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Identification
NameNatamycin
Accession NumberDB00826  (APRD01136)
TypeSmall Molecule
GroupsApproved
Description

Amphoteric macrolide antifungal antibiotic from Streptomyces natalensis or S. chattanoogensis. It is used for a variety of fungal infections, mainly topically. [PubChem]

Structure
Thumb
Synonyms
Natamicina
Natamycin
Natamycine
Natamycinum
Pimaracin
Pimaricin
External Identifiers
  • A-5283
  • Antibiotic A-5283
  • CL 12,625
  • CL 12625
  • E 235
  • E-235
  • INS NO.235
  • INS-235
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Natacynsuspension/ drops50 mg/mLophthalmicAlcon Laboratories, Inc.1980-12-31Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DelvocidNot Available
FukricinSanbe
InfectoMykInfectopharm
N-MycinAristopharma
NatadropsCipla
NatametSun
NatamycynaUnia
NatezhenAlcon
NatophIbn Sina
NatopticFDC
OptinatJayson
PimafucinAstellas
PimafusinElder
PimaricinSenju Seiyaku
Brand mixturesNot Available
SaltsNot Available
Categories
UNII8O0C852CPO
CAS number7681-93-8
WeightAverage: 665.733
Monoisotopic: 665.304740577
Chemical FormulaC33H47NO13
InChI KeyNCXMLFZGDNKEPB-FFPOYIOWSA-N
InChI
InChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1
IUPAC Name
SMILES
[H][C@@]12C[[email protected]](O)C[C@]3(O)C[[email protected]](O)[C@@H](C(O)=O)[C@]([H])(C[C@@H](O[C@]4([H])O[[email protected]](C)[C@@H](O)[[email protected]](N)[C@@H]4O)\C=C\C=C\C=C\C=C\C[C@@H](C)OC(=O)\C=C\[C@@]1([H])O2)O3
Taxonomy
ClassificationNot classified
Pharmacology
IndicationFor the treatment of fungal blepharitis, conjunctivitis, and keratitis caused by susceptible organisms including Fusarium solani keratitis.
PharmacodynamicsNatamycin is an antifungal drug for topical ophthalmic administration. It is a tetraene polyene antibiotic derived from Streptomyces natalensis. It possesses in vitro activity against a variety of yeast and filamentous fungi, including Candida, Aspergillus, Cephalosporium, Fusarium and Penicillium. Although the activity against fungi is dose-related, natamycin is predominantly fungicidal. Natamycin is not effective in vitro against gram-positive or gram-negative bacteria. Topical administration appears to produce effective concentrations of natamycin within the corneal stroma but not in intraocular fluid.
Mechanism of actionLIke other polyene antibiotics, Natamycin inhibits fungal growth by binding to sterols. Specifically, Natamycin binds to ergosterol in the plasma membrane, preventing ergosterol-dependent fusion of vacuoles, as well as membrane fusion and fission. This differs from the mechanism of most other polyene antibiotics, which tend to work by altering fungal membrane permeability instead.
Related Articles
AbsorptionSystemic absorption should not be expected following topical administration, and as with other polyene antibiotics, absorption from the gastrointestinal tract is very poor.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Various Fungus Species
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8512
Blood Brain Barrier-0.9789
Caco-2 permeable-0.6947
P-glycoprotein substrateSubstrate0.5926
P-glycoprotein inhibitor INon-inhibitor0.7063
P-glycoprotein inhibitor IINon-inhibitor0.9224
Renal organic cation transporterNon-inhibitor0.9629
CYP450 2C9 substrateNon-substrate0.7748
CYP450 2D6 substrateNon-substrate0.8576
CYP450 3A4 substrateNon-substrate0.5291
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9154
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8632
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9632
Ames testNon AMES toxic0.6606
CarcinogenicityNon-carcinogens0.9448
BiodegradationNot ready biodegradable0.9718
Rat acute toxicity2.4181 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.994
hERG inhibition (predictor II)Non-inhibitor0.9406
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Alcon laboratories inc
Packagers
Dosage forms
FormRouteStrength
Suspension/ dropsophthalmic50 mg/mL
Prices
Unit descriptionCostUnit
Natacyn eye drops14.16USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point290 dec °CPhysProp
water solubility4100 mg/L (at 21 °C)TOMLIN,C (1994)
logP1.1Not Available
logS-3.21ADME Research, USCD
Predicted Properties
PropertyValueSource
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
References
Synthesis Reference

Michael A. Eisenschink, Phillip T. Olson, “Fermentation process for producing natamycin.” U.S. Patent US5231014, issued July, 1982.

US5231014
General ReferencesNot Available
External Links
ATC CodesA01AB10A07AA03D01AA02G01AA02S01AA10
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNo interactions found.
Food InteractionsNot Available

Targets

1. Ergosterol
Kind
Small molecule
Organism
Candida albicans
Pharmacological action
yes
Actions
binder
References
  1. te Welscher YM, Jones L, van Leeuwen MR, Dijksterhuis J, de Kruijff B, Eitzen G, Breukink E: Natamycin inhibits vacuole fusion at the priming phase via a specific interaction with ergosterol. Antimicrob Agents Chemother. 2010 Jun;54(6):2618-25. doi: 10.1128/AAC.01794-09. Epub 2010 Apr 12. [PubMed:20385867 ]
  2. te Welscher YM, ten Napel HH, Balague MM, Souza CM, Riezman H, de Kruijff B, Breukink E: Natamycin blocks fungal growth by binding specifically to ergosterol without permeabilizing the membrane. J Biol Chem. 2008 Mar 7;283(10):6393-401. doi: 10.1074/jbc.M707821200. Epub 2007 Dec 29. [PubMed:18165687 ]
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Drug created on June 13, 2005 07:24 / Updated on May 10, 2016 09:27