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Home> Encyclopedia >Pharmaceutical Intermediates>Pharmaceuticals and Biochemicals>Pharmaceutical
Flurbiprofen structure
Flurbiprofen structure


Iupac Name:(2R)-2-(3-fluoro-4-phenylphenyl)propanoic acid
CAS No.: 5104-49-4
Molecular Weight:244.265
Modify Date.: 2022-10-30 20:06
Introduction: This product is anti-inflammatory drug for chronic arthritis and pain, inflammation of Deformation joint disease , and pain after surgery and tooth extraction. Mouse oral LD50 of 140mg/kg, rats 640-800mg/kg. View more+
1. Names and Identifiers
1.1 Name
1.2 Synonyms

(-)-Flurbiprofen (+/-)-FLURBIPROFEN (2R)-2-(2-Fluoro-1,1'-biphenyl-4-yl)propanoic acid (2R)-2-(2-Fluoro-4-biphenylyl)propanoic acid (2R)-2-(2-fluorobiphenyl-4-yl)propanoic acid (R)-(&minus)-2-Fluoro-α-methyl-4-biphenylacetic acid (R)-2-Flubiprofen (R)-2-Flurbiprofen (R)-Flurbiprofen [1,1'-Biphenyl]-4-acetic acid, 2-fluoro-α-methyl-, (αR)- 1’-biphenyl)-4-aceticacid,2-fluoro-alpha-methyl-( 1’-biphenyl]-4-aceticacid,2-fluoro-alpha-methyl-[ 2-(2-Fluoro-4-biphenyl)propionicacid 2-(2-fluoro-4-biphenylyl)propionicacid 2-(2-Fluorobiphenyl-4-yl)propionic Acid 2-fluoro-alpha-methyl-4-biphenylaceticaci Adfeed ANSAID ANSIDE Antadys Cebutid EINECS 225-827-6 fp70 froben MFCD00079303 R-(-)-Flurbiprofen R-Flurbiprofen Stayban Zepolas

1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C15H13FO2 (isomer)
1.7 Inchi
1.8 InChkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
2.1 Melting point
110-113 °C
2.1 Boiling point
376.2 °C at 760 mmHg
2.1 Refractive index
2.1 Flash Point
181.3 °C
2.1 Precise Quality
2.1 PSA
2.1 logP
2.1 Solubility
methanol: soluble50mg/mL
2.2 Appearance
White to Almost white powder to crystal
2.3 Storage
Ambient temperatures.
2.4 Color/Form
white to off-white
2.5 pKa
pKa 3.80(H2O) (Uncertain)
2.6 Water Solubility
2.7 StorageTemp
Sealed in dry,Room Temperature
3. Use and Manufacturing
3.1 Usage
This product is anti-inflammatory drug for chronic arthritis and pain, inflammation of Deformation joint disease , and pain after surgery and tooth extraction. Mouse oral LD50 of 140mg/kg, rats 640-800mg/kg.
4. Safety and Handling
4.1 Symbol
4.1 Hazard Codes
4.1 Signal Word
4.1 Risk Statements
4.1 Safety Statements
4.1 Packing Group
4.1 Hazard Class
4.1 Hazard Declaration
UN 2811
4.1 Caution Statement
Missing Phrase - N15.00950417
4.1 WGK Germany

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

2.2 GHS label elements, including precautionary statements

Signal word


Hazard statement(s)

H301 Toxic if swallowed

Precautionary statement(s)

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.


P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P330 Rinse mouth.


P405 Store locked up.


P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification


9. Other Information
9.0 Merck
9.1 Anti-inflammatory analgesics
Flibanserin , also known as flurbiprofen, flurbiprofen, is a potent Phenylalanine anti-inflammatory and antipyretic analgesics,it can inhibit prostaglandin synthesizing cyclooxygenase to have analgesic, anti-inflammatory and antipyretic effects. Its anti-inflammatory and analgesic effects are 250 times and 50 times of aspirin (also known as acetylsalicylic acid) . The oral absorption is rapid , peak plasma concentration achieves after 1.5 hours , half-life is 3.5 hours, it has wide tissue distribution, PPB is 99.4%, it can compete with drugs having a high plasma protein binding rate to bind plasma protein .it Metabolizes in the liver and becomes flurbiprofen hydroxy and its aldehyde acid conjugates. T1/2 is 3.5 h. Urine and fecal excretion,account for approximately 60% and 40% respectively . Age has no effect on drug metabolism. It is Mainly used for rheumatoid arthritis, rheumatoid arthritis, ankylosing spondylitis, osteoarthritis. It is also used in preventing aphakic cystoid patchy edema After surgical removal of the lens, inhibiting pupillary constrictionsurgery, treatment of inflammation after cataract and trabeculoplasty argon laser eye surgery. It Also applies to pain caused by some other reasons such as trauma, sprains, surgery.
9.2 Toxicity
Non-steroidal anti-inflammatory drug (NSAID) has anti-inflammatory, analgesic and antipyretic effects, toxicity ascending ranking is nabumetone, salsalate, sulindac, diclofenac, ibuprofen, one fabric ibuprofen, aspirin, naproxen, tolmetin, flurbiprofen, piroxicam, a phenoxy ibuprofen, indomethacin, mefenamic acid chlorine. Traditional NSAID medications may be the preferred aspirin, if children in the course of treatment can not tolerate its adverse reactions, use of other non-steroidal anti-inflammatory drugs is taken. a selective COX-2 inhibitor Has been developed, which will replace all traditional NSAID. Selective COX-2 inhibitors which has been listed are nimesulide (Nimeng Shu), rofecoxib (Vioxx), celecoxib (Celebrex), etodolac (Rodin), meloxicam. A recent large-scale, international, multi-center, randomized, double-blind technology, prospective study has shown that selective COX-2 inhibitors have few side effects on the gastrointestinal tract, kidneys, having no significant effect on platelet function,it can be used as drug of choice for early combination therapy of JRA children replacing aspirin .
9.3 Adverse reactions
The most common adverse reactions are indigestion, stomach discomfort, occasional headache, skin rash. Peptic ulcer, bronchial asthma patients and pregnant women, lactating women should not take.
Other adverse reactions are nausea, diarrhea, abdominal pain, blurred vision, urinary tract infection symptoms, dermatitis. Few have elevated liver transaminases, continuing medication, may develop, or remain unchanged or disappear. Mild tingling and burning sensations and (or) visual disturbances when it is dropped into the eye.because it leads to platelet aggregation and prolongs bleeding time, it is reported that the application of the drug in the eye surgery increases intraocular hemorrhage Animal experiments, Flibanserin 50~100 mg/kg, medication for three months, can cause renal papillary necrosis. For Humans,it also has this effect.
9.4 Uses
This product is anti-inflammatory drug for chronic arthritis and pain, inflammation of Deformation joint disease , and pain after surgery and tooth extraction. Mouse oral LD50 of 140mg/kg, rats 640-800mg/kg.
9.5 production method
It is obtained by 2-fluoro-linked acetophenone through oxidation, esterification, transesterification, hydrolysis, decarboxylation reaction.
9.6 Chemical Properties
White to Off-White Crystalline Solid
9.7 Uses
An anti-inflammatory used as an analgesic.
9.8 Uses
antiinflammatory, analgesic
9.9 Brand name
Ansaid (Pharmacia & Upjohn).
9.10 Biological Activity
Potent inhibitor of cyclooxygenase (IC 50 values are 0.1 and 0.4 μ M for inhibition of human COX-1 and COX-2 respectively). Analgesic, anti-inflammatory and antipyretic in vivo . Inhibits tumor cell growth in vitro and in vivo . Also inhibits fibroblast proliferation in vitro .
9.11 Description
Flurbiprofen synthesis was originally reported in 1974. During a study of the pharmacological properties of a large number of substituted phenylalkanoic acids, including ibuprofen and ibufenac, the most potent were found to be substituted 2-(4-biphenyl)propionic acids. Further toxicological and pharmacological studies indicated that flurbiprofen possessed the most favorable therapeutic profile, so it was selected for further clinical development. It was not marketed until 1987, when it was introduced as the sodium salt as Ocufen, the first topical NSAID indicated for ophthalmic use in the United States. The indication for Ocufen is the same as that for Profenal—that is, to inhibit intraoperative miosis induced by prostaglandins in cataract surgery.
9.12 Originator
Froben, Boots,UK ,1977
9.13 Indications
Flurbiprofen (Ansaid) is indicated for the treatment of rheumatoid arthritis and osteoarthritis. Its half-life, longer than that of many of the NSAIDs, allows for twice daily dosing.The most common adverse effects of flurbiprofen are similar to those of the other acidic NSAIDs. Flurbiprofen inhibits both COX isoforms about equally.
9.14 Manufacturing Process
A mixture of 3-acetyl-2-fluorobiphenyl, MP 95°C to 96°C, (73.5 g) [prepared from 4.bromo-3-nitroacetophenone (Oelschlage, Ann., 1961, 641, 81) via-4acetyl-2-nitrobiphenyl, MP 106°C to 108°C (Ullman reaction), 4-acetyl-2aminobiphenyl, MP 124°C to 125°C (reduction), and finally the Schiemann reaction], sulfur (17.4 g) and morpholine (87 ml) was refluxed for 16.5 hr, and then the resulting thiomorpholide was hydrolyzed by refluxing with glacial acetic acid (340 ml) concentrated sulfuric acid (54 ml) and water (78 ml) for 24 hr. The cooled solution was diluted with water, and the precipitated crude 2-fluoro-4-biphenylylacetic acid was collected. (A sample was purified by recrystallization to give MP 143°C to 144.5°C; Found (%): C, 73.2; H, 4.8. C14H11FO2 requires C, 73.1; H, 4.8.)
A sodium carbonate solution of the crude acetic acid was washed with ether and then acidified with hydrochloric acid; the required acid was isolated via an ether extraction and was esterified by refluxing for 6 hr with ethanol (370 ml) and concentrated sulfuric acid (15 ml). Excess alcohol was distilled, the residue diluted with water and the required ester isolated in ether. Distillation finally gave ethyl 2-fluoro-4-biphenylacetate, BP 134°C to 136°C/0.25 mm.
This ester (70g) and diethyl carbonate (250 mg) were stirred at 90°C to 100°C while a solution of sodium ethoxide [from sodium (7.8 g) and ethanol (154 ml)] was added over 1 hr. During addition, ethanol was allowed to distill and after addition distillation was continued until the column heat temperature reached 124°C. After cooling the solution to 90°C, dimethyl sulfate (33 ml) was followed by a further 85 ml of diethyl carbonate. This solution was stirred and refluxed for 1 hr and then, when ice cool, was diluted with water and acetic acid (10 ml). The malonate was isolated in ether and fractionally distilled to yield a fraction boiling at 148°C to 153°C/0.075 mm, identified as the alpha-methyl malonate. This was hydrolyzed by refluxing for 1 hr at 2.5 N sodium hydroxide (350 ml) and alcohol (175 ml), excess alcohol was distilled and the residual suspension of sodium salt was acidified with hydrochloric acidto give a precipitate of the alpha-methyl malonic acid. This was decarboxylated by heating at 180°C to 200°C for 30 minutes and recrystallized from petroleum ether (BP 80°C to 100°C) to give 2-(2-fluoro-4biphenylyl)propionic acid, MP 110°C to 111°C
9.15 Brand name
Ansaid (Pharmacia & Upjohn).
9.16 Therapeutic Function
9.17 General Description
Flurbiprofen (Ansaid, Ocufen, Froben), is another drug inthis class indicated for both acute and long-term managementof RA and OA but with a more complex mechanism ofaction. Unlike the other drugs in this class, it does not undergochiral inversion (i.e., the conversion of the “inactive”[R]-enantiomer to the active, [S]-enantiomer). Similar to aspirinand other salicylates, both flurbiprofen enantiomersblock COX-2 induction as well as inhibiting the nuclearfactor-κB-mediated polymorphonuclear leukocyte apoptosissignaling; therefore, both enantiomers are believed to contributeequally to its overall anti-inflammatory action.
(R)-flurbiprofen is actually a strong clinical candidate forthe treatment of Alzheimer disease, because it has beenshown to reduce Aβ42 production by human cells.
9.18 Pharmacokinetics
Flurbiprofen is well absorbed after oral administration, with peak plasma levels being attained within 1.5 hours. Food alters the rate of absorption but not the extent of its bioavailability. It is extensively bound to plasma proteins (99%).and has a plasma half-life of 2 to 4 hours. Metabolism is extensive, with 60 to 70% of flurbiprofen and its metabolites being excreted as sulfate and glucuronide conjugates. Flurbiprofen shows some interesting metabolic patterns, with 40 to 47% as the 4′-hydroxy metabolite, 5% as the 3′,4′-dihydroxy metabolite, 20 to 30% as the 3′-hydroxy- 4′-methoxy metabolite, and the remaining 20 to 25% of the drug being excreted unchanged. None of these metabolites demonstrates significant anti-inflammatory activity.
9.19 Clinical Use
Flurbiprofen is indicated as an oral formulation for the acute or long-term treatment of rheumatoid arthritis and osteoarthritis and as an ophthalmic solution for the inhibition of intraoperative miosis.
9.20 Usage
A cyclooxygenase inhibitor
10. Computational chemical data
  • Molecular Weight: 244.265g/mol
  • Molecular Formula: C15H13FO2
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 244.08995782
  • Monoisotopic Mass: 244.08995782
  • Complexity: 286
  • Rotatable Bond Count: 3
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Topological Polar Surface Area: 37.3
  • Heavy Atom Count: 18
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
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