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MedKoo Cat#: 592666 | Name: Loxoprofen
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Description:

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

Loxoprofen is a nonsteroidal anti-inflammatory drug (NSAID) of the propionic acid class, used primarily for its analgesic, antipyretic, and anti-inflammatory effects. It functions as a prodrug, rapidly converted in vivo to its active trans-alcohol metabolite, which inhibits cyclooxygenase (COX) enzymes and suppresses prostaglandin synthesis. Loxoprofen is widely used in Japan and other Asian countries for the treatment of musculoskeletal pain, arthritis, and postoperative inflammation.

Chemical Structure

Loxoprofen
Loxoprofen
CAS#68767-14-6 (free acid)

Theoretical Analysis

MedKoo Cat#: 592666

Name: Loxoprofen

CAS#: 68767-14-6 (free acid)

Chemical Formula: C15H18O3

Exact Mass: 246.1300

Molecular Weight: 246.31

Elemental Analysis: C, 73.15; H, 7.37; O, 19.49

Price and Availability

Size Price Availability Quantity
5g USD 350.00 2 weeks
10g USD 450.00 2 Weeks
25g USD 750.00 2 Weeks
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Related CAS #
80382-23-6 (sodium) 68767-14-6 (free acid) 226721-96-6 (sodium hydrate)
Synonym
Loxoprofen, Koloxo
IUPAC/Chemical Name
2-(4-((2-Oxocyclopentyl)methyl)phenyl)propanoic acid
InChi Key
YMBXTVYHTMGZDW-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H18O3/c1-10(15(17)18)12-7-5-11(6-8-12)9-13-3-2-4-14(13)16/h5-8,10,13H,2-4,9H2,1H3,(H,17,18)
SMILES Code
CC(C1=CC=C(CC2C(CCC2)=O)C=C1)C(O)=O
Appearance
Solid powder
Purity
>97% (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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Loxoprofen sodium dihydrate is a nonselective COX inhibitor with IC50s of 6.5 and 13.5 μM for COX-1 and COX-2, respectively.
In vitro activity:
Loxoprofen sodium suppressed endothelial AT2R elevation by angiotensin II. Loxoprofen ameliorated Angiotensin II-induced production of ROS, reduced GSH, and NOX-2 and NOX-4 expression. Furthermore, Loxoprofen mitigated Angiotensin II, reduced mitochondrial membrane potential and improved cell viability, and suppressed LDH release by angiotensin II. Reference: Drug Des Devel Ther. 2020 Nov 18;14:5087-5096. https://pubmed.ncbi.nlm.nih.gov/33239867/
In vivo activity:
Atherosclerotic lesion formation was reduced to 63.5% and 41.5% as compared to the control in male and female apoE(-/-) mice treated with loxoprofen sodium respectively. Urinary metabolites of prostaglandin E(2), F(1α), and thromboxane B(2), and platelet aggregation were decreased in mice treated with loxoprofen sodium. Reference: J Clin Biochem Nutr. 2010 Sep;47(2):138-47. https://pubmed.ncbi.nlm.nih.gov/20838569/

Preparing Stock Solutions

The following data is based on the product molecular weight 246.31 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.

Recalculate based on batch purity %
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. Ji C, Yu Y, Zhang M, Yu W, Dong S. Loxoprofen Sodium Alleviates Oxidative Stress and Apoptosis Induced by Angiotensin II in Human Umbilical Vein Endothelial Cells (HUVECs). Drug Des Devel Ther. 2020 Nov 18;14:5087-5096. doi: 10.2147/DDDT.S266175. PMID: 33239867; PMCID: PMC7680688. 2. Hamaguchi M, Seno T, Yamamoto A, Kohno M, Kadoya M, Ishino H, Ashihara E, Kimura S, Tsubakimoto Y, Takata H, Yoshikawa T, Maekawa T, Kawahito Y. Loxoprofen Sodium, a Non-Selective NSAID, Reduces Atherosclerosis in Mice by Reducing Inflammation. J Clin Biochem Nutr. 2010 Sep;47(2):138-47. doi: 10.3164/jcbn.10-33. Epub 2010 Jul 3. PMID: 20838569; PMCID: PMC2935154. 3. Kanda A, Ebihara S, Takahashi H, Sasaki H. Loxoprofen sodium suppresses mouse tumor growth by inhibiting vascular endothelial growth factor. Acta Oncol. 2003;42(1):62-70. doi: 10.1080/0891060310002258. PMID: 12665333.
In vitro protocol:
1. Ji C, Yu Y, Zhang M, Yu W, Dong S. Loxoprofen Sodium Alleviates Oxidative Stress and Apoptosis Induced by Angiotensin II in Human Umbilical Vein Endothelial Cells (HUVECs). Drug Des Devel Ther. 2020 Nov 18;14:5087-5096. doi: 10.2147/DDDT.S266175. PMID: 33239867; PMCID: PMC7680688.
In vivo protocol:
1. Hamaguchi M, Seno T, Yamamoto A, Kohno M, Kadoya M, Ishino H, Ashihara E, Kimura S, Tsubakimoto Y, Takata H, Yoshikawa T, Maekawa T, Kawahito Y. Loxoprofen Sodium, a Non-Selective NSAID, Reduces Atherosclerosis in Mice by Reducing Inflammation. J Clin Biochem Nutr. 2010 Sep;47(2):138-47. doi: 10.3164/jcbn.10-33. Epub 2010 Jul 3. PMID: 20838569; PMCID: PMC2935154. 2. Kanda A, Ebihara S, Takahashi H, Sasaki H. Loxoprofen sodium suppresses mouse tumor growth by inhibiting vascular endothelial growth factor. Acta Oncol. 2003;42(1):62-70. doi: 10.1080/0891060310002258. PMID: 12665333.
1: Onda A, Ogoshi A, Itoh M, Nakagawa T, Kimura M. Comparison of the effects of treatment with celecoxib, loxoprofen, and acetaminophen on postoperative acute pain after arthroscopic knee surgery: A randomized, parallel-group trial. J Orthop Sci. 2016 Mar;21(2):172-7. doi: 10.1016/j.jos.2015.11.005. Epub 2016 Feb 14. PubMed PMID: 26888227. 2: Narumi K, Kobayashi M, Kondo A, Furugen A, Yamada T, Takahashi N, Iseki K. Characterization of loxoprofen transport in Caco-2 cells: the involvement of a proton-dependent transport system in the intestinal transport of loxoprofen. Biopharm Drug Dispos. 2016 Nov;37(8):447-455. doi: 10.1002/bdd.2026. Epub 2016 Sep 19. PubMed PMID: 27514365. 3: Kikuchi H, Aoyagi M, Nagahama K, Yajima Y, Yamamura C, Arai Y, Hirasawa S, Aki S, Inaba N, Tanaka H, Tamura T. Nephrotic-range proteinuria and interstitial nephritis associated with the use of a topical loxoprofen patch. Intern Med. 2014;53(11):1131-5. Epub 2014 Jun 1. PubMed PMID: 24881736. 4: Iwai T, Ichikawa T, Kida M, Goso Y, Kurihara M, Koizumi W, Ishihara K. Protective effect of geranylgeranylacetone against loxoprofen sodium-induced small intestinal lesions in rats. Eur J Pharmacol. 2011 Feb 10;652(1-3):121-5. doi: 10.1016/j.ejphar.2010.11.020. Epub 2010 Dec 2. PubMed PMID: 21130762. 5: Yamakawa N, Suemasu S, Kimoto A, Arai Y, Ishihara T, Yokomizo K, Okamoto Y, Otsuka M, Tanaka K, Mizushima T. Low direct cytotoxicity of loxoprofen on gastric mucosal cells. Biol Pharm Bull. 2010;33(3):398-403. PubMed PMID: 20190399. 6: Hiroshima Y, Kato T, Tajima K. Regression of diffuse large B-cell lymphoma in sphenoid and ethmoid sinuses following treatment with loxoprofen. Leuk Lymphoma. 2016;57(3):721-3. doi: 10.3109/10428194.2015.1070154. Epub 2015 Jul 7. PubMed PMID: 26148875. 7: Hayashi S, Kurata N, Kitahirachi E, Nishimura Y, Amagase K, Yano T, Takeuchi K. Cinacalcet, a calcimimetic, prevents nonsteroidal antiinflammatory drug-induced small intestinal damage in rats. J Physiol Pharmacol. 2013 Aug;64(4):453-63. PubMed PMID: 24101391. 8: Kawano S, Tsuji S, Hayashi N, Takei Y, Nagano K, Fusamoto H, Kamada T. Effects of loxoprofen sodium, a newly synthesized non-steroidal anti-inflammatory drug, and indomethacin on gastric mucosal haemodynamics in the human. J Gastroenterol Hepatol. 1995 Jan-Feb;10(1):81-5. PubMed PMID: 7620114. 9: Nakase H, Itani T, Mimura J, Kawasaki T, Komori H, Hashimoto K, Chiba T. Colonic ulceration caused by administration of loxoprofen sodium. Intern Med. 1999 Mar;38(3):249-51. PubMed PMID: 10337935. 10: Yamamoto T, Kaku M, Sumi H, Yashima Y, Izumino J, Tanimoto K. Effects of loxoprofen on the apical root resorption during orthodontic tooth movement in rats. PLoS One. 2018 Apr 25;13(4):e0194453. doi: 10.1371/journal.pone.0194453. eCollection 2018. PubMed PMID: 29694352; PubMed Central PMCID: PMC5919005. 11: Fujita K, Sakamoto O, Matsumoto M, Kohrogi H, Suga M. [A case of loxoprofen sodium-induced bronchiolitis obliterans organizing pneumonia (BOOP)]. Nihon Kokyuki Gakkai Zasshi. 2003 Dec;41(12):878-83. Japanese. PubMed PMID: 14727549. 12: Kazama I, Sasagawa N, Nakajima T. Complete remission of human parvovirus b19 associated symptoms by loxoprofen in patients with atopic predispositions. Case Rep Med. 2012;2012:703281. doi: 10.1155/2012/703281. Epub 2012 Apr 24. PubMed PMID: 22611409; PubMed Central PMCID: PMC3348632. 13: Uwai Y, Taniguchi R, Motohashi H, Saito H, Okuda M, Inui K. Methotrexate-loxoprofen interaction: involvement of human organic anion transporters hOAT1 and hOAT3. Drug Metab Pharmacokinet. 2004 Oct;19(5):369-74. PubMed PMID: 15548848. 14: Kanda A, Ebihara S, Okazaki T, Yasuda H, Sasaki H. Loxoprofen sodium and survival in older people with advanced non-small cell lung cancer. J Am Geriatr Soc. 2004 Mar;52(3):471-2. PubMed PMID: 14962172. 15: Kanda A, Ebihara S, Takahashi H, Sasaki H. Loxoprofen sodium suppresses mouse tumor growth by inhibiting vascular endothelial growth factor. Acta Oncol. 2003;42(1):62-70. PubMed PMID: 12665333. 16: Izumo T, Kondo M, Mae M, Onizawa S, Nagara N, Nozu T, Tamaoki J, Ohnuki T, Nagai A. [Case of loxoprofen sodium-induced eosinophilic pneumonia that occurred ipsilaterally after VATS lobectomy for lung cancer]. Nihon Kokyuki Gakkai Zasshi. 2007 Oct;45(10):799-803. Japanese. PubMed PMID: 18018630. 17: Oba Y, Watanabe H, Nishimura Y, Ueno S, Nagashima T, Imai Y, Shimpo M, Kario K. A Case of Adult-Onset Acute Rheumatic Fever With Long-Lasting Atrioventricular Block Requiring Permanent Pacemaker Implantation. Int Heart J. 2015;56(6):664-7. doi: 10.1536/ihj.15-091. Epub 2015 Nov 9. PubMed PMID: 26549396. 18: Kanbayashi Y, Konishi H. Predictive Factors for NSAIDs-related Gastrointestinal Toxicity: Can COX-2 Selective Inhibtor Prevent it?. Hepatogastroenterology. 2015 Jun;62(140):787-9. PubMed PMID: 26902001. 19: Boušová I, Skálová L, Souček P, Matoušková P. The modulation of carbonyl reductase 1 by polyphenols. Drug Metab Rev. 2015;47(4):520-33. doi: 10.3109/03602532.2015.1089885. Epub 2015 Sep 29. Review. PubMed PMID: 26415702. 20: Tohyama M, Tamaki Y, Toyama M, Ishimine T, Miyazato A, Nakamoto A, Miyara T, Higa F, Tateyama M, Kawakami K, Nakamura H, Saito A. [A case of loxoprofen-induced pneumonitis pathologically resembling hypersensitivity pneumonitis]. Nihon Kokyuki Gakkai Zasshi. 2002 Feb;40(2):123-8. Japanese. PubMed PMID: 11974866.