Record Information
Version1.0
Creation Date2009-07-21 20:27:19 UTC
Update Date2026-05-14 16:44:58 UTC
Accession NumberCHEM002236
Identification
Common NameNystatin
ClassSmall Molecule
DescriptionNystatin is a polyene antifungal drug to which many molds and yeasts are sensitive, including Candida spp. Nystatin has some toxicity associated with it when given intravenously, but it is not absorbed across intact skin or mucous membranes. It is considered a relatively safe drug for treating oral or gastrointestinal fungal infections.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Anti-Bacterial Agent
  • Antifungal Agent
  • Drug
  • Ester
  • Ionophore
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
(21Z,23E,25E,27E)-20-[(4-Amino-3,5-dihydroxy-6-methyloxan-2-yl)oxy]-4,6,8,11,12,16,18,36-octahydroxy-35,37,38-trimethyl-2,14-dioxo-1-oxacyclooctatriaconta-21,23,25,27,31,33-hexaene-17-carboxylateGenerator
20-[(4-Amino-3,5-dihydroxy-6-methyloxan-2-yl)oxy]-4,6,8,11,12,16,18,36-octahydroxy-35,37,38-trimethyl-2,14-dioxo-1-oxacyclooctatriaconta-21,23,25,27,31,33-hexaene-17-carboxylateGenerator
Chemical FormulaC47H75NO17
Average Molecular Mass926.107 g/mol
Monoisotopic Mass925.503 g/mol
CAS Registry Number1400-61-9
IUPAC 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-amino-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-carboxylic acid
Traditional Name(21Z,23E,25E,27E,31E,33E)-20-[(4-amino-3,5-dihydroxy-6-methyloxan-2-yl)oxy]-4,6,8,11,12,16,18,36-octahydroxy-35,37,38-trimethyl-2,14-dioxo-1-oxacyclooctatriaconta-21,23,25,27,31,33-hexaene-17-carboxylic acid
SMILES[H]C1=C([H])C([H])=C([H])C(C)C(O)C(C)C(C)OC(=O)CC(O)CC(O)CC(O)CCC(O)C(O)CC(=O)CC(O)C(C(O)CC(OC2OC(C)C(O)C(N)C2O)\C([H])=C(\[H])/C(/[H])=C(\[H])/C(/[H])=C(\[H])/C(/[H])=C([H])/CC1)C(O)=O
InChI IdentifierInChI=1S/C47H75NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-35(65-47-45(60)42(48)44(59)30(4)64-47)26-39(56)41(46(61)62)38(55)24-34(52)23-37(54)36(53)20-19-31(49)21-32(50)22-33(51)25-40(57)63-29(3)28(2)43(27)58/h5-6,8,10-18,27-33,35-39,41-45,47,49-51,53-56,58-60H,7,9,19-26,48H2,1-4H3,(H,61,62)/b6-5+,10-8+,13-11+,14-12+,17-15+,18-16-
InChI KeyZDFDJJJGIRGMBE-UZHOVVQJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • Macrolide
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Amino acid
  • Ketone
  • Lactone
  • Cyclic ketone
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Primary amine
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Aldehyde
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point160°C
Boiling PointNot Available
Solubility360 mg/L (at 24°C)
Predicted Properties
PropertyValueSource
Water Solubility0.066 g/LALOGPS
logP-2.8ALOGPS
logP-2.7ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.62ChemAxon
pKa (Strongest Basic)9.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area327.45 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity245.18 m³·mol⁻¹ChemAxon
Polarizability28.72 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0000000696-2dbe48a763da2c51ff0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0010000922-aa0997aef4cbe4d08c7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1002103911-eae0bbc46987f1df1bcfSpectrum
Toxicity Profile
Route of ExposureOral, topical(intravaginal). Nystatin is not absorbed from intact skin or mucous membrane.
Mechanism of ToxicityNystatin interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary for the conversion of lanosterol to ergosterol. This results in inhibition of ergosterol synthesis and increased fungal cellular permeability. Nystatin exerts its antifungal activity by binding to ergosterol found in fungal cell membranes. Binding to ergosterol causes the formation of pores in the membrane. Potassium and other cellular constituents leak from the pores causing cell death.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed to treat cutaneous, vaginal, mucosal and esophageal Candida infections. Nystatin is often used as prophylaxis in patients who are at risk for fungal infections, such as AIDS patients with a low CD4+ count and patients receiving chemotherapy.[Wikipedia]
Minimum Risk LevelNot Available
Health EffectsTachycardia, bronchospasm, facial swelling, and non-specific myalgia have also been rarely reported. Stevens-Johnson syndrome has been reported very rarely. (3)
SymptomsDiarrhea (including one case of bloody diarrhea), nausea, vomiting, gastrointestinal upset/disturbances. Rash, including urticaria has been reported rarely. (3)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID71299651
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General ReferencesNot Available