Identification
- Summary
Natamycin is a macrolide antifungal used to treat fungal infections of the eye.
- Brand Names
- Natacyn
- Generic Name
- Natamycin
- DrugBank Accession Number
- DB00826
- Background
Amphoteric macrolide antifungal antibiotic from Streptomyces natalensis or S. chattanoogensis. It is used for a variety of fungal infections, mainly topically. [PubChem]
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Natamycin (DB00826)
- Weight
- Average: 665.733
Monoisotopic: 665.304740577 - Chemical Formula
- C33H47NO13
- Synonyms
- Natamicina
- Natamycin
- Natamycine
- Natamycinum
- Pimaracin
- Pimaricin
- External IDs
- A-5283
- Antibiotic A-5283
- CL 12,625
- CL 12625
- E 235
- E-235
- INS NO.235
- INS-235
Pharmacology
- Indication
For the treatment of fungal blepharitis, conjunctivitis, and keratitis caused by susceptible organisms including Fusarium solani keratitis.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Natamycin 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 action
Like 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.
Target Actions Organism AErgosterol binderCandida albicans - Absorption
Systemic absorption should not be expected following topical administration, and as with other polyene antibiotics, absorption from the gastrointestinal tract is very poor.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareArticaine The risk or severity of methemoglobinemia can be increased when Natamycin is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Natamycin is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Natamycin is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Natamycin is combined with Bupivacaine. Butacaine The risk or severity of methemoglobinemia can be increased when Natamycin is combined with Butacaine. Butamben The risk or severity of methemoglobinemia can be increased when Natamycin is combined with Butamben. Capsaicin The risk or severity of methemoglobinemia can be increased when Natamycin is combined with Capsaicin. Chloroprocaine The risk or severity of methemoglobinemia can be increased when Natamycin is combined with Chloroprocaine. Cinchocaine The risk or severity of methemoglobinemia can be increased when Natamycin is combined with Cinchocaine. Cisatracurium Natamycin may increase the neuromuscular blocking activities of Cisatracurium. 
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- No interactions found.
Products
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- Delvocid / Fukricin (Sanbe) / InfectoMyk (Infectopharm) / N-Mycin (Aristopharma) / Natadrops (Cipla) / Natamet (Sun) / Natamycyna (Unia) / Natezhen (Alcon) / Natoph (Ibn Sina) / Natoptic (FDC) / Optinat (Jayson) / Pimafucin (Astellas) / Pimafusin (Elder) / Pimaricin (Senju Seiyaku)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Natacyn Suspension / drops 50 mg/1mL Ophthalmic Eyevance Pharmaceuticals, LLC 2021-06-12 Not applicable US 
Natacyn Suspension / drops 50 mg/1mL Ophthalmic ALCON LABORATORIES, INC. 1980-12-31 2022-03-31 US
Categories
- ATC Codes
- G01AA02 — Natamycin
- G01AA — Antibiotics
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- D01AA — Antibiotics
- D01A — ANTIFUNGALS FOR TOPICAL USE
- D01 — ANTIFUNGALS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- A01AB — Antiinfectives and antiseptics for local oral treatment
- A01A — STOMATOLOGICAL PREPARATIONS
- A01 — STOMATOLOGICAL PREPARATIONS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Alimentary Tract and Metabolism
- Anti-Bacterial Agents
- Anti-Infective Agents
- Anti-Infective Agents, Local
- Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
- Antifungal Agents
- Antifungals for Dermatological Use
- Antifungals for Topical Use
- Antiinfectives and Antiseptics for Local Oral Treatment
- Dermatologicals
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Intestinal Antiinfectives
- Lactones
- Ophthalmologicals
- Polyene Antifungal
- Polyene Antimicrobial
- Sensory Organs
- Stomatological Preparations
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- Aminoglycosides
- Alternative Parents
- Macrolides and analogues / Hexoses / O-glycosyl compounds / Beta hydroxy acids and derivatives / Oxanes / Dicarboxylic acids and derivatives / Enoate esters / Amino acids / 1,2-aminoalcohols / Lactones show 13 more
- Substituents
- 1,2-aminoalcohol / Acetal / Alcohol / Aliphatic heteropolycyclic compound / Alpha,beta-unsaturated carboxylic ester / Amine / Amino acid / Amino acid or derivatives / Aminoglycoside core / Beta-hydroxy acid show 29 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Various Fungus Species
Chemical Identifiers
- UNII
- 8O0C852CPO
- CAS number
- 7681-93-8
- InChI Key
- NCXMLFZGDNKEPB-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
- (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0⁵,⁷]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
- SMILES
- [H][C@@]12C[C@H](O)C[C@]3(O)C[C@H](O)[C@@H](C(O)=O)[C@]([H])(C[C@@H](O[C@]4([H])O[C@H](C)[C@@H](O)[C@H](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
References
- Synthesis Reference
Michael A. Eisenschink, Phillip T. Olson, "Fermentation process for producing natamycin." U.S. Patent US5231014, issued July, 1982.
US5231014- General References
- FDA Approved Drug Products: Natacyn (natamycin) suspension [Link]
- External Links
- KEGG Drug
- D00884
- KEGG Compound
- C08073
- PubChem Compound
- 5284447
- PubChem Substance
- 46509171
- ChemSpider
- 10468784
- BindingDB
- 50370755
- 7268
- ChEMBL
- CHEMBL1200656
- ZINC
- ZINC000008220909
- Therapeutic Targets Database
- DAP001331
- PharmGKB
- PA164744325
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Natamycin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Eye Infections, Fungal / Ulcerative keratitis 1 3 Completed Treatment Fungal infections of the cornea / Ulcerative keratitis 1 3 Not Yet Recruiting Treatment Acanthamoeba Keratitis / Fungal infections of the cornea 1 3 Terminated Treatment Fungal infections of the cornea 1 2, 3 Unknown Status Treatment Fungal Infections 1 1, 2 Completed Treatment Fungal infections of the cornea 1 Not Available Unknown Status Treatment Mycotic Corneal Ulcer 1
Pharmacoeconomics
- Manufacturers
- Alcon laboratories inc
- Packagers
- Alcon Laboratories
- Dosage Forms
Form Route Strength Solution / drops Ophthalmic Suspension / drops Ophthalmic 50 mg/1mL Suspension Ophthalmic 5 % Suspension Conjunctival; Ophthalmic 50 mg Solution Ophthalmic 5 % Cream Topical - Prices
Unit description Cost Unit Natacyn eye drops 14.16USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 290 dec °C PhysProp water solubility 4100 mg/L (at 21 °C) TOMLIN,C (1994) logP 1.1 Not Available logS -3.21 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.278 mg/mL ALOGPS logP -3.5 ALOGPS logP -1.7 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 3.58 Chemaxon pKa (Strongest Basic) 9.11 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 13 Chemaxon Hydrogen Donor Count 7 Chemaxon Polar Surface Area 230.99 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 169.88 m3·mol-1 Chemaxon Polarizability 68.58 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8512 Blood Brain Barrier - 0.9789 Caco-2 permeable - 0.6947 P-glycoprotein substrate Substrate 0.5926 P-glycoprotein inhibitor I Non-inhibitor 0.7063 P-glycoprotein inhibitor II Non-inhibitor 0.9224 Renal organic cation transporter Non-inhibitor 0.9629 CYP450 2C9 substrate Non-substrate 0.7748 CYP450 2D6 substrate Non-substrate 0.8576 CYP450 3A4 substrate Non-substrate 0.5291 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9154 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8632 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9632 Ames test Non AMES toxic 0.6606 Carcinogenicity Non-carcinogens 0.9448 Biodegradation Not ready biodegradable 0.9718 Rat acute toxicity 2.4181 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.994 hERG inhibition (predictor II) Non-inhibitor 0.9406
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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Binder
References
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at January 02, 2022 11:53