Narasin | CAS# 55134-13-9 | Antiprotozoal agent

MedKoo Cat#: 571088 | Name: Narasin

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Description:

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

Narasin is a novel agent that inhibits dengue virus replication in vitro through non-cytotoxic mechanisms, thus indicating its potential to be further developed as a therapeutic agent.It is used for the treatment of coccidiosis from a class of protozoa. It also triggers phospholipid scrambling of the erythrocyte cell membrane, an effect partially dependent on Ca2+ entry. It has been shown to foster apoptosis of tumor cells.

Chemical Structure

Narasin

CAS#55134-13-9

Theoretical Analysis

MedKoo Cat#: 571088

Name: Narasin

CAS#: 55134-13-9

Chemical Formula: C43H72O11

Exact Mass: 764.5075

Molecular Weight: 765.04

Elemental Analysis: C, 67.51; H, 9.49; O, 23.00

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 495.00	2 Weeks
25mg	USD 1,650.00	2 Weeks

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Synonym

Narasin; Monteban; A 28086A; A-28086A; A28086A

IUPAC/Chemical Name

2H-Pyran-2-acetic acid, alpha-ethyl-6-(5-(2-(5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro(4.1.5.3)pentadec-13-en-9-yl)-2-hydroxy-1,3-dimethyl-4-oxoheptyl)tetrahydro-3,5-dimethyl-

InChi Key

VHKXXVVRRDYCIK-UHFFFAOYSA-N

InChi Code

InChI=1S/C43H72O11/c1-12-30(35(46)27(8)34(45)28(9)36-23(4)21-24(5)37(51-36)31(13-2)39(47)48)38-25(6)22-26(7)42(52-38)18-15-32(44)43(54-42)20-19-40(11,53-43)33-16-17-41(49,14-3)29(10)50-33/h15,18,23-34,36-38,44-45,49H,12-14,16-17,19-22H2,1-11H3,(H,47,48)

SMILES Code

O=C(O)C(CC)C1C(C)CC(C)C(C(C)C(O)C(C)C(C(C(C(C)CC2C)OC2(C=CC3O)OC43CCC(C)(C5CCC(O)(CC)C(C)O5)O4)CC)=O)O1

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

>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#S20G09M16

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Narasin is a cationic ionophore and coccidiostat agent. Narasin inhibits NF-κB signaling and induces tumor cells apoptosis.

In vitro activity:

A 48 hours exposure of human erythrocytes to narasin (10 and 25 ng/ml) significantly increased the percentage of annexin-V-binding cells. Forward scatter was decreased by 1 ng/ml narasin but not by higher narasin concentrations (10 and 25 ng/ml). Narasin significantly increased Fluo3-fluorescence (10 and 25 ng/ml) and slightly, but significantly increased ceramide abundance (25 ng/ml). Reference: Cell Physiol Biochem. 2015;37(5):1807-16. https://pubmed.ncbi.nlm.nih.gov/26584281/

In vivo activity:

As the inhibition of primary BC tumor metastasis was observed following narasin treatment, the in vivo antitumor activities of narasin were investigated using the nude mouse subcutaneous xenograft model with MCF-7 cells. Intraperitoneal administration of narasin (0.5 and 1.5 mg/kg, 14 days) significantly decreased tumor volume (Fig. 7A) and tumor weight (Fig. 7B) without noticeable weight changes (Fig. 7C). Reference: Mol Med Rep. 2020 Dec;22(6):5113-5124. https://pubmed.ncbi.nlm.nih.gov/33174044/

	Solvent	mg/mL	mM
Solubility
	DMSO	25.0	32.68

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 765.04 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. Chan WY, Hickey EE, Khazandi M, Page SW, Trott DJ, Hill PB. In vitro antimicrobial activity of narasin against common clinical isolates associated with canine otitis externa. Vet Dermatol. 2018 Apr;29(2):149-e57. doi: 10.1111/vde.12516. Epub 2018 Jan 24. PMID: 29363210. 2. Bouguerra G, Bissinger R, Abbès S, Lang F. Stimulation of Eryptosis by Narasin. Cell Physiol Biochem. 2015;37(5):1807-16. doi: 10.1159/000438543. Epub 2015 Nov 13. PMID: 26584281. 3. Chen J, Huang X, Li N, Liu B, Ma Z, Ling J, Yang W, Li T. Narasin inhibits tumor metastasis and growth of ERα‑positive breast cancer cells by inactivation of the TGF‑β/SMAD3 and IL‑6/STAT3 signaling pathways. Mol Med Rep. 2020 Dec;22(6):5113-5124. doi: 10.3892/mmr.2020.11624. Epub 2020 Oct 21. PMID: 33174044; PMCID: PMC7646975.

In vitro protocol:

In vivo protocol:

1. Chen J, Huang X, Li N, Liu B, Ma Z, Ling J, Yang W, Li T. Narasin inhibits tumor metastasis and growth of ERα‑positive breast cancer cells by inactivation of the TGF‑β/SMAD3 and IL‑6/STAT3 signaling pathways. Mol Med Rep. 2020 Dec;22(6):5113-5124. doi: 10.3892/mmr.2020.11624. Epub 2020 Oct 21. PMID: 33174044; PMCID: PMC7646975.

1: Bouguerra G, Bissinger R, Abbès S, Lang F. Stimulation of Eryptosis by Narasin. Cell Physiol Biochem. 2015;37(5):1807-16. doi: 10.1159/000438543. Epub 2015 Nov 13. PubMed PMID: 26584281. 2: Arkfeld EK, Carr SN, Rincker PJ, Gruber SL, Allee GL, Dilger AC, Boler DD. Effects of narasin (Skycis) on live performance and carcass traits of finishing pigs sold in a three-phase marketing system. J Anim Sci. 2015 Oct;93(10):5028-35. doi: 10.2527/jas.2015-9314. PubMed PMID: 26523595. 3: Nilsson O, Myrenås M, Ågren J. Transferable genes putatively conferring elevated minimum inhibitory concentrations of narasin in Enterococcus faecium from Swedish broilers. Vet Microbiol. 2016 Feb 29;184:80-3. doi: 10.1016/j.vetmic.2016.01.012. Epub 2016 Jan 18. PubMed PMID: 26854348. 4: Low JS, Wu KX, Chen KC, Ng MM, Chu JJ. Narasin, a novel antiviral compound that blocks dengue virus protein expression. Antivir Ther. 2011;16(8):1203-18. doi: 10.3851/IMP1884. PubMed PMID: 22155902. 5: Cybulski W, Radko L, Rzeski W. Cytotoxicity of monensin, narasin and salinomycin and their interaction with silybin in HepG2, LMH and L6 cell cultures. Toxicol In Vitro. 2015 Mar;29(2):337-44. doi: 10.1016/j.tiv.2014.11.013. Epub 2014 Dec 9. PubMed PMID: 25500126. 6: Mizinga KM, Burnett TJ, Brunelle SL, Wallace MA, Coleman MR. Determination of Narasin in Chicken Fat: A Bridging Study Comparing the Bioautographic Method (FSIS CLG Method R22) to a Liquid Chromatography with Tandem Mass Spectrometry Method (AOAC Method 2011.24). J AOAC Int. 2016 Mar-Apr;99(2):565-70. doi: 10.5740/jaoacint.15-0005. Epub 2016 Mar 9. PubMed PMID: 26961063. 7: Burnett TJ, Lombardi K, Rodewald JM, Brunelle SL, MacDougall J, Coleman MR. Determination of narasin and monensin in bovine, swine, and chicken tissues by liquid chromatography with tandem mass spectrometry: first action 2011.24. J AOAC Int. 2012 Jul-Aug;95(4):959-91. PubMed PMID: 22970563. 8: Kaldhusdal M, Hetland H, Gjevre AG. Non-soluble fibres and narasin reduce spontaneous gizzard erosion and ulceration in broiler chickens. Avian Pathol. 2012;41(2):227-34. doi: 10.1080/03079457.2012.667559. PubMed PMID: 22515541. 9: Lombardi KR, Burnett TJ, Brunelle SL, Ulrey WD, Coleman MR. Determination and confirmation of narasin and monensin in chicken, swine, and bovine tissues by LC/MS/MS: Final Action 2011.24. J AOAC Int. 2013 Jul-Aug;96(4):902-9. PubMed PMID: 24000767. 10: Nilsson O, Greko C, Bengtsson B, Englund S. Genetic diversity among VRE isolates from Swedish broilers with the coincidental finding of transferrable decreased susceptibility to narasin. J Appl Microbiol. 2012 Apr;112(4):716-22. doi: 10.1111/j.1365-2672.2012.05254.x. Epub 2012 Mar 5. PubMed PMID: 22324455. 11: Novilla MN, Owen NV, Todd GC. The comparative toxicology of narasin in laboratory animals. Vet Hum Toxicol. 1994 Aug;36(4):318-23. PubMed PMID: 7975139. 12: Brennan J, Bagg R, Barnum D, Wilson J, Dick P. Efficacy of narasin in the prevention of necrotic enteritis in broiler chickens. Avian Dis. 2001 Jan-Mar;45(1):210-4. PubMed PMID: 11332485. 13: Jeffers TK, Tonkinson LV, Callender ME. Anticoccidial efficacy of narasin in battery cage trials. Poult Sci. 1988 Jul;67(7):1043-9. PubMed PMID: 3222191. 14: Eggen T, Asp TN, Grave K, Hormazabal V. Uptake and translocation of metformin, ciprofloxacin and narasin in forage- and crop plants. Chemosphere. 2011 Sep;85(1):26-33. doi: 10.1016/j.chemosphere.2011.06.041. Epub 2011 Jul 14. PubMed PMID: 21757221. 15: Brennan J, Skinner J, Barnum DA, Wilson J. The efficacy of bacitracin methylene disalicylate when fed in combination with narasin in the management of necrotic enteritis in broiler chickens. Poult Sci. 2003 Mar;82(3):360-3. PubMed PMID: 12705394. 16: Angelovičová M, Kunová S, Čapla J, Zajac P, Bučko O, Angelovič M. Comparison of fatty acid profile in the chicken meat after feeding with narasin, nicarbazin and salinomycin sodium and phyto-additive substances. J Environ Sci Health B. 2016;51(6):374-82. doi: 10.1080/03601234.2016.1142320. Epub 2016 Mar 7. PubMed PMID: 26950416. 17: Jeffers TK. Resistance and cross-resistance studies with narasin, a new polyether antibiotic anticoccidial drug. Avian Dis. 1981 Apr-Jun;25(2):395-403. PubMed PMID: 7259679. 18: Catherman DR, Szabo J, Batson DB, Cantor AH, Tucker RE, Mitchell GE Jr. Metabolism of narasin in chickens and Japanese quail. Poult Sci. 1991 Jan;70(1):120-5. PubMed PMID: 2017406. 19: Rokka M, Eerola S, Perttilä U, Rossow L, Venäläinen E, Valkonen E, Valaja J, Peltonen K. The residue levels of narasin in eggs of laying hens fed with unmedicated and medicated feed. Mol Nutr Food Res. 2005 Jan;49(1):38-42. PubMed PMID: 15538711. 20: Jeffers TK, Tonkinson LV, Callender ME, Schlegel BF, Reid WM. Anticoccidial efficacy of narasin in floor pen trials. Poult Sci. 1988 Jul;67(7):1050-7. PubMed PMID: 3222192.