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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

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2937024 https://www.ncbi.nlm.nih.gov/pubmed/970297

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 Due to its side effects it was withdrawn from the UK in 1984.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Triiodothyronine metabolism
69.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Flenac

Approved Use

Acute and long-term use in the relief of signs and symptoms of ankylosing spondylitis (delayed-release tablets); acute treatment of migraine attacks with or without aura in adults (oral solution); relief of mild to moderate pain (immediate-release capsules and tablets); relief of signs and symptoms of osteoarthritis and rheumatoid arthritis (immediate-release, ER, and delayed-release tablets); treatment of primary dysmenorrhea (immediate-release tablets).
Palliative
Flenac

Approved Use

Acute and long-term use in the relief of signs and symptoms of ankylosing spondylitis (delayed-release tablets); acute treatment of migraine attacks with or without aura in adults (oral solution); relief of mild to moderate pain (immediate-release capsules and tablets); relief of signs and symptoms of osteoarthritis and rheumatoid arthritis (immediate-release, ER, and delayed-release tablets); treatment of primary dysmenorrhea (immediate-release tablets).
Palliative
Flenac

Approved Use

Acute and long-term use in the relief of signs and symptoms of ankylosing spondylitis (delayed-release tablets); acute treatment of migraine attacks with or without aura in adults (oral solution); relief of mild to moderate pain (immediate-release capsules and tablets); relief of signs and symptoms of osteoarthritis and rheumatoid arthritis (immediate-release, ER, and delayed-release tablets); treatment of primary dysmenorrhea (immediate-release tablets).
PubMed

PubMed

TitleDatePubMed
Penicillamine induced myasthenia reactivated by gold.
1984 Jan 21
Patents

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.
Name Type Language
FENCLOFENAC
INN   MART.   USAN   WHO-DD  
INN   USAN  
Official Name English
Fenclofenac [WHO-DD]
Common Name English
RX-67408
Code English
R 67408
Code English
BENZENEACETIC ACID, 2-(2,4-DICHLOROPHENOXY)-
Common Name English
FENCLOFENAC [MART.]
Common Name English
RX 67408
Code English
R-67408
Code English
(O-(2,4-DICHLOROPHENOXY)PHENYL)ACETIC ACID
Common Name English
fenclofenac [INN]
Common Name English
FENCLOFENAC [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1323
Created by admin on Fri Dec 15 15:35:00 GMT 2023 , Edited by admin on Fri Dec 15 15:35:00 GMT 2023
Code System Code Type Description
CAS
34645-84-6
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PRIMARY
NCI_THESAURUS
C65643
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SMS_ID
100000081267
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MESH
C012970
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FDA UNII
Y01JW64D01
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WIKIPEDIA
FENCLOFENAC
Created by admin on Fri Dec 15 15:35:00 GMT 2023 , Edited by admin on Fri Dec 15 15:35:00 GMT 2023
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INN
3488
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ECHA (EC/EINECS)
252-126-2
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EPA CompTox
DTXSID6048830
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PUBCHEM
65394
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EVMPD
SUB07549MIG
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ChEMBL
CHEMBL15677
Created by admin on Fri Dec 15 15:35:00 GMT 2023 , Edited by admin on Fri Dec 15 15:35:00 GMT 2023
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DRUG CENTRAL
1147
Created by admin on Fri Dec 15 15:35:00 GMT 2023 , Edited by admin on Fri Dec 15 15:35:00 GMT 2023
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