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Basic Information
CAS No.: 22071-15-4
Name: Ketoprofen
Article Data: 84
Molecular Structure:
Molecular Structure of 22071-15-4 (Ketoprofen)
Formula: C16H14O3
Molecular Weight: 254.285
Synonyms: 3-Benzoyl-alpha-methylbenzeneacetic acid;Epatec;Oruvail;Orudis;Ketoprofen (JP14/USP);2-(3-Benzoylphenyl)propionic acid;3-Benzoylhydratropic acid;Profenid;Benzeneacetic acid,3-benzoyl-R-methyl-;LAcide (benzoyl-3-phenyl)-2-propionique;Alrheumate;m-Benzoylhydratropic acid;ISO-K;Orudis (TN);
EINECS: 244-759-8
Density: 1.198 g/cm3
Melting Point: 69-71 °C
Boiling Point: 431.3 °C at 760 mmHg
Flash Point: 147 °C
Solubility: 209mg/L(room temperature)
Appearance: white crystalline solid
Hazard Symbols: ToxicT
Risk Codes: 25-36/37/38-23/24/25
Safety: 26-45-36/37/39
PSA: 54.37000
LogP: 3.10570
Synthetic route
197314-10-6

2-(3-benzoyl-phenyl)-thiopropionic acid S-methyl ester

22071-15-4

ketoprofen

Conditions
ConditionsYield
With potassium hydroxide In acetone for 2h; Heating;100%
362470-63-1

(S)-2-(3-Benzoyl-phenyl)-propionic acid (S)-1-carbamoylmethyl-4,4-dimethyl-2-oxo-pyrrolidin-3-yl ester

22071-15-4

ketoprofen

Conditions
ConditionsYield
With potassium trimethylsilonate In tetrahydrofuran at 20℃; for 12h;99%
201230-82-2

carbon monoxide

63444-57-5

3-benzoylstyrene

22071-15-4

ketoprofen

Conditions
ConditionsYield
With palladium diacetate; catacxium A In 1,4-dioxane at 100℃; for 20h;99%
With palladium diacetate; catacxium A In 1,4-dioxane at 100℃; for 20h;99%
With hydrogenchloride; water; palladium diacetate; catacxium A In 1,4-dioxane at 100℃; under 30003 Torr; for 20h; regioselective reaction;99 %Chromat.
79868-87-4

3-(3-benzoylphenyl)butan-2-one

22071-15-4

ketoprofen

Conditions
ConditionsYield
With sodium hypochlorite at 70℃; for 0.25h;95%
With sodium hypochlorite Yield given;
80078-36-0

dimethyl 2-methyl-2-(3'-benzoyl)phenylpropanedioate

22071-15-4

ketoprofen

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran at 25℃; for 24h;95%
42872-30-0

alpha-(m-benzoylphenyl)propionitrile

22071-15-4

ketoprofen

Conditions
ConditionsYield
With sulfuric acid for 7h; Reflux;92.8%
With sulfuric acid In water; toluene
With sodium hydroxide; sulfuric acid In water; toluene
With sulfuric acid In water; toluene
With sulfuric acid for 7h; Reflux;
1235479-25-0

C18H20O3

22071-15-4

ketoprofen

Conditions
ConditionsYield
Stage #1: C18H20O3 With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide In acetonitrile at 5℃; for 2h; pH=9 - 10;
Stage #2: With hydrogenchloride In ethanol; water at 70℃; for 1h;
91%

2-(3-benzoylphenyl)-propanol

22071-15-4

ketoprofen

Conditions
ConditionsYield
With nitric acid In 1,4-dioxane at 20℃; for 10h;90%
With nitric acid In 1,4-dioxane at 20℃; for 10h;65.6%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite In water; acetonitrile at 35℃; for 24h; aq. phosphate buffer;40%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor; oxygen In water; acetone at 20℃; for 168h; Enzymatic reaction;13%
467225-84-9

S-butyl α-(3-benzoylphenyl)thiopropionate

22071-15-4

ketoprofen

Conditions
ConditionsYield
With potassium hydroxide In acetone for 2h; Heating;89%
216019-59-9

neomenthyldiphenylphosphine

63444-57-5

3-benzoylstyrene

7664-93-9

sulfuric acid

96-22-0

pentan-3-one

22071-15-4

ketoprofen

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; CO; CuCl2; palladium dichloride In tetrahydrofuran; water; toluene88%
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Specification

The Ketoprofen, with the CAS registry number 22071-15-4, is also known as 2-(3-Benzoylphenyl)propionic acid; 2-(meta-Benzoylphenyl) propionic acid; Alrheumat. It belongs to the product categories of Pharmaceuticals;Lipid signaling;Pharmaceutical raw material.Its EINECS number is 244-759-8.This chemical's molecular formula is C16H14O3 and molecular weight is 254.28. What's more,Its systematic name is Ketoprofen.It is a White Crystalline Solid.And it is an ibuprofen-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.

Physical properties about Ketoprofen are:
(1)ACD/LogP: 2.911; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.62; (4)ACD/LogD (pH 7.4): -0.16; (5)ACD/BCF (pH 5.5): 4.93; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 46.90; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.592; (13)Molar Refractivity: 71.795 cm3; (14)Molar Volume: 212.246 cm3; (15)Surface Tension: 49.7709999084473 dyne/cm; (16)Density: 1.198 g/cm3; (17)Flash Point: 228.793 °C; (18)Enthalpy of Vaporization: 72.408 kJ/mol; (19)Boiling Point: 431.316 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

Uses of Ketoprofen :
Ketoprofen is a common NSAID, antipyretic, and analgesic used in horses and other equines. It is also used as a mild painkiller in smaller animals, generally following surgical procedures. It is most commonly used for muscoskeletal pain, joint problems, and soft tissue injury, as well as laminitis. It does not treat the underlying problem, nor does it speed the healing process. It is also used to control fevers and prevent endotoxemia. However, they may mask the symptoms of the underlying problem, and therefore make diagnosis more difficult for a veterinarian.

Safety Information of Ketoprofen:
The Ketoprofen is toxic by inhalation,in contact with skin and if swallowed It is irritating to eyes, respiratory system and skin.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.When you use it ,wear suitable protective clothing, gloves and eye/face protection.In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES:CC(c1cccc(c1)C(=O)c2ccccc2)C(=O)O;
(2)Std. 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);
(3)Std. InChIKey:DKYWVDODHFEZIM-UHFFFAOYSA-N.

The toxicity data of Ketoprofen as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo unreported 300mg/kg/15D- (300mg/kg) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: HEADACHE
New England Journal of Medicine. Vol. 300, Pg. 796, 1979.
guinea pig LD50 intravenous 450mg/kg (450mg/kg)   Journal de Pharmacologie. Vol. 2, Pg. 259, 1971.
guinea pig LD50 oral 1300mg/kg (1300mg/kg)   Journal de Pharmacologie. Vol. 2, Pg. 259, 1971.
human TDLo oral 714ug/kg (.714mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Journal of Clinical Pharmacology. Vol. 24, Pg. 486, 1984.
man TDLo oral 5714ug/kg (5.714mg/kg)   Clinical Rheumatology. Vol. 10, Pg. 215, 1991.
man TDLo oral 5714ug/kg (5.714mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" Clinical Rheumatology. Vol. 10, Pg. 215, 1991.
mouse LD50 intraperitoneal 300mg/kg (300mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 11, Pg. 7, 1976.
mouse LD50 intravenous 500mg/kg (500mg/kg)   Journal de Pharmacologie. Vol. 2, Pg. 259, 1971.
mouse LD50 oral 360mg/kg (360mg/kg)   Polish Journal of Pharmacology and Pharmacy. Vol. 38, Pg. 107, 1986.
mouse LD50 subcutaneous 550mg/kg (550mg/kg)   Journal de Pharmacologie. Vol. 2, Pg. 259, 1971.
rat LD50 intraperitoneal 80mg/kg (80mg/kg)   Drugs in Japan Vol. 6, Pg. 265, 1982.
rat LD50 intravenous 350mg/kg (350mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 222, 1978.
rat LD50 oral 62400ug/kg (62.4mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 34, Pg. 280, 1984.
rat LD50 rectal 84mg/kg (84mg/kg) GASTROINTESTINAL: PERITONITIS

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE
Journal of Toxicological Sciences. Vol. 6, Pg. 209, 1981.
rat LD50 subcutaneous 100mg/kg (100mg/kg)   Journal de Pharmacologie. Vol. 2, Pg. 259, 1971.
women TDLo oral 11mg/kg/12H-I (11mg/kg) SKIN AND APPENDAGES (SKIN): SWEATING: OTHER

CARDIAC: PULSE RATE

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Journal of Clinical Pyschopharmacology. Vol. 19, Pg. 95, 1999.
women TDLo oral 80mg/kg/10D-I (80mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" British Medical Journal. Vol. 292, Pg. 97, 1986.