Used in Particular Diseases
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Ketoprofen

Used in Particular Diseases
Product Name
Ketoprofen
CAS No.
22071-15-4
Chemical Name
Ketoprofen
Synonyms
aneol;Dexal;Topre;Iso-K;ORUDIS;Epatec;Fastum;Lertus;ru4733;Toprec
CBNumber
CB3299418
Molecular Formula
C16H14O3
Formula Weight
254.28
MOL File
22071-15-4.mol
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Ketoprofen Property

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.
pka
pKa 5.94(MeOH/H2O) (Uncertain)
form 
solid
Water Solubility 
209mg/L(room temperature)
Merck 
14,5305
InChIKey
DKYWVDODHFEZIM-UHFFFAOYSA-N
CAS DataBase Reference
22071-15-4(CAS DataBase Reference)
NIST Chemistry Reference
Ketoprofen(22071-15-4)
EPA Substance Registry System
Benzeneacetic acid, 3-benzoyl-.alpha.-methyl- (22071-15-4)
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Safety

Hazard Codes 
T
Risk Statements 
25-36/37/38-23/24/25
Safety Statements 
26-45-36/37/39
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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
34016
Product name
Ketoprofen
Purity
VETRANAL , analytical standard
Packaging
100mg-r
Price
$63.2
Updated
2020/08/18
Sigma-Aldrich
Product number
1356632
Product name
Ketoprofen
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$366
Updated
2020/08/18
TCI Chemical
Product number
K0038
Product name
Ketoprofen
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$171
Updated
2020/06/24
TCI Chemical
Product number
K0038
Product name
Ketoprofen
Purity
>98.0%(HPLC)(T)
Packaging
250g
Price
$986
Updated
2020/06/24
Alfa Aesar
Product number
J62702
Product name
Ketoprofen
Packaging
25g
Price
$248
Updated
2020/06/24
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Ketoprofen Chemical Properties,Usage,Production

Used in Particular Diseases

Acute Gouty Arthritis:
Dosage and Frequency: 75 mg four times a day

Chemical Properties

White Crystalline Solid

Originator

Profenid,Specia,France,1973

Uses

Anti-inflammatory; analgesic

Uses

Natural Vitamin B12. analog

Uses

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

Definition

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

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.

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.

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.

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.

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].

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.

Ketoprofen Preparation Products And Raw materials

Raw materials

Preparation Products

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Ketoprofen Suppliers

Ereal Chemical Co., Ltd.
Tel
0831-6888461
Fax
QQ:97273224
Email
sales@erealchem.com
Country
China
ProdList
36
Advantage
55
Changzhou Bestar Industry Co.,Ltd.
Tel
0519-82309982
Fax
0519-82309985
Email
Lucy@bestarchem.net
Country
China
ProdList
130
Advantage
55
Shanghai Boyle Chemical Co., Ltd.
Tel
Mr Qiu:021-50182298(Demestic market) Miss Xu:021-50180596(Abroad market)
Fax
+86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2214
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
21-61259100-
Fax
86-21-61259102
Email
sh@meryer.com
Country
China
ProdList
40268
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15880
Advantage
69
TAIYUAN RHF CO.,LTD.
Tel
+86 351 7031519
Fax
+86 351 7031519
Email
sales@RHFChem.com
Country
China
ProdList
2347
Advantage
56
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386 / 800-988-0390
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24555
Advantage
81
Beijing dtftchem Technology Co., Ltd.
Tel
13651141086; 86(10)60275028、60275820
Fax
86 (10) 60270825
Email
dtftchem@sina.com
Country
China
ProdList
3393
Advantage
62
Energy Chemical
Tel
021-58432009
Fax
021-58436166-800
Email
sales8178@energy-chemical.com
Country
China
ProdList
44026
Advantage
61
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View Lastest Price from Ketoprofen manufacturers

WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Ketoprofen 22071-15-4
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-09-11
Hebei Guanlang Biotechnology Co., Ltd.
Product
Ketoprofen 22071-15-4
Price
US $100.00/KG
Min. Order
1KG
Purity
99%min
Supply Ability
200TON
Release date
2020-12-09
Longyan Tianhua Biological Technology Co., Ltd
Product
Ketoprofen 22071-15-4
Price
US $25.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
99%
Supply Ability
20 Tons
Release date
2020-10-28

22071-15-4, KetoprofenRelated Search:


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