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

Details

Stereochemistry RACEMIC
Molecular Formula C16H14O3
Molecular Weight 254.2806
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 No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
Effects of nonsteroidal anti-inflammatory drugs on hemostasis in patients with aneurysmal subarachnoid hemorrhage.
1999 Jul
Use of continuous fluid drainage for severe polyhydramnios due to twin to twin transfusion syndrome.
2001
Intravenous ketoprofen in thyroid and parathyroid surgery.
2001 Apr
In vitro distribution of ketoprofen enantiomers in articular tissues of osteoarthritic patients.
2001 Dec
UV-induces formation of hydrogen peroxide based on the photochemistry of ketoprofen.
2001 Feb
Determination of diclofenac sodium, flufenamic acid, indomethacin and ketoprofen by LC-APCI-MS.
2001 Feb
Effects of grinding with microcrystalline cellulose and cyclodextrins on the ketoprofen physicochemical properties.
2001 Feb
Behavioural effects of laparotomy and analgesic effects of ketoprofen and carprofen in rats.
2001 Feb 1
A comparative experimental study of the effects of diclofenac and ketoprofen on the small-bowel mucosa of canines.
2001 Jan
Evaluation and structure-activity relationship of synthesized cyclohexanol derivatives on percutaneous absorption of ketoprofen using artificial neural network.
2001 Jan 16
Novel enzymological profiles of human 11beta-hydroxysteroid dehydrogenase type 1.
2001 Jan 30
Comparison of tissue concentrations after intramuscular and topical administration of ketoprofen.
2001 Jul
Age-related changes in skin permeability of hydrophilic and lipophilic compounds in rats.
2001 Mar
Neuroprotective effects of non-steroidal anti-inflammatory drugs by direct scavenging of nitric oxide radicals.
2001 Mar
[Allergies to ketoprofen gels].
2001 Mar 31
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
Measurement of ketoprofen in horse urine using gas chromatography-mass spectrometry.
2001 Oct
Transdermal delivery of ketoprofen using microemulsions.
2001 Oct 9
[ Ambulatory laparoscopic gynecological surgery in Africa: feasibility].
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. 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 17:13:32 GMT 2023
Edited
by admin
on Fri Dec 15 17:13:32 GMT 2023
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 [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
NSC-758144
Code English
(±)-KETOPROFEN
Common Name English
ANEOL
Brand Name English
HYDRATROPIC ACID, M-BENZOYL-
Common Name English
KETOPROFEN [JAN]
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 [EP IMPURITY]
Common Name English
KETOPROFEN [USAN]
Common Name English
CAPISTEN
Brand Name English
KETOPROFEN [ORANGE BOOK]
Common Name English
ACTRON
Brand Name English
Ketoprofen [WHO-DD]
Common Name English
NEXCEDE
Brand Name English
KETOPROFEN [EP MONOGRAPH]
Common Name English
19583RP
Code English
KETOPROFEN [USP IMPURITY]
Common Name English
ACTRON KETOPROFEN
Brand Name English
Classification Tree Code System Code
WHO-ATC M01AE03
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
WHO-VATC QM01AE53
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
WHO-VATC QM01AE03
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
NDF-RT N0000175722
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
LIVERTOX NBK548678
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
NDF-RT N0000175721
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
WHO-ATC M02AA10
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
NCI_THESAURUS C257
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
NDF-RT N0000000160
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
WHO-VATC QM02AA10
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
CFR 21 CFR 522.1225
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
WHO-ATC M01AE53
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
Code System Code Type Description
CHEBI
6128
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
INN
3284
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
WIKIPEDIA
KETOPROFEN
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
PUBCHEM
3825
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
FDA UNII
90Y4QC304K
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
SMS_ID
100000091768
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
CAS
172964-50-0
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
SUPERSEDED
EVMPD
SUB08374MIG
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
MERCK INDEX
m6622
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY Merck Index
LACTMED
Ketoprofen
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
DRUG CENTRAL
1528
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
CAS
22161-86-0
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
SUPERSEDED
NSC
758144
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
NCI_THESAURUS
C47578
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
DAILYMED
90Y4QC304K
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
ChEMBL
CHEMBL571
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
ECHA (EC/EINECS)
244-759-8
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
RXCUI
6142
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY RxNorm
CAS
22071-15-4
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
CAS
154907-35-4
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
SUPERSEDED
DRUG BANK
DB01009
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
MESH
D007660
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
RS_ITEM_NUM
1356632
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
EPA CompTox
DTXSID6020771
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
IUPHAR
4795
Created by admin on Fri Dec 15 17:13:33 GMT 2023 , Edited by admin on Fri Dec 15 17:13:33 GMT 2023
PRIMARY
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ENANTIOMER -> RACEMATE
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ASSAY (TITRATION)
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC