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Details

Stereochemistry ACHIRAL
Molecular Formula C14H10Cl2O3
Molecular Weight 297.133
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FENCLOFENAC

SMILES

OC(=O)CC1=C(OC2=C(Cl)C=C(Cl)C=C2)C=CC=C1

InChI

InChIKey=IDKAXRLETRCXKS-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C14H10Cl2O3
Molecular Weight 297.133
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Fenclofenac (Flenac) is a non-steroidal anti-inflammatory drug previously used in rheumatism. Fenclofenac was shown to possess anti-inflammatory, antinociceptive and antipyretic properties. Flenac is an acetic acid nonsteroidal antiinflammatory drug (NSAID) with analgesic and antipyretic properties. Flenac is used to treat pain, dysmenorrhea, ocular inflammation, osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, and actinic keratosis. It has mild immunosuppressive effects and may displace thyroid hormone from its binding protein. The antiinflammatory effects of Flenac are believed to be due to inhibition of both leukocyte migration and the enzyme cylooxygenase (COX-1 and COX-2), leading to the peripheral inhibition of prostaglandin synthesis. As prostaglandins sensitize pain receptors, inhibition of their synthesis is responsible for the analgesic effects of Flenac. Antipyretic effects may be due to action on the hypothalamus, resulting in peripheral dilation, increased cutaneous blood flow, and subsequent heat dissipation. Fenclofenac, despite passing animal toxicity tests in 10 animal species (mice, rats, guinea pigs, ferrets, rabbits, cats, dogs, pigs, horses, and monkeys), produced severe liver toxicity in humans. Due to its side effects it was withdrawn from the UK in 1984.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
69.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Flenac
Palliative
Flenac
Palliative
Flenac

Cmax

ValueDoseCo-administeredAnalytePopulation
18.2 μg/mL
200 mg single, oral
FENCLOFENAC plasma
Homo sapiens
45.3 μg/mL
500 mg single, oral
FENCLOFENAC plasma
Homo sapiens
63.5 μg/mL
600 mg single, oral
FENCLOFENAC plasma
Homo sapiens
86.9 μg/mL
600 mg 2 times / day steady-state, oral
FENCLOFENAC plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
457 μg × h/mL
200 mg single, oral
FENCLOFENAC plasma
Homo sapiens
1323 μg × h/mL
500 mg single, oral
FENCLOFENAC plasma
Homo sapiens
1716 μg × h/mL
600 mg single, oral
FENCLOFENAC plasma
Homo sapiens
884 μg × h/mL
600 mg 2 times / day steady-state, oral
FENCLOFENAC plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
24.2 h
200 mg single, oral
FENCLOFENAC plasma
Homo sapiens
32.4 h
500 mg single, oral
FENCLOFENAC plasma
Homo sapiens
27.2 h
600 mg single, oral
FENCLOFENAC plasma
Homo sapiens
25.9 h
600 mg 2 times / day steady-state, oral
FENCLOFENAC plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
0.5%
FENCLOFENAC plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Osteoarthritis Flenac free acid capsules: 35 mg orally 3 times a day Flenac potassium immediate-release tablets: 50 mg orally 2 or 3 times a day Flenac sodium enteric-coated tablets: 50 mg orally 2 or 3 times a day or 75 mg orally 2 times a day Maximum dose: 150 mg daily Flenac sodium extended-release tablets: 100 mg orally once a day
Route of Administration: Oral
In Vitro Use Guide
Fenclofenac inhibited cellular uptake of T3 in rat H4 hepatoma cells with IC50 69 uM.
Substance Class Chemical
Record UNII
Y01JW64D01
Record Status Validated (UNII)
Record Version