| Identification |
| Name |
Neomycin |
| Accession Number |
DB00994
(APRD00013)
|
| Type |
small molecule |
| Groups |
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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- Caswell No. 595
- Neomycin B Sulfate
- Neomycin Sulfate
- Neomycin Sulphate
- Neomycin trisulfate salt hydrate
- USAF CB-19
|
| Brand names |
- Biosol
- Bykomycin
- Endomixin
- Fradiomycin
- Fradiomycin Sulfate
- Fraquinol
- Lidamycin Creme
- Myacine
- Myacyne
- Mycifradin
- Mycifradin-N
- Myciguent
- Neo-Fradin
- Neo-Mantle Creme
- Neo-Rx
- Neobiotic
- Neobrettin
- Neofracin
- Neolate
- Neomix
- Neosulf
- Nivemycin
- Tuttomycin
- Vonamycin Powder V
|
| Brand name mixtures |
- AK Spor liq (gramicidin + neomycin sulfate + polymyxin B sulfate)
- AK Trol Suspension (dexamethasone + neomycin sulfate + polymyxin B sulfate)
- Aminoderm Poudre (glycine + l-cysteine + neomycin sulfate + threonine)
- Anaprime oph gel (flumethasone + neomycin sulfate + polymyxin B sulfate)
- Bacitracin-neomycin polymyxin ont (bacitracin zinc + neomycin sulfate + polymyxin B sulfate)
- Bacitracin-neomycin-polymixin ont (bacitracin zinc + neomycin sulfate + polymyxin B sulfate)
- bacitracin-neomycin-polymyxin oph ont (bacitracin zinc + neomycin sulfate + polymyxin B sulfate)
- beef cattle vit ade premix medicated (neomycin sulfate + oxytetracycline hydrochloride + vitamin A + vitamin D3 + vitamin e)
- Biosol-M-Aquadrops liq (methscopolamine bromide + neomycin sulfate)
- BNPH ont (bacitracin zinc + hydrocortisone acetate + neomycin sulfate + polymyxin B sulfate)
- Calf scour bolus (atropine sulfate + calcium phosphate + hyoscyamine sulfate + kaolin + neomycin sulfate + pectin + sulfaguanidine + sulfathiazole + vitamin A)
- Certreat Scours Oblets (chlortetracycline hydrochloride + neomycin sulfate + nicotinic acid + vitamin A + vitamin D)
- Cicatrin Powder (bacitracin zinc + glycine + l-cysteine + neomycin sulfate + threonine)
- Co-op pinkeye spray (gentian violet + neomycin sulfate)
- Cortisporin (bacitracin zinc + hydrocortisone + neomycin sulfate + polymyxin B sulfate)
- Derma-4 ont (neomycin sulfate + nystatin + thiostrepton (antibiotic of a streptomyces species) + triamcinolone acetonide)
- Dioptrol ointment (dexamethasone + neomycin sulfate + polymyxin B sulfate)
- dioptrol suspension (dexamethasone + neomycin sulfate + polymyxin B sulfate)
- Diosporin ointment (bacitracin zinc + neomycin sulfate + polymyxin B sulfate)
- Enterolyte (calcium chloride dihydrate + magnesium chloride + neomycin sulfate + potassium acetate + sodium acetate + sodium chloride + sulfamethazine)
- FML-Neo oph sus (fluorometholone + neomycin sulfate)
- Forte topical suspension (hydrocortisone acetate + hydrocortisone sodium succinate + neomycin sulfate + penicillin g procaine + polymyxin B sulfate)
- Kaobiotic bolus (kaolin + neomycin sulfate + pectin + sulfadiazine + sulfaguanidine + sulfamerazine + sulfathiazole)
- Kaobiotic tab (kaolin + neomycin sulfate + pectin + sulfadiazine + sulfaguanidine + sulfamerazine + sulfathiazole)
- Kenacomb (gramicidin + neomycin sulfate + nystatin + triamcinolone acetonide)
- Keraplex spray (methyl violet + neomycin sulfate)
- Lidecomb cream (fluocinonide + gramicidin + neomycin sulfate + nystatin)
- Mastitis Care (neomycin sulfate + penicillin g potassium + polymyxin B sulfate + streptomycin sulfate)
- Maxitrol (dexamethasone + neomycin sulfate + polymyxin B sulfate)
- Mecomb Cream 0.1% (gramicidin + neomycin sulfate + nystatin + triamcinolone acetonide)
- Mycitracin oph ont (bacitracin + neomycin sulfate + polymyxin B sulfate)
- Neo Atropec 25 tab (aluminum hydroxide + atropine methylnitrate + kaolin + neomycin sulfate + pectin + sulfacetamide + sulfaguanidine)
- Neo Atropec C tab (aluminum hydroxide + atropine methylnitrate + kaolin + neomycin sulfate + pectin + sulfacetamide + sulfaguanidine)
- Neo Atropec tab (aluminum hydroxide + atropine methylnitrate + kaolin + neomycin sulfate + pectin + sulfacetamide + sulfaguanidine)
- Neo Chlor Powder (neomycin sulfate + tetracycline hydrochloride)
- Neo Darbazine Spansule Capsule no 1 (isopropamide iodide + neomycin sulfate + prochlorperazine maleate)
- Neo Darbazine Spansule no 3 (isopropamide iodide + neomycin sulfate + prochlorperazine maleate)
- Neo Oxymed Powder (neomycin sulfate + oxytetracycline hydrochloride)
- Neo P.P.G. (neomycin sulfate + penicillin g potassium)
- Neo Sulfa-E (calcium chloride + magnesium chloride + neomycin sulfate + potassium acetate + sodium acetate + sodium chloride + sulfamethazine)
- Neo Sulfalyte Bolus (calcium chloride + magnesium chloride + neomycin sulfate + potassium acetate + sodium acetate + sodium chloride + sulfamethazine)
- Neo Terramycin Soluble Powder (neomycin sulfate + oxytetracycline hydrochloride)
- neo-chlor (neomycin sulfate + tetracycline hydrochloride)
- Neo-Cortef (hydrocortisone acetate + neomycin sulfate)
- Neo-Medrol (methylprednisolone acetate + neomycin sulfate)
- Neo-Medrol Acne Lotion (aluminum chlorohydrate + methylprednisolone acetate + neomycin sulfate + sulfur)
- Neo-Oxytetracycline (neomycin sulfate + oxytetracycline hydrochloride)
- Neo-Terramycin 50/50 premix (neomycin sulfate + oxytetracycline hydrochloride)
- Neo-Tet pws (neomycin sulfate + oxytetracycline hydrochloride)
- Neodecadron Eye Ear Solution 0.1% (dexamethasone phosphate + neomycin sulfate)
- Neomix-Pamine Solution (methscopolamine bromide + neomycin sulfate)
- Neopaste (aluminum hydroxide + calcium chloride + magnesium chloride + neomycin sulfate + potassium acetate + sodium acetate + sodium chloride + sulfamethazine + sulfathiazole)
- Neorease (neomycin sulfate + sulfamethazine + sulfathiazole)
- Neosol M Aquadrops (methscopolamine bromide + neomycin sulfate)
- Neospan Mastitis Treatment (neomycin sulfate + penicillin g potassium + polymyxin B sulfate + streptomycin sulfate)
- Neosporin antibiotic cream (gramicidin + neomycin sulfate + polymyxin B sulfate)
- Neosporin Eye-Ear Solution (gramicidin + neomycin sulfate + polymyxin B sulfate)
- Neosporin Irrigating Solution (neomycin sulfate + polymyxin B sulfate)
- Neosporin Ointment (bacitracin zinc + neomycin sulfate + polymyxin B sulfate)
- Neosporin Ophthalmic Ointment (bacitracin zinc + neomycin sulfate + polymyxin B sulfate)
- Neosulf (neomycin sulfate + sulfamethazine + sulfathiazole)
- Neosulf bolus (calcium chloride + magnesium chloride + neomycin sulfate + potassium acetate + sodium acetate + sodium chloride + sulfamethazine)
- Neosulf Plus bolus (calcium chloride + magnesium chloride + neomycin sulfate + potassium acetate + sodium acetate + sodium chloride + sulfamethazine)
- Neosulpec (kaolin + neomycin + pectin + sulfaguanidine + sulfamethazine + sulfathiazole)
- Neotet soluble concentrate (neomycin sulfate + oxytetracycline hydrochloride)
- Neotetramed Powder (neomycin sulfate + tetracycline hydrochloride)
- Neotopic ointment (bacitracin zinc + neomycin sulfate + polymyxin B sulfate)
- Neovast tabs (kaolin + neomycin sulfate + pectin + sulfadiazine + sulfaguanidine + sulfamerazine + sulfathiazole)
- Neox (neomycin sulfate + oxytetracycline hydrochloride)
- Ophtacin ophtalmic ointment (bacitracin zinc + neomycin sulfate + polymyxin B sulfate)
- Ophtacin-H ophtalmic ointment (bacitracin zinc + hydrocortisone acetate + neomycin sulfate + polymyxin B sulfate)
- Optimyxin Plus Oto-opht GTTE (gramicidin + neomycin sulfate + polymyxin B sulfate)
- Optiprime oph gel (neomycin sulfate + polymyxin B sulfate)
- Optisone (neomycin + prednisolone)
- Oribiotic ointment (bacitracin + lidocaine + neomycin sulfate + nystatin + triamcinolone acetonide)
- Otizol HC liq (hydrocortisone acetate + lidocaine hydrochloride + neomycin sulfate)
- P.T. Booster (calcium d-pantothenate + neomycin sulfate + nicotinic acid + pyridoxine hydrochloride + streptomycin sulfate + vitamin A + vitamin B1 + vitamin B12 + vitamin B2 + vitamin D3)
- Panolog cream (neomycin sulfate + nystatin + thiostrepton [antibiotic of a streptomyces species] + triamcinolone acetonide)
- Panolog ointment (neomycin sulfate + nystatin + thiostrepton [antibiotic of a streptomyces species] + triamcinolone acetonide)
- Pinkeye Spray (gentian violet + neomycin sulfate)
- Previte (neomycin sulfate + selenium sulfide + streptomycin sulfate + vitamin A + vitamin D + vitamin e + vitamin K1)
- Proctosone ont (dibucaine hydrochloride + esculin + hydrocortisone acetate + neomycin sulfate)
- Proctosone sup (dibucaine hydrochloride + esculin + hydrocortisone acetate + neomycin sulfate)
- Ratio-Triacomb regular cream (gramicidin + neomycin sulfate + nystatin + triamcinolone acetonide)
- Sandoz Cortimyxin (bacitracin zinc + hydrocortisone + neomycin sulfate + polymyxin B sulfate)
- Scour bolus plus (calcium carbonate + magnesium oxide + menadione sodium bisulfite + neomycin sulfate + potassium acetate + sodium acetate + sodium chloride + streptomycin sulfate + sulfamerazine + sulfamethazine + sulfanilamide + sulfathiazole + vitamin A + vitamin D)
- Scour Solution (methscopolamine bromide + neomycin sulfate)
- Scour solution coop (methscopolamine bromide + neomycin sulfate)
- Scour suspension (atropine sulfate + calcium phosphate + hyoscyamine sulfate + kaolin + neomycin sulfate + pectin + succinylsulfathiazole)
- Scour treat liq (neomycin sulfate + sulfamethazine + sulfathiazole)
- Scour-plug (calcium chloride + magnesium chloride + neomycin sulfate + potassium acetate + sodium acetate + sodium chloride + sulfamethazine)
- Septomixine Forte (dexamethasone + halethazole tartrate + neomycin sulfate + polymyxin B sulfate + tyrothricin)
- Solvaderm ointment (neomycin sulfate + nystatin + thiostrepton [antibiotic of a streptomyces species] + triamcinolone acetonide)
- Spor-HC otic susp (hydrocortisone + neomycin sulfate + polymyxin B sulfate)
- Sulectim plus scour boluses (calcium carbonate + magnesium oxide + menadione sodium bisulfite + neomycin sulfate + potassium acetate + sodium acetate + sodium chloride + streptomycin sulfate + sulfamerazine + sulfamethazine + sulfanilamide + sulfathiazole sodium + vitamin A + vitamin D)
- Sulkamycin S Bolettes (neomycin sulfate + sulfamethazine)
- Synalar Bi-otic solution (fluocinolone acetonide + neomycin sulfate + polymyxin B sulfate)
- Theraderm cream (gramicidin + neomycin sulfate + nystatin + triamcinolone acetonide)
- Tresaderm dermatologic solution (dexamethasone + neomycin sulfate + thiabendazole)
- Triple sulfa plus neomycin (neomycin sulfate + sulfamerazine sodium + sulfamethazine sodium + sulfathiazole sodium)
- Vetropolycin HC ont (bacitracin zinc + hydrocortisone acetate + neomycin sulfate + polymyxin B)
- Vetropolycin ont (bacitracin zinc + neomycin sulfate + polymyxin B sulfate)
- Viaderm KC Cream (gramicidin + neomycin sulfate + nystatin + triamcinolone acetonide)
- Viaderm KC ont (gramicidin + neomycin sulfate + nystatin + triamcinolone acetonide)
- Wound & Pinkeye Spray (gentian violet + neomycin sulfate)
|
| Categories |
- Anti-Bacterial Agents
- Antibiotics
- Aminoglycosides
|
| CAS number |
1404-04-2 |
| Weight |
Average: 614.6437 Monoisotopic: 614.312285588
|
| Chemical Formula |
C23H46N6O13 |
| InChI Key |
InChIKey=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
Plain Text
|
| IUPAC Name |
(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-4-{[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol
|
| SMILES |
NC[C@@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](O)[C@H](N)C[C@H](N)[C@H]3O[C@H]3O[C@H](CN)[C@@H](O)[C@H](O)[C@H]3N)[C@@H]2O)[C@H](N)[C@@H](O)[C@@H]1O
Plain Text
|
| Mass Spec |
Not Available
|
| Taxonomy |
| Kingdom |
Organic |
| Classes |
|
| Substructures |
- Aminoglycosides
- Glycerol and Derivatives
- Hydroxy Compounds
- Pyrans
- Acetals and Derivatives
- Aliphatic and Aryl Amines
- Ethers
- Alcohols and Polyols
- Amino Alcohols
- Heterocyclic compounds
- Carbohydrates
- Furans
|
| Pharmacology |
| Indication |
Topical 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). |
| Pharmacodynamics |
Neomycin 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 action |
Aminoglycosides 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. |
| Absorption |
Poorly 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 distribution |
Not Available |
| Protein binding |
Protein 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 elimination |
The small absorbed fraction is rapidly distributed in the tissues and is excreted by the kidney in keeping with the degree of kidney function. |
| Half life |
2 to 3 hours |
| Clearance |
Not Available |
| Toxicity |
LD50 = 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
|
| Pathways |
| Pathway |
Name |
SMPDB ID |
|
Neomycin Pathway |
SMP00256 |
|
| 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 |
| Form |
Route |
Strength |
| Dressing |
Topical |
|
| Ointment |
Ophthalmic |
|
| Solution / drops |
Ophthalmic |
|
|
| Prices |
| Unit description |
Cost |
Unit |
| Neomycin Sulfate 500 mg tablet |
1.39 USD |
tablet |
| Neomycin 500 mg tablet |
1.25 USD |
tablet |
| Neomycin sulfate powder |
0.84 USD |
g |
| Neo-fradin 125 mg/5 ml soln |
0.12 USD |
ml |
|
| Patents |
Not Available |
| Properties |
| State |
solid |
| Melting point |
6 mg/mL (as sulfate form) |
| Experimental Properties |
| Property |
Value |
Source |
| logP |
-7.8 |
PhysProp |
|
| Predicted Properties |
|
| References |
| Synthesis Reference |
Not Available
|
| General Reference |
Not Available
|
| External Links |
|
| ATC Codes |
- A01AB08
- A07AA01
- B05CA09
- D06AX04
- J01GB05
- R02AB01
- S01AA03
- S02AA07
- S03AA01
- D09AA01
- S01AA07
|
| AHFS Codes |
|
| PDB Entries |
|
| FDA label |
Not Available
|
| MSDS |
show (72.9 KB)
|
| Interactions |
| Drug Interactions |
Not Available |
| Food Interactions |
Not Available |