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-1 127 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10841807	Inhibitor 8297	1.9 nM [IC50]
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10841807	Inhibitor 8297	27.0 nM [IC50]
Interleukin-8 receptors, CXCR1/CXCR2 6 Target ID: CHEMBL2096909 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15974585	Antagonist 2778	50.0 nM [IC50]
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14510637	Inhibitor 8297	0.52 µM [IC50]
Cyclooxygenase-1 127 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14510637	Inhibitor 8297	0.019 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Pain, postoperative 9 Sources: https://clinicaltrials.gov/ct2/show/NCT02568735	Primary	Approved 8429	Keral Approved Use Unknown
Migraine 103 Sources: https://clinicaltrials.gov/ct2/show/NCT02159547	Primary	Approved 8429	Keral Approved Use Unknown
Musculoskeletal pain 10 Sources: https://clinicaltrials.gov/ct2/show/NCT03122314	Primary	Approved 8429	Keral Approved Use Unknown
Pain 614 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c2c99853-1268-4998-a44b-2bf0c0b70fd2	Primary	Approved 8429	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 dysmenorrhea 16 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c2c99853-1268-4998-a44b-2bf0c0b70fd2	Primary	Approved 8429	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
Rheumatoid arthritis 316 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c2c99853-1268-4998-a44b-2bf0c0b70fd2	Primary	Approved 8429	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
Osteoarthritis 157 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c2c99853-1268-4998-a44b-2bf0c0b70fd2	Primary	Approved 8429	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

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 599 OAT2 145 OAT3 642 OAT4 146 MRP2 383 MRP4 204	CYP 270 UGT1A1 418 UGT1A3 422 UGT1A9 380 UGT2B4 249 UGT2B7 389

Drug as perpetrator

Target	Modality	Activity
OAT1 603	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10991954/	yes [IC50 1.3 uM]
MRP2 475	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17005917/	yes [IC50 1.4 uM]
MRP4 238	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17005917/	yes [IC50 11.9 uM]
OAT2 147	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/12388633/	yes [IC50 400 uM]
OAT3 644	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/12388633/	yes [IC50 5.98 uM]
OAT4 146	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/12388633/	yes [IC50 70.3 uM]

Drug as victim

Target	Modality	Activity
CYP 270	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19422321/ Page: 2.0	minor
UGT2B4 249	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0	no
UGT1A1 418	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0	yes
UGT1A3 422	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0	yes
UGT1A9 380	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0	yes
UGT2B7 389	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0	yes

PubMed

Title	Date	PubMed
The feasibility of pain treatment at home after adenoidectomy with ketoprofen tablets in small children.	2000	11012958
Comparison of intravenous and oral ketoprofen for postoperative pain after adenoidectomy in children.	2000 Aug	10992828
R- and S-isomers of nonsteroidal anti-inflammatory drugs differentially regulate cytokine production.	2000 Jun	10903797
Cyclooxygenase-2 expression in lipopolysaccharide-stimulated human monocytes is modulated by cyclic AMP, prostaglandin E(2), and nonsteroidal anti-inflammatory drugs.	2000 Nov 30	11095985
Iatrogenic cost factors incorporating mild and moderate adverse events in the economic comparison of aceclofenac and other NSAIDs.	2001	11548913
Early-morning administration of dexketoprofen-trometamol in morning stiffness induced by nodal osteoarthritis of the hands.	2001	11447775
Release behavior of ketoprofen from poly(acryloyl-L-proline methyl ester) gels having different crosslinked networks.	2001	11416991
Clinical pharmacokinetics of dexketoprofen.	2001	11368291
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.	2001	11228592
Improving gas chromatographic determination of residual solvents in pharmaceuticals by the combined use of headspace solid-phase microextraction and isotopic dilution.	2001 Apr 27	11358250
Simultaneous optimization based on artificial neural networks in ketoprofen hydrogel formula containing O-ethyl-3-butylcyclohexanol as percutaneous absorption enhancer.	2001 Aug	11536204
In vitro distribution of ketoprofen enantiomers in articular tissues of osteoarthritic patients.	2001 Dec	11600284
Analgesic-induced asthma caused by 2.0% ketoprofen adhesive agents, but not by 0.3% agents.	2001 Feb	11300144
Determination of diclofenac sodium, flufenamic acid, indomethacin and ketoprofen by LC-APCI-MS.	2001 Feb	11272315
Determination of nonsteroidal anti-inflammatory drugs in biological fluids by automatic on-line integration of solid-phase extraction and capillary electrophoresis.	2001 Feb	11258759
Five cases of photocontact dermatitis due to topical ketoprofen: photopatch testing and cross-reaction study.	2001 Feb	11169173
Muscle sympathetic nerve responses to physiological changes in prostaglandin production in humans.	2001 Feb	11160062
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
A comparative experimental study of the effects of diclofenac and ketoprofen on the small-bowel mucosa of canines.	2001 Jan	11271513
Efficacy of celecoxib, a cyclooxygenase 2-specific inhibitor, in the treatment of ankylosing spondylitis: a six-week controlled study with comparison against placebo and against a conventional nonsteroidal antiinflammatory drug.	2001 Jan	11212158
Pharmacodynamics and pharmacokinetics of ketoprofen enantiomers in sheep.	2001 Jan	11197566
Effects of anti-inflammatory drugs on lipopolysaccharide-challenged and -unchallenged equine synovial explants.	2001 Jan	11197561
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
Evaluation and structure-activity relationship of synthesized cyclohexanol derivatives on percutaneous absorption of ketoprofen using artificial neural network.	2001 Jan 16	11165080
Novel enzymological profiles of human 11beta-hydroxysteroid dehydrogenase type 1.	2001 Jan 30	11306096
Effect of caffeine on antinociceptive action of ketoprofen in rats.	2001 Jan-Feb	11282174
Allergic reactions due to ibuprofen in children.	2001 Jan-Feb	11207978
Spray-dried microspheres containing ketoprofen formulated into capsules and tablets.	2001 Jan-Feb	11201334
Analgesic profile of peroral and topical ketoprofen upon low pH-induced muscle pain.	2001 Jul	11406335
Evaluation of percutaneous absorption and skin irritation of ketoprofen through rat skin: in vitro and in vivo study.	2001 Jul 17	11427353
Safety and efficacy of preoperative administration of meloxicam, compared with that of ketoprofen and butorphanol in dogs undergoing abdominal surgery.	2001 Jun	11400845
Preparation and evaluation of ketoprofen floating oral delivery system.	2001 Jun 4	11376963
[Acute pancreatitis and ketoprofen].	2001 Jun-Jul	11673744
Neuroprotective effects of non-steroidal anti-inflammatory drugs by direct scavenging of nitric oxide radicals.	2001 Mar	11259508
Effect of lipophilicity on in vivo iontophoretic delivery. I. NSAIDs.	2001 Mar	11256485
NSAIDs bound to methacrylic carriers: microstructural characterization and in vitro release analysis.	2001 Mar 12	11245914
Simultaneous quantification of neutral and acidic pharmaceuticals and pesticides at the low-ng/l level in surface and waste water.	2001 Mar 16	11293584
Chiral resolution of flurbiprofen and ketoprofen enantiomers by HPLC on a glycopeptide-type column chiral stationary phase.	2001 May	11391680
Effect of preincisional ilioinguinal and iliohypogastric nerve block on postoperative analgesic requirement in day-surgery patients undergoing herniorrhaphy under spinal anaesthesia.	2001 May	11309012
Lead-cadmium interaction effect on the responsiveness of rat mesenteric vessels to norepinephrine and angiotensin II.	2001 May 21	11369112
An oral controlled release matrix pellet formulation containing nanocrystalline ketoprofen.	2001 May 21	11337168
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	11697757
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	11564815
Optimized conditions of bio-mimetic artificial membrane permeation assay.	2001 Oct 9	11576780
Comparison of the effects of ketoprofen on platelet function in the presence and absence of aspirin.	2001 Sep	11566459
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 `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

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