethasoneThe risk or severity of adverse effects can be increased when Flumethasone is combined with Antrafenine.Approved, Vet Approved
FlunisolideThe risk or severity of adverse effects can be increased when Flunisolide is combined with Antrafenine.Approved, Investigational
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Fluocinolone Acetonide is combined with Antrafenine.Approved, Investigational, Vet Approved
FluocinonideThe risk or severity of adverse effects can be increased when Fluocinonide is combined with Antrafenine.Approved, Investigational
FluocortoloneThe risk or severity of adverse effects can be increased when Fluocortolone is combined with Antrafenine.Approved, Withdrawn
FluorometholoneThe risk or severity of adverse effects can be increased when Fluorometholone is combined with Antrafenine.Approved, Investigational
FluoxetineFluoxetine may increase the antiplatelet activities of Antrafenine.Approved, Vet Approved
FluprednideneThe risk or severity of adverse effects can be increased when Fluprednidene is combined with Antrafenine.Approved, Withdrawn
FluprednisoloneThe risk or severity of adverse effects can be increased when Fluprednisolone is combined with Antrafenine.Approved
FlurandrenolideThe risk or severity of adverse effects can be increased when Flurandrenolide is combined with Antrafenine.Approved
FluticasoneThe risk or severity of adverse effects can be increased when Fluticasone is combined with Antrafenine.Approved, Experimental, Investigational
Fluticasone furoateThe risk or severity of adverse effects can be increased when Fluticasone furoate is combined with Antrafenine.Approved
Fluticasone propionateThe risk or severity of adverse effects can be increased when Fluticasone propionate is combined with Antrafenine.Approved
FluvoxamineFluvoxamine may increase the antiplatelet activities of Antrafenine.Approved, Investigational
FormestaneThe risk or severity of adverse effects can be increased when Formestane is combined with Antrafenine.Approved, Investigational, Withdrawn
GenisteinAntrafenine may increase the thrombogenic activities of Genistein.Investigational
HalcinonideThe risk or severity of adverse effects can be increased when Halcinonide is combined with Antrafenine.Approved, Investigational, Withdrawn
HE3286The risk or severity of adverse effects can be increased when HE3286 is combined with Antrafenine.Investigational
HexestrolAntrafenine may increase the thrombogenic activities of Hexestrol.Withdrawn
HydrocortisoneThe risk or severity of adverse effects can be increased when Hydrocortisone is combined with Antrafenine.Approved, Vet Approved
IndalpineIndalpine may increase the antiplatelet activities of Antrafenine.Investigational, Withdrawn
IstaroximeThe risk or severity of adverse effects can be increased when Istaroxime is combined with Antrafenine.Investigational
LevomilnacipranLevomilnacipran may increase the antiplatelet activities of Antrafenine.Approved, Investigational
LoteprednolThe risk or severity of adverse effects can be increased when Loteprednol is combined with Antrafenine.Approved
ME-609The risk or severity of adverse effects can be increased when ME-609 is combined with Antrafenine.Investigational
MedrysoneThe risk or severity of adverse effects can be increased when Medrysone is combined with Antrafenine.Approved
MelengestrolThe risk or severity of adverse effects can be increased when Melengestrol is combined with Antrafenine.Vet Approved
MestranolAntrafenine may increase the thrombogenic activities of Mestranol.Approved
MethallenestrilAntrafenine may increase the thrombogenic activities of Methallenestril.Experimental
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Antrafenine.Approved, Vet Approved
MilnacipranMilnacipran may increase the antiplatelet activities of Antrafenine.Approved, Investigational
MometasoneThe risk or severity of adverse effects can be increased when Mometasone is combined with Antrafenine.Approved, Vet Approved
MoxestrolAntrafenine may increase the thrombogenic activities of Moxestrol.Experimental
NCX 1022The risk or severity of adverse effects can be increased when NCX 1022 is combined with Antrafenine.Investigational
NefazodoneNefazodone may increase the antiplatelet activities of Antrafenine.Approved, Withdrawn
Oleoyl-estroneThe risk or severity of adverse effects can be increased when Oleoyl-estrone is combined with Antrafenine.Investigational
ParamethasoneThe risk or severity of adverse effects can be increased when Paramethasone is combined with Antrafenine.Approved
ParoxetineParoxetine may increase the antiplatelet activities of Antrafenine.Approved, Investigational
PhenindioneAntrafenine may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonAntrafenine may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
Polyestradiol phosphateAntrafenine may increase the thrombogenic activities of Polyestradiol phosphate.Approved
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Antrafenine.Approved, Investigational, Nutraceutical
Prasterone sulfateThe risk or severity of adverse effects can be increased when Prasterone sulfate is combined with Antrafenine.Investigational
PrednicarbateThe risk or severity of adverse effects can be increased when Prednicarbate is combined with Antrafenine.Approved, Investigational
PrednisoloneThe risk or severity of adverse effects can be increased when Prednisolone is combined with Antrafenine.Approved, Vet Approved
PrednisoneThe risk or severity of adverse effects can be increased when Prednisone is combined with Antrafenine.Approved, Vet Approved
PregnenoloneThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Antrafenine.Approved, Experimental, Investigational
PromestrieneAntrafenine may increase the thrombogenic activities of Promestriene.Investigational
QuinestrolAntrafenine may increase the thrombogenic activities of Quinestrol.Approved
RimexoloneThe risk or severity of adverse effects can be increased when Rimexolone is combined with Antrafenine.Approved
SecoisolariciresinolAntrafenine may increase the thrombogenic activities of Secoisolariciresinol.Investigational
SertralineSertraline may increase the antiplatelet activities of Antrafenine.Approved
Synthetic Conjugated Estrogens, AAntrafenine may increase the thrombogenic activities of Synthetic Conjugated Estrogens, A.Approved
Synthetic Conjugated Estrogens, BAntrafenine may increase the thrombogenic activities of Synthetic Conjugated Estrogens, B.Approved
TiboloneAntrafenine may increase the thrombogenic activities of Tibolone.Approved, Investigational
TioclomarolAntrafenine may increase the anticoagulant activities of Tioclomarol.Experimental
TixocortolThe risk or severity of adverse effects can be increased when Tixocortol is combined with Antrafenine.Approved, Withdrawn
TriamcinoloneThe risk or severity of adverse effects can be increased when Triamcinolone is combined with Antrafenine.Approved, Vet Approved
UlobetasolThe risk or severity of adverse effects can be increased when Ulobetasol is combined with Antrafenine.Approved
VenlafaxineVenlafaxine may increase the antiplatelet activities of Antrafenine.Approved
WarfarinAntrafenine may increase the anticoagulant activities of Warfarin.Approved
ZeranolAntrafenine may increase the thrombogenic activities of Zeranol.Vet Approved
ZimelidineZimelidine may increase the antiplatelet activities of Antrafenine.Withdrawn
Food Interactions
Not Available

References

Synthesis Reference

Giudicelli, D.P.R.L., Najer, H., Manory, P.M.J. and Dumas, A.P.F.; January 27,1976; assigned to Synthelabo US. Patent 3,935,229.

General References
Not Available
External Links
Human Metabolome Database
HMDB0015488
PubChem Compound
68723
PubChem Substance
46507354
ChemSpider
61973
ChEBI
135841
ChEMBL
CHEMBL345524
PharmGKB
PA164784000
Wikipedia
Antrafenine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)88-90Giudicelli, D.P.R.L., Najer, H., Manory, P.M.J. and Dumas, A.P.F.; January 27,1976; assigned to Synthelabo US. Patent 3,935,229.
Predicted Properties
PropertyValueSource
Water Solubility0.00284 mg/mLALOGPS
logP6.3ALOGPS
logP8.39ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)16.69ChemAxon
pKa (Strongest Basic)7.04ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.7 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity147.01 m3·mol-1ChemAxon
Polarizability55.48 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9969
Blood Brain Barrier+0.9132
Caco-2 permeable-0.5721
P-glycoprotein substrateSubstrate0.5792
P-glycoprotein inhibitor IInhibitor0.8917
P-glycoprotein inhibitor IIInhibitor0.9464
Renal organic cation transporterNon-inhibitor0.5702
CYP450 2C9 substrateNon-substrate0.8703
CYP450 2D6 substrateNon-substrate0.6674
CYP450 3A4 substrateNon-substrate0.5172
CYP450 1A2 substrateInhibitor0.7622
CYP450 2C9 inhibitorInhibitor0.7438
CYP450 2D6 inhibitorNon-inhibitor0.7155
CYP450 2C19 inhibitorInhibitor0.7394
CYP450 3A4 inhibitorInhibitor0.6383
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9305
Ames testNon AMES toxic0.6823
CarcinogenicityNon-carcinogens0.8812
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7506 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8133
hERG inhibition (predictor II)Inhibitor0.8583
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazinanes
Sub Class
Piperazines
Direct Parent
Phenylpiperazines
Alternative Parents
N-arylpiperazines / 4-aminoquinolines / Aminobenzoic acids and derivatives / Benzoic acid esters / Trifluoromethylbenzenes / Aniline and substituted anilines / Dialkylarylamines / Benzoyl derivatives / Aminopyridines and derivatives / N-alkylpiperazines
show 14 more
Substituents
Phenylpiperazine / N-arylpiperazine / Aminoquinoline / 4-aminoquinoline / Aminobenzoic acid or derivatives / Trifluoromethylbenzene / Benzoate ester / Quinoline / Benzoic acid or derivatives / Benzoyl
show 31 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

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. Hassan SM, Olivesi A, Fish A, Turner P: A comparison of antrafenine and aspirin on platelet aggregation and frusemide-induced diuresis. Postgrad Med J. 1982 Jan;58(675):17-9. [PubMed:7088753]
  2. Berry H, Coquelin JP, Gordon A, Seymour D: Antrafenine, naproxen and placebo in osteoarthritis: a comparative study. Br J Rheumatol. 1983 May;22(2):89-94. [PubMed:6342700]
  3. James MJ, Cook-Johnson RJ, Cleland LG: Selective COX-2 inhibitors, eicosanoid synthesis and clinical outcomes: a case study of system failure. Lipids. 2007 Sep;42(9):779-85. Epub 2007 Jun 2. [PubMed:17541796]
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. 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. Albertini R, Aimbire F, Villaverde AB, Silva JA Jr, Costa MS: COX-2 mRNA expression decreases in the subplantar muscle of rat paw subjected to carrageenan-induced inflammation after low level laser therapy. Inflamm Res. 2007 Jun;56(6):228-9. [PubMed:17607546]
  2. Dhir A, Naidu PS, Kulkarni SK: Neuroprotective effect of nimesulide, a preferential COX-2 inhibitor, against pentylenetetrazol (PTZ)-induced chemical kindling and associated biochemical parameters in mice. Seizure. 2007 Dec;16(8):691-7. Epub 2007 Jul 2. [PubMed:17604186]
  3. Kumar P, Padi SS, Naidu PS, Kumar A: Cyclooxygenase inhibition attenuates 3-nitropropionic acid-induced neurotoxicity in rats: possible antioxidant mechanisms. Fundam Clin Pharmacol. 2007 Jun;21(3):297-306. [PubMed:17521299]
  4. White WB: Cardiovascular effects of the selective cyclooxygenase-2 inhibitors. Subcell Biochem. 2007;42:145-58. [PubMed:17612049]
  5. Hassan-Alin M, Naesdal J, Nilsson-Pieschl C, Langstrom G, Andersson T: Lack of Pharmacokinetic Interaction between Esomeprazole and the Nonsteroidal Anti-Inflammatory Drugs Naproxen and Rofecoxib in Healthy Subjects. Clin Drug Investig. 2005;25(11):731-40. [PubMed:17532719]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on July 24, 2007 02:34 / Updated on June 02, 2018 06:48