DEXKETOPROFEN

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21052564https://www.drugs.com/international/dexketoprofen.html
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cyclooxygenase-1 125 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10841807	Inhibitor 8228	1.9 nM [IC50]
Cyclooxygenase-2 192 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10841807	Inhibitor 8228	27.0 nM [IC50]
Interleukin-8 receptors, CXCR1/CXCR2 6 Target ID: CHEMBL2096909 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15974585	Antagonist 2760	50.0 nM [IC50]
Cyclooxygenase-2 192 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14510637	Inhibitor 8228	0.52 µM [IC50]
Cyclooxygenase-1 125 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14510637	Inhibitor 8228	0.019 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Pain, postoperative 9 Sources: https://clinicaltrials.gov/ct2/show/NCT02568735	Primary	Approved 8360	Keral Approved Use Unknown
Migraine 103 Sources: https://clinicaltrials.gov/ct2/show/NCT02159547	Primary	Approved 8360	Keral Approved Use Unknown
Musculoskeletal pain 10 Sources: https://clinicaltrials.gov/ct2/show/NCT03122314	Primary	Approved 8360	Keral Approved Use Unknown
Pain 608 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c2c99853-1268-4998-a44b-2bf0c0b70fd2	Primary	Approved 8360	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 7.2498243E11
Primary dysmenorrhea 16 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c2c99853-1268-4998-a44b-2bf0c0b70fd2	Primary	Approved 8360	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 7.2489599E11
Rheumatoid arthritis 313 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c2c99853-1268-4998-a44b-2bf0c0b70fd2	Primary	Approved 8360	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 7.2489599E11
Osteoarthritis 157 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c2c99853-1268-4998-a44b-2bf0c0b70fd2	Primary	Approved 8360	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 7.2489599E11

C_max

Value	Dose	Co-administered	Analyte	Population
10.1 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7439263	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

Value	Dose	Co-administered	Analyte	Population
21.91 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7439263	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.13 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7439263	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

Dose	Population	Adverse events
12.5 mg single, oral Dose: 12.5 mg Route: oral Route: single Dose: 12.5 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022470s000medr.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022470s000medr.pdf Page: p. 34	Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (mild, 1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022470s000medr.pdf Page: p. 34
2400 mg single, oral Overdose Dose: 2400 mg Route: oral Route: single Dose: 2400 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/019816s011lbl.pdf	unhealthy, 45 years Health Status: unhealthy Age Group: 45 years Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/019816s011lbl.pdf	Other AEs: Epigastric pain... Other AEs: Epigastric pain (mild, 1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/019816s011lbl.pdf
100 mg 1 times / day multiple, topical Dose: 100 mg, 1 times / day Route: topical Route: multiple Dose: 100 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16078335/	unhealthy, adult n = 172 Health Status: unhealthy Condition: tendinitis Age Group: adult Population Size: 172 Sources: https://pubmed.ncbi.nlm.nih.gov/16078335/	Sources: https://pubmed.ncbi.nlm.nih.gov/16078335/
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: https://clinicaltrials.gov/ct2/show/NCT02257970	unhealthy n = 50 Health Status: unhealthy Condition: Lymphedema Population Size: 50 Sources: https://clinicaltrials.gov/ct2/show/NCT02257970	Other AEs: Cellulitis... Other AEs: Cellulitis (below serious, 3 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT02257970
75 ug 3 times / day steady, oral Dose: 75 ug, 3 times / day Route: oral Route: steady Dose: 75 ug, 3 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT02257970	unhealthy n = 19 Health Status: unhealthy Condition: Lymphedema Population Size: 19 Sources: https://clinicaltrials.gov/ct2/show/NCT02257970	Other AEs: Rash... Other AEs: Rash (below serious, 1 patient) Sources: https://clinicaltrials.gov/ct2/show/NCT02257970
75 ug 3 times / day steady, oral Dose: 75 ug, 3 times / day Route: oral Route: steady Dose: 75 ug, 3 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT02257970	unhealthy n = 23 Health Status: unhealthy Condition: Lymphedema Population Size: 23 Sources: https://clinicaltrials.gov/ct2/show/NCT02257970	Other AEs: Cellulitis... Other AEs: Cellulitis (below serious, 1 patient) Sources: https://clinicaltrials.gov/ct2/show/NCT02257970

AEs

AE	Significance	Dose	Population
Rash	mild, 1 patient Disc. AE	12.5 mg single, oral Dose: 12.5 mg Route: oral Route: single Dose: 12.5 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022470s000medr.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022470s000medr.pdf Page: p. 34
Epigastric pain	mild, 1 patient	2400 mg single, oral Overdose Dose: 2400 mg Route: oral Route: single Dose: 2400 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/019816s011lbl.pdf	unhealthy, 45 years Health Status: unhealthy Age Group: 45 years Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/019816s011lbl.pdf
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: https://clinicaltrials.gov/ct2/show/NCT02257970	unhealthy n = 50 Health Status: unhealthy Condition: Lymphedema Population Size: 50 Sources: https://clinicaltrials.gov/ct2/show/NCT02257970
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: https://clinicaltrials.gov/ct2/show/NCT02257970	unhealthy n = 19 Health Status: unhealthy Condition: Lymphedema Population Size: 19 Sources: https://clinicaltrials.gov/ct2/show/NCT02257970
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: https://clinicaltrials.gov/ct2/show/NCT02257970	unhealthy n = 23 Health Status: unhealthy Condition: Lymphedema Population Size: 23 Sources: https://clinicaltrials.gov/ct2/show/NCT02257970

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 595 OAT2 144 OAT3 636 OAT4 145 MRP2 367 MRP4 203	CYP 266 UGT1A1 418 UGT1A3 422 UGT1A9 380 UGT2B4 249 UGT2B7 389

Drug as perpetrator

Target	Modality	Activity
OAT1 599	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/10991954/	yes [IC50 1.3 uM]
MRP2 459	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/17005917/	yes [IC50 1.4 uM]
MRP4 237	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/17005917/	yes [IC50 11.9 uM]
OAT2 146	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/12388633/	yes [IC50 400 uM]
OAT3 638	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/12388633/	yes [IC50 5.98 uM]
OAT4 145	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/12388633/	yes [IC50 70.3 uM]

Drug as victim

Target	Modality	Activity
CYP 266	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/19422321/ Page: 2.0	minor
UGT2B4 249	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0	no
UGT1A1 418	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0	yes
UGT1A3 422	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0	yes
UGT1A9 380	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0	yes
UGT2B7 389	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0	yes

PubMed

Title	Date	PubMed
R- and S-isomers of nonsteroidal anti-inflammatory drugs differentially regulate cytokine production.	2000 Jun	10903797
Modeling cyclooxygenase inhibition. Implication of active site hydration on the selectivity of ketoprofen analogues.	2000 Jun 1	10841807
Photosensitivity to ketoprofen: mechanisms and pharmacoepidemiological data.	2000 May	10830251
Aceclofenac: a reappraisal of its use in the management of pain and rheumatic disease.	2001	11511027
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.	2001	11228592
Interaction between the antinociceptive effect of ketoprofen and adrenergic modulatory systems.	2001 Aug	11580099
Binding constant determination of drugs toward subdomain IIIA of human serum albumin by near-infrared dye-displacement capillary electrophoresis.	2001 Aug	11519955
Investigation of the utility of an in vitro release test for optimizing semisolid dosage forms.	2001 Aug	11485188
UV-induces formation of hydrogen peroxide based on the photochemistry of ketoprofen.	2001 Feb	11272724
Five cases of photocontact dermatitis due to topical ketoprofen: photopatch testing and cross-reaction study.	2001 Feb	11169173
Evidence for significant differences in microsomal drug glucuronidation by canine and human liver and kidney.	2001 Feb	11159800
Double-blind parallel comparison of multiple doses of ketorolac, ketoprofen and placebo administered orally to patients with postoperative dental pain.	2001 Feb 1	11166979
Behavioural effects of laparotomy and analgesic effects of ketoprofen and carprofen in rats.	2001 Feb 1	11166971
Oral ketoprofen in children--could it have been done differently?	2001 Jan	11575403
Pharmacodynamics and pharmacokinetics of ketoprofen enantiomers in sheep.	2001 Jan	11197566
Perioperative intravenous ketoprofen neither prolongs operation time nor delays discharge after adenoidectomy in children.	2001 Jan	11123733
[Dexketoprofen-trometamol and tramadol in acute lumbago].	2001 Jan 11	11217678
Allergic reactions due to ibuprofen in children.	2001 Jan-Feb	11207978
Comparison of tissue concentrations after intramuscular and topical administration of ketoprofen.	2001 Jul	11496958
[Enantiomeric separation of drugs based on macrocyclic antibiotics].	2001 Jul	11475888
Safety and efficacy of preoperative administration of meloxicam, compared with that of ketoprofen and butorphanol in dogs undergoing abdominal surgery.	2001 Jun	11400845
Simultaneous photocontact sensitivity to ketoprofen and oxybenzone.	2001 Jun	11380553
Preparation and evaluation of ketoprofen floating oral delivery system.	2001 Jun 4	11376963
[Ketoprofen-induced acute hepatitis].	2001 Jun-Jul	11673741
In vitro and in vivo evaluation of sustained release chitosan-coated ketoprofen microparticles.	2001 Mar	11265119
[Allergies to ketoprofen gels].	2001 Mar 31	11317922
Chiral resolution of flurbiprofen and ketoprofen enantiomers by HPLC on a glycopeptide-type column chiral stationary phase.	2001 May	11391680
Inhibition of synovial plasma extravasation by preemptive administration of an antiinflammatory irrigation solution in the rat knee.	2001 May	11323366
An oral controlled release matrix pellet formulation containing nanocrystalline ketoprofen.	2001 May 21	11337168
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	11386636
Optimized conditions of bio-mimetic artificial membrane permeation assay.	2001 Oct 9	11576780
Efficacy and safety of ketoprofen lysine salt mouthwash versus benzydamine hydrochloride mouthwash in acute pharyngeal inflammation: a randomized, single-blind study.	2001 Sep	11589263
Incompatibility of prochlorperizine and ketoprofen.	2001 Sep	11550690
Functional characterization of rat organic anion transporter 2 in LLC-PK1 cells.	2001 Sep	11504818

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 `Wed Jul 05 23:22:51 UTC 2023` Edited by `admin` on `Wed Jul 05 23:22:51 UTC 2023`
Record UNII	6KD9E78X68
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEXKETOPROFEN

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