Ketoprofen

Structural formula
	( R ) shape (top) and ( S ) shape (bottom)
General
Non-proprietary name	Ketoprofen
other names	( RS ) -2- (3-Benzoylphenyl) propionic acid ( IUPAC ); (±) - (3-Benzoylphenyl) propionic acid;
Molecular formula	C 16 H 14 O 3
External identifiers / databases
EC number	244-759-8
ECHA InfoCard	100.040.676
PubChem	3825
ChemSpider	3693
DrugBank	DB01009
Wikidata	Q409192
Drug information
ATC code	M01 AE03 ; M02 AA10 ;
Drug class	Non-opioid analgesic
properties
Molar mass	254.28 g mol −1
Physical state	firmly
Melting point	94 ° C
solubility	255 ± 2 mg l −1 (37 ° C, pH 1.2); 529 ± 5 mg l −1 (37 ° C, pH 4.5);
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 301-315-319-335
	P: 261-301 + 310-305 + 351 + 338
Toxicological data	62.4 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ketoprofen , for example under the trade names Fastum Gel and Spondylon , is an analgesic drug from the group of acidic, non-opioid analgesics .

application areas

Ketoprofen is indicated for the symptomatic treatment of pain and inflammation in acute flare-ups of wear-related joint and spinal diseases ( osteoarthritis ) and in acute and chronic joint inflammation ( arthritis ), especially rheumatoid arthritis and inflammatory rheumatic diseases of the spinal column such as ankylosing spondylitis . Ketoprofen has also been used for the experimental treatment of lymphedema in animal studies.

effect

Ketoprofen inhibits the production of prostaglandin by preventing the function of its key enzyme, cyclooxygenase . Clinical studies confirm the different efficacy of the two enantiomers [( R ) form and ( S ) form].

Side effects

Like all acidic antipyretic anti-inflammatory and non-acidic antipyretic analgesics, ketoprofen is poorly tolerated in the gastrointestinal tract . Nausea and vomiting are therefore the most common side effects . Other common side effects are diarrhea and stomach cramps. Light sensitization has been known at least since 1995 .

Contraindication

Ketoprofen is contraindicated in severe liver and kidney diseases.

interaction

Ketoprofen delays blood coagulation , which should be taken into account when taking anticoagulants (e.g. acetylsalicylic acid , warfarin , phenprocoumon ) at the same time . The coagulation values must then be checked. At the same time applied externally to the UV filter stabilizer octocrylene may occur reinforced Photosensibilierung.

Stereoisomerism

Ketoprofen occurs in two enantiomeric forms and is used in therapy as a racemate [1: 1 mixture of the ( S ) - and ( R ) form] as well as the pure enantiomer dexketoprofen ( INN ), which contains the ( S ) Shape represents.

Trade names

Monopreparations

Alrheumun (D), Dolormin pain gel with Ketoprofen (D), Effekton Gel with Ketoprofen (D), Fastum Gel (A, CH), Gabrilen (D), Ketospray (A), Phardol (D), Profenid (A), Spondylon (D), Ketoselect (I), OKI (I).

Combination preparations

with Ceftiofur : Curacef duo (veterinary medicine)

Individual evidence

↑ Entry on ketoprofen. In: Römpp Online . Georg Thieme Verlag, accessed on June 14, 2014.
↑ ^a ^b K. Tsinman, A. Avdeef, O. Tsinman, D. Voloboy: Powder Dissolution Method for Estimating Rotating Disk Intrinsic Dissolution Rates of Low Solubility Drugs in Pharm Res 26 (2009) 2093-2100. doi : 10.1007 / s11095-009-9921-3
↑ ^a ^b ^c Ketoprofen data sheet from Sigma-Aldrich , accessed on April 7, 2011 ( PDF ).

↑ Tian W, Rockson SG, Jiang X, Kim J, Begaye A, Shuffle EM, Tu AB, Cribb M, Nepiyushchikh Z, Feroze AH, Zamanian RT, Dhillon RT, Voelkel NF, Peters-Golden M, Kitajewski J, Dixon JB , Nicolls MR: Leukotriene B4 antagonism ameliorates experimental lymphedema . In: Science Translational Medicine . tape 9 , no. 389 , 2017, p. eaal3920 , doi : 10.1126 / scitranslmed.aal3920 , PMID 28490670 .

↑ PJ Hayball, RL Nation, F. Bochner, LN Sansom, MJ Ahern and MD Smith: The influence of renal function of the enantioselective pharmacokinetics and pharmacodynamics of ketoprofen in patients with rheumatoid arthritis , British Journal of Clinical Pharmacology 36 (1993) 185– 193.

↑ LIGHT AWARENESS THROUGH MEDICINAL PRODUCTS. (No longer available online.) In: at 1995; No. 7: 70 - 2nd medicine telegram, archived from the original on February 3, 2016 ; Retrieved on August 7, 2010 : "Antirheumatics: ... Ketoprofen (ALRHEUMUN et al.)" Info: The archive link was automatically inserted and not yet checked. Please check the original and archive link according to the instructions and then remove this notice.

↑ Committee for Medicinal Products for Human Use (CHMP): Questions and answers on the review of the marketing authorizations for topical formulations of ketoprofen. (83.5 kB; PDF) In: Questions & Answers-EMA / 465107/2010. European Medicines Agency, July 22, 2010, p. 2 , accessed on August 7, 2010 (English): ".... adverse skin reactions when topical ketoprofen is used together with octocrylene."

↑ Red List Online, as of August 2009.

↑ Swiss Medicines Compendium , status; August 2009

↑ AGES-PharmMed, as of February 2016.

[RÖMPP_Online-1] Entry on ketoprofen. In: Römpp Online . Georg Thieme Verlag, accessed on June 14, 2014.

[Tsinman-2] K. Tsinman, A. Avdeef, O. Tsinman, D. Voloboy: Powder Dissolution Method for Estimating Rotating Disk Intrinsic Dissolution Rates of Low Solubility Drugs in Pharm Res 26 (2009) 2093-2100. doi : 10.1007 / s11095-009-9921-3

[sigma-3] Ketoprofen data sheet from Sigma-Aldrich , accessed on April 7, 2011 ( PDF ).

[4] Tian W, Rockson SG, Jiang X, Kim J, Begaye A, Shuffle EM, Tu AB, Cribb M, Nepiyushchikh Z, Feroze AH, Zamanian RT, Dhillon RT, Voelkel NF, Peters-Golden M, Kitajewski J, Dixon JB , Nicolls MR: Leukotriene B4 antagonism ameliorates experimental lymphedema . In: Science Translational Medicine . tape 9 , no. 389 , 2017, p. eaal3920 , doi : 10.1126 / scitranslmed.aal3920 , PMID 28490670 .

[Hayball-5] PJ Hayball, RL Nation, F. Bochner, LN Sansom, MJ Ahern and MD Smith: The influence of renal function of the enantioselective pharmacokinetics and pharmacodynamics of ketoprofen in patients with rheumatoid arthritis , British Journal of Clinical Pharmacology 36 (1993) 185– 193.

[6] LIGHT AWARENESS THROUGH MEDICINAL PRODUCTS. (No longer available online.) In: at 1995; No. 7: 70 - 2nd medicine telegram, archived from the original on February 3, 2016 ; Retrieved on August 7, 2010 : "Antirheumatics: ... Ketoprofen (ALRHEUMUN et al.)" Info: The archive link was automatically inserted and not yet checked. Please check the original and archive link according to the instructions and then remove this notice. @1@ 2

[7] Committee for Medicinal Products for Human Use (CHMP): Questions and answers on the review of the marketing authorizations for topical formulations of ketoprofen. (83.5 kB; PDF) In: Questions & Answers-EMA / 465107/2010. European Medicines Agency, July 22, 2010, p. 2 , accessed on August 7, 2010 (English): ".... adverse skin reactions when topical ketoprofen is used together with octocrylene."

[8] Red List Online, as of August 2009.

[9] Swiss Medicines Compendium , status; August 2009

[10] AGES-PharmMed, as of February 2016.