Natamycin | CAS#7681-93-8 | ergosterol inhibitor

MedKoo Cat#: 540312 | Name: Natamycin

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Description:

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

Natamycin is an ergosterol inhibitor used to treat keratitis. It increases NALP3 inflammasome activaation, activates polyclonal B cells, and inhibits growth of Aspergillus and Fusarium.

Chemical Structure

Natamycin

CAS#7681-93-8

Theoretical Analysis

MedKoo Cat#: 540312

Name: Natamycin

CAS#: 7681-93-8

Chemical Formula: C33H47NO13

Exact Mass: 665.3047

Molecular Weight: 665.73

Elemental Analysis: C, 59.54; H, 7.12; N, 2.10; O, 31.24

Price and Availability

Size	Price	Availability
1g	USD 200.00	2 Weeks
2g	USD 350.00	2 Weeks
5g	USD 700.00	2 Weeks

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Related CAS #

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Synonym

CL 12625; CL12625; CL-12625; Delvocid; Delvolan; Natamycin

IUPAC/Chemical Name

(1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-(((2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid

InChi Key

NCXMLFZGDNKEPB-FFPOYIOWSA-N

InChi Code

InChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1

SMILES Code

OC([C@H]1[C@@]([H])(O[C@](C[C@@H](O)C[C@@]2([C@H](O2)/C=C/3)[H])(C[C@@H]1O)O)C[C@@H](O[C@@]([H])([C@H]4O)O[C@@H]([C@H]([C@@H]4N)O)C)/C=C/C=C/C=C/C=C/C[C@H](OC3=O)C)=O

Appearance

Solid powder

Purity

>95% (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

Instruction

View handling instruction

Biological target:

Natamycin (Pimaricin) is a macrolide antibiotic agent produced by several Streptomyces strains.

In vitro activity:

In contrast to other polyene antibiotics that form pores in the membrane, the mode of action of natamycin has remained obscure but is not related to membrane permeabilization. Here, this study demonstrates that natamycin inhibits growth of yeasts and fungi via the immediate inhibition of amino acid and glucose transport across the plasma membrane. Reference: Proc Natl Acad Sci U S A. 2012 Jul 10;109(28):11156-9. https://pubmed.ncbi.nlm.nih.gov/22733749/

In vivo activity:

In the present study, the effects of natamycin on the activities of some drug metabolizing enzymes in rat liver microsomes were determined in vivo. The activities of CYP2E1, CYP1A1/2 CYP2B1/2 and CYP4A1/2 enzymes significantly decreased after treatment with 1, 3 and 10 mg/kg bw/day, in a dose-dependent manner as compared to control. This effect was not observed after natamycin treatment at dose of 0.3 mg/kg bw/day. Reference: Food Chem Toxicol. 2013 Dec;62:281-4. https://pubmed.ncbi.nlm.nih.gov/24001439/

	Solvent	mg/mL	mM
Solubility
	DMSO	39.2	58.92
	Methanol	1.0	1.50
	Water	1.0	1.50

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 665.73 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. An Y, Jiang J, Zhou L, Shi J, Jin P, Li L, Peng L, He S, Zhang W, Huang C, Zou B, Xie N. Peroxiredoxin 1 is essential for natamycin-triggered apoptosis and protective autophagy in hepatocellular carcinoma. Cancer Lett. 2021 Aug 21;521:210-223. doi: 10.1016/j.canlet.2021.08.023. Epub ahead of print. PMID: 34428517. 2. te Welscher YM, van Leeuwen MR, de Kruijff B, Dijksterhuis J, Breukink E. Polyene antibiotic that inhibits membrane transport proteins. Proc Natl Acad Sci U S A. 2012 Jul 10;109(28):11156-9. doi: 10.1073/pnas.1203375109. Epub 2012 Jun 25. PMID: 22733749; PMCID: PMC3396478. 3. Martínez MA, Martínez-Larrañaga MR, Castellano V, Martínez M, Ares I, Romero A, Anadón A. Effect of natamycin on cytochrome P450 enzymes in rats. Food Chem Toxicol. 2013 Dec;62:281-4. doi: 10.1016/j.fct.2013.08.075. Epub 2013 Aug 31. PMID: 24001439.

In vitro protocol:

In vivo protocol:

1. Martínez MA, Martínez-Larrañaga MR, Castellano V, Martínez M, Ares I, Romero A, Anadón A. Effect of natamycin on cytochrome P450 enzymes in rats. Food Chem Toxicol. 2013 Dec;62:281-4. doi: 10.1016/j.fct.2013.08.075. Epub 2013 Aug 31. PMID: 24001439.

1: Dalhoff AA, Levy SB. Does use of the polyene natamycin as a food preservative jeopardise the clinical efficacy of amphotericin B? A word of concern. Int J Antimicrob Agents. 2015 Jun;45(6):564-7. doi: 10.1016/j.ijantimicag.2015.02.011. Epub 2015 Mar 21. Review. PubMed PMID: 25862309. 2: Prajna NV, Krishnan T, Mascarenhas J, Rajaraman R, Prajna L, Srinivasan M, Raghavan A, Oldenburg CE, Ray KJ, Zegans ME, McLeod SD, Porco TC, Acharya NR, Lietman TM; Mycotic Ulcer Treatment Trial Group. The mycotic ulcer treatment trial: a randomized trial comparing natamycin vs voriconazole. JAMA Ophthalmol. 2013 Apr;131(4):422-9. PubMed PMID: 23710492; PubMed Central PMCID: PMC3769211. 3: Liu SP, Yu P, Yuan PH, Zhou ZX, Bu QT, Mao XM, Li YQ. Sigma factor WhiGch positively regulates natamycin production in Streptomyces chattanoogensis L10. Appl Microbiol Biotechnol. 2015 Mar;99(6):2715-26. doi: 10.1007/s00253-014-6307-1. Epub 2015 Jan 21. PubMed PMID: 25724582. 4: Phan CM, Subbaraman L, Liu S, Gu F, Jones L. In vitro uptake and release of natamycin Dex-b-PLA nanoparticles from model contact lens materials. J Biomater Sci Polym Ed. 2014;25(1):18-31. doi: 10.1080/09205063.2013.830914. Epub 2013 Sep 6. PubMed PMID: 24007402. 5: Liu SP, Yuan PH, Wang YY, Liu XF, Zhou ZX, Bu QT, Yu P, Jiang H, Li YQ. Generation of the natamycin analogs by gene engineering of natamycin biosynthetic genes in Streptomyces chattanoogensis L10. Microbiol Res. 2015 Apr;173:25-33. doi: 10.1016/j.micres.2015.01.013. Epub 2015 Feb 7. PubMed PMID: 25801968. 6: Sharma S, Das S, Virdi A, Fernandes M, Sahu SK, Kumar Koday N, Ali MH, Garg P, Motukupally SR. Re-appraisal of topical 1% voriconazole and 5% natamycin in the treatment of fungal keratitis in a randomised trial. Br J Ophthalmol. 2015 Sep;99(9):1190-5. doi: 10.1136/bjophthalmol-2014-306485. Epub 2015 Mar 4. PubMed PMID: 25740805. 7: Wu H, Liu W, Dong D, Li J, Zhang D, Lu C. SlnM gene overexpression with different promoters on natamycin production in Streptomyces lydicus A02. J Ind Microbiol Biotechnol. 2014 Jan;41(1):163-72. doi: 10.1007/s10295-013-1370-7. Epub 2013 Oct 31. PubMed PMID: 24174215. 8: Phan CM, Subbaraman LN, Jones L. In vitro drug release of natamycin from β-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin-functionalized contact lens materials. J Biomater Sci Polym Ed. 2014;25(17):1907-19. doi: 10.1080/09205063.2014.958016. Epub 2014 Sep 16. PubMed PMID: 25226305. 9: Wang S, Liu F, Hou Z, Zong G, Zhu X, Ling P. Enhancement of natamycin production on Streptomyces gilvosporeus by chromosomal integration of the Vitreoscilla hemoglobin gene (vgb). World J Microbiol Biotechnol. 2014 Apr;30(4):1369-76. doi: 10.1007/s11274-013-1561-4. Epub 2013 Nov 23. PubMed PMID: 24272774. 10: Arima AA, Pavinatto FJ, Oliveira ON Jr, Gonzales ER. The negligible effects of the antifungal natamycin on cholesterol-dipalmitoyl phosphatidylcholine monolayers may explain its low oral and topical toxicity for mammals. Colloids Surf B Biointerfaces. 2014 Oct 1;122:202-8. doi: 10.1016/j.colsurfb.2014.06.058. Epub 2014 Jul 5. PubMed PMID: 25048356. 11: Chandasana H, Prasad YD, Chhonker YS, Chaitanya TK, Mishra NN, Mitra K, Shukla PK, Bhatta RS. Corneal targeted nanoparticles for sustained natamycin delivery and their PK/PD indices: an approach to reduce dose and dosing frequency. Int J Pharm. 2014 Dec 30;477(1-2):317-25. doi: 10.1016/j.ijpharm.2014.10.035. Epub 2014 Oct 16. PubMed PMID: 25455776. 12: Jain A, Shah SG, Chugh A. Cell penetrating peptides as efficient nanocarriers for delivery of antifungal compound, natamycin for the treatment of fungal keratitis. Pharm Res. 2015 Jun;32(6):1920-30. doi: 10.1007/s11095-014-1586-x. Epub 2014 Dec 3. PubMed PMID: 25467959. 13: Mimouni M, Tam G, Paitan Y, Kidron D, Segev F. Safety and efficacy of intrastromal injection of 5% natamycin in experimental fusarium keratitis. J Ocul Pharmacol Ther. 2014 Sep;30(7):543-7. doi: 10.1089/jop.2014.0004. Epub 2014 Jun 11. PubMed PMID: 24919100. 14: Kallinteri LD, Kostoula OK, Savvaidis IN. Efficacy of nisin and/or natamycin to improve the shelf-life of Galotyri cheese. Food Microbiol. 2013 Dec;36(2):176-81. doi: 10.1016/j.fm.2013.05.006. Epub 2013 May 29. PubMed PMID: 24010596. 15: Zeng X, Danquah MK, Jing K, Woo MW, Chen XD, Xie Y, Lu Y. Solubility properties and diffusional extraction behavior of natamycin from Streptomyces gilvosporeus biomass. Biotechnol Prog. 2013 Jan-Feb;29(1):109-15. doi: 10.1002/btpr.1659. Epub 2012 Dec 4. PubMed PMID: 23125192. 16: Sun CQ, Lalitha P, Prajna NV, Karpagam R, Geetha M, O'Brien KS, Oldenburg CE, Ray KJ, McLeod SD, Acharya NR, Lietman TM; Mycotic Ulcer Treatment Trial Group. Association between in vitro susceptibility to natamycin and voriconazole and clinical outcomes in fungal keratitis. Ophthalmology. 2014 Aug;121(8):1495-500.e1. doi: 10.1016/j.ophtha.2014.03.004. Epub 2014 Apr 16. PubMed PMID: 24746358; PubMed Central PMCID: PMC4122634. 17: Li M, Chen S, Li J, Ji Z. Propanol addition improves natamycin biosynthesis of Streptomyces natalensis. Appl Biochem Biotechnol. 2014 Apr;172(7):3424-32. doi: 10.1007/s12010-014-0766-9. Epub 2014 Feb 16. PubMed PMID: 24532463. 18: Balaguer MP, Fajardo P, Gartner H, Gomez-Estaca J, Gavara R, Almenar E, Hernandez-Munoz P. Functional properties and antifungal activity of films based on gliadins containing cinnamaldehyde and natamycin. Int J Food Microbiol. 2014 Mar 3;173:62-71. doi: 10.1016/j.ijfoodmicro.2013.12.013. Epub 2013 Dec 19. PubMed PMID: 24412960. 19: Dervisoglu M, Gul O, Aydemir O, Yazici F, Kahyaoglu T. Natamycin content and quality evaluation of yoghurt from small- and large-scale brands in Turkey. Food Addit Contam Part B Surveill. 2014;7(4):254-60. doi: 10.1080/19393210.2014.901426. Epub 2014 Apr 3. Erratum in: Food Addit Contam Part B Surveill. 2015;8(4):309. PubMed PMID: 25295914. 20: Phan CM, Subbaraman LN, Jones L. In vitro uptake and release of natamycin from conventional and silicone hydrogel contact lens materials. Eye Contact Lens. 2013 Mar;39(2):162-8. doi: 10.1097/ICL.0b013e31827a7a07. PubMed PMID: 23392304.