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Details

Stereochemistry RACEMIC
Molecular Formula C16H14O3
Molecular Weight 254.2806
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of KETOPROFEN

SMILES

CC(C(O)=O)C1=CC(=CC=C1)C(=O)C2=CC=CC=C2

InChI

InChIKey=DKYWVDODHFEZIM-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C16H14O3
Molecular Weight 254.2806
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Ketoprofen is a drug belonging to the family of non-steroidal anti-inflammatory drugs. Ketoprofen, was synthesized in France by Rhône-Poulenc chemists in 1967, and introduced in 1973 in France and the United Kingdom for antiinflammatory use. Ketoprofen selectively inhibits isoform-I of cyclo-oxygenase, COX-1. Ketoprofen has shown to be an excellent choice of drug for the treatment of chronic pain in patients with osteoarthritis, rheumatoid arthritis. In addition Ketoprofen is prescribed for management of pain (acute forms of pain, traumatic and post-surgical pain) and also indicated for treatment of primary dysmenorrhea

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.52 µM [IC50]
0.019 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Iatrogenic cost factors incorporating mild and moderate adverse events in the economic comparison of aceclofenac and other NSAIDs.
2001
Aceclofenac: a reappraisal of its use in the management of pain and rheumatic disease.
2001
Use of continuous fluid drainage for severe polyhydramnios due to twin to twin transfusion syndrome.
2001
[Two complex suicidal poisonings with drugs and their medicolegal aspects].
2001
Early-morning administration of dexketoprofen-trometamol in morning stiffness induced by nodal osteoarthritis of the hands.
2001
Release behavior of ketoprofen from poly(acryloyl-L-proline methyl ester) gels having different crosslinked networks.
2001
Overdose of ketoprofen could be dangerous.
2001 Apr
Interaction between the antinociceptive effect of ketoprofen and adrenergic modulatory systems.
2001 Aug
Simultaneous optimization based on artificial neural networks in ketoprofen hydrogel formula containing O-ethyl-3-butylcyclohexanol as percutaneous absorption enhancer.
2001 Aug
Binding constant determination of drugs toward subdomain IIIA of human serum albumin by near-infrared dye-displacement capillary electrophoresis.
2001 Aug
Investigation of the utility of an in vitro release test for optimizing semisolid dosage forms.
2001 Aug
Sustained release ketoprofen microparticles with ethylcellulose and carboxymethylethylcellulose.
2001 Aug 10
In vitro distribution of ketoprofen enantiomers in articular tissues of osteoarthritic patients.
2001 Dec
Oral ketoprofen in children--could it have been done differently?
2001 Jan
Cytokines and cytokine inducers stimulate prostaglandin E2 entry into the brain.
2001 Jul
Comparison of tissue concentrations after intramuscular and topical administration of ketoprofen.
2001 Jul
[Enantiomeric separation of drugs based on macrocyclic antibiotics].
2001 Jul
Analgesic profile of peroral and topical ketoprofen upon low pH-induced muscle pain.
2001 Jul
Enantioselective inhibition of the binding of rac-profens to human serum albumin induced by lithocholate.
2001 Jul
Evaluation of percutaneous absorption and skin irritation of ketoprofen through rat skin: in vitro and in vivo study.
2001 Jul 17
Stereoselective pharmacokinetics of ketoprofen in llamas following intravenous administration.
2001 Jun
Enantiospecific pharmacokinetics of ketoprofen in plasma and synovial fluid of horses with acute synovitis.
2001 Jun
Safety and efficacy of preoperative administration of meloxicam, compared with that of ketoprofen and butorphanol in dogs undergoing abdominal surgery.
2001 Jun
Simultaneous photocontact sensitivity to ketoprofen and oxybenzone.
2001 Jun
Simultaneous determination of loxoprofen and its diastereomeric alcohol metabolites in human plasma and urine by a simple HPLC-UV detection method.
2001 Jun
Intercalation compounds of hydrotalcite-like anionic clays with antiinflammatory agents--I. Intercalation and in vitro release of ibuprofen.
2001 Jun 4
[Acute pancreatitis and ketoprofen].
2001 Jun-Jul
[Ketoprofen-induced acute hepatitis].
2001 Jun-Jul
I.v. ketoprofen for analgesia after tonsillectomy: comparison of pre- and post-operative administration.
2001 Mar
Thoracoscopy as a nonpharmacotherapeutic research modification for limiting postoperative chest pain.
2001 Mar-Apr
Effect of oxidative stress on the structure and function of human serum albumin.
2001 May
Chiral resolution of flurbiprofen and ketoprofen enantiomers by HPLC on a glycopeptide-type column chiral stationary phase.
2001 May
Screening procedure for detection of non-steroidal anti-inflammatory drugs and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation.
2001 May-Jun
Onset of analgesia for liquigel ibuprofen 400 mg, acetaminophen 1000 mg, ketoprofen 25 mg, and placebo in the treatment of postoperative dental pain.
2001 Nov
Measurement of ketoprofen in horse urine using gas chromatography-mass spectrometry.
2001 Oct
Influence of betacyclodextrin on the release of poorly soluble drugs from inert and hydrophilic heterogeneous polymeric matrices.
2001 Oct
Lipopolysaccharide-induced increase of prostaglandin E(2) is mediated by inducible nitric oxide synthase activation of the constitutive cyclooxygenase and induction of membrane-associated prostaglandin E synthase.
2001 Oct 1
Effects of diclofenac and ketoprofen on nerve conduction velocity in experimental nerve root compression.
2001 Oct 15
Optimized conditions of bio-mimetic artificial membrane permeation assay.
2001 Oct 9
Transdermal delivery of ketoprofen using microemulsions.
2001 Oct 9
[ Ambulatory laparoscopic gynecological surgery in Africa: feasibility].
2001 Sep
Efficacy and safety of ketoprofen lysine salt mouthwash versus benzydamine hydrochloride mouthwash in acute pharyngeal inflammation: a randomized, single-blind study.
2001 Sep
Comparison of the effects of ketoprofen on platelet function in the presence and absence of aspirin.
2001 Sep
Promoting mechanism of menthol derivative, 1-O-ethyl-3-buthylcyclohexanol, on the percutaneous absorption of ketoprofen.
2001 Sep
Incompatibility of prochlorperizine and ketoprofen.
2001 Sep
Photocontact dermatitis to ketoprofen.
2001 Sep
Antihyperalgesic effects of the muscarinic receptor ligand vedaclidine in models involving central sensitization in rats.
2001 Sep
Functional characterization of rat organic anion transporter 2 in LLC-PK1 cells.
2001 Sep
In vitro and in vivo evaluation of polyoxyethylene esters as dermal prodrugs of ketoprofen, naproxen and diclofenac.
2001 Sep
Enhancement of the activity of doxorubicin by inhibition of glutamate transporter.
2001 Sep 15
Patents

Sample Use Guides

In Vivo Use Guide
Rheumatoid Arthritis and Osteoarthritis: 75 mg three times or 50 mg four times a day. The recommended maximum daily dose of ketoprofen capsules is 300 mg/day. Pain and Dysmenorrhea: 25 to 50 mg every 6 to 8 hours as necessary.
Route of Administration: Oral
In Vitro Use Guide
5 mM Ketoprofen (mouse isolated epidermal cells)
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:34:24 UTC 2019
Edited
by admin
on Tue Oct 22 00:34:24 UTC 2019
Record UNII
90Y4QC304K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
KETOPROFEN
EP   GREEN BOOK   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
R.P. 19,583
Code English
(RS)-KETOPROFEN
Common Name English
RU-4733
Code English
KETOPROFEN [EP]
Common Name English
KETOPROFEN [MART.]
Common Name English
ISO-K
Brand Name English
KETOPROFEN [VANDF]
Common Name English
R.P. 19583
Code English
SECTOR
Brand Name English
ORUVAIL
Brand Name English
ALRHEUMAT
Brand Name English
RP-19583
Code English
KETOPROFEN [INN]
Common Name English
KETOPROFEN [USP-RS]
Common Name English
BENZENEACETIC ACID, 3-BENZOYL-.ALPHA.-METHYL-
Systematic Name English
ORUDIS
Brand Name English
(+/-)-M-BENZOYLHYDRATROPIC ACID
Systematic Name English
IDEA-033
Code English
KETOPROFEN [WHO-DD]
Common Name English
(+/-)-KETOPROFEN
Common Name English
BENZENEACETIC ACID, 3-BENZOYL-.ALPHA.-METHYL-,(+/-)-
Common Name English
ANEOL
Brand Name English
HYDRATROPIC ACID, M-BENZOYL-
Common Name English
(+/-)-3-BENZOYL-.ALPHA.-METHYLBENZENEACETIC ACID
Systematic Name English
KETORIN
Brand Name English
KETOPROFEN [GREEN BOOK]
Common Name English
KETOPROFEN [MI]
Common Name English
KETOPROFEN [USAN]
Common Name English
CAPISTEN
Brand Name English
KETOPROFEN [ORANGE BOOK]
Common Name English
ACTRON
Brand Name English
NEXCEDE
Brand Name English
KETOPROFEN [USP]
Common Name English
19583RP
Code English
ACTRON KETOPROFEN
Brand Name English
Classification Tree Code System Code
WHO-ATC M01AE03
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
WHO-VATC QM01AE53
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
WHO-VATC QM01AE03
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
NDF-RT N0000175722
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
LIVERTOX 533
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
NDF-RT N0000175721
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
WHO-ATC M02AA10
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
NCI_THESAURUS C257
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
NDF-RT N0000000160
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
WHO-VATC QM02AA10
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
CFR 21 CFR 522.1225
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
WHO-ATC M01AE53
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
Code System Code Type Description
INN
3284
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
PRIMARY
WIKIPEDIA
KETOPROFEN
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
PRIMARY
PUBCHEM
3825
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
PRIMARY
CAS
172964-50-0
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
SUPERSEDED
EVMPD
SUB08374MIG
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
PRIMARY
MERCK INDEX
M6622
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
PRIMARY Merck Index
CAS
22161-86-0
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
SUPERSEDED
NCI_THESAURUS
C47578
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
PRIMARY
ChEMBL
CHEMBL571
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
PRIMARY
ECHA (EC/EINECS)
244-759-8
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
PRIMARY
RXCUI
6142
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
PRIMARY RxNorm
LactMed
22071-15-4
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
PRIMARY
CAS
22071-15-4
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
PRIMARY
CAS
154907-35-4
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
SUPERSEDED
DRUG BANK
DB01009
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
PRIMARY
MESH
D007660
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
PRIMARY
EPA CompTox
22071-15-4
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
PRIMARY
IUPHAR
4795
Created by admin on Tue Oct 22 00:34:24 UTC 2019 , Edited by admin on Tue Oct 22 00:34:24 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
ENANTIOMER -> RACEMATE
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
TRANSPORTER -> INHIBITOR
Related Record Type Details
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC