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Identification
Name Nystatin
Accession Number DB00646 (APRD01146)
Type small molecule
Groups approved
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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Barstatin 100
Candex
Korostatin
Mycolog-Ii
Mycostatin
Mykacet
Mykinac
Mytrex F
Nadostine
Nilstat
Nyaderm
nystatin dihydrate
Nystatin-Triamcinolone Acetonide
Nystex
Nystop
Pedi-Dri
PMS Nystatin
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Brand mixtures
Brand Name Ingredients
Derma-4 Ont Neomycin Sulfate + Nystatin + Thiostrepton (Antibiotic of a Streptomyces Species) + Triamcinolone Acetonide
Flagystatin Metronidazole + Nystatin
Kenacomb Cream Gramicidin + Neomycin Sulfate + Nystatin + Triamcinolone Acetonide
Kenacomb Mild Cream Gramicidin + Neomycin Sulfate + Nystatin + Triamcinolone Acetonide
Kenacomb Mild Ointment Gramicidin + Neomycin Sulfate + Nystatin + Triamcinolone Acetonide
Kenacomb Ointment Gramicidin + Neomycin Sulfate + Nystatin + Triamcinolone Acetonide
Kenacomb Ont Gramicidin + Neomycin (Neomycin Sulfate) + Nystatin + Triamcinolone Acetonide
Lidecomb Cream Fluocinonide + Gramicidin + Neomycin Sulfate + Nystatin
Mecomb Crm 0.1% Gramicidin + Neomycin (Neomycin Sulfate) + Nystatin + Triamcinolone Acetonide
Solvaderm Ointment Neomycin (Neomycin Sulfate) + Nystatin + Thiostrepton (Antibiotic of a Streptomyces Species) + Triamcinolone Acetonide
Categories
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Ionophores
CAS number 1400-61-9
Weight Average: 926.0949
Monoisotopic: 925.503499979
Chemical Formula C47H75NO17
InChI Key InChIKey=ZDFDJJJGIRGMBE-AFARJNEBSA-N
InChI
InChI=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+/t27?,28?,29?,30-,31?,32?,33?,35?,36?,37?,38?,39?,41?,42+,43?,44-,45+,47?/m1/s1
Plain Text
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
SMILES
C[C@H]1OC(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=C\C=C\CC\C=C\C=C\C=C\C=C\2)C(O)=O)[C@@H](O)[C@@H](N)[C@@H]1O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Aminoglycosides
Substructures
  • Carboxylic Acids and Derivatives
  • Aminoglycosides
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Pyrans
  • Acetates
  • Acetals and Derivatives
  • Lactones
  • Aliphatic and Aryl Amines
  • Ethers
  • Amino Alcohols
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Ketones
Pharmacology
Indication For treatment of cutaneous or mucocutaneous mycotic infections caused by Candida species
Pharmacodynamics 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 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.
Absorption Nystatin is not absorbed from intact skin or mucous membrane.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Fungi
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Bayer pharmaceuticals corp
  • Bristol myers squibb co
  • Alpharma us pharmaceuticals division
  • Lederle laboratories div american cyanamid co
  • Actavis mid atlantic llc
  • Altana inc
  • Perrigo new york inc
  • Taro pharmaceuticals usa inc
  • Teva pharmaceuticals usa inc
  • Vintage pharmaceuticals llc
  • Westwood squibb pharmaceuticals inc
  • Bristol myers squibb
  • Barlan pharmacal co inc
  • Dava pharmaceuticals inc
  • Paddock laboratories inc
  • Coastal pharmaceuticals inc
  • Kv pharmaceutical co
  • Par pharmaceutical inc
  • Upsher smith laboratories inc
  • X gen pharmaceuticals inc
  • Warner chilcott co llc
  • Apothecon inc div bristol myers squibb
  • Glenmark generics inc usa
  • Bausch and lomb pharmaceuticals inc
  • E fougera div altana inc
  • Morton grove pharmaceuticals inc
  • Pharmaderm div altana inc
  • Pharmafair inc
  • Roxane laboratories inc
  • Vintage pharmaceuticals inc
  • Vistapharm inc
  • Wockhardt eu operations (swiss) ag
  • Savage laboratories inc div altana inc
  • Mutual pharmaceutical co inc
  • Quantum pharmics ltd
  • Sandoz inc
  • Usl pharma inc
  • Watson laboratories inc
  • Holland rantos co inc
  • Odyssey pharmaceuticals inc
Packagers
Dosage forms
Form Route Strength
Cream Intravaginal
Cream Topical
Ointment Topical
Powder Topical
Solution / drops Oral
Suspension Oral
Tablet Intravaginal
Tablet Oral
Prices
Unit description Cost Unit
Nystatin 10 billion unit powder 3014.1 USD each
Nystatin 5 billion unit powder 2096.1 USD each
Nystatin 2 billion unit powder 1116.9 USD each
Nystatin 1 billion unit powder 452.08 USD each
Nystat-rx 5 billion unit powder 447.0 USD each
Nystatin 500 million unit powder 130.75 USD each
Pedi-Dri 100000 unit/gm Powder 56.7 gm Bottle 105.87 USD bottle
Nystatin 150mu Bottle 94.5 USD bottle
Nystatin 150 million unit powder 42.25 USD each
Nystatin 150000000 unit powder 42.0 USD each
Nystatin Nystatin Powder 50 Million unit Bottle 39.99 USD bottle
Mycostatin 100000 unit/gm Powder 15 gm Bottle 36.99 USD bottle
Nystop 100000 unit/gm Powder 15 gm Bottle 29.99 USD bottle
Nystatin 50 million unit powder 19.75 USD each
Nystatin 100000 unit/gm Ointment 15 gm Tube 12.99 USD tube
Nystatin 100000 unit/gm Cream 15 gm Tube 6.5 USD tube
Nystatin 100000 unit tablet 5.29 USD tablet
Nystatin vaginal tablet 5.0 USD tablet
Pedi-dri topical powder 1.82 USD g
Nystop 100000 unit/gm powder 1.6 USD g
Nystatin 500000 unit tablet 0.71 USD tablet
Nystatin 500000 unit oral tablet 0.68 USD tablet
Mycostatin 500000 unit orl tablet 0.48 USD tablet
Nystatin 100000 unit/ml Suspension 0.25 USD ml
Ratio-Nystatin 500000 unit Tablet 0.25 USD tablet
Nystatin 100000 unit/gm cream 0.1 USD g
Pms-Nystatin 100000 unit/ml Suspension 0.05 USD ml
Ratio-Nystatin 100000 unit/ml Suspension 0.05 USD ml
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Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 160 °C Not Available
water solubility 360 mg/L (at 24 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP 0.5 Not Available
Predicted Properties
Property Value Source
water solubility 6.60e-02 g/l ALOGPS
logP -2.8 ALOGPS
logP -2.7 ChemAxon
logS -4.2 ALOGPS
pKa (strongest acidic) 3.62 ChemAxon
pKa (strongest basic) 9.11 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 17 ChemAxon
hydrogen donor count 12 ChemAxon
polar surface area 327.45 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 245.18 ChemAxon
polarizability 102.11 ChemAxon
References
Synthesis Reference Not Available
General Reference
  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
External Links
Resource Link
KEGG Drug D00202 Link_out
KEGG Compound C06572 Link_out
PubChem Compound 11953884 Link_out
PubChem Substance 46504780 Link_out
ChemSpider 10128183 Link_out
Therapeutic Targets Database DAP000879 Link_out
PharmGKB PA450666 Link_out
Drug Product Database 792667 Link_out
RxList http://www.rxlist.com/cgi/generic2/nystat.htm Link_out
Drugs.com http://www.drugs.com/cdi/nystatin.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/myc1279.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Nystatin Link_out
ATC Codes
  • A07AA02
  • D01AA01
  • G01AA01
AHFS Codes
  • 84:04.08.28
  • 08:14.28
PDB Entries Not Available
FDA label show (776 KB)
MSDS show (72.5 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Take without regard to meals.
Targets

1. Ergosterol, Candida albicans

Pharmacological action: yes
Actions: binder

References:
  1. Silva L, Coutinho A, Fedorov A, Prieto M: Competitive binding of cholesterol and ergosterol to the polyene antibiotic nystatin. A fluorescence study. Biophys J. 2006 May 15;90(10):3625-31. Epub 2006 Feb 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19