Dexketoprofen

Structural formula
General
Non-proprietary name	Dexketoprofen
other names	( S ) - (+) - 2- (3-Benzoylphenyl) propionic acid; ( S ) -Ketoprofen;
Molecular formula	C 16 H 14 O 3
External identifiers / databases
EC number	606-944-5
ECHA InfoCard	100.118.639
PubChem	667550
ChemSpider	580922
DrugBank	DB09214
Wikidata	Q425440
Drug information
ATC code	M01 AE17
Drug class	Non-opioid analgesic
properties
Molar mass	254.29 g mol −1
Physical state	firmly
Melting point	75-78 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 301-315-319-335-400
	P: 261-273-301 + 310-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dexketoprofen is a pain reliever and anti-inflammatory drug from the group of non-steroidal anti - inflammatory drugs .

Dexketoprofen is an enantiomer of ketoprofen , i. That is, of the two possible, mirror-image molecules of ketoprofen, it is left-handed .

Clinical information

Application areas (indications)

Dexketoprofen is approved for the symptomatic treatment of mild to moderately severe pain, such as pain in the muscles and the musculoskeletal system, rheumatoid arthritis , juvenile arthritis, osteoarthritis, tension headache , mild migraines , acute headache, toothache, pulpitis , gingivitis , acute dysmenorrhea ( menstrual cramps ). The parenteral , supplied ie by injection, drug form ( Sympal Inject 50 mg solution for injection ) suitable for the symptomatic treatment of moderate to severe acute pain such as postoperative pain, renal colic and back pain, when oral administration is not appropriate. If necessary, the drug of moderate to severe postoperative pain in combination with can opioid - analgesics are applied in the recommended adult dose. Comparative clinical studies, especially against ketoprofen, show extensive analgesic equivalence.

Pharmacological properties

In an in vitro study, ( S ) -ketoprofen was the only enantiomer able to prevent the formation of thromboxane B2 in lymphocytes and thus act as a COX inhibitor.

synthesis

The synthesis of dexketoprofen involves an enzymatic resolution and is described in the literature.

Trade names

Monopreparations

Enantyum (A), Ketesse (A, CH), Sympal (D)

Individual evidence

↑ ^a ^b ^c data sheet (S) - (+) - ketoprofen from Sigma-Aldrich , accessed on March 24, 2011 ( PDF ).
↑ Ezcurdia M, et al .: Comparison of the efficacy and tolerability of dexketoprofen and ketoprofen in the treatment of primary dysmenorrhea. In: J Clin Pharmacol . 1998 Dec; 38 (12 Suppl): pp. 65S-73S; PMID 9882084 .
↑ MH Hanna et al .: Comparative study of analgesic efficacy and morphine-sparing effect of intramuscular dexketoprofen trometamol with ketoprofen or placebo after major orthopedic surgery Br J Clin Pharmacol . 2003 February; 55 (2): pp. 126-133; PMID 12580983 ; PMC 1894736 (free full text, PDF).
↑ PJ Hayball et al .: Enantioselective pharmacodynamics of the nonsteroidal antiinflammatory drug ketoprofen: in vitro inhibition of human platelet cyclooxygenase activity. In: Chirality . 4/8/ 1992 : pp 484-487; PMID 1476858 .
^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substances, 4th edition (2000), 2 volumes published by Thieme-Verlag Stuttgart, p. 613, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.
↑ Red List online, as of September 2009.
↑ AM comp. d. Switzerland, as of September 2009.
↑ AGES Pharmaceutical Specialty Register, as of February 2016.

[Sigma-1] ta sheet (S) - (+) - ketoprofen from Sigma-Aldrich , accessed on March 24, 2011 ( PDF ).

[2] Ezcurdia M, et al .: Comparison of the efficacy and tolerability of dexketoprofen and ketoprofen in the treatment of primary dysmenorrhea. In: J Clin Pharmacol . 1998 Dec; 38 (12 Suppl): pp. 65S-73S; PMID 9882084 .

[3] MH Hanna et al .: Comparative study of analgesic efficacy and morphine-sparing effect of intramuscular dexketoprofen trometamol with ketoprofen or placebo after major orthopedic surgery Br J Clin Pharmacol . 2003 February; 55 (2): pp. 126-133; PMID 12580983 ; PMC 1894736 (free full text, PDF).

[4] PJ Hayball et al .: Enantioselective pharmacodynamics of the nonsteroidal antiinflammatory drug ketoprofen: in vitro inhibition of human platelet cyclooxygenase activity. In: Chirality . 4/8/ 1992 : pp 484-487; PMID 1476858 .

[A._Kleemann-5] Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substances, 4th edition (2000), 2 volumes published by Thieme-Verlag Stuttgart, p. 613, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.

[6] Red List online, as of September 2009.

[7] AM comp. d. Switzerland, as of September 2009.

[8] AGES Pharmaceutical Specialty Register, as of February 2016.