Ketoprofen lysine salt | CAS# 57469-78-0 ( lysine salt)| MedKoo

MedKoo Cat#: 530794 | Name: Ketoprofen Lysinate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ketoprofen Lysinate, also known as Ketoprofen lysine salt, is a lysine salt of Ketoprofen, one of the propionic acid class of nonsteroidal anti-inflammatory drugs (NSAID) with analgesic and antipyretic effects. It acts by inhibiting the body's production of prostaglandin.

Chemical Structure

Ketoprofen Lysinate

CAS#57469-78-0 ( lysinate)

Theoretical Analysis

MedKoo Cat#: 530794

Name: Ketoprofen Lysinate

CAS#: 57469-78-0 ( lysinate)

Chemical Formula: C22H28N2O5

Exact Mass: 400.1998

Molecular Weight: 400.48

Elemental Analysis: C, 65.98; H, 7.05; N, 7.00; O, 19.98

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
100mg	USD 750.00	2 Weeks
1g	USD 2,050.00	2 Weeks

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Related CAS #

22071-15-4 (free base) 57469-78-0 ( lysinate) 76690-94-3 (glucuronide) 57495-14-4 (sodium)

Synonym

Ketoprofen lysine salt; Ketoprofen Lysinate;

IUPAC/Chemical Name

L-Lysine, mono(3-benzoyl-alpha-methylbenzeneacetate)

InChi Key

InChI=1S/C16H14O3.C6H14N2O2/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12;7-4-2-1-3-5(8)6(9)10/h2-11H,1H3,(H,18,19);5H,1-4,7-8H2,(H,9,10)/t;5-/m.0/s1

InChi Code

InChI=1S/C16H14O3.C6H14N2O2/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12;7-4-2-1-3-5(8)6(9)10/h2-11H,1H3,(H,18,19);5H,1-4,7-8H2,(H,9,10)/t;5-/m.0/s1

SMILES Code

N[C@@H](CCCCN)C(O)=O.O=C(O)C(C)C1=CC=CC(C(C2=CC=CC=C2)=O)=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ketoprofen (RP-19583) lysinate is a non-steroidal anti-inflammatory agent. Ketoprofen lysinate can inhibit the activity of cyclooxygenase with IC50 values of 2 nM (COX-1) and 26 nM (COX-2).

In vitro activity:

UVB-irradiated KP (ketoprofen) inhibited the cell growth and induced G2/M cell cycle arrest by modulating the levels of cdc2, cyclin B1, Chk1, Tyr15-phosphorylated cdc2 and p21. It also provoked a striking accumulation of cyclin B1-cdc2-p21 complexes, concomitantly with an increase in the levels of Tyr15-phosphorylated cdc2 and p21 protein. The presence of KP accentuated the apoptotic response to UVB radiation in HaCaT cells as evidenced by DAPI staining. Reference: Biochem Biophys Res Commun. 2007 Dec 21;364(3):650-5. https://pubmed.ncbi.nlm.nih.gov/17964538/

In vivo activity:

Ketoprofen reduced the LPS-induced increase of mRNA abundance of tumor necrosis factor α, IL-8, serum amyloid A, and cyclooxygenase-2. Reference: J Dairy Sci. 2018 Dec;101(12):11321-11329. https://pubmed.ncbi.nlm.nih.gov/30243628/

Preparing Stock Solutions

The following data is based on the product molecular weight 400.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Brogliato AR, Antunes CA, Carvalho RS, Monteiro AP, Tinoco RF, Bozza MT, Canetti C, Peters-Golden M, Kunkel SL, Vianna-Jorge R, Benjamim CF. Ketoprofen impairs immunosuppression induced by severe sepsis and reveals an important role for prostaglandin E2. Shock. 2012 Dec;38(6):620-9. doi: 10.1097/SHK.0b013e318272ff8a. PMID: 23143054. 2. 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. Biochem Biophys Res Commun. 2007 Dec 21;364(3):650-5. doi: 10.1016/j.bbrc.2007.10.046. Epub 2007 Oct 17. PMID: 17964538. 3. Dan D, Bruckmaier RM, Wellnitz O. Ketoprofen affects the mammary immune response in dairy cows in vivo and in vitro. J Dairy Sci. 2018 Dec;101(12):11321-11329. doi: 10.3168/jds.2018-15034. Epub 2018 Sep 20. PMID: 30243628. 4. Li KL, Vogel R, Jeffcoat MK, Alfano MC, Smith MA, Collins JG, Offenbacher S. The effect of ketoprofen creams on periodontal disease in rhesus monkeys. J Periodontal Res. 1996 Nov;31(8):525-32. doi: 10.1111/j.1600-0765.1996.tb00516.x. PMID: 8971650.

In vitro protocol:

In vivo protocol:

1. Dan D, Bruckmaier RM, Wellnitz O. Ketoprofen affects the mammary immune response in dairy cows in vivo and in vitro. J Dairy Sci. 2018 Dec;101(12):11321-11329. doi: 10.3168/jds.2018-15034. Epub 2018 Sep 20. PMID: 30243628. 2. Li KL, Vogel R, Jeffcoat MK, Alfano MC, Smith MA, Collins JG, Offenbacher S. The effect of ketoprofen creams on periodontal disease in rhesus monkeys. J Periodontal Res. 1996 Nov;31(8):525-32. doi: 10.1111/j.1600-0765.1996.tb00516.x. PMID: 8971650.

1: Cossellu G, Lanteri V, Lione R, Ugolini A, Gaffuri F, Cozza P, Farronato M. Efficacy of ketoprofen lysine salt and paracetamol/acetaminophen to reduce pain during rapid maxillary expansion: A randomized controlled clinical trial. Int J Paediatr Dent. 2018 Oct 9. doi: 10.1111/ipd.12428. [Epub ahead of print] PubMed PMID: 30298560. 2: Karpova EP, Tulupov DA, Fedotov FA. [The application of different non-steroidal anti-inflammatory drugs for the elimination of pain syndrome during the early postoperative period in the children following the surgical interventions on palatine tonsils]. Vestn Otorinolaringol. 2017;82(5):48-51. doi: 10.17116/otorino201782548-51. Russian. PubMed PMID: 29072664. 3: Brandolini L, d'Angelo M, Antonosante A, Villa S, Cristiano L, Castelli V, Benedetti E, Catanesi M, Aramini A, Luini A, Parashuraman S, Mayo E, Giordano A, Cimini A, Allegretti M. Differential protein modulation by ketoprofen and ibuprofen underlines different cellular response by gastric epithelium. J Cell Physiol. 2018 Mar;233(3):2304-2312. doi: 10.1002/jcp.26102. Epub 2017 Aug 25. PubMed PMID: 28710861. 4: Cerciello A, Auriemma G, Del Gaudio P, Cantarini M, Aquino RP. Natural polysaccharides platforms for oral controlled release of ketoprofen lysine salt. Drug Dev Ind Pharm. 2016 Dec;42(12):2063-2069. Epub 2016 Jun 14. PubMed PMID: 27237337. 5: Cimini A, Brandolini L, Gentile R, Cristiano L, Menghini P, Fidoamore A, Antonosante A, Benedetti E, Giordano A, Allegretti M. Gastroprotective effects of L-lysine salification of ketoprofen in ethanol-injured gastric mucosa. J Cell Physiol. 2015 Apr;230(4):813-20. doi: 10.1002/jcp.24809. PubMed PMID: 25287669. 6: Alekseev VV, Alekseev AV, Gol'dzon GD. [Nonspecific low-back pain: from symptomatic treatment to pathogenesis-based treatment]. Zh Nevrol Psikhiatr Im S S Korsakova. 2014;114(2):51-5. Russian. PubMed PMID: 24662346. 7: Trubetskaia EA, Boĭko AN, Khozova A, Kamchatnov PR, Petrov SV, Otcheskaia OV, Gandzhula PA. [Efficacy of ketoprofen lysine salt (artrosilene) in the treatment of nonspecific vertebrogenic pain syndromes in outpatients]. Zh Nevrol Psikhiatr Im S S Korsakova. 2013;113(1):53-5. Russian. PubMed PMID: 23528496. 8: Durnovo EA, Shashurina SV, Bespalova NA, Khomutinnikova NE, Gliavina IA, Marochkina MS, Iartseva AV. [The clinical estimation of ketoprofen lysine salt effect on the intensitivity of acute pain syndrome in the oral cavity during surgical procedures and postoperative period]. Stomatologiia (Mosk). 2013;92(1):59-62. Russian. PubMed PMID: 23528405. 9: Stigliani M, Aquino RP, Del Gaudio P, Mencherini T, Sansone F, Russo P. Non-steroidal anti-inflammatory drug for pulmonary administration: design and investigation of ketoprofen lysinate fine dry powders. Int J Pharm. 2013 May 1;448(1):198-204. doi: 10.1016/j.ijpharm.2013.03.030. Epub 2013 Mar 23. PubMed PMID: 23528281. 10: Ruperto N, Carozzino L, Jamone R, Freschi F, Picollo G, Zera M, Della Casa Alberighi O, Salvatori E, Del Vecchio A, Dionisio P, Martini A. A randomized, double-blind, placebo-controlled trial of paracetamol and ketoprofren lysine salt for pain control in children with pharyngotonsillitis cared by family pediatricians. Ital J Pediatr. 2011 Sep 29;37:48. doi: 10.1186/1824-7288-37-48. PubMed PMID: 21958958; PubMed Central PMCID: PMC3192740. 11: Anacardio R, Bartolini S, Gentile MM, Bagnasco M, Carlucci G. HPLC investigated physicochemical compatibility between Artrosilene injectable solution and other pharmaceutical products frequently used for combined therapy into elastomeric Baxter LV5 infusion devices. Int J Immunopathol Pharmacol. 2005 Oct-Dec;18(4):791-8. PubMed PMID: 16388729. 12: Carlucci G, Gentile MM, Bartolini S, Anacardio R. Physicochemical compatibility between ketoprofen lysine salt injections (OKi Fiale, PG060) and pharmaceutical products frequently used for combined therapy. Boll Chim Farm. 2004 Jan-Feb;143(1):15-9. PubMed PMID: 15085570. 13: Berardi R, Piga A, Pulita F, Romagnoli E, Pietroselli D, Carle F, Cascinu S, Cellerino R. Effective prevention of 5-fluorouracil-induced superficial phlebitis by ketoprofen lysine salt gel. Am J Med. 2003 Oct 1;115(5):415-7. PubMed PMID: 14553886. 14: Messeri A, Busoni P, Noccioli B, Murolo S, Ivani G, Grossetti R, Gallini C, Maestri L, Fedele G, Novellini R. Analgesic efficacy and tolerability of ketoprofen lysine salt vs paracetamol in common paediatric surgery. A randomized, single-blind, parallel, multicentre trial. Paediatr Anaesth. 2003 Sep;13(7):574-8. PubMed PMID: 12950856. 15: Anacardio R, Perilli O, Bartolini S, Gentile MM, Mazzeo P, Carlucci G. Physicochemical compatibility between ketoprofen lysine salt injections (Artrosilene) and pharmaceutical products frequently used for combined therapy by intravenous administration. J Pharm Biomed Anal. 2003 Aug 21;32(6):1235-41. PubMed PMID: 12907268. 16: Anacardio R, Perilli O, Bartolini S, Gentile MM, Mazzeo P, Carlucci G. Physicochemical compatibility between ketoprofen lysine salt injections (Artrosilene Fiale) and pharmaceutical products frequently used for combined therapy. Boll Chim Farm. 2002 Mar-Apr;141(2):122-7. PubMed PMID: 12135160. 17: Daffonchio L, Novellini R, Bertuglia S. Protective effect of ketoprofen lysine salt on interleukin-1beta and bradykinin induced inflammatory changes in hamster cheek pouch microcirculation. Inflamm Res. 2002 May;51(5):223-8. PubMed PMID: 12056509. 18: Passàli D, Volonté M, Passàli GC, Damiani V, Bellussi L; MISTRAL Italian Study Group. Efficacy and safety of ketoprofen lysine salt mouthwash versus benzydamine hydrochloride mouthwash in acute pharyngeal inflammation: a randomized, single-blind study. Clin Ther. 2001 Sep;23(9):1508-18. PubMed PMID: 11589263. 19: Porzio S, Caselli G, Pellegrini L, Pallottini V, Del Rosario M, Coppola A, Boltri L, Gentile M, Clavenna G, Melillo G. Efficacy of a new topical gel-spray formulation of ketoprofen lysine salt in the rat: percutaneous permeation in vitro and in vivo and pharmacological activity. Pharmacol Res. 1998 Jan;37(1):41-7. PubMed PMID: 9503479. 20: Anfossi P, Villa R, Montesissa C, Carli S. Intramuscular bioavailability of ketoprofen lysine salt in horses. Vet Q. 1997 Jun;19(2):65-8. PubMed PMID: 9225435.