Flurbiprofen

Structural formula
	1: 1 mixture (racemate) of ( R ) -form (top) and ( S ) -form (bottom)
General
Non-proprietary name	Flurbiprofen
other names	( RS ) -2- (2-fluoro-4-biphenylyl) propionic acid; (±) -2- (2-Fluoro-4-biphenylyl) -propionic acid; rac -2- (2-fluoro-4-biphenylyl) propionic acid; ( RS ) -2- (2-fluoro-4-biphenylyl) propanoic acid; (±) -2- (2-Fluoro-4-biphenylyl) propanoic acid; rac -2- (2-fluoro-4-biphenylyl) propanoic acid;
Molecular formula	C 15 H 13 FO 2
External identifiers / databases
EC number	225-827-6
ECHA InfoCard	100.023.479
PubChem	3394
ChemSpider	3277
DrugBank	DB00712
Wikidata	Q419890
Drug information
ATC code	M01 AE09 ; M02 AA19 ; S01 BC04 ;
Drug class	Non-opioid analgesics
properties
Molar mass	244.26 g · mol -1
Physical state	firmly
Melting point	110-112 ° C
pK s value	4.16
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
	P: 301 + 310
Toxicological data	117 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 .

Flurbiprofen is a drug from the group of non-steroidal anti-inflammatory drugs (NSAIDs).

Clinical information

Application areas (indications)

Since flurbiprofen has anti-inflammatory, analgesic and decongestant effects, it has a wide range of applications. It is used, for example, for the local treatment of sore throats, but also for conjunctivitis after an eye operation.

Drug interactions

An enhancement of the effect and an increase in the risk of side effects is favored by taking flurbiprofen at the same time as anticoagulants , glucocorticoids , or diuretics .

Use during pregnancy and breastfeeding

During pregnancy and especially when breastfeeding, flurbiprofen should not be taken or only taken after consulting a doctor, as small amounts of it pass into breast milk.

Adverse effects (side effects)

Common side effects are dry mouth, gastrointestinal discomfort and headache.

Pharmacological properties

Mechanism of action

Flurbiprofen is a nonsteroidal anti-inflammatory drug that inhibits cyclooxygenases . In addition, its ( R ) -isomer in particular has a gamma-secretase-inhibiting effect.

metabolism

Flurbiprofen is mainly metabolized in the liver by the enzyme cytochrome P450 2C9 . The active metabolite is 4-hydroxyflurbiprofen.

Chemistry and stereoisomerism

Several multistep syntheses are described in the literature. Flurbiprofen is chiral and has a stereogenic center. It is used as a 1: 1 mixture ( racemate ) of the ( R ) form and the ( S ) form. The pure right-handed form is ( R ) -Flurbiprofen - the eutomer - has the non-proprietary name Tarenflurbil .

Trade names

Monopreparations

Benactiv Gola (I), Dobendan Direkt (D), Froben (CH), Ocuflur (D), Strepsils (A, D, CH)

Individual evidence

↑ ^a ^b ^c Flurbiprofen data sheet at Sigma-Aldrich , accessed on April 2, 2011 ( PDF ).

↑ ^a ^b Entry on Flurbiprofen. In: Römpp Online . Georg Thieme Verlag, accessed on May 29, 2014.

↑ Beher D, Clarke EE, Wrigley JD, et al. : Selected non-steroidal anti-inflammatory drugs and their derivatives target gamma-secretase at a novel site. Evidence for an allosteric mechanism . In: J. Biol. Chem. . 279, No. 42, October 2004, pp. 43419-26. doi : 10.1074 / jbc.M404937200 . PMID 15304503 .

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

↑ Red List Online, as of August 2009.

↑ Am Comp. d. Switzerland, as of August 2009.

↑ AGES-PharmMed, as of August 2009.

[sigma-1] Flurbiprofen data sheet at Sigma-Aldrich , accessed on April 2, 2011 ( PDF ).

[RÖMPP_Online-2] Entry on Flurbiprofen. In: Römpp Online . Georg Thieme Verlag, accessed on May 29, 2014.

[pmid15304503-3] Beher D, Clarke EE, Wrigley JD, et al. : Selected non-steroidal anti-inflammatory drugs and their derivatives target gamma-secretase at a novel site. Evidence for an allosteric mechanism . In: J. Biol. Chem. . 279, No. 42, October 2004, pp. 43419-26. doi : 10.1074 / jbc.M404937200 . PMID 15304503 .

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

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

[6] Am Comp. d. Switzerland, as of August 2009.

[7] AGES-PharmMed, as of August 2009.