Nystatin
(1S,3R,4R,7R,9R,11R,15S,16R,17R,18S,19E,21E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-azaniumyl-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylate
Grundinformationen
- CAS
1400-61-9- Standard-SMILES
C[C@@H]1[C@H](O)[C@@H](C)/C=C/C=C/CC/C=C/C=C/C=C/C=C/[C@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H]([NH3+])[C@@H]2O)C[C@@H]2O[C@](O)(C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)C[C@@H](O)CC(=O)O[C@H]1C)C[C@H](O)[C@H]2C(=O)[O-]- InChIKey
VQOXZBDYSJBXMA-NQTDYLQESA-N- Summenformel
- C47H75NO17
- Durchschnittliche Molmasse
- 926,1 g/mol
- Monoisotopische Masse
- 925,50349992
Überblick
Nystatin is a polyene antifungal drug that has broad-spectrum fungicidal and fungistatic activity against a number of yeasts and fungi, most notably Candida species. It is one of the most effective antifungal agents synthesized by bacteria, in this case a strain of Streptomyces noursei, and is closely related to [amphotericin B], differing only slightly in structure. Nystatin has a greater antifungal activity than amphotericin B - parenterally administered nystatin, however, is associated with significant toxicity and is not available in a formulation appropriate for systemic use. As it undergoes very little absorption following oral or topical administration, nystatin's efficacy is limited to the treatment/prevention of cutaneous, mucocutaneous, and gastrointestinal fungal infections.
Namen und Bezeichner
- Bevorzugter Name
- (1S,3R,4R,7R,9R,11R,15S,16R,17R,18S,19E,21E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-azaniumyl-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylate
- IUPAC
- (1S,3R,4R,7R,9R,11R,15S,16R,17R,18S,19E,21E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-azaniumyl-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylate
- Lokaler Name
- Nystatin
- Englischer Name
- Nystatin
- Summenformel
- C47H75NO17
- Molmasse
- 926.09
Namen und Synonyme
nystatineMYCOSTATINNYSFUNGINNystainNystatin CRSNystexNystopnilstatNystatin (Fungicidin)nystan
Datenbank-Bezeichner
- CAS
1400-61-9、34786-70-4- PubChem CID
- 91820523
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,5
- Polarare Oberfläche (TPSA)
- 324 Ų
- H-Brücken-Donoren
- 11
- H-Brücken-Akzeptoren
- 17
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 65
- Formalladung
- 0
- Komplexität
- 1.610
Experimentelle und physikochemische Eigenschaften
LipidsPolyketides [PK] -> Polyenes [PK06]
Physikochemische Eigenschaften
- Schmelzpunkt
- 155 °C · >155°C (dec.)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- 2 O: · H2O: insoluble
- Aggregatzustand
- suspension
- pka
- 5.72 · pKa 5.72(MeOH/2-methoxyethanol/ H2O) (Uncertain);8.64 (Uncertain)
- Farbe
- yellow
- Geruch (Odor)
- ofcereals odor
- Biologische Quelle
- Streptomyces noursei
- Wasserlöslichkeit
- 0.36 g/L · 0.36g/L(24 ºC)
- Merck
- 13 · 13,6770
- Specific Activity
- 4 · ≥4,400USP units/mg
- Henry's Law Constant
- 4.9 · 4.9×104 mol/(m3Pa) at 25℃, HSDB (2015)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- F
- 10-8-23
- wgk
- 3
- hs_code
- 38210000
- RTECS-Nr.
- RF5950000
- risk_code
- 11-34
- Toxizität
- LD50 i.p. in mice: ~200 mg/kg (Seneca)
- hazard_code
- F,C
- safety_code
- 22-24/25-45-36/37/39-26-16
- hazard_class
- 3
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 1400-61-9(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
Protein BindingNystatin is not absorbed into the systemic circulation and is therefore not subject to plasma protein binding.
Pharmacodynamics
Nystatin is an antifungal that is both fungistatic and fungicidal in vitro against a wide variety of yeasts and yeast-like fungi. It exerts its antifungal effects via disruption of the fungal cell membrane. Resistance to nystatin is minimal in _Candida albicans_, but tends to develop in other species of _Candida_. Nystatin carries no significant activity against bacteria, protozoa, or viruses. It carries significant systemic toxicity and is currently unavailable in a formula appropriate for systemic use - its efficacy is currently restricted, therefore, to topical, oral, and gastrointestinal infections.
Mechanism of Action
Nystatin is a channel-forming ionophore, meaning it exerts its therapeutic effect via formation of a membrane-spanning pore in the fungal plasma membrane. The formation of this pore results in a change in membrane permeability that allows for leakage of intracellular contents and the subsequent disruption of electrochemical gradients necessary for proper cell function. Selectivity for fungal cells over mammalian cells is due to nystatin’s greater binding affinity for ergosterol, a key sterol found in fungal cell walls, as opposed to its mammalian counterpart, cholesterol.
Metabolism/MetabolitesBecause nystatin undergoes little-to-no systemic absorption it is not metabolized to any appreciable extent.
Absorption, Distribution and Excretion
Systemic absorption of nystatin is minimal following oral administration, and no detectable plasma concentrations are attained following topical or vaginal administration.
The majority of orally administered nystatin is eliminated unchanged in the feces.
Nystatin is not absorbed into the systemic circulation and thus does not undergo distribution.
Anwendungen
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