Ketoprofen

Iupac Name：2-(3-benzoylphenyl)propanoic acid

CAS No.: 22071-15-4

Molecular Weight：254.285

Modify Date.: 2022-11-03 14:12

Introduction: 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. View more+

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1. Names and Identifiers

1.1 Name: Ketoprofen
1.2 Synonyms: (±)-Ketoprofen 19583 RP 19583rp 2-(3-Benzoylphenyl)propanoic acid 2-(3-benzoylphenyl)propionic acid 2-(3-benzoyl-phenyl)propionic acid 2-(3-benzoylphenyl)-propionicaci 2-(m-Benzoylphenyl)propionic acid 2-(meta-benzoylphenyl) propionic acid aneol benzeneacetic acid, 3-benzoyl-a-methyl- Benzeneacetic acid, 3-benzoyl-α-methyl- Dexal EINECS 244-759-8 Enantyum Epatec Fastum Iso-K Kefenid Ketoflam Ketopron Ketoprophene Lertus M-BENZOYLHYDRATROPIC ACID Menamin Meprofen MFCD00055790 ORUDIS Orugesic ORUVAIL Oscorel Racemic Ketoprofen racemic-Ketoprofen RARECHEM AL BO 1306 ru4733 Topre Toprec Toprek UNII:90Y4QC304K

1.3 CAS No.: 22071-15-4

1.4 CID: 3825

1.5 EINECS(EC#): 244-759-8

1.6 Molecular Formula: C16H14O3 (isomer)

1.7 Inchi: InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)

1.8 InChkey: DKYWVDODHFEZIM-UHFFFAOYSA-N

1.9 Canonical Smiles: CC(C1=CC(=CC=C1)C(=O)C2=CC=CC=C2)C(=O)O

1.10 Isomers Smiles: CC(C1=CC(=CC=C1)C(=O)C2=CC=CC=C2)C(=O)O

2. Properties

2.1 Density: 1.198

2.1 Melting point: 69-71 °C

2.1 Boiling point: 431.3 °C at 760 mmHg

2.1 Refractive index: 1.592

2.1 Flash Point: 147℃

2.1 Precise Quality: 254.09400

2.1 PSA: 54.37000

2.1 logP: 3.10570

2.1 Solubility: Slightly soluble in chloroform and methanol.

2.2 Appearance: white or almost white, crystalline powder.

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: White Crystalline Solid

2.5 Contact Allergens: Ketoprofen is an anti-inflammatory drug, used bothtopically and systemically. It is above all a photoaller-gen, responsible for photoallergic or photo-worsenedcontact dermatitis, with sun-induced, progressive,severe, and durable reactions. Recurrent photosensitiv-ity is possible for many years. Photosensitivities areexpected to thiophene-phenylketone derivatives suchas tiaprofenic acid and suprofen, to ketoprofen esterssuch 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.

2.6 pKa: pKa 5.94(MeOH/H2O) (Uncertain)

2.7 Water Solubility: practically insoluble in water ,freely soluble in acetone, in ethanol(96 percent) and in methylene chloride

2.8 StorageTemp: 2-8°C

3. Use and Manufacturing

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

3.2 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.

3.3 Usage: Anti-inflammatory; analgesic

4. Safety and Handling

4.1 Symbol: GHS06;

4.1 Hazard Codes: T

4.1 Signal Word: DANGER

4.1 Risk Statements: R25;R36/37/38

4.1 Safety Statements: 26-45-36/37/39

4.1 Packing Group: III

4.1 Hazard Class: 6.1(b)

4.1 Hazard Declaration: H301; H315; H319; H335

4.1 RIDADR: 25kgs

4.1 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.

4.2 Caution Statement: P261-P301 + P310-P305 + P351 + P338

4.2 WGK Germany: 3

4.2 RTECS: UE7570000

4.2 Toxicity: LD50 orally in rats: 101 mg/kg (Ueno)

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H301 Toxic if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : 400 MHz in CDCl3

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

22071-15-4Total: 73 Synthesis Route

71-43-2 200 Suppliers

22071-15-4 353 Suppliers

Literatures:
Tetrahedron, , vol. 50, # 27 p. 8117 - 8126
Yield: null

585-76-2 178 Suppliers

22071-15-4 353 Suppliers

Literatures:
Gazzetta Chimica Italiana, , vol. 122, # 12 p. 511 - 514
Yield: null

100-44-7 207 Suppliers

22071-15-4 353 Suppliers

Literatures:
Synthetic Communications, , vol. 18, # 18 p. 2259 - 2266
Yield: null

View all

8. Precursor and Product

precursor:

79868-87-4

79868-86-3

70125-82-5

2835-78-1

60658-04-0

80078-36-0

57872-48-7

71-43-2

2142-63-4

1504-06-9

2243-80-3

2084-24-4

71574-82-8

19829-31-3

21262-52-2

1711-09-7

75116-77-7

1016-77-9

70006-55-2

22161-82-6

121-90-4

100-44-7

73275-86-2

106-45-6

585-76-2

View all

product :

59512-16-2

66067-43-4

586-42-5

66067-44-5

59960-32-6

319482-67-2

579-18-0

67173-18-6

126489-64-3

9. Other Information

9.0 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.

9.1 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.

9.2 Originator: Profenid,Specia,France,1973

9.3 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.

9.4 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.

9.5 Therapeutic Function: Antiinflammatory

9.6 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.

9.7 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.

9.8 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.

9.9 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.

9.10 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.

9.11 Chemical 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) [104–106].

9.12 Usage: It is used as a anti-inflammatory; analgesic and an antipyretic drug cause the hypothalamus to override an interleukin-induced increase in temperature. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.

9.13 Merck: 14,5305

9.14 Used in Particular Diseases: Acute Gouty Arthritis:
Dosage and Frequency: 75 mg four times a day

9.15 Chemical Properties: White Crystalline Solid

9.16 Uses: Natural Vitamin B12. analog

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

9.18 Uses: Anti-inflammatory; analgesic

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

9.20 Brand name: Actron (Bayer); Orudis (Wyeth); Oruvail (Wyeth).

9.21 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.

9.22 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.

9.23 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.

10. Computational chemical data

Molecular Weight: 254.285g/mol
Molecular Formula: C₁₆H₁₄O₃
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 254.094294304
Monoisotopic Mass: 254.094294304
Complexity: 331
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 54.4
Heavy Atom Count: 19
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
CACTVS Substructure Key Fingerprint: AAADccB4MAAAAAAAAAAAAAAAAAAAAAAAAAAwYAAAAAAAAAABQAAAGgAACAAADQSAmAAyCIAAAgCIAqDSCAACAAAkAAAIiAEAAMgIIDKAFRCAYQAkwAEIiYeIyPCOgAACAAAAAAAAAAQAAAAAAAAAAAAAAA==

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