U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C16H14O3
Molecular Weight 254.2812
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of KETOPROFEN

SMILES

CC(c1cccc(c1)C(=O)c2ccccc2)C(=O)O

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

Description
Curator's Comment:: https://clinicaltrials.gov/ct2/show/NCT02159547 | https://www.ncbi.nlm.nih.gov/pubmed/28540716 | https://clinicaltrials.gov/ct2/show/NCT03122314 | https://www.ncbi.nlm.nih.gov/pubmed/28326850 | https://clinicaltrials.gov/ct2/show/NCT02092012

Dexketoprofen is a nonsteroidal anti-inflammatory drug (NSAID), manufactured by Menarini under the tradename Keral. Dexketoprofen is indicated for short-term treatment of mild to moderate pain, including dysmenorrhoea. Dexketoprofen works by blocking the action of a substance in the body called cyclo-oxygenase, which is involved in the production of chemicals in the body called prostaglandins. Prostaglandins are produced in response to injury or certain diseases and would otherwise go on to cause swelling, inflammation, and pain. By blocking cyclo-oxygenase, dexketoprofen prevents the production of prostaglandins and therefore reduces inflammation and pain. Along with peripheral analgesic action, it possesses central analgesic action. Dexketoprofen may cause dizziness, and patients should not, therefore, drive or operate heavy machinery or vehicles until they are familiar with how dexketoprofen affects them. Concomitant use of alcohol and other sedatives may potentiate this effect. In a small subset of individuals, the dizziness may be intolerable and require the transition to an alternative treatment.

CNS Activity

Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/9176993

Originator

Curator's Comment:: 1967

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Keral
Primary
Keral
Primary
Keral
Primary
KETOPROFEN

Approved Use

Ketoprofen capsules USP are indicated for the management of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Ketoprofen capsules USP are indicated for the management of pain. Ketoprofen capsules USP are also indicated for treatment of primary dysmenorrhea.

Launch Date

724982400000
Primary
KETOPROFEN

Approved Use

Ketoprofen capsules USP are indicated for the management of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Ketoprofen capsules USP are indicated for the management of pain. Ketoprofen capsules USP are also indicated for treatment of primary dysmenorrhea.

Launch Date

724896000000
Primary
KETOPROFEN

Approved Use

Ketoprofen capsules USP are indicated for the management of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Ketoprofen capsules USP are indicated for the management of pain. Ketoprofen capsules USP are also indicated for treatment of primary dysmenorrhea.

Launch Date

724896000000
Primary
KETOPROFEN

Approved Use

Ketoprofen capsules USP are indicated for the management of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Ketoprofen capsules USP are indicated for the management of pain. Ketoprofen capsules USP are also indicated for treatment of primary dysmenorrhea.

Launch Date

724896000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
10.1 μg/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
KETOPROFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
21.91 μg × h/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
KETOPROFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.13 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
KETOPROFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
12.5 mg single, oral
Dose: 12.5 mg
Route: oral
Route: single
Dose: 12.5 mg
Sources:
unhealthy, 36.8 years (range: 18 - 65 years)
Health Status: unhealthy
Age Group: 36.8 years (range: 18 - 65 years)
Sex: M+F
Sources:
Disc. AE: Rash...
AEs leading to
discontinuation/dose reduction:
Rash (mild, 1 patient)
Sources:
2400 mg single, oral
Overdose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
unhealthy, 45 years
Health Status: unhealthy
Age Group: 45 years
Sex: F
Sources:
Other AEs: Epigastric pain...
Other AEs:
Epigastric pain (mild, 1 patient)
Sources:
100 mg 1 times / day multiple, topical
Dose: 100 mg, 1 times / day
Route: topical
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
100 ug 3 times / day steady, oral
Dose: 100 ug, 3 times / day
Route: oral
Route: steady
Dose: 100 ug, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Other AEs: Cellulitis...
Other AEs:
Cellulitis (below serious, 3 patients)
Sources:
75 ug 3 times / day steady, oral
Dose: 75 ug, 3 times / day
Route: oral
Route: steady
Dose: 75 ug, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Other AEs: Cellulitis...
Other AEs:
Cellulitis (below serious, 1 patient)
Sources:
75 ug 3 times / day steady, oral
Dose: 75 ug, 3 times / day
Route: oral
Route: steady
Dose: 75 ug, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Other AEs: Rash...
Other AEs:
Rash (below serious, 1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Rash mild, 1 patient
Disc. AE
12.5 mg single, oral
Dose: 12.5 mg
Route: oral
Route: single
Dose: 12.5 mg
Sources:
unhealthy, 36.8 years (range: 18 - 65 years)
Health Status: unhealthy
Age Group: 36.8 years (range: 18 - 65 years)
Sex: M+F
Sources:
Epigastric pain mild, 1 patient
2400 mg single, oral
Overdose
Dose: 2400 mg
Route: oral
Route: single
Dose: 2400 mg
Sources:
unhealthy, 45 years
Health Status: unhealthy
Age Group: 45 years
Sex: F
Sources:
Cellulitis below serious, 3 patients
100 ug 3 times / day steady, oral
Dose: 100 ug, 3 times / day
Route: oral
Route: steady
Dose: 100 ug, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Cellulitis below serious, 1 patient
75 ug 3 times / day steady, oral
Dose: 75 ug, 3 times / day
Route: oral
Route: steady
Dose: 75 ug, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Rash below serious, 1 patient
75 ug 3 times / day steady, oral
Dose: 75 ug, 3 times / day
Route: oral
Route: steady
Dose: 75 ug, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
Drug as perpetrator​

Drug as perpetrator​

Drug as victim
Sourcing
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
Overdose of ketoprofen could be dangerous.
2001 Apr
Intravenous ketoprofen in thyroid and parathyroid surgery.
2001 Apr
Improving gas chromatographic determination of residual solvents in pharmaceuticals by the combined use of headspace solid-phase microextraction and isotopic dilution.
2001 Apr 27
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
Analgesic-induced asthma caused by 2.0% ketoprofen adhesive agents, but not by 0.3% agents.
2001 Feb
Oral ketoprofen in children--could it have been done differently?
2001 Jan
Novel enzymological profiles of human 11beta-hydroxysteroid dehydrogenase type 1.
2001 Jan 30
Effect of caffeine on antinociceptive action of ketoprofen in rats.
2001 Jan-Feb
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
Simultaneous determination of loxoprofen and its diastereomeric alcohol metabolites in human plasma and urine by a simple HPLC-UV detection method.
2001 Jun
Selective inhibition of interleukin-8-induced neutrophil chemotaxis by ketoprofen isomers.
2001 Jun 1
Intercalation compounds of hydrotalcite-like anionic clays with antiinflammatory agents--I. Intercalation and in vitro release of ibuprofen.
2001 Jun 4
Preparation and evaluation of ketoprofen floating oral delivery system.
2001 Jun 4
I.v. ketoprofen for analgesia after tonsillectomy: comparison of pre- and post-operative administration.
2001 Mar
Simultaneous quantification of neutral and acidic pharmaceuticals and pesticides at the low-ng/l level in surface and waste water.
2001 Mar 16
[Allergies to ketoprofen gels].
2001 Mar 31
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
Effect of ketoprofen on muscle function and sEMG activity after eccentric exercise.
2001 May
Inhibition of synovial plasma extravasation by preemptive administration of an antiinflammatory irrigation solution in the rat knee.
2001 May
Effect of preincisional ilioinguinal and iliohypogastric nerve block on postoperative analgesic requirement in day-surgery patients undergoing herniorrhaphy under spinal anaesthesia.
2001 May
Lead-cadmium interaction effect on the responsiveness of rat mesenteric vessels to norepinephrine and angiotensin II.
2001 May 21
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
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
Patents

Sample Use Guides

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.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment:: In cultivation of freshly isolated epidermal cells, 5 mM Ketoprofen inhibited the culture-promoted expression of PCl-augmented expression of major histocompatibility complex class II and CD86 on Langerhans cells
5 mM Ketoprofen (mouse isolated epidermal cells)
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
BENZENEACETIC ACID, 3-BENZOYL-.ALPHA.-METHYL-
Systematic Name English
ORUDIS
Brand Name English
KETOPROFEN [USP MONOGRAPH]
Common Name English
(+/-)-M-BENZOYLHYDRATROPIC ACID
Systematic Name English
IDEA-033
Code English
KETOPROFEN [WHO-DD]
Common Name English
NSC-758144
Code English
(+/-)-KETOPROFEN
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 [EP MONOGRAPH]
Common 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 Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
WHO-VATC QM01AE53
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
WHO-VATC QM01AE03
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
NDF-RT N0000175722
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
LIVERTOX 533
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
NDF-RT N0000175721
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
WHO-ATC M02AA10
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
NCI_THESAURUS C257
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
NDF-RT N0000000160
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
WHO-VATC QM02AA10
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
CFR 21 CFR 522.1225
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
WHO-ATC M01AE53
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
Code System Code Type Description
INN
3284
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY
WIKIPEDIA
KETOPROFEN
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY
PUBCHEM
3825
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY
FDA UNII
90Y4QC304K
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY
CAS
172964-50-0
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
SUPERSEDED
EVMPD
SUB08374MIG
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY
MERCK INDEX
M6622
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY Merck Index
LACTMED
Ketoprofen
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY
USP_CATALOG
1356632
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY USP-RS
DRUG CENTRAL
1528
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY
CAS
22161-86-0
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
SUPERSEDED
NCI_THESAURUS
C47578
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL571
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY
ECHA (EC/EINECS)
244-759-8
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY
RXCUI
6142
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY RxNorm
CAS
22071-15-4
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY
CAS
154907-35-4
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
SUPERSEDED
DRUG BANK
DB01009
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY
MESH
D007660
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY
EPA CompTox
22071-15-4
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY
IUPHAR
4795
Created by admin on Fri Jun 25 21:04:45 UTC 2021 , Edited by admin on Fri Jun 25 21:04:45 UTC 2021
PRIMARY