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Withdrawn NSAID drug used in rheumatism
Fenclofenac
Names
Preferred IUPAC name
[2-(2,4-Dichlorophenoxy)phenyl]acetic acid
Identifiers
ChEMBL
ChemSpider
ECHA InfoCard
100.047.373
UNII
InChI=1S/C14H10Cl2O3/c15-10-5-6-13(11(16)8-10)19-12-4-2-1-3-9(12)7-14(17)18/h1-6,8H,7H2,(H,17,18)
Key: IDKAXRLETRCXKS-UHFFFAOYSA-N
InChI=1/C14H10Cl2O3/c15-10-5-6-13(11(16)8-10)19-12-4-2-1-3-9(12)7-14(17)18/h1-6,8H,7H2,(H,17,18)
Key: IDKAXRLETRCXKS-UHFFFAOYAG
OC(=O)Cc1ccccc1Oc2ccc(Cl)cc2Cl
Properties
C14 H10 Cl2 O3
Molar mass
297.1 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Fenclofenac is a
nonsteroidal anti-inflammatory drug (NSAID) previously used in
rheumatism . It has mild
immunosuppressive effects
[1] and may displace
thyroid hormone from its
binding protein .
[2]
[3] It can also cause
lichen planus .
[4]
Due to its side effects it was withdrawn from the UK and US in the 1980s.
References
^ Spiers EM, Watson NT, Beck JS, Chapman IV, Dettmar PW (November 1993). "The effect of fenclofenac on the regeneration of lymphocytes in rats following total body irradiation". Int. J. Immunopharmacol . 15 (8): 865–9.
doi :
10.1016/0192-0561(93)90003-h .
PMID
7902830 .
^ Allen PA, Taylor RT (December 1980).
"Fenclofenac and thyroid function tests" . Br Med J . 281 (6255): 1642.
doi :
10.1136/bmj.281.6255.1642 .
PMC
1715072 .
PMID
7448557 .
^ Taylor R, Clark F, Griffiths ID, Weeke J (October 1980).
"Prospective study of effect of fenclofenac on thyroid function tests" . Br Med J . 281 (6245): 911–2.
doi :
10.1136/bmj.281.6245.911 .
PMC
1714224 .
PMID
7427506 .
^ Ferguson MM, Wiesenfeld D, MacDonald DG (1984). "Oral mucosal lichenoid eruption due to fenclofenac". J Oral Med . 39 (1): 39–40.
PMID
6232357 .
Receptor (
ligands )
DP (D2 ) Tooltip Prostaglandin D2 receptor
DP1 Tooltip Prostaglandin D2 receptor 1
DP2 Tooltip Prostaglandin D2 receptor 2
EP (E2 ) Tooltip Prostaglandin E2 receptor
EP1 Tooltip Prostaglandin EP1 receptor
EP2 Tooltip Prostaglandin EP2 receptor
EP3 Tooltip Prostaglandin EP3 receptor
EP4 Tooltip Prostaglandin EP4 receptor Unsorted
FP (F2α ) Tooltip Prostaglandin F receptor
IP (I2 ) Tooltip Prostacyclin receptor
TP (TXA2 ) Tooltip Thromboxane receptor Unsorted
Enzyme (
inhibitors )
COX (
PTGS )
PGD2 S Tooltip Prostaglandin D synthase
PGES Tooltip Prostaglandin E synthase
PGFS Tooltip Prostaglandin F synthase
PGI2 S Tooltip Prostacyclin synthase
TXAS Tooltip Thromboxane A synthase
Others