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(S)-(+)-Ketoprofen

Product Name
(S)-(+)-Ketoprofen
CAS No.
22161-81-5
Chemical Name
(S)-(+)-Ketoprofen
Synonyms
Dexketoprofen;(S)-KETOPROFEN;(2S)-2-(3-Benzoylphenyl)propanoic acid;Keral;Dexktoprofen;Dexketoprofe;exketoprofen;(+)-Ketoprofen;Dexketoprofen API;(S)-(+)-KETOPROFEN
CBNumber
CB8356545
Molecular Formula
C16H14O3
Formula Weight
254.28
MOL File
22161-81-5.mol
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(S)-(+)-Ketoprofen Property

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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H400Very toxic to aquatic life

Precautionary statements

P273Avoid release to the environment.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
471909
Product name
(S)-(+)-Ketoprofen
Purity
AldrichCPR
Packaging
1g
Price
$136
Updated
2024/03/01
Cayman Chemical
Product number
16407
Product name
(S)-Ketoprofen
Purity
≥98%
Packaging
1g
Price
$93
Updated
2024/03/01
Cayman Chemical
Product number
16407
Product name
(S)-Ketoprofen
Purity
≥98%
Packaging
5g
Price
$305
Updated
2024/03/01
Cayman Chemical
Product number
16407
Product name
(S)-Ketoprofen
Purity
≥98%
Packaging
100mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
16407
Product name
(S)-Ketoprofen
Purity
≥98%
Packaging
500mg
Price
$63
Updated
2024/03/01
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(S)-(+)-Ketoprofen Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from (S)-(+)-Ketoprofen manufacturers

WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
(S)-(+)-Ketoprofen 22161-81-5
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-11-09
WUHAN FORTUNA CHEMICAL CO., LTD
Product
(S)-(+)-Ketoprofen 22161-81-5
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
98.5%-101%
Supply Ability
100KGS
Release date
2021-07-16
Henan Bao Enluo International TradeCo.,LTD
Product
(S)-(+)-Ketoprofen 22161-81-5
Price
US $100.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000tons
Release date
2023-08-21

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  • Enzymes, Inhibitors, and Substrates
  • Cyclooxygenase Inhibitors
  • Cyclooxygenase (COX) Enzymes
  • Organic Building Blocks
  • Biochemicals and Reagents
  • BioChemical
  • Asymmetric Synthesis
  • Application Index
  • Carboxylic Acids
  • Cell Signaling Enzymes
  • Chiral Building Blocks
  • Other APIs
  • Aromatics
  • Chiral Reagents
  • Chiral Compound
  • Intermediates & Fine Chemicals
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