natamycin

Also known as CL-12625, PMR, E235, myprozine, pimaricin, antibiotic A-5283

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.

Key facts

Drug.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
Drug.image: Natamycin.svg
Drug.image_class: skin-invert-image
Drug.image2: Natamycin ball-and-stick.png
Drug.image_class2: bg-transparent
Drug.tradename: Natacyn, others
Drug.routes_of_administration: Eye drops
Drug.ATC_prefix: A01
Drug.ATC_suffix: AB10
Drug.ATC_supplemental: , , ,
Drug.CAS_number: 7681-93-8
Drug.PubChem: 441382
Drug.DrugBank: DB00826
Drug.ChemSpiderID: 10468784
Drug.UNII: 8O0C852CPO
Drug.KEGG: C08073
Drug.ChEMBL: 1200656
Drug.C: 33

via Wikipedia infobox

Chemical data

Formula: C33H47NO13
Molecular weight: 665.7 g/mol
IUPAC 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-methyloxan-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
SMILES: C[C@@H]1C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@@H]3[C@H](O3)/C=C/C(=O)O1)O)O)O)C(=O)O)O[C@H]4[C@H]([C@H]([C@@H]([C@H](O4)C)O)N)O
InChIKey: NCXMLFZGDNKEPB-FFPOYIOWSA-N
XLogP: -1.3
Polar surface area: 231 Å²
H-bond donors: 7
H-bond acceptors: 14
Formal charge: 0

via PubChem

Research

1,401 papers

Natamycin Ocular Delivery: Challenges and Advancements in Ocular Therapeutics.Advances in therapy · 2023
Natamycin versus voriconazole for fungal keratitis.Medwave · 2018
[Advances in the biosynthesis of natamycin and its regulatory mechanisms].Sheng wu gong cheng xue bao = Chinese journal of biotechnology · 2021
Semisynthetic Amides of Polyene Antibiotic Natamycin.ACS infectious diseases · 2023
Intrastromal natamycin: A well-aimed arrow in a difficult battle.Indian journal of ophthalmology · 2021

via PubMed

Wikidata facts

Mass: 665.305

Show 6 more facts

chemical formula: C₃₃H₄₇NO₁₃
defined daily dose: 20
World Health Organisation international non-proprietary name: natamycin
canonical SMILES: CC1CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC3C(O3)C=CC(=O)O1)O)O)O)C(=O)O)OC4C(C(C(C(O4)C)O)N)O
isomeric SMILES: C[C@@H]1C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@@H]3[C@H](O3)/C=C/C(=O)O1)O)O)O)C(=O)O)O[C@H]4[C@H]([C@H]([C@@H]([C@H](O4)C)O)N)O
Commons category: Natamycin

Sources (8)

via Wikidata · CC0

~7 min read

Article

9 sections

Contents

Uses
Medical
Food
Safety
Mechanism of action
Biochemistry
History
Society and culture
References

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.