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MedKoo Cat#: 592802 | Name: Amfenac

Description:

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

Amfenac promotes apoptosis in ARPE-19 cell culture.

Chemical Structure

Amfenac
Amfenac
CAS#51579-82-9 (free)

Theoretical Analysis

MedKoo Cat#: 592802

Name: Amfenac

CAS#: 51579-82-9 (free)

Chemical Formula: C15H13NO3

Exact Mass: 255.0895

Molecular Weight: 255.27

Elemental Analysis: C, 70.58; H, 5.13; N, 5.49; O, 18.80

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
61618-27-7 (sodium hydrate) 61941-56-8 (sodium) 51579-82-9 (free)
Synonym
Amfenac; NSC 309467; NSC-309467; NSC309467
IUPAC/Chemical Name
2-(2-amino-3-benzoylphenyl)acetic acid
InChi Key
SOYCMDCMZDHQFP-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H13NO3/c16-14-11(9-13(17)18)7-4-8-12(14)15(19)10-5-2-1-3-6-10/h1-8H,9,16H2,(H,17,18)
SMILES Code
O=C(O)CC1=CC=CC(C(C2=CC=CC=C2)=O)=C1N
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 255.27 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
1: Argun M, Tök L, Uğuz AC, Çelik Ö, Tök ÖY, Naziroğlu M. Melatonin and amfenac modulate calcium entry, apoptosis, and oxidative stress in ARPE-19 cell culture exposed to blue light irradiation (405 nm). Eye (Lond). 2014 Jun;28(6):752-60. doi: 10.1038/eye.2014.50. Epub 2014 Mar 7. PubMed PMID: 24603419; PubMed Central PMCID: PMC4058615. 2: Chastain JE, Sanders ME, Curtis MA, Chemuturi NV, Gadd ME, Kapin MA, Markwardt KL, Dahlin DC. Distribution of topical ocular nepafenac and its active metabolite amfenac to the posterior segment of the eye. Exp Eye Res. 2016 Apr;145:58-67. doi: 10.1016/j.exer.2015.10.009. Epub 2015 Oct 22. PubMed PMID: 26474497. 3: Yanni SE, Clark ML, Yang R, Bingaman DP, Penn JS. The effects of nepafenac and amfenac on retinal angiogenesis. Brain Res Bull. 2010 Feb 15;81(2-3):310-9. doi: 10.1016/j.brainresbull.2009.10.018. Epub 2009 Nov 6. PubMed PMID: 19897019; PubMed Central PMCID: PMC2815002. 4: Hiranuma T, Kato S, Hachisu M. Analgesic action of amfenac Na, a non-steroidal anti-inflammatory agent. J Pharmacobiodyn. 1988 Sep;11(9):612-9. PubMed PMID: 3265150. 5: Jain AK, Hunley CC, Kuebel J, McMahon FG, Ryan JJ. Analgesic efficacy of amfenac, aspirin and placebo after extraction of impacted teeth. Pharmacotherapy. 1986 Sep-Oct;6(5):236-40. PubMed PMID: 3540874. 6: Walters T, Raizman M, Ernest P, Gayton J, Lehmann R. In vivo pharmacokinetics and in vitro pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac. J Cataract Refract Surg. 2007 Sep;33(9):1539-45. PubMed PMID: 17720067. 7: Bucci FA Jr, Waterbury LD. Re: Pharmacokinetics and pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac. J Cataract Refract Surg. 2008 Aug;34(8):1226; author reply 1226-7. doi: 10.1016/j.jcrs.2008.05.019. PubMed PMID: 18655957. 8: Fernandes BF, Marshall JC, Di Cesare S, Logan P, Maloney S, Burnier MN Jr. Amfenac increases the radiosensitivity of uveal melanoma cell lines. Eye (Lond). 2008 May;22(5):701-6. Epub 2007 Nov 30. PubMed PMID: 18049486. 9: Kato Y, Shimokawa M, Yokoyama T, Mohri K. Simultaneous determination of amfenac sodium and its metabolite (7-benzoyl-2-oxindole) in human plasma by high-performance liquid chromatography. J Chromatogr. 1993 Jun 23;616(1):67-71. PubMed PMID: 8376494. 10: Kida T, Kozai S, Takahashi H, Isaka M, Tokushige H, Sakamoto T. Pharmacokinetics and efficacy of topically applied nonsteroidal anti-inflammatory drugs in retinochoroidal tissues in rabbits. PLoS One. 2014 May 5;9(5):e96481. doi: 10.1371/journal.pone.0096481. eCollection 2014. PubMed PMID: 24796327; PubMed Central PMCID: PMC4010472. 11: Sasaki H, Odaki M, Yokota M, Kawaoto H, Watanabe H, Itoh T, Ishiwatari N, Wada T, Seki M, Takeda U, et al. Toxicological studies on Amfenac sodium (AHR-5850) (I) Acute toxicities in mice and rats. J Toxicol Sci. 1984 Feb;9(1):87-99. PubMed PMID: 6471132. 12: Matsumoto T, Yuda Y, Sekizawa Y, Takano T. Effect of a non-steroidal anti-inflammatory drug (amfenac sodium) on polymorphonuclear leukocytes. Pharmacol Res Commun. 1982 Jun;14(6):523-32. PubMed PMID: 7122676. 13: Bucolo C, Marrazzo G, Platania CB, Romano GL, Drago F, Salomone S. Effects of topical indomethacin, bromfenac and nepafenac on lipopolysaccharide-induced ocular inflammation. J Pharm Pharmacol. 2014 Jul;66(7):954-60. doi: 10.1111/jphp.12224. Epub 2014 Feb 12. PubMed PMID: 24697218. 14: Jones BM, Neville MW. Nepafenac: an ophthalmic nonsteroidal antiinflammatory drug for pain after cataract surgery. Ann Pharmacother. 2013 Jun;47(6):892-6. doi: 10.1345/aph.1R757. Epub 2013 May 28. Review. PubMed PMID: 23715071. 15: de Souza Filho JP, Correa ZM, Marshall JC, Anteka E, Coutinho AB, Martins MC, Burnier MN. The effect of a selective cyclooxygenase-2 (COX-2) inhibitor on the proliferation rate of retinoblastoma cell lines. Eye (Lond). 2006 May;20(5):598-601. PubMed PMID: 16123787. 16: Ruiz J, López M, Milà J, Lozoya E, Lozano JJ, Pouplana R. QSAR and conformational analysis of the antiinflammatory agent amfenac and analogues. J Comput Aided Mol Des. 1993 Apr;7(2):183-98. PubMed PMID: 8320556. 17: Bucci FA Jr, Waterbury LD. A randomized comparison of to-aqueous penetration of ketorolac 0.45%, bromfenac 0.09% and nepafenac 0.1% in cataract patients undergoing phacoemulsification. Curr Med Res Opin. 2011 Dec;27(12):2235-9. doi: 10.1185/03007995.2011.626018. Epub 2011 Oct 12. PubMed PMID: 21992076. 18: Marshall JC, Caissie AL, Cruess SR, Cools-Lartigue J, Burnier MN Jr. The effects of a cyclooxygenase-2 (COX-2) expression and inhibition on human uveal melanoma cell proliferation and macrophage nitric oxide production. J Carcinog. 2007 Nov 27;6:17. PubMed PMID: 18042295; PubMed Central PMCID: PMC2222223. 19: Lal N, Kumar J, Erdahl WE, Pfeiffer DR, Gadd ME, Graff G, Yanni JM. Differential effects of non-steroidal anti-inflammatory drugs on mitochondrial dysfunction during oxidative stress. Arch Biochem Biophys. 2009 Oct 1;490(1):1-8. PubMed PMID: 19810214. 20: Yuda Y, Tanaka J, Suzuki K, Igarashi K, Satoh T. Inhibitory effects of non-steroidal anti-inflammatory drugs on superoxide generation. Chem Pharm Bull (Tokyo). 1991 Apr;39(4):1075-7. PubMed PMID: 1654219.