Ketoprofen | CAS# 22071-15-4 (free base)

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

MedKoo CAT#: 318080

CAS#: 22071-15-4 (free base)

Description: Ketoprofen is 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

CAS# 22071-15-4 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318080
Name: Ketoprofen
CAS#: 22071-15-4 (free base)
Chemical Formula: C16H14O3
Exact Mass: 254.09
Molecular Weight: 254.281
Elemental Analysis: C, 75.57; H, 5.55; O, 18.88

Price and Availability

Size	Price	Availability
1g	USD 250	Ready to ship
2g	USD 350	Ready to ship
5g	USD 550	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Ketoprofen, Profenid, Orudis, Alrheumun, Capisten

IUPAC/Chemical Name: 2-(3-benzoylphenyl)propanoic acid

InChi Key: DKYWVDODHFEZIM-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)

SMILES Code: CC(C1=CC=CC(C(C2=CC=CC=C2)=O)=C1)C(O)=O

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, not in water

Shelf Life: >2 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

Certificate of Analysis:

View CoA: current batch, Lot#A21M12B03

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	Ketoprofen can inhibits 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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	30.0	117.98
	DMSO	60.3	237.27
	Ethanol	35.5	139.61
	PBS (pH 7.2)	0.5	1.97

Preparing Stock Solutions

The following data is based on the product molecular weight 254.28 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:	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.
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.

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1: Damulin IV. [Treatment of back pain (ketoprofen and other methods)]. Zh Nevrol Psikhiatr Im S S Korsakova. 2014;114(2):81-6. Review. Russian. PubMed PMID: 24730046.

2: Sarzi-Puttini P, Atzeni F, Lanata L, Bagnasco M. Efficacy of ketoprofen vs. ibuprofen and diclofenac: a systematic review of the literature and meta-analysis. Clin Exp Rheumatol. 2013 Sep-Oct;31(5):731-8. Epub 2013 May 17. Review. PubMed PMID: 23711416.

3: Shohin IE, Kulinich JI, Ramenskaya GV, Abrahamsson B, Kopp S, Langguth P, Polli JE, Shah VP, Groot DW, Barends DM, Dressman JB. Biowaiver monographs for immediate-release solid oral dosage forms: ketoprofen. J Pharm Sci. 2012 Oct;101(10):3593-603. doi: 10.1002/jps.23233. Epub 2012 Jul 11. Review. PubMed PMID: 22786667.

4: Gigante A, Tagarro I. Non-steroidal anti-inflammatory drugs and gastroprotection with proton pump inhibitors: a focus on ketoprofen/omeprazole. Clin Drug Investig. 2012 Apr 1;32(4):221-33. doi: 10.2165/11596670-000000000-00000. Review. PubMed PMID: 22350497.

5: Coaccioli S. Ketoprofen 2.5% gel: a clinical overview. Eur Rev Med Pharmacol Sci. 2011 Aug;15(8):943-9. Review. PubMed PMID: 21845805.

6: Adachi H, Ioppolo F, Paoloni M, Santilli V. Physical characteristics, pharmacological properties and clinical efficacy of the ketoprofen patch: a new patch formulation. Eur Rev Med Pharmacol Sci. 2011 Jul;15(7):823-30. Review. PubMed PMID: 21780552.

7: Kokki H. Ketoprofen pharmacokinetics, efficacy, and tolerability in pediatric patients. Paediatr Drugs. 2010 Oct 1;12(5):313-29. doi: 10.2165/11534910-000000000-00000. Review. PubMed PMID: 20799760.

8: Sarzi-Puttini P, Atzeni F, Lanata L, Bagnasco M, Colombo M, Fischer F, D'Imporzano M. Pain and ketoprofen: what is its role in clinical practice? Reumatismo. 2010 Jul-Sep;62(3):172-88. Review. PubMed PMID: 21052564.

9: Cantisani C, Grieco T, Faina V, Mattozzi C, Bohnenberger H, Silvestri E, Calvieri S. Ketoprofen allergic reactions. Recent Pat Inflamm Allergy Drug Discov. 2010 Jan;4(1):58-64. Review. PubMed PMID: 19832694.

10: Barden J, Derry S, McQuay HJ, Moore RA. Single dose oral ketoprofen and dexketoprofen for acute postoperative pain in adults. Cochrane Database Syst Rev. 2009 Oct 7;(4):CD007355. doi: 10.1002/14651858.CD007355.pub2. Review. PubMed PMID: 19821407; PubMed Central PMCID: PMC4171124.

11: Mazières B. Topical ketoprofen patch. Drugs R D. 2005;6(6):337-44. Review. PubMed PMID: 16274258.

12: Mullangi R, Yao M, Srinivas NR. Resolution of enantiomers of ketoprofen by HPLC: a review. Biomed Chromatogr. 2003 Oct;17(7):423-34. Review. PubMed PMID: 14598325.

13: Veyrac G, Paulin M, Milpied B, Bourin M, Jolliet P. [Results of a French nationwide survey of cutaneous side effects of ketoprofen gel reported between September 1996 and August 2000]. Therapie. 2002 Jan-Feb;57(1):55-64. Review. French. PubMed PMID: 12090148.

14: Ouchi A, Zandomeneghi G, Zandomeneghi M. Complexation with albumins of chiral aromatic substrates and their chemistry in ground and excited states. Catalytic and chirality recognition properties of the protein in the cases of binaphthol, its photoisomers, and ketoprofen. Chirality. 2002 Jan;14(1):1-11. Review. PubMed PMID: 11748793.

15: Sugiura M, Hayakawa R, Kato Y, Sugiura K, Ueda H. 4 cases of photocontact dermatitis due to ketoprofen. Contact Dermatitis. 2000 Jul;43(1):16-9. Review. PubMed PMID: 10902583.

16: Schumacher HR Jr. Ketoprofen extended-release capsules: a new formulation for the treatment of osteoarthritis and rheumatoid arthritis. Clin Ther. 1994 Mar-Apr;16(2):145-59. Review. PubMed PMID: 8062310.

17: Serrano G, Fortea JM, Latasa JM, Millan F, Janes C, Bosca F, Miranda MA. Photosensitivity induced by fibric acid derivatives and its relation to photocontact dermatitis to ketoprofen. J Am Acad Dermatol. 1992 Aug;27(2 Pt 1):204-8. Review. PubMed PMID: 1430357.

18: Jamali F, Brocks DR. Clinical pharmacokinetics of ketoprofen and its enantiomers. Clin Pharmacokinet. 1990 Sep;19(3):197-217. Review. PubMed PMID: 2203580.

19: Sunshine A, Olson NZ. Analgesic efficacy of ketoprofen in postpartum, general surgery, and chronic cancer pain. J Clin Pharmacol. 1988 Dec;28(12 Suppl):S47-54. Review. PubMed PMID: 3072358.

20: Williams RL, Upton RA. The clinical pharmacology of ketoprofen. J Clin Pharmacol. 1988 Dec;28(12 Suppl):S13-22. Review. PubMed PMID: 3072352.

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