Natamycin

Natamycin
Clinical data
Trade names	Natacyn, others
AHFS/Drugs.com	Monograph
Routes of; administration	Eye drops
ATC code	A01AB10 (WHO) A07AA03 (WHO), D01AA02 (WHO), G01AA02 (WHO), S01AA10 (WHO);
Identifiers
	IUPAC name (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(3-amino-3,6-dideoxy-D-mannopyranosyl)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;
CAS Number	7681-93-8;
PubChem CID	441382;
DrugBank	DB00826;
ChemSpider	10468784;
UNII	8O0C852CPO;
KEGG	C08073;
ChEMBL	ChEMBL1200656;
E number	E235 (preservatives)
CompTox Dashboard (EPA)	DTXSID6021163 ;
ECHA InfoCard	100.028.803
Chemical and physical data
Formula	C33H47NO13
Molar mass	665.733 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.35 g/ml g/cm3
Melting point	Darkens at ±200 °C with vigorous decomposition at 280-300 °C
Solubility in water	0.39 mg/ml
	SMILES OC(=O)[C@@H]3[C@@H](O)C[C@@]2(O)C[C@@H](O)C[C@H]4O[C@@H]4/C=C/C(=O)O[C@H](C)C\C=C\C=C\C=C\C=C\[C@H](O[C@@H]1O[C@H](C)[C@@H](O)[C@H](N)[C@@H]1O)C[C@@H]3O2;
	InChI 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; ; Key:NCXMLFZGDNKEPB-FFPOYIOWSA-N;

Natamycin, also known as pimaricin, is an antifungal medication used to treat fungal infections around the eye.^[1]^[2] This includes infections of the eyelids, conjunctiva, and cornea.^[1] It is used as eyedrops.^[1] Natamycin is also used in the food industry as a preservative.^[2]

Allergic reactions may occur.^[1] It is unclear if medical use during pregnancy or breastfeeding is safe.^[1] It is in the macrolide and polyene families of medications.^[1] It results in fungal death by altering the cell membrane.^[1]

Natamycin was discovered in 1955 and approved for medical use in the United States in 1978.^[1]^[2] It is on the World Health Organization's List of Essential Medicines.^[3] It is produced by fermentation of certain types of the bacterium Streptomyces.^[1]^[4]

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "Natamycin". The American Society of Health-System Pharmacists. Retrieved 8 December 2017.
^ ^a ^b ^c Davidson PM, Juneja VK, Branen J (2001). "Antimicrobial Agents". In Branen AL, Davidson PM, Salminen S, Thorngate J (eds.). Food Additives. CRC Press. pp. 599–600. ISBN 9780824741709.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ Aparicio JF, Barreales EG, Payero TD, Vicente CM, de Pedro A, Santos-Aberturas J (January 2016). "Biotechnological production and application of the antibiotic pimaricin: biosynthesis and its regulation". Applied Microbiology and Biotechnology. 100 (1): 61–78. doi:10.1007/s00253-015-7077-0. PMC 4700089. PMID 26512010.