S-(+)-Ketoprofen

Names

[ Name ]:
S-(+)-Ketoprofen

[Synonym ]:
S-ketoprofen
(S)-Ketoprofen
(2S)-2-(3-Benzoylphenyl)propanoic acid
(S)-3-Benzoyl-a-methylbenzeneacetic Acid
MFCD00673316
Benzeneacetic acid, 3-benzoyl-α-methyl-, (αS)-
(+)-(S)-m-Benzoylhydratropic acid
Dexketoprofen
(+)-3-Benzoylhydratropic acid
Keral
(S)-(+)-2-(3-Benzoylphenyl)propionic acid
(+)-Ketoprofen
(S)-(+)-Ketoprofen
S-(+)-Ketoprofen
(2S)-2-(3-Benzoylphenyl)propionic Acid

Biological Activity

[Description]:

S-(+)-Ketoprofen is a potent inhibitor of both COX-1 and COX-2 with IC50s of 1.9 and 27 nM, respectively.

[Related Catalog]:

Research Areas >> Inflammation/Immunology

[Target]

COX-1:13 μM (IC50)

COX-2:370 μM (IC50)

[In Vitro]

S-(+)-Ketoprofen (Compound 1) is a potent inhibitor of both COX-1 and COX-2 with IC50s of 1.9 and 27 nM, respectively[1].

[References]

[1]. Palomer A, et al. Modeling cyclooxygenase inhibition. Implication of active site hydration on the selectivity ofketoprofen analogues. J Med Chem. 2000 Jun 1;43(11):2280-4.

[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 ]:
75-78ºC(lit.)

[ 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

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CY1572790

CHEMICAL NAME :: Benzeneacetic acid, 3-benzoyl-alpha-methyl-, (S)-

CAS REGISTRY NUMBER :: 22161-81-5

LAST UPDATED :: 199606

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C16-H14-O3

MOLECULAR WEIGHT :: 254.30

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 225 mg/kg/90D-I

TOXIC EFFECTS :: Gastrointestinal - other changes

REFERENCE :: TOXID9 Toxicologist. (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway, Akron, OH 44311) V.1- 1981- Volume(issue)/page/year: 30,101,1996

Safety Information

[ Symbol ]:

GHS06, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H315-H319-H335-H400

[ Precautionary Statements ]:
P261-P273-P301 + P310-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

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

[ Safety Phrases ]:
26-60-61

[ RIDADR ]:
UN 2811 6

[ WGK Germany ]:
3

[ RTECS ]:
CY1572790

[ Hazard Class ]:
6.1

[ HS Code ]:
2942000000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2942000000

Articles

Hologram QSAR model for the prediction of human oral bioavailability.

Bioorg. Med. Chem. 15 , 7738-45, (2007)

A drug intended for use in humans should have an ideal balance of pharmacokinetics and safety, as well as potency and selectivity. Unfavorable pharmacokinetics can negatively affect the clinical devel...

2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors.

J. Med. Chem. 48 , 4312-31, (2005)

The CXC chemokine CXCL8/IL-8 plays a major role in the activation and recruitment of polymorphonuclear (PMN) cells at inflammatory sites. CXCL8 activates PMNs by binding the seven-transmembrane (7-TM)...

Scope of partial least-squares regression applied to the enantiomeric composition determination of ketoprofen from strongly overlapped chromatographic profiles.

J. Sep. Sci. 38 , 2423-30, (2015)

Valuable quantitative information could be obtained from strongly overlapped chromatographic profiles of two enantiomers by using proper chemometric methods. Complete separation profiles where the pea...