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Identification
NameNeomycin
Accession NumberDB00994  (APRD00013)
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

A component of neomycin that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). Neomycin is a bactericidal aminoglycoside antibiotic that binds to the 30S ribosome of susceptible organisms. Binding interferes with mRNA binding and acceptor tRNA sites and results in the production of non-functional or toxic peptides.

Structure
Thumb
SynonymsNot Available
External Identifiers
  • Caswell No. 595
  • USAF CB-19
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mycifradin Sulfate Oral Solutionsolution125 mgoralPharmacia & Upjohn Inc1957-12-312000-08-02Canada
Mycifradin Sulfate Tablets 0.5 Gmtablet500 mgoralPharmacia & Upjohn Inc1953-12-312000-08-02Canada
Myciguent Ointmentointment.5 %topicalThe Upjohn Company Of Canada1951-12-311998-08-12Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Neo-fradinsolution87.5 mg/5mLoralX Gen Pharmaceuticals, Inc.2002-05-23Not applicableUs
Neomycin Sulfatetablet500 mg/1oralTeva Pharmaceuticals USA Inc1990-09-30Not applicableUs
Neomycin Sulfatetablet500 mg/1oralGolden State Medical Supply, Inc.2011-01-03Not applicableUs
Neomycin Sulfatetablet500 mg/1oralBreckenridge Pharmaceutical, Inc.2011-01-03Not applicableUs
Neomycin Sulfatetablet500 mg/1oralHI TECH PHARMACAL CO INC2010-03-12Not applicableUs
Neomycin Sulfatetablet500 mg/1oralX Gen Pharmaceuticals, Inc.2010-03-12Not applicableUs
Neomycin Sulfatetablet500 mg/1oralMajor Pharmaceuticals2009-09-14Not applicableUs
Neomycin Sulfatetablet500 mg/1oralECI Pharmaceuticals, LLC2016-01-16Not applicableUs
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Antibioticointment3.5 mg/gtopicalPromex, LLC2013-12-05Not applicableUs
Antibioticointment3.5 mg/gtopicalMorales Distributors Inc2012-09-25Not applicableUs
Antibioticointment3.5 mg/gtopicalKareway Product, Inc.2011-08-11Not applicableUs
Antibiotic Ointmentointment3.5 mg/gtopicalNeo Pharm Co., Ltd.2010-08-26Not applicableUs
Baclezenecream5 mg/.9gtopicalCurazene, Llc2014-06-19Not applicableUs
Family Care Antibioticointment3.5 mg/gtopicalUNITED EXCHANGE CORP.2012-11-30Not applicableUs
Family Care Triple Antibiotic Pain Reliefointment3.5 mg/gtopicalUNITED EXCHANGE CORP.2012-02-07Not applicableUs
Pomada De Sulfaointment3.5 mg/57gtopicalMenper Distributors, Inc.2012-02-21Not applicableUs
Single Antibiotic With Neomycinointment3.5 mg/gtopicalSafetec of America2008-11-13Not applicableUs
Vitacilinaointment3.5 mg/gtopicalTeresa Cecena Dba Genesis2015-05-15Not applicableUs
Vitacilina Neomycin Sulfate First Aid Antibioticointment3.5 mg/gtopicalCompania Internacional de Comercio, S.A. de C.V.2012-08-28Not applicableUs
Water-jel Neomycin Antibioticointment3.5 mg/gtopicalWater Jel Technologies2010-03-31Not applicableUs
Unapproved/Other Products Not Available
International Brands
NameCompany
MyacyneNot Available
MycifradinNot Available
MyciguentNot Available
Neo-RxNot Available
NeobioticNot Available
NivemycinNot Available
Brand mixtures
NameLabellerIngredients
10 Person AnsiGenuine First Aid LLC
25 Person AnsiGenuine First Aid LLC
50 Person AnsiGenuine First Aid LLC
Acme First Aid Contains 404 PiecesAcme United Corp.
Acme Small Cuts and BurnsAcme United Corp.
AerosootheAero Healthcare Us Llc
American Red Cross First Aid KitTomy International
Aminoderm PoudreDesbergers LtÉe, Division Of Technilab Inc.
AntibioticRite Aid Corporation
Antibiotic and Pain ReliefRite Aid Corporation
Antibiotic and Pain Relief Maximum StrengthCVS Pharmacy
Antibiotic Ear (neo/polym/hc)Physicians Total Care, Inc.
Antibiotic Maximum StrengthWalgreen Company
Antibiotic Original StrengthCVS Pharmacy
Antibiotic Plus Pain ReliefSafeway
Antibiotic Plus Pain Relief Maximum StrengthRite Aid Corporation
Arc First Aid Contains 1000 PiecesAmerican Red Cross
Arc First Aid Contains 404 PiecesAmerican Red Cross
Atopalm First Aid Triple AntibioticNeoPharm Co., Ltd.
Atopalm First Aid Triple Antibiotic Protection Moisturizing and Pain ReliefNeoPharm Co., Ltd.
Bacitracin Zinc, Neomycin Sulfate and Polymyxin B SulfateGalentic Pharma (India) Private Limited
Berkley and Jensen Triple AntibioticBJWC
Biotic-plusProvision Medical
Budpak Triple Antibiotic Maximum StrengthBudpak Inc.
Cardinal Health First Aid AntibioticCardinal Health
Care One Maximum Strength First Aid AntibioticFoodhold U.S.A. Llc
Careall Triple AntibioticNew World Imports, Inc
Careone Antibiotic Plus Pain ReliefAmerican Sales Company
Careone Original Strength Triple AntibioticFoodhold U.S.A. Llc
Careone Triple AntibioticAmerican Sales Company
Childrens Double Antibiotic With Pain ReliefWalgreen Company
Cicatrin PowderGlaxosmithkline Inc
Coly-mycin SPar Pharmaceutical, Inc.
CortisporinPhysicians Total Care, Inc.
Cortisporin-TCPar Pharmaceutical, Inc.
CortomycinMajor Pharmaceuticals
CuadridermaPro Mex Llc
Cvp Triple AntibioticSalado Sales, Inc
Daymark Fak-35 First AidCmc Group
Dg Health AntibioticDolgencorp Inc
Dg Health Triple AntibioticDolgencorp Inc
Dioptrol OintmentDioptic Pharmaceuticals Inc
Dioptrol SuspensionDioptic Pharmaceuticals Inc
Diosporin OintmentDioptic Pharmaceuticals Inc
Double Antibiotic Plus Pain Relief Maximum StrengthFred's Inc.
Dr Bells PomadeGenomma Lab Usa Inc.
Dr Teals Triple AntibioticAdvanced Beauty Systems, Inc.
Equaline Antibiotic Plus Pain ReliefSupervalu Inc
Equaline Antibiotic Plus Pain Relief for KidsSupervalu Inc
Equaline First Aid AntibioticSupervalu Inc
Equaline Triple AntibioticSupervalu Inc
Equaline Triple Antibiotic PlusSupervalu Inc
Equate Antibiotic Plus Pain ReliefWal Mart Stores Inc
Exchange Select First Aid Triple Anitbiotic Pain RelievingArmy & Air Force Exchange Service
Exchange Select Triple AntibioticArmy & Air Force Exchange Service
Face Values Triple AntibioticHarmon Stores Inc.
Family Care Triple AntibioticUNITED EXCHANGE CORP.
Family Care Triple Antibiotic Plus Pain ReliefUNITED EXCHANGE CORP.
Family WellnessZhejiang Jingwei Pharmaceutical Co., Ltd.
Family Wellness Triple Antibiotic Plus Pain ReliefFamily Dollar
First Aid AntibioticHy Vee Inc
First Aid Antibiotic Pain Relief Maximum StrengthRite Aid
First Aid Antibiotic Plus Pain Relief Maximum StrengthRite Aid
First Aid Pocket Pack - 40 PiecesReady America, Inc.
First Aid Triple AntibioticRite Aid
First Aid Triple Antibiotic and Pain Relief Maximum StrengthLif Elabs, A Division Of Atico International Usa, Inc.
First Aid Triple Antibiotic With Pain RelieverCintas First Aid & Safety
First Aid Value Pack - 77 PiecesReady America, Inc.
FML-neo Oph SusAllergan Inc
Formucare Triple Antibiotic Original StrengthAccess Business Group LLC
Fulton Street Market Triple Antibiotic Original StrengthAccess Business Group LLC
Genuine First Aid - Auto First AidGenuine First Aid, LLC
Genuine First Aid - Home First AidGenuine First Aid, LLC
Genuine First Aid Emergency Preparedness Contains 167 Pieces HardcaseGenuine First Aid LLC
Genuine First Aid Industrial First AidGenuine First Aid, LLC
Genuine Triple AntibioticGenuine First Aid LLC
Gfa First AidGenuine First Aid, LLC
Gfa First Aid 16 Unit Metal CaseGenuine First Aid, LLC
Gfa First Aid 24 Unit Metal CaseGenuine First Aid, LLC
Gfa First Aid 36 Unit Metal CaseGenuine First Aid, LLC
Gfa First Aid Kit Essentials - 33 PiecesGenuine First Aid, LLC
Good Neighbor Pharmacy Antibiotic and Pain ReliefAmerisource Bergen
Good Neighbor Pharmacy Emergency Preparedness and First Aid Contains 167 PiecesAmerisource Bergen
Good Neighbor Pharmacy First AidAmerisource Bergen
Good Neighbor Pharmacy Triple AntibioticAmerisource Bergen
Good Neighbor Pharmacy Triple Antibiotic Plus Pain ReliefAmerisource Bergen
Good Sense First Aid AntibioticL. Perrigo Company
Good Sense Triple AntibioticL Perrigo Company
Good Sense Triple Antibiotic and Pain ReliefL. Perrigo Company
Goodsense Antibiotic Plus Pain ReliefGeiss, Destin & Dunn, Inc.
H E Buddy Antibiotic Maximum Strength Plus Pain ReliefH E B
Healthy Accents Triple AntibioticDZA Brands LLC
Kenacomb CreamWestwood Squibb, Division Of Bristol Myers Squibb Canada Inc.
Kenacomb Mild CreamWestwood Squibb, Division Of Bristol Myers Squibb Canada Inc.
Kenacomb Mild OintmentWestwood Squibb, Division Of Bristol Myers Squibb Canada Inc.
Kenacomb OintmentWestwood Squibb, Division Of Bristol Myers Squibb Canada Inc.
Kenacomb OntSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.
Leader Triple AntibioticCardinal Health
Leader Triple Antibiotic PlusCardinal Health
Lidecomb CreamMedicis Canada Ltd.
LincolnLincoln Pharmaceutical Ltd.
Live Better Triple AntibioticThe Great Atlantic & Pacific Tea Company
Live Better Triple Antibiotic Plus Pain ReliefThe Great Atlantic & Pacific Tea Company
Livebetter Antibiotic Plus Pain ReliefThe Great Atlantic & Pacific Tea Company
Lucky Supersoft First AidDelta Brands, Inc
Makesense First AidCherry Hill Sales Co
Market Basket First Aid Triple AntibioticDavion, Inc.
MaxitrolAlcon Laboratories, Inc.
Maxitrol OntAlcon Canada Inc
Mecomb Crm 0.1%Medic Laboratory LtÉe
Medi-firstMedique Products
Medichoice Triple AntibioticOwens & Minor Inc.
Medpride First AidShield Line LLC
Meijer Antibiotic Plus Pain ReliefMeijer Distribution Inc
Meijer Triple AntibioticMeijer Distribution Inc
Meijer Triple Antibiotic PlusMEIJER, INC.
Meijer Triple Antibiotic Plus Pain ReliefMeijer Distribution Inc
MethedexMajor Pharmaceuticals
Mountain Series Weekender MedicalTender Corporation Dba Adventure Medical Kits
Multi Antibiotic With Pain Relief Maximum StrengthWalgreen Company
Neo PolycinPaddock Laboratories, LLC
Neo Polycin HCPaddock Laboratories, LLC
Neo-cortef 0.5% OintmentPfizer Canada Inc
Neo-cortef 1% OintmentPfizer Canada Inc
Neo-cortef Eye Ear Drops Sterile SuspensionPharmacia & Upjohn Inc
Neo-medrolPfizer Canada Inc
Neo-medrol Acne LotionPfizer Canada Inc
Neo-poly-bacButler Animal Health Supply
Neo-poly-bac HydroButler Animal Health Supply
Neo-poly-dexButler Animal Health Supply
Neo-polycinRebel Distributors Corp
Neo-polycin HCFera Pharmaceuticals
Neo-synalarMedimetriks Pharmaceuticals
NeocidinMajor Pharmaceuticals
Neodecadron Eye Ear Soln 0.1%Merck Frosst Canada & Cie, Merck Frosst Canada & Co.
Neomycin and Polymyxin B SulfatesWatson Laboratories, Inc.
Neomycin and Polymyxin B Sulfates and Bacitracin ZincRxv
Neomycin and Polymyxin B Sulfates and Bacitracin Zinc With Hydrocortisone AcetateRebel Distributors Corp
Neomycin and Polymyxin B Sulfates and DexamethasonePaddock Laboratories, LLC
Neomycin and Polymyxin B Sulfates and GramicidinRebel Distributors Corp
Neomycin and Polymyxin B Sulfates and HydrocortisoneBlenheim Pharmacal, Inc
Neomycin and Polymyxin B Sulfates, and Bacitracin ZincHenry Schein Inc.
Neomycin and Polymyxin B Sulfates, Bacitracin Zinc and HydrocortisoneMwi/Vet One
Neomycin and Polymyxin B Sulfates, Bacitracin Zinc, and HydrocortisoneHenry Schein Inc.
Neomycin Polymyxin B Sulfates and DexamethasoneMwi/Vet One
Neomycin Sulfate, Polymyxin B Sulfate and Bacitracin ZincSTAT Rx USA LLC
Neomycin Sulfate, Polymyxin B Sulfate and DexamethasoneSTAT RX LLC USA
Neomycin, Polymyxin B Sulfates and HydrocortisonePhysicians Total Care, Inc.
NeosporinMonarch Pharmaceuticals, Inc.
Neosporin Antibiotic CreamGlaxosmithkline Inc
Neosporin Eye-ear SolutionGlaxosmithkline Inc
Neosporin G.U.Pfizer Laboratories Div Pfizer Inc
Neosporin Irrigating SolutionGlaxosmithkline Inc
Neosporin OintmentGlaxosmithkline Inc
Neosporin Ophthalmic OintmentGlaxosmithkline Inc
Neosporin OriginalJohnson & Johnson Consumer Products Company, Division of Johnson & Johnson Consumer Companies, Inc.
Neosporin Pain Itch ScarJohnson & Johnson Consumer Inc.
Neosporin Plus Pain ReliefJohnson & Johnson Consumer Inc.
Neosporin Plus Pain Relief First Aid Antibiotic Pain Relieving for KidsJohnson & Johnson Consumer Inc.
Neosporin Plus Pain Relief First Aid Antibiotic/pain RelievingJohnson & Johnson Consumer Inc.
Neosporin Plus Pain Relief Neo To GoJohnson & Johnson Consumer Products Company, Division of Johnson & Johnson Consumer Companies, Inc.
Neosporin Plus Pain Relief Neo To Go First Aid Antibiotic Pain RelievingJohnson & Johnson Consumer Products Company, Division of Johnson & Johnson Consumer Companies, Inc.
Neotopic OintmentTechnilab Pharma Inc.
North Triple AntibioticNorth Safety Products
NpdPhoenix Pharmaceutical, Inc.
Odan-sporOdan Laboratories Ltd
Odan-spor-HCOdan Laboratories Ltd
Odan-trolOdan Laboratories Ltd
Optimyxin Plus Oto-opht GtteSandoz Canada Incorporated
Otizol HC LiqLab Nadeau LtÉe, Division Of Technilab Inc.
Our Family Triple AntibioticNash Finch Company
Paraid Triple AntibioticMcure Health Solutions Inc.
Pentrexcilina Triple AntibioticOpmx Llc
Pomada De LA Campana Triple Antibiotic Pain ReliefGenomma Lab Usa, Inc.
Premier Value Antibiotic Plus Pain ReliefChain Drug Consortium
Premier Value Triple AntibioticChain Drug Consortium
Premier Value Triple Antibiotic PlusTAI GUK PHARM. CO., LTD.
ProcomycinPhysicians Science & Nature Inc.
Procuretriple Antibiotic Triple AntibioticTWIN MED, LLC
Publix AntibioticPublix Super Markets Inc
Publix Antibiotic Plus Pain ReliefPublix Super Markets Inc
Quality Choice Maximum Strength Triple AntibioticChain Drug Marketing Association Inc
Quality Choice Triple AntibioticChain Drug Marketing Association Inc
Quality Choice Triple Antibiotic Plus Pain RelieverChain Drug Marketing Association Inc
Ratio-triacombTeva Canada Limited
Ready America First Aid Outdoor- 107 PiecesGenuine First Aid, LLC
Ready America First Aid Pocket - 33 PiecesGenuine First Aid, LLC
Repara Triple AntibioticPSS World Medical, Inc.
Safeway Antibiotic Plus Pain ReliefSAFEWAY INC
Sandoz CortimyxinSandoz Canada Incorporated
Schein Triple AntibioticHenry Schein, Inc.
Select Medical Products Triple AntibioticPSS World Medical, Inc.
Sheffield Triple AntibioticFaria LLC dba Sheffield Pharmaceuticals
Sheffield Triple Antibiotic Plus Pain ReliefFaria LLC dba Sheffield Pharmaceuticals
Shopko Antibiotic Plus Pain ReliefShopko Stores Operating Co., LLC
Shopko Triple AntibioticShopko Stores Operating Co., LLC
Shopko Triple Antibiotic PlusUNITED EXCHANGE CORP.
Shopko Triple Antibiotic Plus Pain ReliefShopko Stores Operating Co., LLC
Shoprite Triple AntibioticWakefern Food Corporation
Signature Care First Aid AntibioticSafeway
Signature Care Triple AntibioticSafeway
Small Cuts and BurnsGenuine First Aid LLC
Smart Sense Antibiotic Maximum StrengthKmart Corporation
Smart Sense Triple AntibioticKmart Corporation
Smart Sense Triple Antibitotic Plus Pain ReliefKmart Corporation
Sunmark Antibiotic Plus Pain ReliefMc Kesson
Sunmark Triple AntibioticMc Kesson
Sunmark Triple Antibiotic Plus Pain ReliefMc Kesson
Synalar Bi-otic SolutionMedicis Canada Ltd.
Theraderm CreamBimeda Mtc Animal Health Inc
Theraplusplus PlusZhejiang Jingwei Pharmaceutical Co., Ltd.
Topcare Antibiotic Plus Pain ReliefTopco Associates LLC
Topcare Triple AntibioticTopco Associates LLC
Topcare Triple Antibiotic Plus Pain ReliefTopco Associates LLC
TribioticHART Health
Tribioticlc Lc LcHART Health
Triple AntibioticE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.
Triple Antibiotic and Pain Relief Maximum StrengthCVS Pharmacy
Triple Antibiotic Extra StrengthPersonal Care Products, Inc.
Triple Antibiotic First AidUniversal Distribution Center LLC
Triple Antibiotic First Aid AntibioticNatureplex LLC
Triple Antibiotic HCPhoenix Pharmaceutical, Inc.
Triple Antibiotic Maximum StrengthBudpak Inc.
Triple Antibiotic OintmentG&W Laboratories, Inc.
Triple Antibiotic PlusG&W Laboratories, Inc.
Triple Antibiotic Plus Maximum StrengthH E B
Triple Antibiotic Plus Pain ReliefMeijer Distribution Inc
Triple Antibiotic Plus Pain Relief Maximum StrengthKroger Company
Triple Antibiotic With Pain Relief Maximum StrengthWalgreen Company
Ultra Seal Triple AntibioticUltra Seal Corporation
Up and Up AntibioticTarget Corporation
Up and Up Antibiotic Plus Pain ReliefTarget Corporation
Up and Up First Aid Antibiotic Pain RelievingTarget Corporation
Viaderm Kc CrmTaro Pharmaceuticals Inc
Viaderm Kc OntTaro Pharmaceuticals Inc
Walgreens Maximum Strength Triple Antibiotic With Pain ReliefWALGREEN CO.
Walgreens Triple AntibioticWalgreen Company
Walgreenstriple AntibioticWalgreen Company
Water-jel 3-IN-1 AntibioticWater Jel Technologies
Well At Walg Triple Antibiotic Well At WalgreensWalgreens
Western Family Antibiotic Plus Pain ReliefWestern Family Foods Inc
Western Family Triple AntibioticWestern Family Foods Inc
Western Family Triple Antibiotic Plus Pain ReliefWestern Family Foods Inc
Winco Maximum Strength Triple AntibioticWin Co Foods, Llc
Winco Original Strength Triple AntibioticWin Co Foods, Llc
Salts
Name/CASStructureProperties
Neomycin palmitate
ThumbNot applicableDBSALT001620
Neomycin sulfate
Thumb
  • InChI Key: OIXVKQDWLFHVGR-CITJEJKVSA-N
  • Monoisotopic Mass: 712.27966483
  • Average Mass: 712.722
DBSALT000472
Categories
UNIII16QD7X297
CAS number1404-04-2
WeightAverage: 614.6437
Monoisotopic: 614.312285588
Chemical FormulaC23H46N6O13
InChI KeyInChIKey=PGBHMTALBVVCIT-VCIWKGPPSA-N
InChI
InChI=1S/C23H46N6O13/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22/h5-23,30-36H,1-4,24-29H2/t5-,6+,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1
IUPAC Name
(2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(2R,3S,4R,5S)-5-{[(1R,2R,3S,5R,6S)-3,5-diamino-2-{[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-hydroxycyclohexyl]oxy}-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}oxane-3,4-diol
SMILES
NC[C@@H]1O[[email protected]](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](O)[[email protected]](N)C[[email protected]](N)[[email protected]]3O[[email protected]]3O[[email protected]](CN)[C@@H](O)[[email protected]](O)[[email protected]]3N)[C@@H]2O)[[email protected]](N)[C@@H](O)[C@@H]1O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as amino sugars. These are sugars having one alcoholic hydroxy group replaced by an amino group; systematically known as x-amino-x-deoxymonosaccharides. These compounds do not include Glycosylamines.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct ParentAmino sugars
Alternative Parents
Substituents
  • 4,5-disubstituted 2-deoxystreptamine
  • Aminoglycoside core
  • 2-deoxystreptamine aminoglycoside
  • Neamine core
  • Glucosamine
  • Amino sugar
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Cyclohexylamine
  • Cyclohexanol
  • Oxane
  • Oxolane
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationTopical uses include treatment for superficial eye infections caused by susceptible bacteria (used in combination with other antiinfectives), treatment of otitis externa caused by susceptible bacteria, treatment or prevention of bacterial infections in skin lesions, and use as a continuous short-term irrigant or rinse to prevent bacteriuria and gram negative rod bacteremia in abacteriuric patients with indwelling catheters. May be used orally to treat hepatic encephalopathy, as a perioperative prophylactic agent, and as an adjunct to fluid and electrolyte replacement in the treatment of diarrhea caused to enteropathogenic E. coli (EPEC).
PharmacodynamicsNeomycin is an aminoglycoside antibiotic. Aminoglycosides work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. In addition, some mycobacteria, including the bacteria that cause tuberculosis, are susceptible to aminoglycosides. Infections caused by Gram-positive bacteria can also be treated with aminoglycosides, but other types of antibiotics are more potent and less damaging to the host. In the past the aminoglycosides have been used in conjunction with penicillin-related antibiotics in streptococcal infections for their synergistic effects, particularly in endocarditis. Aminoglycosides are mostly ineffective against anaerobic bacteria, fungi and viruses.
Mechanism of actionAminoglycosides like neomycin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Specifically neomycin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes.
Related Articles
AbsorptionPoorly absorbed from the normal gastrointestinal tract. Although only approximately 3% of neomycin is absorbed through intact intestinal mucosa, significant amounts may be absorbed through ulcerated or denuded mucosa or if inflammation is present.
Volume of distributionNot Available
Protein bindingProtein binding studies have shown that the degree of aminoglycoside protein binding is low and, depending upon the methods used for testing, may be between 0% and 30%.
Metabolism

Neomycin undergoes negligible biotransformation after parenteral administration.

Route of eliminationThe small absorbed fraction is rapidly distributed in the tissues and is excreted by the kidney in keeping with the degree of kidney function.
Half life2 to 3 hours
ClearanceNot Available
ToxicityLD50 = 200 mg/kg (rat). Because of low absorption, it is unlikely that acute overdosage would occur with oral neomycin. However, prolonged administration could result in sufficient systemic drug levels to produce neurotoxicity, ototoxicity and/or nephrotoxicity. Nephrotoxicity occurs via drug accumulation in renal proximal tubular cells resulting in cellular damage. Tubular cells may regenerate despite continued exposure and nephrotoxicity is usually mild reversible. Neomycin is the most toxic aminoglycoside agent, which is thought to be due to its large number of cationic amino groups. Otoxocity occurs via drug accumulation in the endolymph and perilymph of the inner ear causing irreversible damage to hair cells in the cochlea or summit of ampullar cristae in the vestibular complex. High frequency hearing loss is followed by low frequency hearing loss. Further toxicity may cause retrograde degeneration of the auditory nerve. Vestibular toxicity may result in vertigo, nausea and vomiting, dizziness and loss of balance.
Affected organisms
  • Enteric bacteria and other eubacteria
  • Escherichia coli
  • Klebsiella
  • Enterobacter
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8617
Blood Brain Barrier-0.9659
Caco-2 permeable-0.7502
P-glycoprotein substrateNon-substrate0.5164
P-glycoprotein inhibitor INon-inhibitor0.8023
P-glycoprotein inhibitor IINon-inhibitor0.8764
Renal organic cation transporterNon-inhibitor0.7886
CYP450 2C9 substrateNon-substrate0.8231
CYP450 2D6 substrateNon-substrate0.8041
CYP450 3A4 substrateNon-substrate0.6473
CYP450 1A2 substrateNon-inhibitor0.9157
CYP450 2C9 inhibitorNon-inhibitor0.9147
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9034
CYP450 3A4 inhibitorNon-inhibitor0.9471
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8446
Ames testNon AMES toxic0.6934
CarcinogenicityNon-carcinogens0.9505
BiodegradationNot ready biodegradable0.8587
Rat acute toxicity1.4850 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9728
hERG inhibition (predictor II)Non-inhibitor0.81
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • X gen pharmaceuticals inc
  • Pharmacia and upjohn co
  • Pfizer laboratories div pfizer inc
  • Bristol myers squibb co
  • Lannett co inc
  • Eli lilly and co
  • Oman pharmaceutical products co llc
  • Roxane laboratories inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
Packagers
Dosage forms
FormRouteStrength
Kit
Powdertopical
Ointmenttopical3.5 mg/g
Creamtopical5 mg/.9g
Suspensiontopical
Suspensionauricular (otic)
Suspension/ dropsauricular (otic)
Ointmentophthalmic; topical
Ointmenttopical
Sticktopical
Ointmentophthalmic
Suspensionophthalmic
Solution/ dropsophthalmic
Creamtopical
Solutionoral125 mg
Tabletoral500 mg
Ointmenttopical.5 %
Suspensionophthalmic; otic
Solutionoral87.5 mg/5mL
Lotiontopical
Suspension/ dropsophthalmic
Liquidophthalmic; otic
Irrigantirrigation
Solutionirrigation
Solutionauricular (otic)
Solution/ dropsauricular (otic)
Tabletoral500 mg/1
Solutionophthalmic
Solutionophthalmic; otic
Solutionurethral
Liquidophthalmic
Dropsophthalmic; otic
Suspensionotic
Ointmenttopical3.5 mg/57g
Solutionotic
Prices
Unit descriptionCostUnit
Neomycin Sulfate 500 mg tablet1.39USD tablet
Neomycin 500 mg tablet1.25USD tablet
Neomycin sulfate powder0.84USD g
Neo-fradin 125 mg/5 ml soln0.12USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point6 mg/mL (as sulfate form)Not Available
logP-7.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility64.7 mg/mLALOGPS
logP-2.8ALOGPS
logP-8.4ChemAxon
logS-0.98ALOGPS
pKa (Strongest Acidic)12.29ChemAxon
pKa (Strongest Basic)9.97ChemAxon
Physiological Charge6ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area353.11 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity135.9 m3·mol-1ChemAxon
Polarizability60.87 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Jaehoon Yu, Jongkook Lee, Miyun Kwon, Ae Pae, Hun Koh, “Heterodimeric conjugates of neomycin-oxazolidinone, their preparation and their use.” U.S. Patent US20050222055, issued October 06, 2005.

US20050222055
General ReferencesNot Available
External Links
ATC CodesA07AA51J01GB05S03AA01S01AA03D06AX04B05CA09A07AA01A01AB08S02AA07R02AB01
AHFS Codes
  • 52:04.04
  • 84:04.04
PDB Entries
FDA labelNot Available
MSDSDownload (72.9 KB)
Interactions
Drug Interactions
Drug
AcarboseThe risk or severity of adverse effects can be increased when Neomycin is combined with Acarbose.
AcenocoumarolNeomycin may increase the anticoagulant activities of Acenocoumarol.
Alendronic acidNeomycin may increase the activities of Alendronate.
AmdinocillinThe serum concentration of Neomycin can be decreased when it is combined with Amdinocillin.
AmoxicillinThe serum concentration of Neomycin can be decreased when it is combined with Amoxicillin.
Amphotericin BAmphotericin B may increase the nephrotoxic activities of Neomycin.
AmpicillinThe serum concentration of Neomycin can be decreased when it is combined with Ampicillin.
Atracurium besylateNeomycin may increase the activities of Atracurium besylate.
AvibactamAvibactam may increase the nephrotoxic activities of Neomycin.
AzidocillinThe serum concentration of Neomycin can be decreased when it is combined with Azidocillin.
AzlocillinThe serum concentration of Neomycin can be decreased when it is combined with Azlocillin.
BacampicillinThe serum concentration of Neomycin can be decreased when it is combined with Bacampicillin.
BacitracinNeomycin may increase the nephrotoxic activities of Bacitracin.
BenzylpenicillinThe serum concentration of Neomycin can be decreased when it is combined with Benzylpenicillin.
Botulinum Toxin Type ANeomycin may increase the neuromuscular blocking activities of Botulinum Toxin Type A.
Botulinum Toxin Type BNeomycin may increase the neuromuscular blocking activities of Botulinum Toxin Type B.
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Neomycin.
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Neomycin.
CarbenicillinThe serum concentration of Neomycin can be decreased when it is combined with Carbenicillin.
CarboplatinNeomycin may increase the ototoxic activities of Carboplatin.
CefaclorCefaclor may increase the nephrotoxic activities of Neomycin.
CefdinirCefdinir may increase the nephrotoxic activities of Neomycin.
CefepimeCefepime may increase the nephrotoxic activities of Neomycin.
CefiximeCefixime may increase the nephrotoxic activities of Neomycin.
CefmenoximeCefmenoxime may increase the nephrotoxic activities of Neomycin.
CefotaximeCefotaxime may increase the nephrotoxic activities of Neomycin.
CefotetanCefotetan may increase the nephrotoxic activities of Neomycin.
CefoxitinCefoxitin may increase the nephrotoxic activities of Neomycin.
CefpodoximeCefpodoxime may increase the nephrotoxic activities of Neomycin.
CefprozilCefprozil may increase the nephrotoxic activities of Neomycin.
CeftazidimeCeftazidime may increase the nephrotoxic activities of Neomycin.
CeftibutenCeftibuten may increase the nephrotoxic activities of Neomycin.
CeftriaxoneCeftriaxone may increase the nephrotoxic activities of Neomycin.
CefuroximeCefuroxime may increase the nephrotoxic activities of Neomycin.
CelecoxibCelecoxib may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
Cisatracurium besylateNeomycin may increase the activities of Cisatracurium besylate.
CisplatinCisplatin may increase the nephrotoxic activities of Neomycin.
ClavulanateThe serum concentration of Neomycin can be decreased when it is combined with Clavulanate.
ClodronateNeomycin may increase the activities of Clodronate.
CloxacillinThe serum concentration of Neomycin can be decreased when it is combined with Cloxacillin.
ColistimethateNeomycin may increase the nephrotoxic activities of Colistimethate.
ColistinNeomycin may increase the nephrotoxic activities of Colistin.
CyclacillinThe serum concentration of Neomycin can be decreased when it is combined with Cyclacillin.
CyclosporineNeomycin may increase the nephrotoxic activities of Cyclosporine.
DiclofenacDiclofenac may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
DicloxacillinThe serum concentration of Neomycin can be decreased when it is combined with Dicloxacillin.
DicoumarolNeomycin may increase the anticoagulant activities of Dicoumarol.
DiflunisalDiflunisal may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Neomycin.
Etacrynic acidThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Neomycin.
EtodolacEtodolac may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
FenoprofenFenoprofen may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
FloctafenineFloctafenine may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
FlucloxacillinThe serum concentration of Neomycin can be decreased when it is combined with Flucloxacillin.
FlurbiprofenFlurbiprofen may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
FoscarnetFoscarnet may increase the nephrotoxic activities of Neomycin.
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Neomycin.
HetacillinThe serum concentration of Neomycin can be decreased when it is combined with Hetacillin.
IbandronateNeomycin may increase the activities of Ibandronate.
IbuprofenIbuprofen may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
IndomethacinIndomethacin may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
InfliximabInfliximab may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
KetoprofenKetoprofen may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
KetorolacKetorolac may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
MannitolMannitol may increase the nephrotoxic activities of Neomycin.
MecamylamineNeomycin may increase the neuromuscular blocking activities of Mecamylamine.
Mefenamic acidMefenamic acid may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
MeloxicamMeloxicam may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
MeticillinThe serum concentration of Neomycin can be decreased when it is combined with Meticillin.
MezlocillinThe serum concentration of Neomycin can be decreased when it is combined with Mezlocillin.
NabumetoneNabumetone may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
NafcillinThe serum concentration of Neomycin can be decreased when it is combined with Nafcillin.
NaproxenNaproxen may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
OxacillinThe serum concentration of Neomycin can be decreased when it is combined with Oxacillin.
OxaprozinOxaprozin may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
PamidronateNeomycin may increase the activities of Pamidronate.
PancuroniumNeomycin may increase the activities of Pancuronium.
PhenoxymethylpenicillinThe serum concentration of Neomycin can be decreased when it is combined with Phenoxymethylpenicillin.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Neomycin.
PiperacillinThe serum concentration of Neomycin can be decreased when it is combined with Piperacillin.
PiroxicamPiroxicam may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
PivampicillinThe serum concentration of Neomycin can be decreased when it is combined with Pivampicillin.
PivmecillinamThe serum concentration of Neomycin can be decreased when it is combined with Pivmecillinam.
RisedronateNeomycin may increase the activities of Risedronate.
RocuroniumNeomycin may increase the activities of Rocuronium.
SorafenibThe serum concentration of Sorafenib can be decreased when it is combined with Neomycin.
SuccinylcholineNeomycin may increase the activities of Succinylcholine.
SulindacSulindac may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
TenofovirThe serum concentration of Neomycin can be increased when it is combined with Tenofovir.
Tiaprofenic acidTiaprofenic acid may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
TicarcillinThe serum concentration of Neomycin can be decreased when it is combined with Ticarcillin.
TiludronateNeomycin may increase the activities of Tiludronate.
TolmetinTolmetin may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Neomycin.
VancomycinVancomycin may increase the nephrotoxic activities of Neomycin.
VecuroniumNeomycin may increase the activities of Vecuronium.
WarfarinNeomycin may increase the anticoagulant activities of Warfarin.
Zoledronic acidNeomycin may increase the activities of Zoledronate.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Trna binding
Specific Function:
With S4 and S5 plays an important role in translational accuracy.Interacts with and stabilizes bases of the 16S rRNA that are involved in tRNA selection in the A site and with the mRNA backbone. Located at the interface of the 30S and 50S subunits, it traverses the body of the 30S subunit contacting proteins on the other side and probably holding the rRNA structure together. The combined cluste...
Gene Name:
rpsL
Uniprot ID:
P0A7S3
Molecular Weight:
13736.995 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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:17016423 ]
  3. Gill AE, Amyes SG: The contribution of a novel ribosomal S12 mutation to aminoglycoside resistance of Escherichia coli mutants. J Chemother. 2004 Aug;16(4):347-9. [PubMed:15332709 ]
  4. Eisenstein BI, Beachey EH, Ofek I: Influence of sublethal concentrations of antibiotics on the expression of the mannose-specific ligand of Escherichia coli. Infect Immun. 1980 Apr;28(1):154-9. [PubMed:6103875 ]
2. 16S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
yes
Actions
inhibitor
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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:17016423 ]
  3. Roy U, Nair D: Biodiversity of organotin resistant Pseudomonas from west coast of India. Ecotoxicology. 2007 Mar;16(2):253-61. Epub 2006 Nov 28. [PubMed:17131180 ]
  4. Wachino J, Shibayama K, Kurokawa H, Kimura K, Yamane K, Suzuki S, Shibata N, Ike Y, Arakawa Y: Novel plasmid-mediated 16S rRNA m1A1408 methyltransferase, NpmA, found in a clinically isolated Escherichia coli strain resistant to structurally diverse aminoglycosides. Antimicrob Agents Chemother. 2007 Dec;51(12):4401-9. Epub 2007 Sep 17. [PubMed:17875999 ]
  5. Brown JM, Cowley KD, Manninen KI, McNeil MM: Phenotypic and molecular epidemiologic evaluation of a Nocardia farcinica mastitis epizootic. Vet Microbiol. 2007 Nov 15;125(1-2):66-72. Epub 2007 May 6. [PubMed:17553640 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23