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Respiratory system drug stubs
Flurbiprofen
Другие языки:

Flurbiprofen

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Flurbiprofen
Flurbiprofen.svg
Clinical data
Trade names Ansaid, Ocufen, Strepfen
Other names (±)-2-fluoro-α-methyl-(1,1'-biphenyl)-4-acetic acid
AHFS/Drugs.com Monograph
MedlinePlus a687005
Pregnancy
category
  • AU: B2
Routes of
administration		 By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding > 99%
Metabolism Liver (CYP2C9)
Elimination half-life 4.7-5.7 hours
Excretion Kidney
Identifiers
  • (RS)-2-(2-fluorobiphenyl-4-yl)propanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard 100.023.479
Chemical and physical data
Formula C15H13FO2
Molar mass 244.265 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
Melting point 117 °C (243 °F)
  • Fc2cc(ccc2c1ccccc1)C(C(=O)O)C
  • InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18) checkY
  • Key:SYTBZMRGLBWNTM-UHFFFAOYSA-N checkY
  (verify)

Flurbiprofen is a member of the phenylalkanoic acid derivative family of nonsteroidal anti-inflammatory drugs (NSAIDs). It is primarily indicated as a pre-operative anti-miotic (in an ophthalmic solution) as well as orally for arthritis or dental pain. Side effects are analogous to those of ibuprofen.

It was derived from propionic acid by the research arm of Boots UK during the 1960s, a period which also included the discovery of ibuprofen, indometacin, diclofenac, naproxen, ketoprofen, and sulindac.

It was patented in 1964 by Boots UK and approved for medical use in 1987. It was approved in the US in 1988; the first generic was approved in 1994.

Adverse effects

In October 2020, the U.S. Food and Drug Administration (FDA) required the drug label to be updated for all nonsteroidal anti-inflammatory medications to describe the risk of kidney problems in unborn babies that result in low amniotic fluid. They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.

Society and culture

Brand names

As of 2016 the drug was available worldwide as drops for ophthalmic use and as tablets, both in various strengths, under many brand names which include: Acustop Cataplasma, Adofeed, Anazin, Anflupin, Anorcid, Ansaid, Antadys, Antafen, Antipain, Baenazin, Benactiv, Biprofin, Biprotec, Bro-Z, Brufen, Brufoz, Cebutid, Clinadol, Coryfin, Dispain, Edolfene, Eyeflur, Falken, Fiera, Flu Ro Fen, Flubifix, Flufen, Flugalin, Flupe, Flur di fen, Fluractive, Fluran, Flurbi Pap, Flurbic, Flurbiprofen, Flurbiprofène, Flurbiprofeno, Flurflex, Flurofen, Fluroptic, Fo Bi Pu Luo Fun, Forphen, Fortine, Froben, Frolix, Fubifen, Fubiprofen, Fubofen, Fukon, Fulruban, Furofen, Kai Fen, Kavoflog, Kotton, Lefenine, Majezik, Maprofen, Maxaljin, Maximus, Meiprofen, Neliacan, Nibelon, Nirolex Gola, Ocufen, Ocuflur, Optifen, Orofaringeo, Painil, Profen, Projezik, Ropion, Sigmaprofen, Stayban, Strefen, Strepfen, Strepflam, Strepsils (various formulations), Sulan, Tie Shr Shu, TransAct, Upnon, Urbifen, Yakuban, Zepolas, Zeralgo, Zero-P, and Zeton.

Synthesis

Patent quotation: "It has anti-inflammatory activity which is about 240 times that of aspirin and analgesic activity which is about 180 times that of aspirin in standard laboratory tests."

Thieme Improved method: Patented method:

The Malonic ester synthesis between 2,4-Difluoronitrobenzene [446-35-5] (1) and Diethyl methylmalonate [609-08-5] (2) gives Diethyl (3-fluoro-4-nitrophenyl)methylmalonate [78543-06-3] (3). The catalytic hydrogenation of the nitro group gives Diethyl (4-amino-3-fluorophenyl)methylmalonate [78543-08-5] (4). Sandmeyer reaction of the diazonium salt with benzene (5) apparently gives CID:13065233 (6). Saponification of the esters gives 2-(2-Fluorobiphenyl-4-yl)-2,3-dimethylbutanedioic acid [42771-82-4] (7). Boiling in acid causes decarboxylation, completing the synthesis of Flurbiprofen (8).

Further reading



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