(S)-(+)-Ketoprofen
(S)-(+)-Ketoprofen Basic information
- Product Name:
- (S)-(+)-Ketoprofen
- Synonyms:
-
- (+)-hydratropicaci
- (S)-(+)-KETOPROFEN
- (S)-KETOPROFEN
- (S)-(+)-3-BENZOYL-ALPHA-METHYLBENZENE-ACETIC ACID
- [S]-2-[3-BENZOYLPHENYL]PROPIONIC ACID
- Dexketoprofen
- 3-(1-Hydrocarboxyethyl)benzophenone
- Dexktoprofen
- CAS:
- 22161-81-5
- MF:
- C16H14O3
- MW:
- 254.28
- EINECS:
- 606-944-5
- Product Categories:
-
- Other APIs
- Aromatics
- Chiral Compound
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Chiral Reagents
- Mol File:
- 22161-81-5.mol
(S)-(+)-Ketoprofen Chemical Properties
- 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
- pka
- 4.23±0.10(Predicted)
- form
- White solid.
- color
- White to off-white
- optical activity
- [α]22/D +49°, c = 1 in methanol
- CAS DataBase Reference
- 22161-81-5(CAS DataBase Reference)
Safety Information
- Hazard Codes
- Xn,T
- Risk Statements
- 22-36/37/38-50/53-25
- Safety Statements
- 26-60-61-45
- RIDADR
- UN 2811 6.1/PG 3
- WGK Germany
- 3
- RTECS
- CY1572790
MSDS
- Language:English Provider:SigmaAldrich
(S)-(+)-Ketoprofen Usage And Synthesis
Chemical Properties
White Solid
Uses
COX inhibitor
Uses
Anti-inflammatory; analgesic
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].
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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(S)-(+)-Ketoprofen(22161-81-5)Related Product Information
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- (RS)-Ketoprofen,KETOPROFEN EPK(CRM STANDARD),KETOPROFEN, USP23,KETOPROFEN(RG),KETOPROFEN(2-(3-BENZOYLPHENYL)PROPIONICACID),Racemic ketoprofen,KETOPROFEN,BP
- Folic acid
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- 3-(4-Hydroxyphenyl)propionic acid
- (S)-(+)-2-Phenylpropionic acid
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- Propionic anhydride
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- Desmethyl Ketoprofen
- rac-4'-Methyl Ketoprofen
- Allethrin
- Ascoric Acid
- KETOPROFEN TROMETHAMINE AMIDE
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