Basic information
- CAS
52882-37-8- Standard SMILES
C[C@@H]1C/C=C/C=C/C=C/C=C/[C@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H](N)[C@@H]2O)C[C@@H]2O[C@](O)(C[C@@H](O)C[C@H]3O[C@@H]3/C=C/C(=O)O1)C[C@H](O)[C@H]2C(=O)O- InChIKey
NCXMLFZGDNKEPB-FFPOYIOWSA-N- Molecular formula
- C33H47O13N
- Average molar mass
- 665.7 g/mol
- Monoisotopic mass
- 665.30474055
Overview
Natamycin is a Polyene Antimicrobial.
Names & identifiers
- Preferred name
- Natamycin
- IUPAC
- (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
Names & synonyms
NATAMYCINpimaricin7681-93-8NatamicinaNatamycinePimaracinNatamycinumPimarizinMyprozinePimafucinTennecetinNatacyn
Show more names
DelvolanPimaricineDelvocidMycophytSynogilAntibiotic A-5283CL 12,6258O0C852CPO
Database identifiers
- CAS
52882-37-8、7681-93-8- PubChem CID
- 5284447
- DTXSID
DTXSID6021163- ChEMBL
CHEMBL1200656- UNII
- 8O0C852CPO
- EC Number
- 231-683-5
Properties
Computed structural properties
- XLogP
- -1.3
- Topological polar surface area
- 231 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 3
- Heavy atoms
- 47
- Formal charge
- 0
- Complexity
- 1,220
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
pH5,5-7,5 (1 % w/v solution in previously neutralised mixture of 20 parts dimethylformamide and 80 parts of water)
Pesticides
Other Treatment
Active substance -> EU Pesticides database: Pending
Food AdditivesFUMIGANT -> FDA Substance added to food
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antibacterial Agents; Anti-Infective Agents, Local; Antifungal Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Ophthalmological preparations > Anti-infective agents
Optical Rotation[α]D/20 + 250° to + 295° (a 1 % w/v solution in glacial acetic acid, at 20 °C and calculated with reference to the dried material)
Physical DescriptionWhite to creamy-white crystalline powder
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (6 of 6) of all reports.
Not Classified
Aggregated GHS information provided per 6 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Directive (EC) No 2/1995 (Repealed by Reg. EC No 1333/2008 (amended))
Natamycin: Does not have an individual approval but may be used under an appropriate group standard
Other Safety Information
IMAP assessments - Pimaricin: Environment tier I assessment
IMAP assessments - 6,11,28-Trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid, 22-[(3-amino-3,6-dideoxy-.beta.-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-: Environment tier I assessment
Hazard Classes and CategoriesNot Classified
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Chemistry & industry
Pharmacology
ATC Code
S - Sensory organs
A - Alimentary tract and metabolism
D - Dermatologicals
A - Alimentary tract and metabolism
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
Pharmacodynamics
Natamycin is an antifungal drug for topical ophthalmic administration. It is a tetraene polyene antibiotic derived from <i>Streptomyces natalensis</i>. It possesses in vitro activity against a variety of yeast and filamentous fungi, including <i>Candida</i>, <i>Aspergillus</i>, <i>Cephalosporium</i>, <i>Fusarium</i> and <i>Penicillium</i>. Although the activity against fungi is dose-related, natamycin is predominantly fungicidal. Natamycin is not effective in vitro against gram-positive or gram-negative bacteria. Topical administration appears to produce effective concentrations of natamycin within the corneal stroma but not in intraocular fluid.
Mechanism of Action
Like other polyene antibiotics, Natamycin inhibits fungal growth by binding to sterols. Specifically, Natamycin binds to ergosterol in the plasma membrane, preventing ergosterol-dependent fusion of vacuoles, as well as membrane fusion and fission. This differs from the mechanism of most other polyene antibiotics, which tend to work by altering fungal membrane permeability instead.
FDA Pharmacological Classification
8O0C852CPO
NATAMYCIN
Established Pharmacologic Class [EPC] - Polyene Antimicrobial
Chemical Structure [CS] - Polyenes
Natamycin is a Polyene Antimicrobial.
NATAMYCIN
MeSH Pharmacological Classification
Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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