Natamycin
Grundinformationen
- 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- Summenformel
- C33H47O13N
- Durchschnittliche Molmasse
- 665,7 g/mol
- Monoisotopische Masse
- 665,30474055
Überblick
Natamycin is a Polyene Antimicrobial.
Namen und Bezeichner
- Bevorzugter 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
Namen und Synonyme
NATAMYCINpimaricin7681-93-8NatamicinaNatamycinePimaracinNatamycinumPimarizinMyprozinePimafucinTennecetinNatacyn
Weitere Namen anzeigen
DelvolanPimaricineDelvocidMycophytSynogilAntibiotic A-5283CL 12,6258O0C852CPO
Datenbank-Bezeichner
- CAS
52882-37-8、7681-93-8- PubChem CID
- 5284447
- DTXSID
DTXSID6021163- ChEMBL
CHEMBL1200656- UNII
- 8O0C852CPO
- EC Number
- 231-683-5
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -1,3
- Polarare Oberfläche (TPSA)
- 231 Ų
- H-Brücken-Donoren
- 7
- H-Brücken-Akzeptoren
- 14
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 47
- Formalladung
- 0
- Komplexität
- 1.220
Experimentelle und physikochemische Eigenschaften
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
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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.
Gefahrenhinweise
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
Toxikologische Informationen
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Chemie und Industrie
Pharmakologische Informationen
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.
Zugehörige Reaktionen
0
Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.
Notizen zur Verbindung
Wird geladen…