KETOPROFEN SODIUM

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H13O3.Na
Molecular Weight	276.2624
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CC(C([O-])=O)C1=CC=CC(=C1)C(=O)C2=CC=CC=C2

InChI

InChIKey=OAPDLBHLMVYMCW-UHFFFAOYSA-M

InChI=1S/C16H14O3.Na/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);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C16H13O3
Molecular Weight	253.2726
Charge	-1
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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
Release behavior of ketoprofen from poly(acryloyl-L-proline methyl ester) gels having different crosslinked networks.	2001	11416991
Clinical pharmacokinetics of dexketoprofen.	2001	11368291
Overdose of ketoprofen could be dangerous.	2001 Apr	11573649
Intravenous ketoprofen in thyroid and parathyroid surgery.	2001 Apr	11273950
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
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
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
UV-induces formation of hydrogen peroxide based on the photochemistry of ketoprofen.	2001 Feb	11272724
Determination of diclofenac sodium, flufenamic acid, indomethacin and ketoprofen by LC-APCI-MS.	2001 Feb	11272315
Effects of grinding with microcrystalline cellulose and cyclodextrins on the ketoprofen physicochemical properties.	2001 Feb	11266223
Determination of nonsteroidal anti-inflammatory drugs in biological fluids by automatic on-line integration of solid-phase extraction and capillary electrophoresis.	2001 Feb	11258759
Crystal structure of the NADP(H)-dependent ketose reductase from Bemisia argentifolii at 2.3 A resolution.	2001 Feb 16	11237597
Oral ketoprofen in children--could it have been done differently?	2001 Jan	11575403
A comparative experimental study of the effects of diclofenac and ketoprofen on the small-bowel mucosa of canines.	2001 Jan	11271513
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
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
Evaluation of percutaneous absorption and skin irritation of ketoprofen through rat skin: in vitro and in vivo study.	2001 Jul 17	11427353
Stereoselective pharmacokinetics of ketoprofen in llamas following intravenous administration.	2001 Jun	11442802
Enantiospecific pharmacokinetics of ketoprofen in plasma and synovial fluid of horses with acute synovitis.	2001 Jun	11442795
Safety and efficacy of preoperative administration of meloxicam, compared with that of ketoprofen and butorphanol in dogs undergoing abdominal surgery.	2001 Jun	11400845
Simultaneous determination of loxoprofen and its diastereomeric alcohol metabolites in human plasma and urine by a simple HPLC-UV detection method.	2001 Jun	11377045
Intercalation compounds of hydrotalcite-like anionic clays with antiinflammatory agents--I. Intercalation and in vitro release of ibuprofen.	2001 Jun 4	11376964
[Acute pancreatitis and ketoprofen].	2001 Jun-Jul	11673744
I.v. ketoprofen for analgesia after tonsillectomy: comparison of pre- and post-operative administration.	2001 Mar	11573528
[Addition of clonidine to 0.5% lidocaine for intravenous locoregional anesthesia].	2001 Mar	11332061
In vitro and in vivo evaluation of sustained release chitosan-coated ketoprofen microparticles.	2001 Mar	11265119
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
[Allergies to ketoprofen gels].	2001 Mar 31	11317922
Thoracoscopy as a nonpharmacotherapeutic research modification for limiting postoperative chest pain.	2001 Mar-Apr	11396618
Effect of oxidative stress on the structure and function of human serum albumin.	2001 May	11465418
Inhibition of synovial plasma extravasation by preemptive administration of an antiinflammatory irrigation solution in the rat knee.	2001 May	11323366
Effect of preincisional ilioinguinal and iliohypogastric nerve block on postoperative analgesic requirement in day-surgery patients undergoing herniorrhaphy under spinal anaesthesia.	2001 May	11309012
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
Influence of betacyclodextrin on the release of poorly soluble drugs from inert and hydrophilic heterogeneous polymeric matrices.	2001 Oct	11519784
Effects of diclofenac and ketoprofen on nerve conduction velocity in experimental nerve root compression.	2001 Oct 15	11598507
Optimized conditions of bio-mimetic artificial membrane permeation assay.	2001 Oct 9	11576780
Transdermal delivery of ketoprofen using microemulsions.	2001 Oct 9	11576778
Efficacy and safety of ketoprofen lysine salt mouthwash versus benzydamine hydrochloride mouthwash in acute pharyngeal inflammation: a randomized, single-blind study.	2001 Sep	11589263
Comparison of the effects of ketoprofen on platelet function in the presence and absence of aspirin.	2001 Sep	11566459
Photocontact dermatitis to ketoprofen.	2001 Sep	11526526
Antihyperalgesic effects of the muscarinic receptor ligand vedaclidine in models involving central sensitization in rats.	2001 Sep	11514081
In vitro and in vivo evaluation of polyoxyethylene esters as dermal prodrugs of ketoprofen, naproxen and diclofenac.	2001 Sep	11500258

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 `Thu Jul 06 00:44:25 UTC 2023` Edited by `admin` on `Thu Jul 06 00:44:25 UTC 2023`
Record UNII	5R10M39KS7
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

KETOPROFEN SODIUM

Common Name

English

2-(3-BENZOYLPHENYL)PROPIONIC ACID SODIUM SALT

Common Name

English

Ketoprofen sodium [WHO-DD]

Common Name

English

BENZENEACETIC ACID, 3-BENZOYL-.ALPHA.-METHYL-, SODIUM SALT (1:1)

Systematic Name

English

DIRACTIN

Brand Name

English

BENZENEACETIC ACID, 3-BENZOYL-.ALPHA.-METHYL-, SODIUM SALT

Common Name

English

SODIUM KETOPROFEN

Common Name

English

Code System Code Type Description

EVMPD

SUB26651