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Showing drug card for Nystatin (DB00646)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:03:51
Primary Accession Number DB00646
Secondary Accession Number
  • APRD01146
Name Nystatin
Drug Type
  • Approved
  • Small Molecule
Description Nystatin 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.
Synonyms Not Available
Brand Names
  1. Barstatin 100
  2. Candex
  3. Korostatin
  4. Myco-Triacet Ii
  5. Mycolog-Ii
  6. Mycostatin
  7. Mykacet
  8. Mykinac
  9. Mytrex F
  10. Nadostine
  11. Nilstat
  12. Nyaderm
  13. Nysert
  14. Nystaform
  15. Nystatin sodium
  16. Nystatin, sodium salt
  17. Nystatin-Triamcinolone Acetonide
  18. Nystex
  19. Nystop
  20. PMS Nystatin
  21. Pedi-Dri
  22. Sodium nystatin
  23. nystatin dihydrate
Brand Mixtures
  1. Derma-4 Ont (Neomycin Sulfate + Nystatin + Thiostrepton (Antibiotic of a Streptomyces Species) + Triamcinolone Acetonide)
  2. Flagystatin (Metronidazole + Nystatin)
  3. Kenacomb Cream (Gramicidin + Neomycin Sulfate + Nystatin + Triamcinolone Acetonide)
  4. Kenacomb Mild Cream (Gramicidin + Neomycin Sulfate + Nystatin + Triamcinolone Acetonide)
  5. Kenacomb Mild Ointment (Gramicidin + Neomycin Sulfate + Nystatin + Triamcinolone Acetonide)
  6. Kenacomb Ointment (Gramicidin + Neomycin Sulfate + Nystatin + Triamcinolone Acetonide)
  7. Kenacomb Ont (Gramicidin + Neomycin (Neomycin Sulfate) + Nystatin + Triamcinolone Acetonide)
  8. Lidecomb Cream (Fluocinonide + Gramicidin + Neomycin Sulfate + Nystatin)
  9. Mecomb Crm 0.1% (Gramicidin + Neomycin (Neomycin Sulfate) + Nystatin + Triamcinolone Acetonide)
  10. Solvaderm Ointment (Neomycin (Neomycin Sulfate) + Nystatin + Thiostrepton (Antibiotic of a Streptomyces Species) + Triamcinolone Acetonide)
Chemical IUPAC Name (21E,23E,25E,27E,31E,33E)-20-[(3S,4S,5S,6R)-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
Chemical Formula C47H75NO17
Chemical Structure Structure
CAS Registry Number 1400-61-9
InChI Identifier InChI=1/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+/t27?,28?,29?,30-,31?,32?,33?,35?,36?,37?,38?,39?,41?,42+,43?,44-,45+,47?/m1/s1/f/h61H
InChI Key ZDFDJJJGIRGMBE-AXSLEXJYDP
KEGG Drug D00202 Link Image
KEGG Compound C06572 Link Image
PubChem Compound 11953884 Link Image
PubChem Substance 8801 Link Image
ChEBI ID Not Available
PharmGKB ID PA450666 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00792667 Link Image
RxList Link http://www.rxlist.com/cgi/generic2/nystat.htm Link Image
PDRhealth Link http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/myc1279.shtml Link Image
Wikipedia Link http://en.wikipedia.org/wiki/Nystatin Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 926.0949
Monoisotopic Molecular Weight 925.5035
State Solid
Melting Point 160oC
Experimental Water Solubility 360 mg/L Source: PhysProp
Predicted Water Solubility 6.60e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 0.5 Source: PhysProp
Predicted LogP -2.81 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.15 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES C[C@H]1OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@H](O)[C@@H](O)CC(=O)C[C@@H](O)[C@@H]([C@@H](O)C[C@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H](N)[C@@H]2O)\C=C\C=C\C=C\C=C\CC\C=C\C=C\[C@H](C)[C@H](O)[C@H]1C)C(O)=O
Canonical SMILES CC1OC(=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=CC=CC=CC=CCCC=CC=CC(C)C(O)C1C)C(O)=O
Drug Category
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Ionophores
ATC Codes
AHFS Codes
  • 08:14.28
  • 84:04.08.28
Indication For treatment of cutaneous or mucocutaneous mycotic infections caused by Candida species
Pharmacology Nystatin is an antibiotic which is both fungistatic and fungicidal in vitro against a wide variety of yeasts and yeast-like fungi, including Candida albicans, C. parapsilosis, C. tropicalis, C. guilliermondi, C. pseudotropicalis, C. krusei, Torulopsis glabrata, Tricophyton rubrum, T. mentagrophytes. Nystatin acts by binding to sterols in the cell membrane of susceptible species resulting in a change in membrane permeability and the subsequent leakage of intracellular components. On repeated subculturing with increasing levels of nystatin, Candida albicans does not develop resistance to nystatin. Generally, resistance to nystatin does not develop during therapy. However, other species of Candida (C. tropicalis, C. guilliermondi, C. krusei, and C. stellatoides) become quite resistant on treatment with nystatin and simultaneously become cross resistant to amphotericin as well. This resistance is lost when the antibiotic is removed. Nystatin exhibits no appreciable activity against bacteria, protozoa, or viruses.
Mechanism of Action Nystatin 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.
Absorption Nystatin is not absorbed from intact skin or mucous membrane
Toxicity Not Available
Protein Binding Not Available
Biotransformation Not Available
Half Life Not Available
Dosage Forms
Form Route
Cream Intravaginal
Cream Topical
Ointment Topical
Powder Topical
Solution / drops Oral
Suspension Oral
Tablet Intravaginal
Tablet Oral
Patient Information Not Available
Contraindications Show Link Image
Interactions Not Available
Drug Interactions Not Available
Food Interactions
  • Take without regard to meals.
Pathways Not Available
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. [PubMed Link Image]
  2. Drugs.com Link Image
  3. Wikipedia Link Image
  4. RxList Link Image
  5. PDRhealth Link Image
Organisms Affected
  • Fungi
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 3A4 (CYP3A4)
Targets
  1. Cytochrome P450 51
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 3A4 (CYP3A4)
Enzyme 1 Gene Name CYP3A4
Enzyme 1 SwissProt ID P08684 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P08684|CP3A4_HUMAN Cytochrome P450 3A4 (EC 1.14.13.67) 
ALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNILSYHKGFCMFD
MECHKKYGKVWGFYDGQQPVLAITDPDMIKTVLVKECYSVFTNRRPFGPVGFMKSAISIA
EDEEWKRLRSLLSPTFTSGKLKEMVPIIAQYGDVLVRNLRREAETGKPVTLKDVFGAYSM
DVITSTSFGVNIDSLNNPQDPFVENTKKLLRFDFLDPFFLSITVFPFLIPILEVLNICVF
PREVTNFLRKSVKRMKESRLEDTQKHRVDFLQLMIDSQNSKETESHKALSDLELVAQSII
FIFAGYETTSSVLSFIMYELATHPDVQQKLQEEIDAVLPNKAPPTYDTVLQMEYLDMVVN
ETLRLFPIAMRLERVCKKDVEINGMFIPKGWVVMIPSYALHRDPKYWTEPEKFLPERFSK
KNKDNIDPYIYTPFGSGPRNCIGMRFALMNMKLALIRVLQNFSFKPCKETQIPLKLSLGG
LLQPEKPVVLKVESRDGTVSGA
Drug Target 1 [top]
Target 1 ID 260
Target 1 Name Cytochrome P450 51
Target 1 Synonyms
  1. CYPLI
  2. EC 1.14.13.70
  3. Lanosterol 14-alpha demethylase
  4. P450-14DM
  5. P450-LIA1
  6. Sterol 14- alpha demethylase
Target 1 Gene Name ERG11
Target 1 Protein Sequence >Cytochrome P450 51 
MAIVETVIDGINYFLSLSVTQQISILLGVPFVYNLVWQYLYSLRKDRAPLVFYWIPWFGS
AASYGQQPYEFFESCRQKYGDVFSFMLLGKIMTVYLGPKGHEFVFNAKLSDVSAEDAYKH
LTTPVFGKGVIYDCPNSRLMEQKKFAKFALTTDSFKRYVPKIREEILNYFVTDESFKLKE
KTHGVANVMKTQPEITIFTASRSLFGDEMRRIFDRSFAQLYSDLDKGFTPINFVFPNLPL
PHYWRRDAAQKKISATYMKEIKSRRERGDIDPNRDLIDSLLIHSTYKDGVKMTDQEIANL
LIGILMGGQHTSASTSAWFLLHLGEKPHLQDVIYQEVVELLKEKGGDLNDLTYEDLQKLP
SVNNTIKETLRMHMPLHSIFRKVTNPLRIPETNYIVPKGHYVLVSPGYAHTSERYFDNPE
DFDPTRWDTAAAKANSVSFNSSDEVDYGFGKVSKGVSSPYLPFGGGRHRCIGEQFAYVQL
GTILTTFVYNLRWTIDGYKVPDPDYSSMVVLPTEPAEIIWEKRETCMF
Target 1 Number of Residues 536
Target 1 Molecular Weight 60676
Target 1 Theoretical pI 7.19
Target 1 GO Classification
Function
tetrapyrrole binding
heme binding
binding
ion binding
cation binding
transition metal ion binding
iron ion binding
catalytic activity
oxidoreductase activity
monooxygenase activity
Process
physiological process
metabolism
cellular metabolism
generation of precursor metabolites and energy
electron transport
Component
Not Available
Target 1 General Function Secondary metabolites biosynthesis, transport and catabolism
Target 1 Specific Function Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol
Target 1 Pathways Not Available
Target 1 Reactions
  • obtusifoliol + 3 O2 + 3 NADPH + 3 H+ = 4alpha-methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-ol + formate + 3 NADP+ + 4 H2O
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 15-37; 50-69
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 578119 Link Image
Target 1 UniProtKB/Swiss-Prot ID P10613 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name CP51_CANAL Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location Not Available
Target 1 Gene Sequence >1587 bp 
ATGGCTATTGTTGAAACTGTCATTGATGGCATTAATTATTTTTTGTCCCTTAGTGTTACA
CAACAGATCAGTATATTATTAGGGGTTCCATTTGTTTACAACTTAGTATGGCAATATTTA
TATTCATTAAGAAAAGATAGAGCTCCATTAGTGTTTTATTGGATTCCTTGGTTTGGTTCT
GCAGCTTCATATGGTCAACAACCTTATGAATTTTTCGAATCATGTCGTCAAAAGTATGGT
GATGTATTTTCATTTATGTTATTAGGGAAAATTATGACGGTTTATTTAGGTCCAAAAGGT
CATGAATTTGTTTTTAATGCTAAATTATCTGATGTTTCTGCTGAAGATGCTTATAAACAT
TTAACTACTCCAGTTTTCGGTAAAGGGGTTATTTATGATTGTCCAAATTCCAGATTAATG
GAACAAAAAAAATTTGCTAAATTTGCTTTGACTACTGATTCATTTAAAAGATATGTTCCT
AAGATTAGAGAAGAAATTTTGAATTATTTTGTTACTGATGAAAGTTTCAAATTGAAAGAA
AAAACTCATGGGGTTGCCAATGTTATGAAAACTCAACCAGAAATTACTATTTTCACTGCT
TCAAGATCTTTATTTGGTGATGAAATGAGAAGAATTTTTGACCGTTCATTTGCTCAACTA
TATTCTGATTTAGATAAAGGTTTTACCCCTATTAATTTTGTTTTCCCTAATTTACCTTTA
CCTCATTATTGGAGACGTGATGCTGCTCAAAAGAAAATCTCTGCTACTTATATGAAAGAA
ATTAAACTGAGAAGAGAACGTGGTGATATTGATCCAAATCGTGATTTAATTGATTCCTTA
TTGATTCATTCAACTTATAAAGATGGTGTGAAAATGACTGATCAAGAAATTGCTAATCTT
TTAATTGGTATTCTTATGGGTGGTCAACATACTTCTGCTTCTACTTCTGCTTGGTTCTTG
TTACATTTAGGTGAAAAACCTCATTTACAAGATGTTATTTATCAAGAAGTTGTTGAATTA
TTGAAAGAAAAAGGTGGTGATTTGAATGATTTGACTTATGAAGATTTACAAAAATTACCA
TCAGTCAATAACACTATTAAGGAAACTCTCAGAATGCATATGCCATTACATTCTATTTTT
AGAAAAGTTACTAACCCATTAAGAATCCCTGAAACCAATTATATTGTTCCAAAAGGTCAT
TATGTTTTAGTTTCTCCAGGTTATGCTCATACTAGTGAAAGATATTTTGATAACCCTGAA
GATTTTGATCCAACTAGATGGGATACTGCTGCTGCCAAAGCTAATTCTGTTTCATTTAAC
TCTTCTGATGAAGTTGATTATGGGTTTGGGAAAGTTTCTAAAGGGGTTTCTTCACCTTAT
TTACCATTTGGTGGTGGTAGACATAGATGTATTGGGGAACAATTTGCTTATGTTCAATTA
GGAACCATTTTAACTACTTTTGTTTATAATTTAAGATGGACTATTGATGGTTATAAAGTG
CCTGACCCTGATTATAGTTCAATGGTGGTTTTACCTACTGAACCAGCAGAAATCATTTGG
GAAAAAAGAGAAACTTGTATGTTTTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Lai MH, Kirsch DR: Nucleotide sequence of cytochrome P450 L1A1 (lanosterol 14 alpha-demethylase) from Candida albicans. Nucleic Acids Res. 1989 Jan 25;17(2):804. [PubMed Link Image]
  2. Boscott PE, Grant GH: Modeling cytochrome P450 14 alpha demethylase (Candida albicans) from P450cam. J Mol Graph. 1994 Sep;12(3):185-92, 195. [PubMed Link Image]
  3. White TC: The presence of an R467K amino acid substitution and loss of allelic variation correlate with an azole-resistant lanosterol 14alpha demethylase in Candida albicans. Antimicrob Agents Chemother. 1997 Jul;41(7):1488-94. [PubMed Link Image]
  4. Loffler J, Kelly SL, Hebart H, Schumacher U, Lass-Florl C, Einsele H: Molecular analysis of cyp51 from fluconazole-resistant Candida albicans strains. FEMS Microbiol Lett. 1997 Jun 15;151(2):263-8. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
  3. Lorenz RT, Parks LW: Physiological effects of fenpropimorph on wild-type Saccharomyces cerevisiae and fenpropimorph-resistant mutants. Antimicrob Agents Chemother. 1991 Aug;35(8):1532-7. [PubMed Link Image]

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