Identification

Name
Nystatin
Accession Number
DB00646  (APRD01146)
Type
Small Molecule
Groups
Approved, Vet 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
Synonyms
  • Nistatina
  • NYS
  • Nystatin
  • Nystatine
  • Nystatinum
Product Ingredients
IngredientUNIICASInChI Key
Nystatin dihydrateNot AvailableNot AvailableNot applicable
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MestatinCream25000 unitVaginalMedic Laboratory LtÉe1980-12-311996-09-09Canada
Mycostatin Oral Suspension 100000iuLiquid100000 unitOralSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.1972-12-312003-07-28Canada
Mycostatin Oral Tab 500000iuTablet500000 unitOralSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.1955-12-312002-07-30Canada
Mycostatin Vaginal Crm 25000unitCream25000 unitVaginalSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.1973-12-312005-08-01Canada
Nadostine Sus 100000iu/mlSuspension100000 unitOralLab Nadeau LtÉe, Division Of Technilab Inc.1974-12-312004-08-03Canada
Nadostine Tab 100000unitTablet100000 unitVaginalLab Nadeau LtÉe, Division Of Technilab Inc.1973-12-312004-08-03Canada
Nadostine Tab 500000unitTablet500000 unitOralLab Nadeau LtÉe, Division Of Technilab Inc.1973-12-311999-09-28Canada
Nilstat 25000units/gCream25000 unitVaginalTechnilab Pharma Inc.1974-12-312004-08-03Canada
Nilstat Oral Dps 100000iu/mlSolution / drops100000 unitOralLederle Cyanamid Canada Inc.1970-12-311997-01-29Canada
Nilstat Orl Tab 500000unitTablet500000 unitOralLederle Cyanamid Canada Inc.1970-12-311997-01-29Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dom-nystatin SuspensionSuspension100000 unitOralDominion Pharmacal1998-08-05Not applicableCanada
Ftp-nystatinSolution / drops100000 unitOralFtp Pharmacal Inc.1998-10-092004-08-03Canada
Jamp-nystatin Oral Suspension USPSuspension100000 unitOralJamp Pharma Corporation2015-01-09Not applicableCanada
MycostatinCream100000 [USP'U]/1gTopicalE.R. Squibb & Sons, L.L.C.2007-01-012007-06-30Us
MycostatinPowder100000 [USP'U]/1gTopicalE.R. Squibb & Sons, L.L.C.2009-06-012010-03-31Us
NyamycPowder100000 [USP'U]/1gTopicalUpsher-Smith Laboratories, LLC2005-05-03Not applicableUs
NyataKit100000 U/1gTopicalCrown Laboratories2015-12-172016-10-03Us
Nyata Nystatin PowderKit100000 U/1gTopicalCrown Laboratories2016-12-082017-01-02Us
NystatinSuspension100000 [USP'U]/1mLOralVista Pharm, Inc.2012-05-01Not applicableUs
NystatinCream100000 [USP'U]/1gTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.1979-02-01Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Candistatin Topical Powder - 100000 Unit/gPowder100000 unitTopicalBristol Myers Squibb1996-12-312008-04-25Canada
Mycostatin Crm 100000unit/gmCream100000 unitTopicalSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.1970-12-312006-09-06Canada
Mycostatin Ont 100000iu/gmOintment100000 unitTopicalSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.1955-12-312002-07-30Canada
Mycostatin Topical Pwr 100,000units/gmPowder100000 unitTopicalConvatec, Division Of Bristol Myers Squibb Canada Co.1994-12-312008-11-12Canada
Nadostine Crm 100000iu/gmCream100000 unitTopicalLab Nadeau LtÉe, Division Of Technilab Inc.1974-12-312004-08-03Canada
Nadostine Ont 100000iu/gmOintment100000 unitTopicalLab Nadeau LtÉe, Division Of Technilab Inc.1974-12-312004-08-03Canada
Nilstat Top Crm 100000unit/gmCream100000 unitTopicalLederle Cyanamid Canada Inc.1979-12-311997-01-29Canada
Nilstat Top Ont 100000unit/gmOintment100000 unitTopicalLederle Cyanamid Canada Inc.1979-12-311997-01-29Canada
Nyaderm Crm 100000unit/gmCream100000 unitTopicalTaro Pharmaceuticals, Inc.1979-12-31Not applicableCanada
Nyaderm Ont 100000unit/gmOintment100000 unitTopicalTaro Pharmaceuticals, Inc.1979-12-31Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
FlagystatinNystatin (100000 unit) + Metronidazole (500 mg)SuppositoryVaginalAventis Pharma Ltd.1972-12-312004-07-30Canada
Flagystatin CreamNystatin (100000 unit) + Metronidazole (500 mg)CreamVaginalSanofi Aventis1976-12-31Not applicableCanada
Flagystatin Vaginal OvuleNystatin (100000 unit) + Metronidazole (500 mg)SuppositoryVaginalSanofi Aventis1979-12-31Not applicableCanada
Kenacomb CreamNystatin (100000 unit) + Gramicidin D (.25 mg) + Neomycin sulfate (2.5 mg) + Triamcinolone acetonide (1 mg)CreamTopicalWestwood Squibb, Division Of Bristol Myers Squibb Canada Inc.1965-12-312004-08-05Canada
Kenacomb Mild CreamNystatin (100000 unit) + Gramicidin D (.25 mg) + Neomycin sulfate (2.5 mg) + Triamcinolone acetonide (.25 mg)CreamTopicalWestwood Squibb, Division Of Bristol Myers Squibb Canada Inc.1968-12-312004-08-05Canada
Kenacomb Mild OintmentNystatin (100000 unit) + Gramicidin D (.25 mg) + Neomycin sulfate (2.5 mg) + Triamcinolone acetonide (.25 mg)OintmentTopicalWestwood Squibb, Division Of Bristol Myers Squibb Canada Inc.1968-12-312004-08-05Canada
Kenacomb OintmentNystatin (100000 unit) + Gramicidin D (.25 mg) + Neomycin sulfate (2.5 mg) + Triamcinolone acetonide (1 mg)OintmentTopicalWestwood Squibb, Division Of Bristol Myers Squibb Canada Inc.1996-07-312004-08-05Canada
Kenacomb OntNystatin (100000 unit) + Gramicidin D (.25 mg) + Neomycin (2.5 mg) + Triamcinolone acetonide (1 mg)OintmentTopicalSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.1965-12-311997-08-14Canada
Lidecomb CreamNystatin (100000 unit) + Fluocinonide (0.5 mg) + Gramicidin D (0.25 mg) + Neomycin sulfate (5 mg)CreamTopicalMedicis Pharmaceutical Corporation1980-12-311998-09-25Canada
Mecomb Crm 0.1%Nystatin (100000 unit) + Gramicidin D (.25 mg) + Neomycin (2.5 mg) + Triamcinolone acetonide (1 mg)CreamTopicalMedic Laboratory LtÉe1979-12-312003-07-17Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
FIRST BXN MouthwashNystatin (6.75 mg/1mL) + Diphenhydramine hydrochloride (0.84 mg/1mL) + Lidocaine hydrochloride (6.75 mg/1mL)KitOralCutisPharma, Inc2009-09-08Not applicableUs
FIRST Dukes Mouthwash CompoundingNystatin (0.6 g/0.6g) + Diphenhydramine hydrochloride (0.525 g/0.525g) + Hydrocortisone (0.06 g/0.06g)KitOralCutisPharma, Inc.2010-12-15Not applicableUs
FIRST Marys Mouthwash CompoundingNystatin (1.2 g/1.2g) + Diphenhydramine hydrochloride (0.45 g/0.45g) + Hydrocortisone (0.06 g/0.06g) + Tetracycline hydrochloride (1.5 g/1.5g)KitOralCutisPharma, Inc.2010-12-15Not applicableUs
International/Other Brands
Adiclair (Ardeypharm) / Afunginal (Euro Generics) / Biofanal (Pfleger) / Candacide (Be-Tabs Pharmaceuticals) / Candermil (LKM) / Candex (Square) / Candidias (Fabra) / Candistat (Ambalal Sarabhai Enterprises) / Candistin (Pharos) / Canstat (Aspen Pharmacare) / Cazetin (Ifars) / Diaper NZ (Cheminter) / Dipni (Omega) / Enystin (Kalbe) / Fukangning (Deyer) / Fungatin (Ferron) / Fungicidin Leciva (Zentiva) / Fungistin (Beximco) / Fungostatin (Nobel) / Funistatin (Nobel) / Gynostatin (Iqfarma) / Kandistatin (Metiska) / Kenalon (Ta Fong) / Lederlind (Riemser) / Ledernyst (Riemser) / Lystin (Biolab) / Mycostatin (Bristol Myers Squibb) / Nilstat (Glenmark) / Nyaderm (Taro) / Nystan (Bristol Myers Squibb)
Categories
UNII
BDF1O1C72E
CAS number
1400-61-9
Weight
Average: 926.0949
Monoisotopic: 925.503499979
Chemical Formula
C47H75NO17
InChI Key
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
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

Pharmacology

Indication

For treatment of cutaneous or mucocutaneous mycotic infections caused by Candida species

Associated Conditions
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.

TargetActionsOrganism
AErgosterol
binder
Candida albicans
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Nystatin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Nystatin is combined with (S)-Warfarin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Nystatin.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Nystatin.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Nystatin.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Nystatin.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Nystatin.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Nystatin.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Nystatin.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Nystatin.
Food Interactions
  • Take without regard to meals.

References

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:7534361]
External Links
Human Metabolome Database
HMDB0014784
KEGG Drug
D00202
KEGG Compound
C06572
PubChem Compound
11953884
PubChem Substance
46504780
ChemSpider
10128183
ChEBI
7660
ChEMBL
CHEMBL229383
Therapeutic Targets Database
DAP000879
PharmGKB
PA450666
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Nystatin
ATC Codes
G01AA01 — NystatinA07AA02 — NystatinD01AA01 — NystatinG01AA51 — Nystatin, combinations
AHFS Codes
  • 84:04.08.28 — Polyenes
  • 08:14.28 — Polyenes
FDA label
Download (776 KB)
MSDS
Download (72.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
1, 2CompletedTreatmentKidney Diseases / Transplantation, Kidney1
2CompletedTreatmentStomatitis, Denture1
2Unknown StatusTreatmentAnastomotic Leakage1
2, 3WithdrawnTreatmentMinor burns1
3CompletedSupportive CareChronic Myeloproliferative Disorders / Infection NOS / Leukemias / Malignant Lymphomas / Multiple Myeloma and Plasma Cell Neoplasm / Myelodysplastic Syndromes1
3CompletedTreatmentGastrointestinal Diseases / Oral Candidiasis / Vesicular Stomatitis1
3CompletedTreatmentInfection, Human Immunodeficiency Virus I1
3CompletedTreatmentOral Candidiasis1
3RecruitingPreventionCritical Illness / Sepsis / Shock, Septic / Ventilator-associated Bacterial Pneumonia1
4CompletedHealth Services ResearchChronic Renal Failure (CRF)1
4CompletedPreventionCritical Illness / Fungal Prophylaxis / General Surgery / Prophylaxis of Candida Infections1
4CompletedPreventionFungal Infections Systemic1
4CompletedPreventionVery Low Birth Weight Infants1
4CompletedTreatmentPhotochemotherapy Reaction1
4CompletedTreatmentVaginal Inflammation1
4Unknown StatusPreventionAnticandidal Property of Saccharomyces Boulardii on Very Low Birth Weight Infants1
Not AvailableCompletedPreventionOral Lichen Planus / Prophylaxis of Candida Infections1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Oral Candidiasis3
Not AvailableUnknown StatusNot AvailableStomatitis, Denture1

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
  • Actavis Group
  • Advanced Pharmaceutical Services Inc.
  • Aidarex Pharmacuticals LLC
  • Apothecon
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Bausch & Lomb Inc.
  • Bryant Ranch Prepack
  • Cardinal Health
  • Contract Pharm
  • Cutis Pharma Inc.
  • Dept Health Central Pharmacy
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Duramed
  • E. Fougera and Co.
  • E.R. Squibb and Sons LLC
  • Gallipot
  • Glenmark Generics Ltd.
  • Major Pharmaceuticals
  • Medisca Inc.
  • Metrics Inc.
  • Midlothian Labs
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mutual Pharmaceutical Co.
  • Novopharm Ltd.
  • Nycomed Inc.
  • Odyssey Pharmaceuticals Inc.
  • Paddock Labs
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • PD-Rx Pharmaceuticals Inc.
  • PEDiNOL
  • Perrigo Co.
  • Pharmaceutical Association
  • Pharmaceutics International Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Pliva Inc.
  • Precision Dose Inc.
  • Preferred Pharmaceuticals Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Sandoz
  • Savage Labs
  • Stat Scripts LLC
  • Taro Pharmaceuticals USA
  • Teva Pharmaceutical Industries Ltd.
  • USL Pharma Inc.
  • Vintage Pharmaceuticals Inc.
  • Vistapharm Inc.
  • Wockhardt Ltd.
  • Xactdose Inc.
  • X-Gen Pharmaceuticals
Dosage forms
FormRouteStrength
KitOral
CreamVaginal
SuppositoryVaginal
Solution / dropsOral100000 unit
PowderTopical100000 [USP'U]/1g
LiquidOral100000 unit
PowderTopical100000 unit
SuspensionOral100000 unit
TabletVaginal100000 unit
TabletOral500000 unit
CreamVaginal100000 unit
CreamVaginal25000 unit
KitTopical100000 U/1g
CreamTopical100000 mg/1g
CreamTopical100000 [USP'U]/1g
InsertVaginal100000 [USP'U]/1
OintmentTopical100000 [USP'U]/1g
OintmentTopical100000 U/1g
PowderTopical100000
PowderTopical100000 1/1g
PowderTopical100000 U/1g
Powder, for suspensionOral5000
SuspensionOral100000
SuspensionOral100000 [USP'U]/1mL
SuspensionOral100000 [iU]/1mL
SuspensionOral100000 [USP'U]/15mL
SuspensionOral500000 [USP'U]/5mL
Tablet, coatedOral500000 [USP'U]/1
Tablet, film coatedOral500000 [USP'U]/1
Kit100000 [USP'U]/1g
CreamTopical100000 unit
OintmentTopical100000 unit
CreamTopical
OintmentTopical
Prices
Unit descriptionCostUnit
Nystatin 10 billion unit powder3014.1USD each
Nystatin 5 billion unit powder2096.1USD each
Nystatin 2 billion unit powder1116.9USD each
Nystatin 1 billion unit powder452.08USD each
Nystat-rx 5 billion unit powder447.0USD each
Nystatin 500 million unit powder130.75USD each
Pedi-Dri 100000 unit/gm Powder 56.7 gm Bottle105.87USD bottle
Nystatin 150mu Bottle94.5USD bottle
Nystatin 150 million unit powder42.25USD each
Nystatin 150000000 unit powder42.0USD each
Nystatin Nystatin Powder 50 Million unit Bottle39.99USD bottle
Mycostatin 100000 unit/gm Powder 15 gm Bottle36.99USD bottle
Nystop 100000 unit/gm Powder 15 gm Bottle29.99USD bottle
Nystatin 50 million unit powder19.75USD each
Nystatin 100000 unit/gm Ointment 15 gm Tube12.99USD tube
Nystatin 100000 unit/gm Cream 15 gm Tube6.5USD tube
Nystatin 100000 unit tablet5.29USD tablet
Nystatin vaginal tablet5.0USD tablet
Pedi-dri topical powder1.82USD g
Nystop 100000 unit/gm powder1.6USD g
Nystatin 500000 unit tablet0.71USD tablet
Nystatin 500000 unit oral tablet0.68USD tablet
Mycostatin 500000 unit orl tablet0.48USD tablet
Nystatin 100000 unit/ml Suspension0.25USD ml
Ratio-Nystatin 500000 unit Tablet0.25USD tablet
Nystatin 100000 unit/gm cream0.1USD g
Pms-Nystatin 100000 unit/ml Suspension0.05USD ml
Ratio-Nystatin 100000 unit/ml Suspension0.05USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)160 °C (decomposes)MSDS
water solubility360 mg/L (at 24 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.066 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity245.18 m3·mol-1ChemAxon
Polarizability102.11 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8641
Blood Brain Barrier-0.9581
Caco-2 permeable-0.741
P-glycoprotein substrateSubstrate0.5182
P-glycoprotein inhibitor INon-inhibitor0.814
P-glycoprotein inhibitor IINon-inhibitor0.6721
Renal organic cation transporterNon-inhibitor0.96
CYP450 2C9 substrateNon-substrate0.8313
CYP450 2D6 substrateNon-substrate0.867
CYP450 3A4 substrateNon-substrate0.5273
CYP450 1A2 substrateNon-inhibitor0.916
CYP450 2C9 inhibitorNon-inhibitor0.9374
CYP450 2D6 inhibitorNon-inhibitor0.9354
CYP450 2C19 inhibitorNon-inhibitor0.9243
CYP450 3A4 inhibitorNon-inhibitor0.931
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.987
Ames testNon AMES toxic0.8992
CarcinogenicityNon-carcinogens0.9731
BiodegradationNot ready biodegradable0.8601
Rat acute toxicity2.1245 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9462
hERG inhibition (predictor II)Non-inhibitor0.8971
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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 / Secondary alcohols / 1,2-aminoalcohols / Amino acids / Carboxylic acid esters
show 10 more
Substituents
Aminoglycoside core / Macrolide / Hexose monosaccharide / Glycosyl compound / O-glycosyl compound / Beta-hydroxy acid / Dicarboxylic acid or derivatives / Hydroxy acid / Monosaccharide / Oxane
show 25 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
nystatins (CHEBI:7660) / Plyenes (C06572) / Polyenes (LMPK06000001)

Targets

1. Ergosterol
Kind
Small molecule
Organism
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:16500971]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Kuper JI, D'Aprile M: Drug-Drug interactions of clinical significance in the treatment of patients with Mycobacterium avium complex disease. Clin Pharmacokinet. 2000 Sep;39(3):203-14. [PubMed:11020135]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [PubMed:22541068]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [PubMed:22541068]

Drug created on June 13, 2005 07:24 / Updated on November 17, 2018 07:11