Nystatin (T3D2847)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2009-07-21 20:27:19 UTC
Update Date2014-12-24 20:25:52 UTC
Accession NumberT3D2847
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.
Compound Type
  • Amine
  • Anti-Bacterial Agent
  • Antifungal Agent
  • Drug
  • Ester
  • Ionophore
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Adiclair
Afunginal
Biofanal
Candacide
Candermil
Candex
Candidias
Candistat
Candistin
Canstat
Cazetin
Diaper NZ
Dipni
Enystin
Fukangning
Fungatin
Fungicidin Leciva
Fungistin
Fungostatin
Funistatin
Gynostatin
Kandistatin
Kenalon
Lederlind
Ledernyst
Lystin
Mycostatin
Nilstat
Nistatina
Nyaderm
Nyamyc
NYS
Nystan
Nystatine
Nystatinum
Nystop
Pedi-Dri
Chemical FormulaC47H75NO17
Average Molecular Mass926.095 g/mol
Monoisotopic Mass925.503 g/mol
CAS Registry Number1400-61-9
IUPAC Name20-[(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
Traditional Name20-[(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
SMILESCC1OC(OC2CC(O)C(C(O)CC(=O)CC(O)C(O)CCC(O)CC(O)CC(O)CC(=O)OC(C)C(C)C(O)C(C)C=CC=CCCC=CC=CC=CC=C2)C(O)=O)C(O)C(N)C1O
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 KeyInChIKey=ZDFDJJJGIRGMBE-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
  • Amino acid
  • Ketone
  • Lactone
  • Carboxylic acid ester
  • Secondary alcohol
  • Cyclic ketone
  • Carboxylic acid
  • Organoheterocyclic compound
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Polyol
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Alcohol
  • Organopnictogen 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)
LogP0.5
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
Polarizability100.28 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0000000594-7f42f3e1bd5597881f4c2019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-0000000930-367c50b1acf216d54ad52019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0000000900-7c278ee472df77d70ec92019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08g0-2000000496-774431ed75efe06401c12019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08ir-0000000490-8f81c2a4e4a2977923e32019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-1000000900-94ba1a7b1c2cf5359def2019-02-23View Spectrum
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00646
HMDB IDHMDB14784
PubChem Compound ID11953884
ChEMBL IDCHEMBL229383
ChemSpider ID10128183
KEGG IDC06572
UniProt IDNot Available
OMIM ID
ChEBI ID7660
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNystatin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNystatin
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. Akaike N, Harata N: Nystatin perforated patch recording and its applications to analyses of intracellular mechanisms. Jpn J Physiol. 1994;44(5):433-73. [7534361 ]
  2. Drugs.com [Link]
  3. RxiList. Nystatin [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available