ketoprofen

Names

[ CAS No. ]:
22071-15-4

[ Name ]:
ketoprofen

[Synonym ]:
2-(3-benzoyl-phenyl)propionic acid
Ketoprophene
Ketopron
UNII:90Y4QC304K
Epatec
Lertus
Ketoprofen
Dexal
Menamin
Meprofen
Fastum
MFCD00055790
racemic-Ketoprofen
Orugesic
Iso-K
Oscorel
2-(m-Benzoylphenyl)propionic acid
Oruvail
Toprec
Racemic Ketoprofen
Toprek
2-(3-Benzoylphenyl)propanoic acid
Kefenid
Ketoflam
Orudis
Benzeneacetic acid, 3-benzoyl-α-methyl-
benzeneacetic acid, 3-benzoyl-a-methyl-
ru4733
EINECS 244-759-8
Enantyum
(±)-Ketoprofen
Topre
2-(3-benzoylphenyl)propionic acid
aneol

Biological Activity

[Description]:

Ketoprofen is a non-steroidal antiinflammatory agent, acting as a potent inhibitor of COX, with IC50s of 2 nM and 26 nM for COX-1 and COX-2 in human blood monocytes, respectively.

[Related Catalog]:

Research Areas >> Inflammation/Immunology

[Target]

COX-1:2 nM (IC50, in human blood monocytes)

COX-2:26 nM (IC50, in human blood monocytes)

[In Vitro]

Ketoprofen (Compound 2) is a non-steroidal antiinflammatory agent, acting as a potent inhibitor of COX, with IC50s of 2 nM and 26 nM for COX-1 and COX-2 in human blood monocytes, respectively[1].

[In Vivo]

Ketoprofen (0.32-10 mg/kg, s.c) dose-dependently inhibits acid-induced depression of nesting (IC50, 2.05 mg/kg), and reverses CFA-induced such depression at 0.1-10 mg/kg, with an IC50 of 0.18 mg/kg in mice[2].

[Animal admin]

First, Ketoprofen (0.1-1.0 mg/kg) and morphine (0.1-1.0 mg/kg) are evaluated for their effectiveness to block U69,593-induced depression of nesting. For these studies, Ketoprofen or morphine is administered 30 min before nesting, 1.0 mg/kg U69,593 is administered 15 min before nesting, and each set of conditions is tested in a group of six mice[2].

[References]

[1]. Palomer A, et al. Structure-based design of cyclooxygenase-2 selectivity into ketoprofen. Bioorg Med Chem Lett. 2002 Feb 25;12(4):533-7.

[2]. Negus SS, et al. Effects of ketoprofen, morphine, and kappa opioids on pain-related depression of nesting in mice. Pain. 2015 Jun;156(6):1153-60.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
431.3±28.0 °C at 760 mmHg

[ Melting Point ]:
93-96°C

[ Molecular Formula ]:
C₁₆H₁₄O₃

[ Molecular Weight ]:
254.281

[ Flash Point ]:
228.8±20.5 °C

[ Exact Mass ]:
254.094299

[ PSA ]:
54.37000

[ LogP ]:
2.81

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.592

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UE7570000

CHEMICAL NAME :: Propionic acid, 2-(3-benzoylphenyl)-

CAS REGISTRY NUMBER :: 22071-15-4

LAST UPDATED :: 199801

DATA ITEMS CITED :: 23

MOLECULAR FORMULA :: C16-H14-O3

MOLECULAR WEIGHT :: 254.30

WISWESSER LINE NOTATION :: QVY1&R CVR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 5714 ug/kg

TOXIC EFFECTS :: Liver - hepatitis (hepatocellular necrosis), zonal Liver - jaundice (or hyperbilirubinemia) hepatocellular Nutritional and Gross Metabolic - body temperature increase

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 714 ug/kg

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 80 mg/kg/10D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 300 mg/kg/15D-I

TOXIC EFFECTS :: Brain and Coverings - other degenerative changes Behavioral - headache Gastrointestinal - nausea or vomiting

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 62400 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 80 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 350 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Rectal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 84 mg/kg

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from small intestine Gastrointestinal - peritonitis

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 360 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 550 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 1300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 450 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 300 mg/kg/30D-C

TOXIC EFFECTS :: Endocrine - changes in spleen weight Blood - other changes Related to Chronic Data - changes in testicular weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1080 mg/kg/26W-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes Gastrointestinal - other changes Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Rectal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 300 mg/kg/30D-C

TOXIC EFFECTS :: Blood - pigmented or nucleated red blood cells Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 900 mg/kg/5D-I

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1092 mg/kg/13W-I

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from duodenum Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1 mg/kg

SEX/DURATION :: female 21 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 50 mg/kg

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 393,123,1997

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H315-H319-H335

[ Precautionary Statements ]:
P261-P301 + P310-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R25;R36/37/38

[ Safety Phrases ]:
S26-S45-S36/37/39

[ RIDADR ]:
2811

[ RTECS ]:
UE7570000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2916392000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918300090

[ Summary ]:
2918300090 other carboxylic acids with aldehyde or ketone function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

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