(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

form 

White solid.

pka

4.23±0.10(Predicted)

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

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(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.

(S)-(+)-Ketoprofen(22161-81-5)Related Product Information

• Imidocarb dipropionate
• (RS)-Ketoprofen,KETOPROFEN EPK(CRM STANDARD),KETOPROFEN, USP23,KETOPROFEN(RG),KETOPROFEN(2-(3-BENZOYLPHENYL)PROPIONICACID),Racemic ketoprofen,KETOPROFEN,BP
• Folic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Nandrolone phenylpropionate
• 3-(4-Hydroxyphenyl)propionic acid
• (S)-(+)-2-Phenylpropionic acid
• Citric acid
• L-Ketoprofen trometamol
• Propionic anhydride
• Propionic acid
• Desmethyl Ketoprofen
• rac-4'-Methyl Ketoprofen
• Allethrin
• Ascoric Acid
• KETOPROFEN TROMETHAMINE AMIDE
• 3-(CYANOMETHYL)BENZOIC ACID
• 3-ACETYLBENZOPHENONE