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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H14O3
Molecular Weight 254.2806
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXKETOPROFEN

SMILES

C[C@H](C(O)=O)C1=CC(=CC=C1)C(=O)C2=CC=CC=C2

InChI

InChIKey=DKYWVDODHFEZIM-NSHDSACASA-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)/t11-/m0/s1

HIDE SMILES / InChI

Molecular Formula C16H14O3
Molecular Weight 254.2806
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including 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

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.9 nM [IC50]
27.0 nM [IC50]
50.0 nM [IC50]
0.52 µM [IC50]
0.019 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Keral

Approved Use

Unknown
Primary
Keral

Approved Use

Unknown
Primary
Keral

Approved Use

Unknown
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

1992
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

1992
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

1992
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

1992
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: Page: p. 34
unhealthy, 36.8 years (range: 18 - 65 years)
n = 90
Health Status: unhealthy
Age Group: 36.8 years (range: 18 - 65 years)
Sex: M+F
Population Size: 90
Sources: Page: p. 34
Disc. AE: Rash...
AEs leading to
discontinuation/dose reduction:
Rash (mild, 1 patient)
Sources: Page: p. 34
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
n = 172
Health Status: unhealthy
Condition: tendinitis
Age Group: adult
Population Size: 172
Sources:
100 ug 3 times / day steady, oral (max)
Dose: 100 ug, 3 times / day
Route: oral
Route: steady
Dose: 100 ug, 3 times / day
Sources:
unhealthy
n = 50
Health Status: unhealthy
Condition: Lymphedema
Population Size: 50
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
n = 19
Health Status: unhealthy
Condition: Lymphedema
Population Size: 19
Sources:
Other AEs: Rash...
Other AEs:
Rash (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
n = 23
Health Status: unhealthy
Condition: Lymphedema
Population Size: 23
Sources:
Other AEs: Cellulitis...
Other AEs:
Cellulitis (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: Page: p. 34
unhealthy, 36.8 years (range: 18 - 65 years)
n = 90
Health Status: unhealthy
Age Group: 36.8 years (range: 18 - 65 years)
Sex: M+F
Population Size: 90
Sources: Page: p. 34
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 (max)
Dose: 100 ug, 3 times / day
Route: oral
Route: steady
Dose: 100 ug, 3 times / day
Sources:
unhealthy
n = 50
Health Status: unhealthy
Condition: Lymphedema
Population Size: 50
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
n = 19
Health Status: unhealthy
Condition: Lymphedema
Population Size: 19
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
n = 23
Health Status: unhealthy
Condition: Lymphedema
Population Size: 23
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
Drug as perpetrator​

Drug as perpetrator​

Drug as victim
PubMed

PubMed

TitleDatePubMed
Iatrogenic cost factors incorporating mild and moderate adverse events in the economic comparison of aceclofenac and other NSAIDs.
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
Clinical pharmacokinetics of dexketoprofen.
2001
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
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
Preparation and evaluation of ketoprofen floating oral delivery system.
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
Lead-cadmium interaction effect on the responsiveness of rat mesenteric vessels to norepinephrine and angiotensin II.
2001 May 21
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

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
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)
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:54:23 GMT 2023
Edited
by admin
on Fri Dec 15 15:54:23 GMT 2023
Record UNII
6KD9E78X68
Record Status Validated (UNII)
Record Version
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Name Type Language
DEXKETOPROFEN
INN   WHO-DD  
INN  
Official Name English
ARVELES
Brand Name English
dexketoprofen [INN]
Common Name English
BENZENEACETIC ACID, 3-BENZOYL-.ALPHA.-METHYL-, (.ALPHA.S)-
Systematic Name English
BENZENEACETIC ACID, 3-BENZOYL-.ALPHA.-METHYL-, (S)-
Common Name English
Dexketoprofen [WHO-DD]
Common Name English
(S)-2-(3-BENZOYLPHENYL)PROPANOIC ACID
Systematic Name English
(S)-KETOPROFEN
Common Name English
(.ALPHA.S)-3-BENZOYL-.ALPHA.-METHYLBENZENEACETIC ACID
Common Name English
(2S)-2-(3-BENZOYLPHENYL)PROPIONIC ACID
Systematic Name English
(+)-KETOPROFEN
Common Name English
(+)-2-(3-BENZOYLPHENYL)PROPIONIC ACID
Systematic Name English
(+)-(S)-M-BENZOYLHYDRATROPIC ACID
Systematic Name English
(S)-(+)-2-(3-BENZOYLPHENYL)PROPIONIC ACID
Systematic Name English
KETOPROFEN, (S)-
Common Name English
HYDRATROPIC ACID, M-BENZOYL-, (+)-
Common Name English
Classification Tree Code System Code
WHO-ATC M02AA27
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
WHO-VATC QM01AE17
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
WHO-ATC M01AE17
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
NCI_THESAURUS C257
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
WHO-ATC N02AJ14
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID40905141
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
PRIMARY
EVMPD
SUB07034MIG
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
PRIMARY
INN
7120
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
PRIMARY
RXCUI
237162
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
PRIMARY RxNorm
SMS_ID
100000083407
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
PRIMARY
DRUG CENTRAL
833
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
PRIMARY
NCI_THESAURUS
C87321
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
PRIMARY
DRUG BANK
DB09214
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
PRIMARY
CAS
22161-81-5
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
PRIMARY
WIKIPEDIA
DEXKETOPROFEN
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
PRIMARY
FDA UNII
6KD9E78X68
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
PRIMARY
PUBCHEM
667550
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
PRIMARY
ChEMBL
CHEMBL75435
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
PRIMARY
CHEBI
76128
Created by admin on Fri Dec 15 15:54:23 GMT 2023 , Edited by admin on Fri Dec 15 15:54:23 GMT 2023
PRIMARY
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