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. This includes infections of the eyelids, conjunctiva, and cornea. It is used as eyedrops. Natamycin is also used in the food industry as a preservative.

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

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

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