ChemicalBook--->CAS DataBase List--->22071-15-4

22071-15-4

22071-15-4 Structure

22071-15-4 Structure
IdentificationMore
[Name]

Ketoprofen
[CAS]

22071-15-4
[Synonyms]

2-(3-BENZOYLPHENYL)PROPANOIC ACID
2-(3-BENZOYLPHENYL)PROPIONIC ACID
2-(meta-benzoylphenyl) propionic acid
3-BENZOYL-ALPHA-METHYL-BENZENEACETIC ACID
alrheumat
KETOPROFEN
M-BENZOYLHYDRATROPIC ACID
ORUDIS
ORUVAIL
RARECHEM AL BO 1306
19583 RP
19583rp
2-(3-benzoylphenyl)-propionicaci
2-(m-Benzoylphenyl)propionic acid
2-(m-benzoylphenyl)propionicacid
3-benzoyl-alpha-methyl-benzeneaceticaci
3-Benzoylhydratropic acid
3-benzoylhydratropicacid
acide(benzoyl-3-phenyl)-2-propionique
Alrheumun
[EINECS(EC#)]

244-759-8
[Molecular Formula]

C16H14O3
[MDL Number]

MFCD00055790
[Molecular Weight]

254.28
[MOL File]

22071-15-4.mol
Chemical PropertiesBack Directory
[Appearance]

White Crystalline Solid
[Melting point ]

93-96°C
[Boiling point ]

357.5°C (rough estimate)
[density ]

1.1565 (rough estimate)
[refractive index ]

1.5600 (estimate)
[storage temp. ]

0-6°C
[solubility ]

Slightly soluble in chloroform and methanol.
[form ]

solid
[pka]

pKa 5.94(MeOH/H2O) (Uncertain)
[color ]

White to Off-White
[Water Solubility ]

209mg/L(room temperature)
[Usage]

Anti-inflammatory; analgesic
[Merck ]

5305
[Contact allergens]

Ketoprofen is an anti-inflammatory drug, used both topically and systemically. It is above all a photoaller- gen, responsible for photoallergic or photo-worsened contact dermatitis, with sun-induced, progressive, severe, and durable reactions. Recurrent photosensitiv- ity is possible for many years. Photosensitivities are expected to thiophene-phenylketone derivatives such as tiaprofenic acid and suprofen, to ketoprofen esters such as piketoprofen, and to benzophenone derivatives (see above) such as fenofibrate and benzophenone-3. Concomitant photosensitivities without clinical rel- evance have been observed to fenticlor, tetrachloro- salicylanilide, triclosan, tribromsalan, and bithionol.
[InChIKey]

DKYWVDODHFEZIM-UHFFFAOYSA-N
[CAS DataBase Reference]

22071-15-4(CAS DataBase Reference)
[NIST Chemistry Reference]

Ketoprofen(22071-15-4)
[EPA Substance Registry System]

22071-15-4(EPA Substance)
Hazard InformationBack Directory
[Chemical Properties]

White Crystalline Solid
[Uses]

Anti-inflammatory; analgesic
[Uses]

Ketoprofen, a propionic acid derivative, is a nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties.
[Uses]

Natural Vitamin B12. analog
[Definition]

ChEBI: An oxo monocarboxylic acid that consists of propionic acid substituted by a 3-benzoylphenyl group at position 2.
[Description]

Ketoprofen (3-benzoyl-α-methylphenylacetic acid) is a 2-arylpropionic acid potent non-steroidal anti-inflammatory drug. It was first synthesized by French chemist Rhone Poulenc in 1967. In 1973, it was introduced into France and the United States as an anti-inflammatory drug. It has good effects on rheumatism, rheumatoid arthritis, myelitis and gout, and its anti-inflammatory effect is stronger than that of ibuprofen. Ibuprofen. At the same dose, its anti-inflammatory and analgesic effect is 150 times that of aspirin, its antipyretic effect is 4 times that of indomethacin and 100 times that of aspirin. Because ketoprofen has high efficacy, short half-life, It has the advantages of simple metabolism and few and mild adverse reactions, and has been widely used in the treatment of various types of pain, inflammatory symptoms, colds and post-operative anti-inflammatory analgesia.
[Description]

Ketoprofen is a chemical that comes in the form of a white crystalline powder; odorless or nearly odorless. It is very soluble in methanol, soluble in ethanol, acetone or ether, and almost insoluble in water. The melting point is about 93-96 °C. For the arylalkanoic acid compounds. Has analgesic, anti-inflammatory and antipyretic effects. The anti-inflammatory effect is stronger than that of ibuprofen, with less side effects and low toxicity. Oral and easily absorbed from the gastrointestinal tract. After 1 administration, the peak plasma concentration can be reached in about 0.5 to 2 hours. t 1/2 is 1.6 to 1.9 hours. In the blood and plasma protein binding force is extremely strong. The excretion rate from urine is 30% to 90% within 24 hours. Mainly excreted in the form of glucuronic acid conjugates. For rheumatoid arthritis, rheumatoid arthritis, osteoarthritis, ankylosing spondylitis and gout, etc.
[Originator]

Profenid,Specia,France,1973
[Indications]

Ketoprofen (Orudis) is indicated for use in rheumatoid and osteoarthritis, for mild to moderate pain, and in dysmenorrhea. The most frequently reported side effects are GI (dyspepsia, nausea, abdominal pain, diarrhea, constipation, and flatulence) and CNS related (headache, excitation). Edema and increased blood urea nitrogen have also been noted in more than 3% of patients. Ketoprofen can cause fluid retention and increases in plasma creatinine, particularly in the elderly and in patients taking diuretics.
[Manufacturing Process]

In an initial step, the sodium derivative of ethyl (3-benzoylphenyl) cyanoacetate is prepared as follows: (3-benzoylphenyl)acetonitrile (170 9) is dissolved in ethyl carbonate (900 g). There is added, over a period of 2 hours, a sodium ethoxide solution [prepared from sodium (17.7 g) and anhydrous ethanol (400 cc)], the reaction mixture being heated at about 105° to 115°C and ethanol being continuously distilled. A product precipitates. Toluene (500 cc) is added, and then, after distillation of 50 cc of toluene, the product is allowed to cool. Diethyl ether (600 cc) is added and the mixture is stirred for 1 hour. The crystals which form are filtered off and washed with diethyl ether (600 cc) to give the sodium derivative of ethyl (3-benzoylphenyl)cyanoacetate (131 g).
Then, ethyl methyl(3-benzoylphenyl)cyanoacetate employed as an intermediate material is prepared as follows: The sodium derivative of ethyl (3-benzoylphenyl)cyanoacetate (131 g) is dissolved in anhydrous ethanol (2 liters). Methyl iodide (236 g) is added and the mixture is heated under reflux for 22 hours, and then concentrated to dryness under reduced pressure (10 mm Hg). The residue is taken up in methylene chloride (900 cc) and water (500 cc) and acidified with 4N hydrochloric acid (10 cc). The methylene chloride solution is decanted, washed with water (400 cc) and dried over anhydrous sodium sulfate. The methylene chloride solution is filtered through a column containing alumina (1,500 g). Elution is effected with methylene chloride (6 liters), and the solvent is evaporated under reduced pressure (10 mm Hg) to give ethyl methyl(3-benzoylphenyl)cyanoacetate (48 g) in the form of an oil.
In the final production preparation, a mixture of ethyl methyl(3- benzoylphenyl)cyanoacetate (48 g), concentrated sulfuric acid (125 cc) and water (125 cc) is heated under reflux under nitrogen for 4 hours, and water (180 cc) is then added. The reaction mixture is extracted with diethyl ether (300 cc) and the ethereal solution is extracted with N sodium hydroxide (300 cc). The alkaline solution is treated with decolorizing charcoal (2 g) and then acidified with concentrated hydrochloric acid (40 cc). An oil separates out, which is extracted with methylene chloride (450 cc), washed with water (100 cc) and dried over anhydrous sodium sulfate. The product is concentrated to dryness under reduced pressure (20 mm Hg) to give a brown oil (33.8 g).
This oil is dissolved in benzene (100 cc) and chromatographed through silica (430 g). After elution with ethyl acetate, there is collected a fraction of 21 liters, which is concentrated to dryness under reduced pressure (20 mm Hg). The crystalline residue (32.5 g) is recrystallized from acetonitrile (100 cc) and a product (16.4 g), MP 94°C, is obtained. On recrystallization from a mixture of benzene (60 cc) and petroleum ether (200 cc), there is finally obtained 2- (3-benzoylphenyl)propionic acid (13.5 g), MP 94°C.
[Brand name]

Actron (Bayer); Orudis (Wyeth); Oruvail (Wyeth).
[Therapeutic Function]

Antiinflammatory
[General Description]

Ketoprofen (Orudis, Rhodis) and suprofen (Profenal) areclosely related to fenoprofen in their structures, properties,and indications. Even though ketoprofen has been approvedfor OTC use (Orudis KT, Actron), its GI side effects aresimilar to indomethacin, and therefore its useshould be closely monitored, especially in patients with GIor renal problems.
[Biochem/physiol Actions]

It serves as an efficient drug to treat ankylosing spondylitis, rheumatoid arthritis and osteoarthritis. It also has antipyretic and analgesic effects. Ketoprofen prevents the action of prostaglandin synthetase.
[Pharmacokinetics]

Ketoprofen is rapidly and nearly completely absorbed on oral administration, reaching peak plasma levels within 0.5 to 2 hours. It is highly plasma protein bound (99%) despite a lower acidity (pKa = 5.9) than some other NSAIDs. Wide variation in plasma half-lives has been reported. It is metabolized by glucuronidation of the carboxylic acid, CYP3A4 and CYP2C9 hydroxylation of the benzoyl ring, and reduction of the keto function.
[Pharmacology]

The pharmacologically active isomer is mainly the S(+)- enantiomer, which is available in some countries as the trometamol (2-amino-2-(hydroxymethyl)- 1,3-propanediol) salt. As compared to the racemate, absorption of the S(+)-isomer is said to be faster, leading to an earlier onset of action . The peak plasma concentration after oral administration occurs within 2 h. Ketoprofen is bound to plasma protein up to 99% and shows a plasma elimination half-life of 1.5to 4 h.
[Clinical Use]

Ketoprofen, unlike many NSAIDs, inhibits the synthesis of leukotrienes and leukocyte migration into inflamed joints in addition to inhibiting the biosynthesis of prostaglandins. It stabilizes the lysosomal membrane during inflammation, resulting in decreased tissue destruction. Antibradykinin activity also has been observed. Bradykinin is released during inflammation and can activate peripheral pain receptors. In addition to anti-inflammatory activity, ketoprofen also possesses antipyretic and analgetic properties. Although it is less potent than indomethacin as an anti-inflammatory agent and an analgetic, its ability to produce gastric lesions is about the same.
[Safety Profile]

Poison by ingestion,subcutaneous, intravenous, rectal, and intraperitoneal routes. Human systemic effects by an unspecified route:headache, nausea or vomiting, and degenerative changesin the brain, changes in kidney tubules. An experimentalteratogen.
[Synthesis]

Ketoprofen, 2-(3-benzoyl)propionic acid (3.2.37), is synthesized from 3-methylbenzophenone, which undergoes bromination and forms 3-bromo-methylbenzophenone (3.2.33). The reduction of the resulting product by sodium cyanide gives 3-cyanomethylbenzophenone (3.2.34), which is reacted with the diethyl ester of carbonic acid in the presence of sodium ethoxide. The resulting cyanoacetic ester derivative (3.2.25) is alkylated by methyl iodide and the resulting product (3.2.36) undergoes acidic hydrolysis, forming ketoprofen (3.2.37) [104¨C106].

Synthesis_22071-15-4

[Veterinary Drugs and Treatments]

Ketoprofen is labeled for use in horses for the alleviation of inflammation and pain associated with musculoskeletal disorders. Like flunixin (and other NSAIDs), ketoprofen potentially has many other uses in a variety of species and conditions. There are approved dosage forms for dogs and cats in Europe and Canada. Some consider ketoprofen to be the NSAID of choice for use short-term for analgesia in cats.
[Drug interactions]

Concomitant use of alcohol or other NSAIDs after taking ketoprofen can increase gastrointestinal side effects and may cause ulcers. When ketoprofen is used together with aspirin or other salicylic acid drugs, the efficacy cannot be increased, but the incidence of gastrointestinal side effects and bleeding tendency increases. Concomitant use of ketoprofen with anticoagulants increases the risk of bleeding. Ketoprofen can enhance the effect of antidiabetic drugs and reduce the antihypertensive effect of antihypertensive drugs; ketoprofen and corticosteroids can be used together, which can significantly reduce the symptoms of inflammation. Ketoprofen should not be used with methotrexate to prevent poisoning. When ketoprofen is used with probenecid, verapamil, and nifedipine, the dose should be reduced; when ketoprofen is used with digoxin, the dose of digoxin should be adjusted.
[Metabolism]

Two processes are involved in the biotransformation of ketoprofen: one very minor (hydroxylation), and the other largely predominant (conjugation with glucuronic acid). Less than 1% of the dose of ketoprofen administered is recovered in unchanged form in the urine, whereas the glucuronide metabolite accounts for about 65-75%. The drug is excreted as metabolites essentially by the urinary route. The rate of excretion is rapid, since 50% of the dose administered is eliminated in the first 6 hours.
[storage]

Store at -20°C
Safety DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

R25:Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
[RIDADR ]

2811
[WGK Germany ]

3
[RTECS ]

UE7570000
[TSCA ]

Yes
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

29183000
[Toxicity]

LD50 orally in rats: 101 mg/kg (Ueno)
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

2-(3-Benzoylphenyl)propionic acid(22071-15-4).msds
Questions And AnswerBack Directory
[Used in Particular Diseases]

Acute Gouty Arthritis:
Dosage and Frequency: 75 mg four times a day
Spectrum DetailBack Directory
[Spectrum Detail]

Ketoprofen(22071-15-4)MS
Ketoprofen(22071-15-4)1HNMR
Ketoprofen(22071-15-4)13CNMR
Ketoprofen(22071-15-4)IR1
Ketoprofen(22071-15-4)IR2
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

22071-15-4(sigmaaldrich)
[TCI AMERICA]

Ketoprofen,>98.0%(T)(22071-15-4)
22071-15-4 suppliers list
Company Name: Baoji Guokang Bio-Technology Co., Ltd.
Tel: 0917-3909592 13892490616 , 13892490616
Website: http://www.gk-bio.com
Company Name: Liaoning Pharmaceutical Innovation Co., Ltd
Tel: +8616588669988 , +8616588669988
Website: https://www.pipharma.com.cn/
Company Name: Hebei Guanlang Biotechnology Co,.LTD
Tel: +8619930503252 , +8619930503252
Website: https://www.chemicalbook.com/manufacturer/hebei-crovell-biotech-455/
Company Name: Sigma Audley
Tel: +86-18336680971 +86-18126314766 , +86-18126314766
Website:
Company Name: Capot Chemical Co.,Ltd.
Tel: 571-85586718 +8613336195806 , +8613336195806
Website: http://www.capotchem.com
Company Name: Shanghai Bojing Chemical Co.,Ltd.
Tel: +86-86-02137122233 +8613795318958 , +8613795318958
Website: www.bj-chem.com
Company Name: Henan Tianfu Chemical Co.,Ltd.
Tel: +86-0371-55170693 +86-19937530512 , +86-19937530512
Website: https://www.tianfuchem.com/
Company Name: Hangzhou FandaChem Co.,Ltd.
Tel: 008657128800458; +8615858145714 , +8615858145714
Website: http://www.fandachem.com
Company Name: Hubei XinRunde Chemical Co., Ltd.
Tel: +8615102730682
Website: www.chemicalbook.com/ShowSupplierProductsList30595/0_EN.htm
Company Name: ATK CHEMICAL COMPANY LIMITED
Tel: +undefined-21-51877795
Website: www.atkchemical.com
Company Name: Hefei TNJ Chemical Industry Co.,Ltd.
Tel: +86-0551-65418679 +86-18949832763 , +86-18949832763
Website: http://www.tnjchem.com
Company Name: Shanxi Naipu Import and Export Co.,Ltd
Tel: +86-13734021967 +8613734021967 , +8613734021967
Website: https://www.chemicalbook.com/manufacturer/Chisure/
Company Name: career henan chemical co
Tel: +86-0371-86658258
Website: https://www.coreychem.com/
Company Name: SHANDONG ZHI SHANG CHEMICAL CO.LTD
Tel: +86 18953170293 , +86 18953170293
Website: https://www.zhishangchem.com/
Company Name: Hubei Jusheng Technology Co.,Ltd.
Tel: 18871490254
Website: www.hubeijusheng.com
Company Name: Hebei Guanlang Biotechnology Co., Ltd.
Tel: +86-19930503282 , +86-19930503282
Website: https://www.chemicalbook.com/manufacturer/crovell/
Company Name: Xiamen AmoyChem Co., Ltd
Tel: +86-592-6051114 +8618959220845 , +8618959220845
Website: http://www.amoychem.com/
Company Name: Shanghai Longyu Biotechnology Co., Ltd.
Tel: +8615821988213 , +8615821988213
Website: https://www.chemicalbook.com/manufacturer/shanghai-longyu-biotechnology-164/
Tags:22071-15-4 Related Product Information
15687-27-1 55896-93-0 622-47-9 99-04-7 614-75-5 79-09-4 77-92-9 104-01-8 123-62-6 156-38-7 22161-81-5 59-30-3 1797984-80-5 66067-44-5 5689-33-8 1777830-05-3 1257296-76-6 21288-34-6