| Identification | More | [Name]
(S)-(+)-Ketoprofen | [CAS]
22161-81-5 | [Synonyms]
[S]-2-[3-BENZOYLPHENYL]PROPIONIC ACID
(S)-(+)-3-BENZOYL-ALPHA-METHYLBENZENE-ACETIC ACID
(S)-(+)-KETOPROFEN
(S)-KETOPROFEN
(+)-hydratropicaci
Dexketoprofen
3-(1-Hydrocarboxyethyl)benzophenone
Dexktoprofen
(S)-(+)-3-Benzoyl-a-methylbenzeneacetic Acid
Dexketoprofe
(s)-(+)-3-benzoyl-α-methylbenzeneacetic acid
(+)-(S)-m-Benzoylhydratropic acid
(2S)-2-(3-Benzoylphenyl)propionic acid
Benzeneacetic acid, 3-benzoyl-a-methyl-, (aS)-(9CI)
Benzeneacetic acid, 3-benzoyl-a-methyl-, (S)-
Hydratropic acid, m-benzoyl-, (+)-(8CI)
(S)-(+)-3-Benzoyl-α-methylbenzeneacetic acid, (S)-2-(3-Benzoylphenyl)propionic acid
(2S)-2-(3-Benzoylphenyl)propanoic acid
(S)-2-(3-Benzoylphenyl)propanoic acid | [EINECS(EC#)]
606-944-5 | [Molecular Formula]
C16H14O3 | [MDL Number]
MFCD00673316 | [Molecular Weight]
254.28 | [MOL File]
22161-81-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
75-78 °C(lit.)
| [Boiling point ]
431.3±28.0 °C(Predicted) | [density ]
1.198±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
insoluble in H2O; ≥10.6 mg/mL in DMSO; ≥20.55 mg/mL in EtOH | [form ]
White solid. | [pka]
4.23±0.10(Predicted) | [color ]
White to off-white | [optical activity]
[α]22/D +49°, c = 1 in methanol | [Usage]
Anti-inflammatory; analgesic | [CAS DataBase Reference]
22161-81-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R25:Toxic if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
CY1572790
|
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
Anti-inflammatory; analgesic | [Uses]
COX inhibitor | [Definition]
ChEBI: A monocarboxylic acid that is (S)-hydratropic acid substituted at position 3 on the phenyl ring by a benzoyl group. A cyclooxygenase inhibitor, it is used to relieve short-term pain, such as muscular pain, dental pain and dysmenorrhoea. | [Biological Activity]
(s)-ketoprofen, a dual cox1/2 inhibitor, can be used as a nonsteroidal anti-inflammatory drug to treat arthritis-related inflammatory pains. ketoprofen is photolabile and undergoes degradation when irradiated by sunlight to induce various skin diseases [1]. | [Clinical Use]
#N/A | [in vitro]
the combination of uvb irradiation with ketoprofen dose-dependently induced the cytotoxicity and suppressed dna synthesis in hacat cells. uvb-irradiated kp inhibited the cell growth and induced g2/m cell cycle arrest by regulating the levels of cdc2, cyclin b1, chk1, tyr15-phosphorylated cdc2 and p21. the dapi staining results has revealed that kp accentuated the apoptotic response to uvb radiation in hacat cells [1]. | [in vivo]
in a placebo-controlled, double-blind study in the rhesus monkeys macaca mulatta with periodontal disease, administeration of kp at 1% level in suitable topical vehicles to the gingiva once daily at a standard dose of 1.8 ml per monkey for 6 months effectively inhibited gcf-ltb4 and gcf-pge2 and positively altered alveolar bone activity [2]. ketoprofen at a dose of 3.63 mg/kg bwt (phenylbutazone equimolar dose) showed significant analgesic effects and reduced hoof pain and lameness to a greater extent [3]. treatment with ketoprofen (40 and 80 mg/kg diet) greatly reduced the incidence of transitional cell carcinoma of the urinary bladder by >70% from that seen in dietary mice [4]. | [Drug interactions]
Potentially hazardous interactions with other drugs
ACE inhibitors and angiotensin-II antagonists:
antagonism of hypotensive effect; increased risk of
nephrotoxicity and hyperkalaemia
Analgesics: avoid concomitant use of 2 or more
NSAIDs, including aspirin (increased side effects);avoid with ketorolac (increased risk of side effects
and haemorrhage).
Antibacterials: possibly increased risk of convulsions
with quinolones
Anticoagulants: effects of coumarins and
phenindione enhanced; possibly increased risk of
bleeding with heparins, dabigatran and edoxaban -
avoid long term use with edoxaban
Antidepressants: increased risk of bleeding with
SSRIs and venlaflaxine.
Antidiabetic agents: effects of sulphonylureas enhanced.
Antiepileptics: possibly increased phenytoin
concentration.
Antivirals: increased risk of haematological toxicity
with zidovudine; concentration possibly increased by
ritonavir.
Ciclosporin: may potentiate nephrotoxicity.
Cytotoxics: reduced excretion of methotrexate;
increased risk of bleeding with erlotinib.
Diuretics: increased risk of nephrotoxicity;
antagonism of diuretic effect, hyperkalaemia with
potassium-sparing diuretics.
Lithium: excretion decreased.
Pentoxifylline: increased risk of bleeding
Probenecid: excretion reduced by probenecid.
Tacrolimus: increased risk of nephrotoxicity | [Metabolism]
Dexketoprofen is the S-enantiomer of ketoprofen.The
main elimination route for dexketoprofen is glucuronide
conjugation in the liver followed by renal excretion. | [References]
[1]. liu s, mizu h, yamauchi h. molecular response to phototoxic stress of uvb-irradiated ketoprofen through arresting cell cycle in g2/m phase and inducing apoptosis[j]. biochemical and biophysical research communications, 2007, 364(3): 650-655.
[2]. li k l, vogel r, jeffcoat m k, et al. the effect of ketoprofen creams on periodontal disease in rhesus monkeys[j]. journal of periodontal research, 1996, 31(8): 525-532.
[3]. owens j g, kamerling s g, stanton s r, et al. effects of ketoprofen and phenylbutazone on chronic hoof pain and lameness in the horse[j]. equine veterinary journal, 1995, 27(4): 296-300.
[4]. hawk e t, kelloff g j, mccormick d l. differential activity of aspirin, ketoprofen and sulindac as cancer chemopreventive agents in the mouse urinary bladder[j]. carcinogenesis, 1996, 17(5): 1435-1438. |
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