Ketoprofen - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (3)Enzymes (2)Carriers (1)Transporters (6)

Targets (3)Enzymes (2)Carriers (1)Transporters (6)Biointeractions (11)

Identification

Name

Ketoprofen

Accession Number

DB01009 (APRD01059, DB05823, DB05335)

Type

Small Molecule

Groups

Approved, Vet Approved

Description

Ketoprofen, a propionic acid derivative, is a nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

2-(3-Benzoylphenyl)propionic acid

3-Benzoyl-alpha-methylbenzeneacetic acid

3-Benzoyl-α-methylbenzeneacetic acid

3-Benzoylhydratropic acid

Ketoprofen

L'Acide (benzoyl-3-phenyl)-2-propionique

m-Benzoylhydratropic acid

Orudis (tn)

External IDs

Not Available

Product Ingredients

Ingredient	UNII	CAS	InChI Key	Details
Ketoprofen sodium	5R10M39KS7	57495-14-4	OAPDLBHLMVYMCW-UHFFFAOYSA-M	Details

Approved Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ketoprofen	Capsule	50 mg	Oral	Aa Pharma Inc	1989-12-31	Not applicable	Canada
Ketoprofen SR	Tablet, extended release	200 mg	Oral	Aa Pharma Inc	1995-12-31	Not applicable	Canada
Ketoprofen Suppositories	Suppository	50 mg	Rectal	Pharmel Inc	Not applicable	Not applicable	Canada
Ketoprofen Suppositories	Suppository	100 mg	Rectal	Pharmel Inc	1998-06-04	Not applicable	Canada
Ketoprofen-E	Tablet, delayed release	100 mg	Oral	Aa Pharma Inc	1989-12-31	Not applicable	Canada
Ketoprofen-E	Tablet, delayed release	50 mg	Oral	Aa Pharma Inc	1989-12-31	Not applicable	Canada
Ketoprofen-E Ect 100mg	Tablet, delayed release	100 mg	Oral	Pro Doc Limitee	1996-12-31	2009-07-23	Canada
Ketoprofen-E Ect 50mg	Tablet, delayed release	50 mg	Oral	Pro Doc Limitee	1995-12-31	2009-07-23	Canada
Ketoprofen-SR - Srt 200mg	Tablet, extended release	200 mg	Oral	Pro Doc Limitee	1997-09-18	2009-07-23	Canada
Novo-keto Suppositories 100mg	Suppository	100 mg	Rectal	Novopharm Limited	1996-12-31	2005-08-10	Canada
Novo-keto-EC Tab 100mg	Tablet, delayed release	100 mg	Oral	Novopharm Limited	1992-12-31	2005-08-10	Canada
Novo-keto-EC Tab 50mg	Tablet, delayed release	50 mg	Oral	Novopharm Limited	1992-12-31	2005-08-10	Canada
Nu-ketoprofen Cap 50mg	Capsule	50 mg	Oral	Nu Pharm Inc	1993-12-31	2012-09-04	Canada
Nu-ketoprofen-E Ect 100mg	Tablet, delayed release	100 mg	Oral	Nu Pharm Inc	1994-12-31	2012-09-04	Canada
Nu-ketoprofen-E Ect 50mg	Tablet, delayed release	50 mg	Oral	Nu Pharm Inc	1994-12-31	2012-09-04	Canada
Orafen - Sup RT 100mg	Suppository	100 mg	Rectal	Technilab Pharma Inc.	1996-12-31	2004-08-03	Canada
Orudis 100	Suppository	100 mg	Rectal	Aventis Pharma Ltd.	1979-12-31	2003-07-22	Canada
Orudis 50	Suppository	50 mg	Rectal	Aventis Pharma Ltd.	1991-12-31	2003-07-22	Canada
Orudis Cap 50mg	Capsule	50 mg	Oral	Aventis Pharma Ltd.	1979-12-31	2004-07-30	Canada
Orudis E-100	Tablet, delayed release	100 mg	Oral	Aventis Pharma Ltd.	1987-12-31	2003-07-22	Canada
Orudis E-50	Tablet, delayed release	50 mg	Oral	Aventis Pharma Ltd.	1983-12-31	2004-07-30	Canada
Orudis SR-200	Tablet, extended release	200 mg	Oral	Aventis Pharma Ltd.	1988-12-31	2005-08-01	Canada
Oruvail 150	Capsule, extended release	150 mg	Oral	Aventis Pharma Ltd.	1991-12-31	2003-07-22	Canada
Oruvail 200	Capsule, extended release	200 mg	Oral	Aventis Pharma Ltd.	1991-12-31	2003-07-22	Canada
PMS-ketoprofen	Suppository	50 mg	Rectal	Pharmascience Inc	1995-12-31	Not applicable	Canada
PMS-ketoprofen	Suppository	100 mg	Rectal	Pharmascience Inc	1993-12-31	Not applicable	Canada
PMS-ketoprofen Capsules	Capsule	50 mg	Oral	Pharmascience Inc	1995-12-31	Not applicable	Canada
PMS-ketoprofen E-100 - Ect	Tablet, delayed release	100 mg	Oral	Pharmascience Inc	1995-12-31	Not applicable	Canada
PMS-ketoprofen E-50 - Ect 50mg	Tablet, delayed release	50 mg	Oral	Pharmascience Inc	1995-12-31	Not applicable	Canada
Rhodis	Suppository	100 mg	Rectal	Sanofi Aventis	1988-12-31	2006-07-28	Canada
Rhodis Cap 50mg	Capsule	50 mg	Oral	Rhodiapharm Inc	1988-12-31	2005-08-01	Canada
Rhodis EC	Tablet, delayed release	50 mg	Oral	Sanofi Aventis	1988-12-31	2006-07-28	Canada
Rhodis EC	Tablet, delayed release	100 mg	Oral	Sanofi Aventis	1988-12-31	2007-01-11	Canada
Rhodis SR 200mg	Tablet, extended release	200 mg	Oral	Rhodiapharm Inc	1995-12-31	2005-08-01	Canada
Rhovail 150	Capsule, extended release	150 mg	Oral	Rhodiapharm Inc	1995-12-31	2005-08-01	Canada
Rhovail 200	Capsule, extended release	200 mg	Oral	Rhodiapharm Inc	1995-12-31	2005-08-01	Canada

Approved Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ketoprofen	Capsule	50 mg/1	Oral	Mylan Pharmaceuticals	1997-01-15	Not applicable	US
Ketoprofen	Capsule	50 mg/1	Oral	Pd Rx Pharmaceuticals, Inc.	1993-01-01	Not applicable	US
Ketoprofen	Capsule	75 mg/1	Oral	Rebel Distributors	2011-01-18	Not applicable	US
Ketoprofen	Capsule	75 mg/1	Oral	A S Medication Solutions	1993-01-01	2017-06-20	US
Ketoprofen	Capsule	75 mg/1	Oral	Nucare Pharmaceuticals, Inc.	1993-01-01	Not applicable	US
Ketoprofen	Capsule, extended release	200 mg/1	Oral	Physicians Total Care, Inc.	2009-06-23	Not applicable	US
Ketoprofen	Capsule	75 mg/1	Oral	Preferreed Pharmaceuticals Inc.	2011-01-18	Not applicable	US
Ketoprofen	Capsule	50 mg/1	Oral	Stat Rx USA	2011-01-18	Not applicable	US
Ketoprofen	Capsule	50 mg/1	Oral	Teva	1993-01-01	Not applicable	US
Ketoprofen	Capsule	50 mg/1	Oral	H.J. Harkins Company	2011-01-18	Not applicable	US
Ketoprofen	Capsule	75 mg/1	Oral	Rebel Distributors	2010-04-20	Not applicable	US
Ketoprofen	Capsule	50 mg/1	Oral	bryant ranch prepack	1993-01-01	Not applicable	US
Ketoprofen	Capsule	75 mg/1	Oral	Proficient Rx LP	1993-01-01	Not applicable	US
Ketoprofen	Capsule	50 mg/1	Oral	Preferreed Pharmaceuticals Inc.	2016-05-31	Not applicable	US
Ketoprofen	Capsule	75 mg/1	Oral	Mylan Pharmaceuticals	1997-01-15	Not applicable	US
Ketoprofen	Capsule	50 mg/1	Oral	A S Medication Solutions	1993-01-01	2017-06-20	US
Ketoprofen	Capsule	50 mg/1	Oral	Av Kare, Inc.	2013-07-08	2016-03-11	US
Ketoprofen	Capsule	50 mg/1	Oral	Physicians Total Care, Inc.	1997-02-14	Not applicable	US
Ketoprofen	Capsule	75 mg/1	Oral	Teva	1993-01-01	Not applicable	US
Ketoprofen	Capsule	75 mg/1	Oral	Pd Rx Pharmaceuticals, Inc.	2011-01-18	Not applicable	US
Ketoprofen	Capsule	75 mg/1	Oral	Stat Rx USA	2011-01-18	Not applicable	US
Ketoprofen	Capsule	75 mg/1	Oral	Aidarex Pharmaceuticals LLC	1993-01-01	Not applicable	US
Ketoprofen	Tablet	75 mg/1	Oral	Red Pharm Drug, Inc.	2011-01-18	Not applicable	US
Ketoprofen	Capsule	50 mg/1	Oral	Aidarex Pharmaceuticals LLC	1993-01-01	Not applicable	US
Ketoprofen	Capsule, extended release	200 mg/1	Oral	Mylan Pharmaceuticals	2003-09-04	Not applicable	US
Ketoprofen	Capsule	50 mg/1	Oral	Avera Mc Kennan Hospital	2015-10-28	Not applicable	US
Ketoprofen	Capsule	75 mg/1	Oral	Av Kare, Inc.	2013-07-08	2016-03-11	US
Ketoprofen	Capsule	75 mg/1	Oral	Physicians Total Care, Inc.	2005-08-15	Not applicable	US
Ketoprofen	Capsule	75 mg/1	Oral	bryant ranch prepack	1993-01-01	Not applicable	US
Ketoprofen	Capsule	50 mg/1	Oral	Pd Rx Pharmaceuticals, Inc.	2010-04-20	Not applicable	US
Ketoprofen	Capsule	50 mg/1	Oral	Rebel Distributors	2010-04-20	Not applicable	US

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Vopac - Ketoprofen, Lidocaine Hydrochloride Pac	Kit			Sircle Laboratories, Llc	2015-03-01	Not applicable	US

International Brands

Name	Company
Actron	Not Available
Alrheumun	Teofarma
Capisten	Kissei
Epatec	Zeria Shinyaku
Fastum	Menarini
Menamin	Daiko Seiyaku
Orudis	Abbott
Orudis KT	Sanofi
Orugesic	Sanofi
Oruvail	Wyeth
Oscorel	Sanofi
Profenid	Sanofi
Toprec	Sanofi

Brand mixtures

Not Available

Categories

UNII

90Y4QC304K

CAS number

22071-15-4

Weight

Average: 254.2806
Monoisotopic: 254.094294314

Chemical Formula

C₁₆H₁₄O₃

InChI Key

DKYWVDODHFEZIM-UHFFFAOYSA-N

InChI

InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)

IUPAC Name

2-(3-benzoylphenyl)propanoic acid

SMILES

CC(C(O)=O)C1=CC(=CC=C1)C(=O)C1=CC=CC=C1

Pharmacology

Indication

For symptomatic treatment of acute and chronic rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, primary dysmenorrhea and mild to moderate pain associated with musculotendinous trauma (sprains and strains), postoperative (including dental surgery) or postpartum pain.

Structured Indications

Pharmacodynamics

Ketoprofen is a nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties. Ketoprofen has pharmacologic actions similar to those of other prototypical NSAIDs, which inhibit prostaglandin synthesis. Ketoprofen is used to treat rheumatoid arthritis, osteoarthritis, dysmenorrhea, and alleviate moderate pain.

Mechanism of action

The anti-inflammatory effects of ketoprofen are believed to be due to inhibition cylooxygenase-2 (COX-2), an enzyme involved in prostaglandin synthesis via the arachidonic acid pathway. This results in decreased levels of prostaglandins that mediate pain, fever and inflammation. Ketoprofen is a non-specific cyclooxygenase inhibitor and inhibition of COX-1 is thought to confer some of its side effects, such as GI upset and ulceration. Ketoprofen is thought to have anti-bradykinin activity, as well as lysosomal membrane-stabilizing action. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Prostaglandin G/H synthase 1	Protein	unknown	inhibitor	Human	P23219	details
Prostaglandin G/H synthase 2	Protein	yes	inhibitor	Human	P35354	details
C-X-C chemokine receptor type 1	Protein	unknown	other	Human	P25024	details

Absorption

Ketoprofen is rapidly and well-absorbed orally, with peak plasma levels occurring within 0.5 to 2 hours.

Volume of distribution

Not Available

Protein binding

99% bound, primarily to albumin

Metabolism

Rapidly and extensively metabolized in the liver, primarily via conjugation to glucuronic acid. No active metabolites have been identified.

Substrate	Enzymes	Product
Ketoprofen	Not Available	Ketoprofen glucuronide	Details

Route of elimination

In a 24 hour period, approximately 80% of an administered dose of ketoprofen is excreted in the urine, primarily as the glucuronide metabolite.

Half life

Conventional capsules: 1.1-4 hours

Extended release capsules: 5.4 hours due to delayed absorption (intrinsic clearance is same as conventional capsules)

Clearance

Oral-dose cl=6.9 +/- 0.8 L/h [Ketoprofen Immediate-release capsules (4 × 50 mg)]
Oral-dose cl=6.8 +/- 1.8 L/h [Ketoprofen Extended-release capsules (1 × 200 mg)]
0.08 L/kg/h
0.7 L/kg/h [alcoholic cirrhosis patients]

Toxicity

LD₅₀=62.4 mg/kg (rat, oral).

Symptoms of overdose include drowsiness, vomiting and abdominal pain.

Side effects are usually mild and mainly involved the GI tract. Most common adverse GI effect is dyspepsia (11% of patients). May cause nausea, diarrhea, abdominal pain, constipation and flatulence in greater than 3% of patients.

Affected organisms

Humans and other mammals

Pathways

Pathway	Category	SMPDB ID
Ketoprofen Action Pathway	Drug action	SMP00085

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
16-Bromoepiandrosterone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with 16-Bromoepiandrosterone.	Investigational
19-norandrostenedione	The risk or severity of adverse effects can be increased when Ketoprofen is combined with 19-norandrostenedione.	Experimental, Illicit
5-androstenedione	The risk or severity of adverse effects can be increased when Ketoprofen is combined with 5-androstenedione.	Experimental, Illicit
Abciximab	Ketoprofen may increase the anticoagulant activities of Abciximab.	Approved
Abiraterone	The metabolism of Ketoprofen can be decreased when combined with Abiraterone.	Approved
Acebutolol	Ketoprofen may decrease the antihypertensive activities of Acebutolol.	Approved
Aceclofenac	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Aceclofenac.	Approved
Acenocoumarol	Ketoprofen may increase the anticoagulant activities of Acenocoumarol.	Approved
Acetylsalicylic acid	The risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Ketoprofen.	Approved, Vet Approved
Aclarubicin	Ketoprofen may decrease the excretion rate of Aclarubicin which could result in a higher serum level.	Investigational
Adapalene	The risk or severity of adverse effects can be increased when Adapalene is combined with Ketoprofen.	Approved
Alclometasone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Alclometasone.	Approved
Aldosterone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Aldosterone.	Experimental
Alendronic acid	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Alendronic acid.	Approved
Aliskiren	Ketoprofen may decrease the antihypertensive activities of Aliskiren.	Approved, Investigational
Alprenolol	Ketoprofen may decrease the antihypertensive activities of Alprenolol.	Approved, Withdrawn
Alprostadil	The therapeutic efficacy of Alprostadil can be decreased when used in combination with Ketoprofen.	Approved, Investigational
Amcinonide	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Amcinonide.	Approved
Amikacin	Ketoprofen may decrease the excretion rate of Amikacin which could result in a higher serum level.	Approved, Vet Approved
Amiloride	Ketoprofen may decrease the antihypertensive activities of Amiloride.	Approved
Amiodarone	The metabolism of Ketoprofen can be decreased when combined with Amiodarone.	Approved, Investigational
Amodiaquine	The serum concentration of Amodiaquine can be increased when it is combined with Ketoprofen.	Approved
Amrubicin	Ketoprofen may decrease the excretion rate of Amrubicin which could result in a higher serum level.	Approved, Investigational
Ancrod	Ketoprofen may increase the anticoagulant activities of Ancrod.	Investigational
Andrographolide	The risk or severity of adverse effects can be increased when Ketoprofen is combined with HMPL-004.	Investigational
Androstenedione	The risk or severity of adverse effects can be increased when Ketoprofen is combined with 4-Androstenedione.	Experimental, Illicit
Antipyrine	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Antipyrine.	Approved
Antithrombin III human	Ketoprofen may increase the anticoagulant activities of Antithrombin III human.	Approved
Apixaban	Ketoprofen may increase the anticoagulant activities of Apixaban.	Approved
Apramycin	Ketoprofen may decrease the excretion rate of Apramycin which could result in a higher serum level.	Experimental, Vet Approved
Apremilast	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Apremilast.	Approved, Investigational
Aprepitant	The metabolism of Ketoprofen can be increased when combined with Aprepitant.	Approved, Investigational
Arbekacin	Ketoprofen may decrease the excretion rate of Arbekacin which could result in a higher serum level.	Approved
Ardeparin	Ketoprofen may increase the anticoagulant activities of Ardeparin.	Approved, Withdrawn
Argatroban	Ketoprofen may increase the anticoagulant activities of Argatroban.	Approved, Investigational
Arotinolol	Ketoprofen may decrease the antihypertensive activities of Arotinolol.	Approved
Atenolol	Ketoprofen may decrease the antihypertensive activities of Atenolol.	Approved
Azapropazone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Azapropazone.	Withdrawn
Azelastine	The risk or severity of adverse effects can be increased when Azelastine is combined with Ketoprofen.	Approved
Azilsartan medoxomil	The risk or severity of adverse effects can be increased when Azilsartan medoxomil is combined with Ketoprofen.	Approved
Balsalazide	Ketoprofen may increase the nephrotoxic activities of Balsalazide.	Approved, Investigational
Becaplermin	Ketoprofen may increase the anticoagulant activities of Becaplermin.	Approved, Investigational
Beclomethasone dipropionate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Beclomethasone dipropionate.	Approved, Investigational
Befunolol	Ketoprofen may decrease the antihypertensive activities of Befunolol.	Experimental
Benazepril	The risk or severity of adverse effects can be increased when Benazepril is combined with Ketoprofen.	Approved, Investigational
Bendroflumethiazide	The therapeutic efficacy of Bendroflumethiazide can be decreased when used in combination with Ketoprofen.	Approved
Benoxaprofen	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Benoxaprofen.	Withdrawn
Beraprost	The therapeutic efficacy of Beraprost can be decreased when used in combination with Ketoprofen.	Investigational
Betamethasone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Betamethasone.	Approved, Vet Approved
Betaxolol	Ketoprofen may decrease the antihypertensive activities of Betaxolol.	Approved
Betulinic Acid	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Betulinic Acid.	Investigational
Bevantolol	Ketoprofen may decrease the antihypertensive activities of Bevantolol.	Approved
Bimatoprost	The therapeutic efficacy of Bimatoprost can be decreased when used in combination with Ketoprofen.	Approved, Investigational
Bisoprolol	Ketoprofen may decrease the antihypertensive activities of Bisoprolol.	Approved
Bivalirudin	Ketoprofen may increase the anticoagulant activities of Bivalirudin.	Approved, Investigational
Bopindolol	Ketoprofen may decrease the antihypertensive activities of Bopindolol.	Approved
Bromfenac	The risk or severity of adverse effects can be increased when Bromfenac is combined with Ketoprofen.	Approved
Budesonide	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Budesonide.	Approved
Bufuralol	Ketoprofen may decrease the antihypertensive activities of Bufuralol.	Experimental, Investigational
Bumetanide	Ketoprofen may decrease the diuretic activities of Bumetanide.	Approved
Bupranolol	Ketoprofen may decrease the antihypertensive activities of Bupranolol.	Approved
Candesartan	The risk or severity of adverse effects can be increased when Candesartan is combined with Ketoprofen.	Approved
Candoxatril	The risk or severity of adverse effects can be increased when Candoxatril is combined with Ketoprofen.	Experimental
Capecitabine	The metabolism of Ketoprofen can be decreased when combined with Capecitabine.	Approved, Investigational
Captopril	The risk or severity of adverse effects can be increased when Captopril is combined with Ketoprofen.	Approved
Carbamazepine	The metabolism of Ketoprofen can be increased when combined with Carbamazepine.	Approved, Investigational
Carboprost Tromethamine	The therapeutic efficacy of Carboprost Tromethamine can be decreased when used in combination with Ketoprofen.	Approved
Carprofen	The risk or severity of adverse effects can be increased when Carprofen is combined with Ketoprofen.	Approved, Vet Approved, Withdrawn
Carteolol	Ketoprofen may decrease the antihypertensive activities of Carteolol.	Approved
Carvedilol	Ketoprofen may decrease the antihypertensive activities of Carvedilol.	Approved, Investigational
Castanospermine	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Castanospermine.	Experimental
Celecoxib	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Celecoxib.	Approved, Investigational
Celiprolol	Ketoprofen may decrease the antihypertensive activities of Celiprolol.	Approved, Investigational
Ceritinib	The serum concentration of Ketoprofen can be increased when it is combined with Ceritinib.	Approved
Certoparin	Ketoprofen may increase the anticoagulant activities of Certoparin.	Approved
Chloroquine	The risk or severity of adverse effects can be increased when Chloroquine is combined with Ketoprofen.	Approved, Vet Approved
Chlorothiazide	The therapeutic efficacy of Chlorothiazide can be decreased when used in combination with Ketoprofen.	Approved, Vet Approved
Chlorthalidone	The therapeutic efficacy of Chlorthalidone can be decreased when used in combination with Ketoprofen.	Approved
Cholecalciferol	The metabolism of Ketoprofen can be decreased when combined with Cholecalciferol.	Approved, Nutraceutical
Cholestyramine	Cholestyramine can cause a decrease in the absorption of Ketoprofen resulting in a reduced serum concentration and potentially a decrease in efficacy.	Approved
Choline magnesium trisalicylate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Trisalicylate-choline.	Approved
Ciclesonide	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Ciclesonide.	Approved, Investigational
Cilazapril	The risk or severity of adverse effects can be increased when Cilazapril is combined with Ketoprofen.	Approved
Cinoxacin	Ketoprofen may increase the neuroexcitatory activities of Cinoxacin.	Approved, Withdrawn
Ciprofloxacin	Ketoprofen may increase the neuroexcitatory activities of Ciprofloxacin.	Approved, Investigational
Citric Acid	Ketoprofen may increase the anticoagulant activities of Citric Acid.	Nutraceutical, Vet Approved
Clobetasol propionate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Clobetasol propionate.	Approved
Clocortolone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Clocortolone.	Approved
Clodronic Acid	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Clodronate.	Approved, Investigational, Vet Approved
Clonixin	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Clonixin.	Approved
Clotrimazole	The metabolism of Ketoprofen can be decreased when combined with Clotrimazole.	Approved, Vet Approved
Colesevelam	Colesevelam can cause a decrease in the absorption of Ketoprofen resulting in a reduced serum concentration and potentially a decrease in efficacy.	Approved
Colestipol	Colestipol can cause a decrease in the absorption of Ketoprofen resulting in a reduced serum concentration and potentially a decrease in efficacy.	Approved
Cortisone acetate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Cortisone acetate.	Approved
Cyclosporine	Ketoprofen may increase the nephrotoxic activities of Cyclosporine.	Approved, Investigational, Vet Approved
Cyclosporine	The metabolism of Ketoprofen can be decreased when combined with Cyclosporine.	Approved, Investigational, Vet Approved
Dabigatran etexilate	Ketoprofen may increase the anticoagulant activities of Dabigatran etexilate.	Approved
Dabrafenib	The serum concentration of Ketoprofen can be decreased when it is combined with Dabrafenib.	Approved
Dalteparin	Ketoprofen may increase the anticoagulant activities of Dalteparin.	Approved
Daunorubicin	Ketoprofen may decrease the excretion rate of Daunorubicin which could result in a higher serum level.	Approved
Deferasirox	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Deferasirox.	Approved, Investigational
Delavirdine	The metabolism of Ketoprofen can be decreased when combined with Delavirdine.	Approved
Desirudin	Ketoprofen may increase the anticoagulant activities of Desirudin.	Approved
Desmopressin	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Desmopressin.	Approved
Desoximetasone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Desoximetasone.	Approved
Desoxycorticosterone Pivalate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Desoxycorticosterone Pivalate.	Experimental, Vet Approved
Dexamethasone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Dexamethasone.	Approved, Investigational, Vet Approved
Dexketoprofen	The risk or severity of adverse effects can be increased when Dexketoprofen is combined with Ketoprofen.	Approved
Dextran	Ketoprofen may increase the anticoagulant activities of Dextran.	Approved, Vet Approved
Dextran 40	Ketoprofen may increase the anticoagulant activities of Dextran 40.	Approved
Diclofenac	The risk or severity of adverse effects can be increased when Diclofenac is combined with Ketoprofen.	Approved, Vet Approved
Dicoumarol	Ketoprofen may increase the anticoagulant activities of Dicoumarol.	Approved
Diflorasone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Diflorasone.	Approved
Diflunisal	The risk or severity of adverse effects can be increased when Diflunisal is combined with Ketoprofen.	Approved
Difluocortolone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Difluocortolone.	Approved
Difluprednate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Difluprednate.	Approved
Digoxin	The serum concentration of Digoxin can be increased when it is combined with Ketoprofen.	Approved
Dinoprost Tromethamine	The therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Ketoprofen.	Approved, Vet Approved
Dinoprostone	The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Ketoprofen.	Approved
Doxorubicin	Ketoprofen may decrease the excretion rate of Doxorubicin which could result in a higher serum level.	Approved, Investigational
Drospirenone	Ketoprofen may increase the hyperkalemic activities of Drospirenone.	Approved
Droxicam	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Droxicam.	Approved
Edetic Acid	Ketoprofen may increase the anticoagulant activities of Edetic Acid.	Approved, Vet Approved
Edoxaban	Ketoprofen may increase the anticoagulant activities of Edoxaban.	Approved
Efavirenz	The metabolism of Ketoprofen can be decreased when combined with Efavirenz.	Approved, Investigational
Enalapril	The risk or severity of adverse effects can be increased when Enalapril is combined with Ketoprofen.	Approved, Vet Approved
Enalaprilat	The risk or severity of adverse effects can be increased when Enalaprilat is combined with Ketoprofen.	Approved
Enoxacin	Ketoprofen may increase the neuroexcitatory activities of Enoxacin.	Approved
Enoxaparin	Ketoprofen may increase the anticoagulant activities of Enoxaparin.	Approved
Epirizole	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Epirizole.	Approved
Epirubicin	Ketoprofen may decrease the excretion rate of Epirubicin which could result in a higher serum level.	Approved
Eplerenone	Ketoprofen may decrease the antihypertensive activities of Eplerenone.	Approved
Epoprostenol	The therapeutic efficacy of Epoprostenol can be decreased when used in combination with Ketoprofen.	Approved
Eprosartan	The risk or severity of adverse effects can be increased when Eprosartan is combined with Ketoprofen.	Approved
Equilenin	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Equilenin.	Experimental
Equilin	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Equilin.	Approved
Esmolol	Ketoprofen may decrease the antihypertensive activities of Esmolol.	Approved
Estrone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Estrone.	Approved
Estrone sulfate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Estrone sulfate.	Approved
Etacrynic acid	Ketoprofen may decrease the diuretic activities of Etacrynic acid.	Approved
Etanercept	The risk or severity of adverse effects can be increased when Etanercept is combined with Ketoprofen.	Approved, Investigational
Ethyl biscoumacetate	Ketoprofen may increase the anticoagulant activities of Ethyl biscoumacetate.	Withdrawn
Etidronic acid	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Etidronic acid.	Approved
Etodolac	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Etodolac.	Approved, Investigational, Vet Approved
Etofenamate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Etofenamate.	Approved
Etoricoxib	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Etoricoxib.	Approved, Investigational
Etravirine	The metabolism of Ketoprofen can be decreased when combined with Etravirine.	Approved
Fenbufen	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Fenbufen.	Approved
Fenoprofen	The risk or severity of adverse effects can be increased when Fenoprofen is combined with Ketoprofen.	Approved
Fleroxacin	Ketoprofen may increase the neuroexcitatory activities of Fleroxacin.	Approved
Floctafenine	The risk or severity of adverse effects can be increased when Floctafenine is combined with Ketoprofen.	Approved, Withdrawn
Floxuridine	The metabolism of Ketoprofen can be decreased when combined with Floxuridine.	Approved
Fluconazole	The metabolism of Ketoprofen can be decreased when combined with Fluconazole.	Approved
Fludrocortisone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Fludrocortisone.	Approved
Flumequine	Ketoprofen may increase the neuroexcitatory activities of Flumequine.	Withdrawn
Flumethasone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Flumethasone.	Approved, Vet Approved
Flunisolide	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Flunisolide.	Approved, Investigational
Fluocinolone Acetonide	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Fluocinolone Acetonide.	Approved, Investigational, Vet Approved
Fluocinonide	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Fluocinonide.	Approved, Investigational
Fluocortolone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Fluocortolone.	Approved, Withdrawn
Fluorometholone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Fluorometholone.	Approved
Fluorouracil	The metabolism of Ketoprofen can be decreased when combined with Fluorouracil.	Approved
Fluprednidene	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Fluprednidene.	Approved, Withdrawn
Flurandrenolide	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Flurandrenolide.	Approved
Flurbiprofen	The risk or severity of adverse effects can be increased when Flurbiprofen is combined with Ketoprofen.	Approved, Investigational
Fluticasone furoate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Fluticasone furoate.	Approved
Fluticasone Propionate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Fluticasone Propionate.	Approved
Fluvastatin	The metabolism of Ketoprofen can be decreased when combined with Fluvastatin.	Approved
Fluvoxamine	The metabolism of Ketoprofen can be decreased when combined with Fluvoxamine.	Approved, Investigational
Folic Acid	The therapeutic efficacy of Folic Acid can be decreased when used in combination with Ketoprofen.	Approved, Nutraceutical, Vet Approved
Fondaparinux sodium	Ketoprofen may increase the anticoagulant activities of Fondaparinux sodium.	Approved, Investigational
Forasartan	The risk or severity of adverse effects can be increased when Forasartan is combined with Ketoprofen.	Experimental
Formestane	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Formestane.	Approved, Investigational, Withdrawn
Fosinopril	The risk or severity of adverse effects can be increased when Fosinopril is combined with Ketoprofen.	Approved
Fosphenytoin	The metabolism of Ketoprofen can be increased when combined with Fosphenytoin.	Approved
Framycetin	Ketoprofen may decrease the excretion rate of Framycetin which could result in a higher serum level.	Approved
Furosemide	Ketoprofen may decrease the diuretic activities of Furosemide.	Approved, Vet Approved
Gabexate	Ketoprofen may increase the anticoagulant activities of Gabexate.	Investigational
Gatifloxacin	Ketoprofen may increase the neuroexcitatory activities of Gatifloxacin.	Approved, Investigational
Gemeprost	The therapeutic efficacy of Gemeprost can be decreased when used in combination with Ketoprofen.	Approved, Withdrawn
Gemfibrozil	The metabolism of Ketoprofen can be decreased when combined with Gemfibrozil.	Approved
Gemifloxacin	Ketoprofen may increase the neuroexcitatory activities of Gemifloxacin.	Approved, Investigational
Geneticin	Ketoprofen may decrease the excretion rate of Geneticin which could result in a higher serum level.	Experimental
Gentamicin	Ketoprofen may decrease the excretion rate of Gentamicin which could result in a higher serum level.	Approved, Vet Approved
GENTAMICIN C1A	Ketoprofen may decrease the excretion rate of GENTAMICIN C1A which could result in a higher serum level.	Experimental
Grepafloxacin	Ketoprofen may increase the neuroexcitatory activities of Grepafloxacin.	Withdrawn
Haloperidol	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Haloperidol.	Approved
HE3286	The risk or severity of adverse effects can be increased when Ketoprofen is combined with HE3286.	Investigational
Heparin	Ketoprofen may increase the anticoagulant activities of Heparin.	Approved, Investigational
Hydralazine	Ketoprofen may decrease the antihypertensive activities of Hydralazine.	Approved
Hydrochlorothiazide	The therapeutic efficacy of Hydrochlorothiazide can be decreased when used in combination with Ketoprofen.	Approved, Vet Approved
Hydrocortisone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Hydrocortisone.	Approved, Vet Approved
Hydroflumethiazide	The therapeutic efficacy of Hydroflumethiazide can be decreased when used in combination with Ketoprofen.	Approved
Ibandronate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Ibandronate.	Approved, Investigational
Ibuprofen	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Ibuprofen.	Approved
Ibuproxam	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Ibuproxam.	Withdrawn
Icatibant	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Icatibant.	Approved
Idarubicin	Ketoprofen may decrease the excretion rate of Idarubicin which could result in a higher serum level.	Approved
Iloprost	The therapeutic efficacy of Iloprost can be decreased when used in combination with Ketoprofen.	Approved, Investigational
Indapamide	The therapeutic efficacy of Indapamide can be decreased when used in combination with Ketoprofen.	Approved
Indenolol	Ketoprofen may decrease the antihypertensive activities of Indenolol.	Withdrawn
Indinavir	The metabolism of Ketoprofen can be decreased when combined with Indinavir.	Approved
Indomethacin	The risk or severity of adverse effects can be increased when Indomethacin is combined with Ketoprofen.	Approved, Investigational
Indoprofen	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Indoprofen.	Withdrawn
Irbesartan	The metabolism of Ketoprofen can be decreased when combined with Irbesartan.	Approved, Investigational
Isoxicam	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Isoxicam.	Withdrawn
Kanamycin	Ketoprofen may decrease the excretion rate of Kanamycin which could result in a higher serum level.	Approved, Vet Approved
Kebuzone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Kebuzone.	Experimental
Ketoconazole	The metabolism of Ketoprofen can be decreased when combined with Ketoconazole.	Approved, Investigational
Ketorolac	The risk or severity of adverse effects can be increased when Ketorolac is combined with Ketoprofen.	Approved
Labetalol	Ketoprofen may decrease the antihypertensive activities of Labetalol.	Approved
Latanoprost	The therapeutic efficacy of Latanoprost can be decreased when used in combination with Ketoprofen.	Approved, Investigational
Leflunomide	The metabolism of Ketoprofen can be decreased when combined with Leflunomide.	Approved, Investigational
Lepirudin	Ketoprofen may increase the anticoagulant activities of Lepirudin.	Approved
Levobunolol	Ketoprofen may decrease the antihypertensive activities of Levobunolol.	Approved
Levofloxacin	Ketoprofen may increase the neuroexcitatory activities of Levofloxacin.	Approved, Investigational
Limaprost	The therapeutic efficacy of Limaprost can be decreased when used in combination with Ketoprofen.	Approved
Lisinopril	The risk or severity of adverse effects can be increased when Lisinopril is combined with Ketoprofen.	Approved, Investigational
Lithium	The serum concentration of Lithium can be increased when it is combined with Ketoprofen.	Approved
Lomefloxacin	Ketoprofen may increase the neuroexcitatory activities of Lomefloxacin.	Approved
Lornoxicam	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Lornoxicam.	Approved
Losartan	The metabolism of Ketoprofen can be decreased when combined with Losartan.	Approved
Lovastatin	The metabolism of Ketoprofen can be decreased when combined with Lovastatin.	Approved, Investigational
Loxoprofen	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Loxoprofen.	Approved
Lubiprostone	The therapeutic efficacy of Lubiprostone can be decreased when used in combination with Ketoprofen.	Approved, Investigational
Lumacaftor	The serum concentration of Ketoprofen can be decreased when it is combined with Lumacaftor.	Approved
Lumiracoxib	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Lumiracoxib.	Approved, Investigational
Magnesium salicylate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Magnesium salicylate.	Approved
Masoprocol	The risk or severity of adverse effects can be increased when Masoprocol is combined with Ketoprofen.	Approved
ME-609	The risk or severity of adverse effects can be increased when Ketoprofen is combined with ME-609.	Investigational
Meclofenamic acid	The risk or severity of adverse effects can be increased when Meclofenamic acid is combined with Ketoprofen.	Approved, Vet Approved
Medrysone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Medrysone.	Approved
Mefenamic acid	The risk or severity of adverse effects can be increased when Mefenamic acid is combined with Ketoprofen.	Approved
Meloxicam	The risk or severity of adverse effects can be increased when Meloxicam is combined with Ketoprofen.	Approved, Vet Approved
Mesalazine	Ketoprofen may increase the nephrotoxic activities of Mesalazine.	Approved
Metamizole	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Metamizole.	Withdrawn
Methotrexate	The serum concentration of Methotrexate can be increased when it is combined with Ketoprofen.	Approved
Methyclothiazide	The therapeutic efficacy of Methyclothiazide can be decreased when used in combination with Ketoprofen.	Approved
Methylprednisolone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Methylprednisolone.	Approved, Vet Approved
Metipranolol	Ketoprofen may decrease the antihypertensive activities of Metipranolol.	Approved
Metolazone	The therapeutic efficacy of Metolazone can be decreased when used in combination with Ketoprofen.	Approved
Metoprolol	Ketoprofen may decrease the antihypertensive activities of Metoprolol.	Approved, Investigational
Metrizamide	Ketoprofen may decrease the excretion rate of Metrizamide which could result in a higher serum level.	Approved
Mifepristone	The serum concentration of Ketoprofen can be increased when it is combined with Mifepristone.	Approved, Investigational
Misoprostol	The therapeutic efficacy of Misoprostol can be decreased when used in combination with Ketoprofen.	Approved
Moexipril	The risk or severity of adverse effects can be increased when Moexipril is combined with Ketoprofen.	Approved
Mometasone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Mometasone.	Approved, Vet Approved
Morniflumate	The risk or severity of adverse effects can be increased when Morniflumate is combined with Ketoprofen.	Approved
Moxifloxacin	Ketoprofen may increase the neuroexcitatory activities of Moxifloxacin.	Approved, Investigational
Mycophenolate mofetil	The risk or severity of adverse effects can be increased when Mycophenolate mofetil is combined with Ketoprofen.	Approved, Investigational
Mycophenolic acid	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Mycophenolic acid.	Approved
Nabumetone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Nabumetone.	Approved
Nadolol	Ketoprofen may decrease the antihypertensive activities of Nadolol.	Approved
Nadroparin	Ketoprofen may increase the anticoagulant activities of Nadroparin.	Approved
Nafamostat	Ketoprofen may increase the anticoagulant activities of Nafamostat.	Approved, Investigational
Naftifine	The risk or severity of adverse effects can be increased when Naftifine is combined with Ketoprofen.	Approved
Nalidixic Acid	Ketoprofen may increase the neuroexcitatory activities of Nalidixic Acid.	Approved
Naproxen	The risk or severity of adverse effects can be increased when Naproxen is combined with Ketoprofen.	Approved, Vet Approved
NCX 1022	The risk or severity of adverse effects can be increased when Ketoprofen is combined with NCX 1022.	Investigational
NCX 4016	The risk or severity of adverse effects can be increased when Ketoprofen is combined with NCX 4016.	Investigational
Neamine	Ketoprofen may decrease the excretion rate of Neamine which could result in a higher serum level.	Experimental
Neomycin	Ketoprofen may decrease the excretion rate of Neomycin which could result in a higher serum level.	Approved, Vet Approved
Nepafenac	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Nepafenac.	Approved
Netilmicin	Ketoprofen may decrease the excretion rate of Netilmicin which could result in a higher serum level.	Approved
Nicardipine	The metabolism of Ketoprofen can be decreased when combined with Nicardipine.	Approved
Niflumic Acid	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Niflumic Acid.	Approved
Nimesulide	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Nimesulide.	Approved, Withdrawn
Norfloxacin	Ketoprofen may increase the neuroexcitatory activities of Norfloxacin.	Approved
Ofloxacin	Ketoprofen may increase the neuroexcitatory activities of Ofloxacin.	Approved
Oleoyl estrone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Oleoyl estrone.	Investigational
Olmesartan	The risk or severity of adverse effects can be increased when Olmesartan is combined with Ketoprofen.	Approved, Investigational
Olopatadine	The risk or severity of adverse effects can be increased when Olopatadine is combined with Ketoprofen.	Approved
Olsalazine	Ketoprofen may increase the nephrotoxic activities of Olsalazine.	Approved
Omacetaxine mepesuccinate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Omacetaxine mepesuccinate.	Approved
Omapatrilat	The risk or severity of adverse effects can be increased when Omapatrilat is combined with Ketoprofen.	Investigational
Omeprazole	The metabolism of Ketoprofen can be decreased when combined with Omeprazole.	Approved, Investigational, Vet Approved
Oxaprozin	The risk or severity of adverse effects can be increased when Oxaprozin is combined with Ketoprofen.	Approved
Oxprenolol	Ketoprofen may decrease the antihypertensive activities of Oxprenolol.	Approved
Oxyphenbutazone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Oxyphenbutazone.	Withdrawn
Pamidronate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Pamidronate.	Approved
Paramethasone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Paramethasone.	Approved
Parecoxib	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Parecoxib.	Approved
Paromomycin	Ketoprofen may decrease the excretion rate of Paromomycin which could result in a higher serum level.	Approved, Investigational
Pefloxacin	Ketoprofen may increase the neuroexcitatory activities of Pefloxacin.	Approved
Penbutolol	Ketoprofen may decrease the antihypertensive activities of Penbutolol.	Approved, Investigational
Pentosan Polysulfate	Ketoprofen may increase the anticoagulant activities of Pentosan Polysulfate.	Approved
Perindopril	The risk or severity of adverse effects can be increased when Perindopril is combined with Ketoprofen.	Approved
Phenindione	Ketoprofen may increase the anticoagulant activities of Phenindione.	Approved
Phenobarbital	The metabolism of Ketoprofen can be increased when combined with Phenobarbital.	Approved
Phenprocoumon	Ketoprofen may increase the anticoagulant activities of Phenprocoumon.	Approved
Phenylbutazone	The risk or severity of adverse effects can be increased when Phenylbutazone is combined with Ketoprofen.	Approved, Vet Approved
Phenytoin	The metabolism of Ketoprofen can be increased when combined with Phenytoin.	Approved, Vet Approved
Pimecrolimus	The risk or severity of adverse effects can be increased when Pimecrolimus is combined with Ketoprofen.	Approved, Investigational
Pindolol	Ketoprofen may decrease the antihypertensive activities of Pindolol.	Approved
Pirarubicin	Ketoprofen may decrease the excretion rate of Pirarubicin which could result in a higher serum level.	Investigational
Piretanide	Ketoprofen may decrease the diuretic activities of Piretanide.	Experimental
Pirfenidone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Pirfenidone.	Investigational
Piroxicam	The risk or severity of adverse effects can be increased when Piroxicam is combined with Ketoprofen.	Approved, Investigational
Plicamycin	Ketoprofen may decrease the excretion rate of Plicamycin which could result in a higher serum level.	Approved, Withdrawn
Polythiazide	The therapeutic efficacy of Polythiazide can be decreased when used in combination with Ketoprofen.	Approved
Practolol	Ketoprofen may decrease the antihypertensive activities of Practolol.	Approved
Pralatrexate	The serum concentration of Pralatrexate can be increased when it is combined with Ketoprofen.	Approved
Prasterone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Prasterone.	Approved, Nutraceutical
Prasterone sulfate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with dehydroepiandrosterone sulfate.	Investigational
Prednicarbate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Prednicarbate.	Approved
Prednisolone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Prednisolone.	Approved, Vet Approved
Prednisone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Prednisone.	Approved, Vet Approved
Pregnenolone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Pregnenolone.	Experimental
Primidone	The metabolism of Ketoprofen can be increased when combined with Primidone.	Approved, Vet Approved
Probenecid	The serum concentration of Ketoprofen can be increased when it is combined with Probenecid.	Approved
Propacetamol	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Propacetamol.	Approved
Propranolol	Ketoprofen may decrease the antihypertensive activities of Propranolol.	Approved, Investigational
Prostaglandin B2	The therapeutic efficacy of Prostaglandin B2 can be decreased when used in combination with Ketoprofen.	Experimental
Prostaglandin G2	The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Ketoprofen.	Experimental
Protein S human	Ketoprofen may increase the anticoagulant activities of Protein S human.	Approved
PTC299	The risk or severity of adverse effects can be increased when Ketoprofen is combined with PTC299.	Investigational
Puromycin	Ketoprofen may decrease the excretion rate of Puromycin which could result in a higher serum level.	Experimental
Pyrimethamine	The metabolism of Ketoprofen can be decreased when combined with Pyrimethamine.	Approved, Vet Approved
Quinapril	The risk or severity of adverse effects can be increased when Quinapril is combined with Ketoprofen.	Approved, Investigational
Quinethazone	The therapeutic efficacy of Quinethazone can be decreased when used in combination with Ketoprofen.	Approved
Quinine	The metabolism of Ketoprofen can be decreased when combined with Quinine.	Approved
Ramipril	The risk or severity of adverse effects can be increased when Ramipril is combined with Ketoprofen.	Approved
Rescinnamine	The risk or severity of adverse effects can be increased when Rescinnamine is combined with Ketoprofen.	Approved
Resveratrol	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Resveratrol.	Experimental, Investigational
Reviparin	Ketoprofen may increase the anticoagulant activities of Reviparin.	Approved
Ribostamycin	Ketoprofen may decrease the excretion rate of Ribostamycin which could result in a higher serum level.	Approved
Rifampicin	The metabolism of Ketoprofen can be increased when combined with Rifampicin.	Approved
Rifapentine	The metabolism of Ketoprofen can be increased when combined with Rifapentine.	Approved
Rimexolone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Rimexolone.	Approved
Risedronate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Risedronate.	Approved, Investigational
Rivaroxaban	Ketoprofen may increase the anticoagulant activities of Rivaroxaban.	Approved
Rofecoxib	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Rofecoxib.	Investigational, Withdrawn
Rosoxacin	Ketoprofen may increase the neuroexcitatory activities of Rosoxacin.	Approved
Sacubitril	The risk or severity of adverse effects can be increased when Sacubitril is combined with Ketoprofen.	Approved
Salicylamide	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Salicylamide.	Approved
Salicylic acid	The risk or severity of adverse effects can be increased when Salicylic acid is combined with Ketoprofen.	Approved, Vet Approved
Salsalate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Salsalate.	Approved
Saprisartan	The risk or severity of adverse effects can be increased when Saprisartan is combined with Ketoprofen.	Experimental
Secobarbital	The metabolism of Ketoprofen can be increased when combined with Secobarbital.	Approved, Vet Approved
Sildenafil	The metabolism of Ketoprofen can be decreased when combined with Sildenafil.	Approved, Investigational
Sorafenib	The metabolism of Ketoprofen can be decreased when combined with Sorafenib.	Approved, Investigational
Sotalol	Ketoprofen may decrease the antihypertensive activities of Sotalol.	Approved
SP1049C	Ketoprofen may decrease the excretion rate of SP1049C which could result in a higher serum level.	Investigational
Sparfloxacin	Ketoprofen may increase the neuroexcitatory activities of Sparfloxacin.	Approved
Spectinomycin	Ketoprofen may decrease the excretion rate of Spectinomycin which could result in a higher serum level.	Approved, Vet Approved
Spirapril	The risk or severity of adverse effects can be increased when Spirapril is combined with Ketoprofen.	Approved
Spironolactone	Ketoprofen may decrease the antihypertensive activities of Spironolactone.	Approved
SRT501	The risk or severity of adverse effects can be increased when Ketoprofen is combined with SRT501.	Investigational
Streptomycin	Ketoprofen may decrease the excretion rate of Streptomycin which could result in a higher serum level.	Approved, Vet Approved
Streptozocin	Ketoprofen may decrease the excretion rate of Streptozocin which could result in a higher serum level.	Approved
Sulfadiazine	The metabolism of Ketoprofen can be decreased when combined with Sulfadiazine.	Approved, Vet Approved
Sulfamethoxazole	The metabolism of Ketoprofen can be decreased when combined with Sulfamethoxazole.	Approved
Sulfasalazine	Ketoprofen may increase the nephrotoxic activities of Sulfasalazine.	Approved
Sulfisoxazole	The metabolism of Ketoprofen can be decreased when combined with Sulfisoxazole.	Approved, Vet Approved
Sulindac	The risk or severity of adverse effects can be increased when Sulindac is combined with Ketoprofen.	Approved
Sulodexide	Ketoprofen may increase the anticoagulant activities of Sulodexide.	Approved, Investigational
Suprofen	The risk or severity of adverse effects can be increased when Suprofen is combined with Ketoprofen.	Approved, Withdrawn
Tacrolimus	Ketoprofen may increase the nephrotoxic activities of Tacrolimus.	Approved, Investigational
Tafluprost	The therapeutic efficacy of Tafluprost can be decreased when used in combination with Ketoprofen.	Approved
Talniflumate	The risk or severity of adverse effects can be increased when Talniflumate is combined with Ketoprofen.	Approved
Tasosartan	The risk or severity of adverse effects can be increased when Tasosartan is combined with Ketoprofen.	Approved
Technetium Tc-99m medronate	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Technetium Tc-99m Medronate.	Approved
Telmisartan	The risk or severity of adverse effects can be increased when Telmisartan is combined with Ketoprofen.	Approved, Investigational
Temafloxacin	Ketoprofen may increase the neuroexcitatory activities of Temafloxacin.	Withdrawn
Temocapril	The risk or severity of adverse effects can be increased when Temocapril is combined with Ketoprofen.	Experimental, Investigational
Tenofovir	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Tenofovir.	Approved, Investigational
Tenoxicam	The risk or severity of adverse effects can be increased when Tenoxicam is combined with Ketoprofen.	Approved
Teriflunomide	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Teriflunomide.	Approved
Tiaprofenic acid	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Tiaprofenic acid.	Approved
Ticagrelor	The metabolism of Ketoprofen can be decreased when combined with Ticagrelor.	Approved
Ticlopidine	The metabolism of Ketoprofen can be decreased when combined with Ticlopidine.	Approved
Tiludronic acid	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Tiludronate.	Approved, Vet Approved
Timolol	Ketoprofen may decrease the antihypertensive activities of Timolol.	Approved
Tixocortol	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Tixocortol.	Approved
Tobramycin	Ketoprofen may decrease the excretion rate of Tobramycin which could result in a higher serum level.	Approved, Investigational
Tolbutamide	The metabolism of Ketoprofen can be decreased when combined with Tolbutamide.	Approved
Tolfenamic Acid	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Tolfenamic Acid.	Approved
Tolmetin	The risk or severity of adverse effects can be increased when Tolmetin is combined with Ketoprofen.	Approved
Torasemide	Ketoprofen may decrease the diuretic activities of Torasemide.	Approved
Trandolapril	The risk or severity of adverse effects can be increased when Trandolapril is combined with Ketoprofen.	Approved
Tranilast	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Tranilast.	Approved, Investigational
Travoprost	The therapeutic efficacy of Travoprost can be decreased when used in combination with Ketoprofen.	Approved
Treprostinil	The risk or severity of adverse effects can be increased when Treprostinil is combined with Ketoprofen.	Approved, Investigational
Triamcinolone	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Triamcinolone.	Approved, Vet Approved
Triamterene	Ketoprofen may decrease the antihypertensive activities of Triamterene.	Approved
Trichlormethiazide	The therapeutic efficacy of Trichlormethiazide can be decreased when used in combination with Ketoprofen.	Approved, Vet Approved
Trimethoprim	The metabolism of Ketoprofen can be decreased when combined with Trimethoprim.	Approved, Vet Approved
Trovafloxacin	Ketoprofen may increase the neuroexcitatory activities of Trovafloxacin.	Approved, Withdrawn
Unoprostone	The therapeutic efficacy of Unoprostone can be decreased when used in combination with Ketoprofen.	Approved
Valdecoxib	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Valdecoxib.	Investigational, Withdrawn
Valproic Acid	The metabolism of Ketoprofen can be decreased when combined with Valproic Acid.	Approved, Investigational
Valrubicin	Ketoprofen may decrease the excretion rate of Valrubicin which could result in a higher serum level.	Approved
Valsartan	The metabolism of Ketoprofen can be decreased when combined with Valsartan.	Approved, Investigational
Vancomycin	The serum concentration of Vancomycin can be increased when it is combined with Ketoprofen.	Approved
Voriconazole	The metabolism of Ketoprofen can be decreased when combined with Voriconazole.	Approved, Investigational
Warfarin	Ketoprofen may increase the anticoagulant activities of Warfarin.	Approved
Ximelagatran	Ketoprofen may increase the anticoagulant activities of Ximelagatran.	Approved, Investigational, Withdrawn
Zafirlukast	The metabolism of Ketoprofen can be decreased when combined with Zafirlukast.	Approved, Investigational
Zaltoprofen	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Zaltoprofen.	Approved
Zileuton	The risk or severity of adverse effects can be increased when Zileuton is combined with Ketoprofen.	Approved, Investigational, Withdrawn
Zoledronic acid	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Zoledronic acid.	Approved
Zomepirac	The risk or severity of adverse effects can be increased when Ketoprofen is combined with Zomepirac.	Withdrawn
Zorubicin	Ketoprofen may decrease the excretion rate of Zorubicin which could result in a higher serum level.	Experimental

Food Interactions

Avoid alcohol.
Food prolongs rate of absorption and decreases peak plasma concentration. Extent of absorption is not affected.
Take with food to reduce gastric irritation.

References

Synthesis Reference

Attilio Citterio, Daniele Fancelli, "Method of preparing ketoprofen." U.S. Patent US4845281, issued December, 1982.

US4845281

General References

Kantor TG: Ketoprofen: a review of its pharmacologic and clinical properties. Pharmacotherapy. 1986 May-Jun;6(3):93-103. [PubMed:3526298 ]
Mazieres B: Topical ketoprofen patch. Drugs R D. 2005;6(6):337-44. [PubMed:16274258 ]

External Links

Resource	Link
Human Metabolome Database (HMDB)	HMDB15144
KEGG Drug	D00132
KEGG Compound	C01716
PubChem Compound	3825
PubChem Substance	46505715
ChemSpider	3693
BindingDB	50022271
ChEBI	6128
ChEMBL	CHEMBL571
Therapeutic Targets Database	DAP000623
PharmGKB	PA450149
Drug Product Database	2327
RxList	http://www.rxlist.com/cgi/generic/ketoprof.htm
Drugs.com	http://www.drugs.com/cdi/ketoprofen.html
PDRhealth	http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/oru1313.shtml
Wikipedia	Ketoprofen

ATC Codes

M01AE53

M02AA10

M01AE03

AHFS Codes

28:08.04.92

PDB Entries

Not Available

FDA label

Download (160 KB)

MSDS

Download (75.9 KB)

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Treatment	Painful musculoskeletal conditions	1
1	Recruiting	Treatment	Renal Colic	1
2	Completed	Not Available	Osteoarthritis of the Knees	1
2	Completed	Treatment	Osteoarthritis of the Knees	1
2	Completed	Treatment	Tendonitis of the Shoulder, Elbow, or Knee	1
2	Recruiting	Treatment	Neoplasms, Upper Aerodigestive Tract / Uterine Cervical Cancer	1
2	Unknown Status	Treatment	Post-Operative Pain / Surgery, Cardiac	1
2, 3	Completed	Treatment	Female Genital Diseases	1
3	Completed	Not Available	Ankle Sprains	1
3	Completed	Prevention	Migraines	1
3	Completed	Treatment	Ankle Sprains	1
3	Completed	Treatment	Bursitis / Tendonitis	1
3	Completed	Treatment	Low Back Pain (LBP)	1
3	Completed	Treatment	Muscle Strain / Sprains	1
3	Completed	Treatment	Osteoarthritis of the Knees	1
3	Completed	Treatment	Pain	3
3	Completed	Treatment	Synovitis of osteoarthritis	1
3	Not Yet Recruiting	Prevention	Pain Relief	1
3	Not Yet Recruiting	Treatment	Painful musculoskeletal conditions	2
3	Recruiting	Prevention	Pain Relief	1
3	Recruiting	Treatment	Prophylaxis against postoperative nausea and vomiting	1
3	Terminated	Treatment	Bursitis / Tendonitis	1
3	Unknown Status	Treatment	Migraines	1
3	Unknown Status	Treatment	Muscular Atrophy / Sprains / Tendonitis	1
3	Withdrawn	Treatment	Acute Pain (Flare) Associated With Osteoarthritis (OA) of the Knee	1
4	Completed	Supportive Care	Other Surgical Procedures / Pain	1
4	Completed	Treatment	Ankle Sprains	1
4	Completed	Treatment	Caesarian Section	1
4	Completed	Treatment	Children / Postoperative pain / Recovery of Function	1
4	Completed	Treatment	General Surgery	1
4	Completed	Treatment	Gonarthrosis / Low Back Pain (LBP)	1
4	Completed	Treatment	Pain	1
4	Completed	Treatment	Sciatica	1
4	Not Yet Recruiting	Treatment	Acute Renal Colic / Renal Colic	1
4	Recruiting	Treatment	Analgesia, Postoperative	1
4	Recruiting	Treatment	Ankle Sprains	1
4	Recruiting	Treatment	Cesarean Section / Pain Management / Pain, Neuropathic	1
4	Recruiting	Treatment	Mechanical Low Back Pain	1
4	Terminated	Treatment	Pharyngotonsillitis	1
Not Available	Completed	Diagnostic	Dermatitis, Photocontact	1
Not Available	Completed	Treatment	Migraines	1
Not Available	Completed	Treatment	Pregnancy Termination	1

Pharmacoeconomics

Manufacturers

Elan pharmaceutical research corp
Mylan pharmaceuticals inc
Watson laboratories inc florida
Wyeth pharmaceuticals inc
Heritage pharmaceuticals inc
Sandoz inc
Teva pharmaceuticals usa inc
Wyeth ayerst laboratories
Novartis consumer health inc
Bayer healthcare llc
L perrigo co
Wyeth consumer healthcare

Packagers

Aidarex Pharmacuticals LLC
Apothecary Shop Wholesale
A-S Medication Solutions LLC
Bryant Ranch Prepack
Corepharma LLC
Direct Dispensing Inc.
Dispensing Solutions
Diversified Healthcare Services Inc.
Elan Pharmaceuticals Inc.
H.J. Harkins Co. Inc.
Innoviant Pharmacy Inc.
Letco Medical Inc.
Major Pharmaceuticals
Medisca Inc.
Murfreesboro Pharmaceutical Nursing Supply
Mylan
Nucare Pharmaceuticals Inc.
Palmetto Pharmaceuticals Inc.
PD-Rx Pharmaceuticals Inc.
Pharma Pac LLC
Pharmedix
Physicians Total Care Inc.
Preferred Pharmaceuticals Inc.
Prescription Dispensing Service Inc.
Professional Co.
Qualitest
Rebel Distributors Corp.
Sandhills Packaging Inc.
Southwood Pharmaceuticals
Teva Pharmaceutical Industries Ltd.
Watson Pharmaceuticals

Dosage forms

Form	Route	Strength
Capsule	Oral	50 mg/1
Capsule	Oral	50 mg
Capsule	Oral	75 mg/1
Capsule, extended release	Oral	200 mg/1
Tablet	Oral	75 mg/1
Tablet, extended release	Oral	200 mg
Tablet, delayed release	Oral	100 mg
Tablet, delayed release	Oral	50 mg
Capsule, extended release	Oral	150 mg
Capsule, extended release	Oral	200 mg
Suppository	Rectal	100 mg
Suppository	Rectal	50 mg
Kit

Prices

Unit description	Cost	Unit
Ketoprofen powder	43.74USD	g
Ketoprofen micronized powder	3.84USD	g
Ketoprofen CR 200 mg 24 Hour Capsule	2.8USD	capsule
Orudis 75 mg capsule	1.58USD	capsule
Apo-Keto Sr 200 mg Sustained-Release Tablet	1.46USD	tablet
Ketoprofen 75 mg capsule	1.12USD	capsule
Pms-Ketoprofen 100 mg Suppository	1.1USD	suppository
Ketoprofen 50 mg capsule	1.0USD	capsule
Apo-Keto-E 100 mg Enteric-Coated Tablet	0.71USD	tablet
Apo-Keto 50 mg Capsule	0.35USD	capsule
Apo-Keto-E 50 mg Enteric-Coated Tablet	0.35USD	tablet
Orudis kt 12.5 mg tablet	0.3USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	94 °C	U.S. Patent 3,641,127.
water solubility	51 mg/L (at 22 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	3.12	SANGSTER (1993)
logS	-3.7	ADME Research, USCD
pKa	4.45	SANGSTER (1994)

Predicted Properties

Property	Value	Source
Water Solubility	0.0213 mg/mL	ALOGPS
logP	3.29	ALOGPS
logP	3.61	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.88	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.52 m³·mol^-1	ChemAxon
Polarizability	26.56 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9928
Blood Brain Barrier	+	0.9382
Caco-2 permeable	+	0.8866
P-glycoprotein substrate	Non-substrate	0.7132
P-glycoprotein inhibitor I	Non-inhibitor	0.9168
P-glycoprotein inhibitor II	Non-inhibitor	0.9589
Renal organic cation transporter	Non-inhibitor	0.8818
CYP450 2C9 substrate	Non-substrate	0.7183
CYP450 2D6 substrate	Non-substrate	0.9598
CYP450 3A4 substrate	Non-substrate	0.7685
CYP450 1A2 substrate	Non-inhibitor	0.9046
CYP450 2C9 inhibitor	Non-inhibitor	0.907
CYP450 2D6 inhibitor	Non-inhibitor	0.9604
CYP450 2C19 inhibitor	Non-inhibitor	0.9465
CYP450 3A4 inhibitor	Non-inhibitor	0.9598
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9438
Ames test	Non AMES toxic	0.9801
Carcinogenicity	Non-carcinogens	0.6299
Biodegradation	Ready biodegradable	0.6701
Rat acute toxicity	2.2378 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9661
hERG inhibition (predictor II)	Non-inhibitor	0.9595

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0390000000-a31eea165d399e00a838	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-0900000000-520a79bdaf7ce3ec476c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-0900000000-3aa1f85f9b6550cc9147	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-0900000000-d582a4bd39cf003e73e3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-0900000000-5a1b8d289986b0103991	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0390000000-66208a90d621bcbafe58	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-0900000000-e3e8663a70e4a78219d3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0090000000-adc690db13d79d7e088b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF , negative	splash10-0a4i-0090000000-dc927e8f8991af0b9c62	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0090000000-2f4539685044ce030904	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0090000000-e4776b39ad9777a106d6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0190000000-cd73850fa213100eea4f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a6u-0940000000-b2b661b497cc37bb54d7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0090000000-60f88de41010fba22c8b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0090000000-8b462ef2178ab7ffdf4f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0290000000-a6f4442004890a1099fa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0960000000-ea2a1b4ccfd466afd1d7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0900000000-ffa78d310365a0a9dd0e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-2900000000-3f15ff6dad9be8084701	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Benzenoids

Sub Class

Benzene and substituted derivatives

Direct Parent

Benzophenones

Alternative Parents

Diphenylmethanes / Aryl-phenylketones / Phenylpropanoic acids / Benzoyl derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives

Substituents

Benzophenone / Aryl-phenylketone / Diphenylmethane / 2-phenylpropanoic-acid / Benzoyl / Aryl ketone / Ketone / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzophenones, oxo monocarboxylic acid (CHEBI:6128 )

Targets

Details

1. Prostaglandin G/H synthase 1

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

Parsadaniantz SM, Lebeau A, Duval P, Grimaldi B, Terlain B, Kerdelhue B: Effects of the inhibition of cyclo-oxygenase 1 or 2 or 5-lipoxygenase on the activation of the hypothalamic-pituitary-adrenal axis induced by interleukin-1beta in the male Rat. J Neuroendocrinol. 2000 Aug;12(8):766-73. [PubMed:10929089 ]
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 ]
Zuniga J, Fuenzalida M, Guerrero A, Illanes J, Dabancens A, Diaz E, Lemus D: Effects of steroidal and non steroidal drugs on the neovascularization response induced by tumoral TA3 supernatant on CAM from chick embryo. Biol Res. 2003;36(2):233-40. [PubMed:14513718 ]
Martic M, Tatic I, Markovic S, Kujundzic N, Kostrun S: Synthesis, biological activity and molecular modeling studies of novel COX-1 inhibitors. Eur J Med Chem. 2004 Feb;39(2):141-51. [PubMed:14987823 ]
Levoin N, Blondeau C, Guillaume C, Grandcolas L, Chretien F, Jouzeau JY, Benoit E, Chapleur Y, Netter P, Lapicque F: Elucidation of the mechanism of inhibition of cyclooxygenases by acyl-coenzyme A and acylglucuronic conjugates of ketoprofen. Biochem Pharmacol. 2004 Nov 15;68(10):1957-69. [PubMed:15476667 ]

Details

2. Prostaglandin G/H synthase 2

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

Kay-Mugford P, Benn SJ, LaMarre J, Conlon P: In vitro effects of nonsteroidal anti-inflammatory drugs on cyclooxygenase activity in dogs. Am J Vet Res. 2000 Jul;61(7):802-10. [PubMed:10895904 ]
Sommerauer M, Ates M, Guhring H, Brune K, Amann R, Peskar BA: Ketoprofen-induced cyclooxygenase inhibition in renal medulla and platelets of rats treated with caffeine. Pharmacology. 2001;63(4):234-9. [PubMed:11729362 ]
Levoin N, Chretien F, Lapicque F, Chapleur Y: Synthesis and biological testing of Acyl-CoA-ketoprofen conjugates as selective irreversible inhibitors of COX-2. Bioorg Med Chem. 2002 Mar;10(3):753-7. [PubMed:11814865 ]
Zuniga J, Fuenzalida M, Guerrero A, Illanes J, Dabancens A, Diaz E, Lemus D: Effects of steroidal and non steroidal drugs on the neovascularization response induced by tumoral TA3 supernatant on CAM from chick embryo. Biol Res. 2003;36(2):233-40. [PubMed:14513718 ]
Wilson JE, Chandrasekharan NV, Westover KD, Eager KB, Simmons DL: Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. Am J Vet Res. 2004 Jun;65(6):810-8. [PubMed:15198222 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Details

3. C-X-C chemokine receptor type 1

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: other

General Function:: Interleukin-8 receptor activity
Specific Function:: Receptor to interleukin-8, which is a powerful neutrophils chemotactic factor. Binding of IL-8 to the receptor causes activation of neutrophils. This response is mediated via a G-protein that activate a phosphatidylinositol-calcium second messenger system. This receptor binds to IL-8 with a high affinity and to MGSA (GRO) with a low affinity.
Gene Name:: CXCR1
Uniprot ID:: P25024
Molecular Weight:: 39790.735 Da

References

Allegretti M, Bertini R, Cesta MC, Bizzarri C, Di Bitondo R, Di Cioccio V, Galliera E, Berdini V, Topai A, Zampella G, Russo V, Di Bello N, Nano G, Nicolini L, Locati M, Fantucci P, Florio S, Colotta F: 2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors. J Med Chem. 2005 Jun 30;48(13):4312-31. [PubMed:15974585 ]
Bizzarri C, Pagliei S, Brandolini L, Mascagni P, Caselli G, Transidico P, Sozzani S, Bertini R: Selective inhibition of interleukin-8-induced neutrophil chemotaxis by ketoprofen isomers. Biochem Pharmacol. 2001 Jun 1;61(11):1429-37. [PubMed:11331079 ]
Wang LM, Toyoshima A, Mineshita S, Wang XX, Yamamoto T, Nomura Y, Yang L, Koikei Y, Shiba K, Honda Y: The anti-inflammatory effects of ketoprofen in animal experiments. Drugs Exp Clin Res. 1997;23(1):1-6. [PubMed:9093816 ]

Enzymes

Details

1. Cytochrome P450 2C9

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: substrateinhibitor

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

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 ]
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 ]

Details

2. Cytochrome P450 2C8

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor

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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular Weight:: 55824.275 Da

References

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 ]

Carriers

Details

1. Serum albumin

Kind: Protein
Organism: Human
Pharmacological action: 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

Bertucci C: Enantioselective inhibition of the binding of rac-profens to human serum albumin induced by lithocholate. Chirality. 2001 Jul;13(7):372-8. [PubMed:11400191 ]
Lagrange F, Penhourcq F, Matoga M, Bannwarth B: Binding of ketoprofen enantiomers in various human albumin preparations. J Pharm Biomed Anal. 2000 Oct;23(5):793-802. [PubMed:11022905 ]
Li F, Zhou D, Guo X: Study on the protein binding of ketoprofen using capillary electrophoresis frontal analysis compared with liquid chromatography frontal analysis. J Chromatogr Sci. 2003 Mar;41(3):137-41. [PubMed:12725696 ]
Zhou D, Li F: [Study of protein binding in ketoprofen using liquid chromatography frontal analysis in comparison with capillary electrophoresis frontal analysis]. Se Pu. 2004 Nov;22(6):601-4. [PubMed:15807110 ]

Transporters

Details

1. Multidrug resistance-associated protein 4

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

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 ]

Details

2. Solute carrier organic anion transporter family member 1A2

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor

General Function:: Sodium-independent organic anion transmembrane transporter activity
Specific Function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibited by the grapefruit juice component naringin.
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular Weight:: 74144.105 Da

References

Shitara Y, Sugiyama D, Kusuhara H, Kato Y, Abe T, Meier PJ, Itoh T, Sugiyama Y: Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. Pharm Res. 2002 Feb;19(2):147-53. [PubMed:11883641 ]

Details

3. Solute carrier family 22 member 6

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

Cihlar T, Ho ES: Fluorescence-based assay for the interaction of small molecules with the human renal organic anion transporter 1. Anal Biochem. 2000 Jul 15;283(1):49-55. [PubMed:10929807 ]
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 ]
Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]
Uwai Y, Saito H, Inui K: Interaction between methotrexate and nonsteroidal anti-inflammatory drugs in organic anion transporter. Eur J Pharmacol. 2000 Dec 1;409(1):31-6. [PubMed:11099697 ]
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 ]

Details

4. Solute carrier family 22 member 8

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor

General Function:: Sodium-independent organic anion transmembrane transporter activity
Specific Function:: Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:: SLC22A8
Uniprot ID:: Q8TCC7
Molecular Weight:: 59855.585 Da

References

Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]
Ohtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T: Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. J Neurochem. 2002 Oct;83(1):57-66. [PubMed:12358729 ]

Details

5. Solute carrier family 22 member 11

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor

General Function:: Sodium-independent organic anion transmembrane transporter activity
Specific Function:: Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name:: SLC22A11
Uniprot ID:: Q9NSA0
Molecular Weight:: 59970.945 Da

References

Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]

Details

6. Solute carrier family 22 member 7

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor

General Function:: Sodium-independent organic anion transmembrane transporter activity
Specific Function:: Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha-ketoglutarate.
Gene Name:: SLC22A7
Uniprot ID:: Q9Y694
Molecular Weight:: 60025.025 Da

References

Sekine T, Cha SH, Tsuda M, Apiwattanakul N, Nakajima N, Kanai Y, Endou H: Identification of multispecific organic anion transporter 2 expressed predominantly in the liver. FEBS Lett. 1998 Jun 12;429(2):179-82. [PubMed:9650585 ]
Morita N, Kusuhara H, Sekine T, Endou H, Sugiyama Y: Functional characterization of rat organic anion transporter 2 in LLC-PK1 cells. J Pharmacol Exp Ther. 2001 Sep;298(3):1179-84. [PubMed:11504818 ]
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 ]
Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]

Drug created on June 13, 2005 07:24 / Updated on June 11, 2017 15:46

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Structure for DB01009 (Ketoprofen)

Targets

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Enzymes

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Carriers

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Transporters

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