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

MedKoo CAT#: 540312

CAS#: 7681-93-8

Description: 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.


Price and Availability

Size
Price

50mg
USD 200
Size
Price

100mg
USD 345
Size
Price

1g
USD 850

Natamycin purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 540312
Name: Natamycin
CAS#: 7681-93-8
Chemical Formula: C33H47NO14
Exact Mass: 681.2997
Molecular Weight: 681.73
Elemental Analysis: C, 58.14; H, 6.95; N, 2.05; O, 32.86


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

IUPAC/Chemical Name: (2E,8E,10E,12E,14E)-16-(((2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-18,20,24-trihydroxy-6-methyl-4,22-dioxo-5,27-dioxabicyclo[24.1.0]heptacosa-2,8,10,12,14-pentaen-19-yl hydrogen carbonate

InChi Key: OEEHRJFLJYDOII-DWQLXOFXSA-N

InChi Code: InChI=1S/C33H47NO14/c1-18-10-8-6-4-3-5-7-9-11-22(46-32-30(41)28(34)29(40)19(2)45-32)17-24(38)31(48-33(42)43)23(37)15-20(35)14-21(36)16-26-25(47-26)12-13-27(39)44-18/h3-9,11-13,18-19,21-26,28-32,36-38,40-41H,10,14-17,34H2,1-2H3,(H,42,43)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18?,19-,21?,22?,23?,24?,25?,26?,28+,29-,30+,31?,32+/m1/s1

SMILES Code: O=C(O)OC1C(O)CC(CC(O)CC2C(O2)/C=C/C(OC(C)C/C=C/C=C/C=C/C=C/C(O[C@H]3[C@H]([C@@H](N)[C@@H]([C@@H](C)O3)O)O)CC1O)=O)=O


Technical Data

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).

Harmonized System Code:
293490


References

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.