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2D Structure
Also known as: Neomycin sulfate, 1405-10-3, Neomycin trisulfate hydrate, Akos016010116
Molecular Formula
C23H48N6O17S
Molecular Weight
712.7  g/mol
InChI Key
OIXVKQDWLFHVGR-VTSVPHRWSA-N

Aminoglycoside antibiotic complex produced by Streptomyces fradiae. It is composed of neomycins A, B, and C, and acts by inhibiting translation during protein synthesis.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2R,3R,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2S,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4R,5R)-4-[(3R,4R,5R,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol;sulfuric acid
2.1.2 InChI
InChI=1S/C23H46N6O13.H2O4S/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;1-5(2,3)4/h5-23,30-36H,1-4,24-29H2;(H2,1,2,3,4)/t5-,6+,7-,8+,9-,10-,11-,12+,13+,14+,15-,16-,17-,18-,19+,20+,21-,22?,23+;/m1./s1
2.1.3 InChI Key
OIXVKQDWLFHVGR-VTSVPHRWSA-N
2.1.4 Canonical SMILES
C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)N)OC3C(C(C(O3)CO)OC4C(C(C(C(O4)CN)O)O)N)O)O)N.OS(=O)(=O)O
2.1.5 Isomeric SMILES
C1[C@H]([C@@H]([C@@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@H]([C@H](O2)CN)O)O)N)O[C@H]3[C@@H]([C@H]([C@H](O3)CO)OC4[C@@H]([C@H]([C@H]([C@@H](O4)CN)O)O)N)O)O)N.OS(=O)(=O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Neomycin

2. Neomycin Palmitate

3. Neomycin Sulfate

2.2.2 Depositor-Supplied Synonyms

1. Neomycin Sulfate

2. 1405-10-3

3. Neomycin Trisulfate Hydrate

4. Akos016010116

2.3 Create Date
2013-05-31
3 Chemical and Physical Properties
Molecular Weight 712.7 g/mol
Molecular Formula C23H48N6O17S
Hydrogen Bond Donor Count15
Hydrogen Bond Acceptor Count23
Rotatable Bond Count9
Exact Mass712.27966526 g/mol
Monoisotopic Mass712.27966526 g/mol
Topological Polar Surface Area436 Ų
Heavy Atom Count47
Formal Charge0
Complexity953
Isotope Atom Count0
Defined Atom Stereocenter Count18
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameNeomycin sulfate
Drug LabelNeomycin Sulfate Tablets, USP, for oral administration, contain neomycin which is an antibiotic obtained from the metabolic products of the actinomycete Streptomycesfradiae. Structurally, neomycin sulfate may be represented as follows:Chemically, i...
Active IngredientNeomycin sulfate
Dosage FormTablet
RouteOral
Strength500mg
Market StatusPrescription
CompanyOman Pharm Products; Teva; X Gen Pharms

2 of 2  
Drug NameNeomycin sulfate
Drug LabelNeomycin Sulfate Tablets, USP, for oral administration, contain neomycin which is an antibiotic obtained from the metabolic products of the actinomycete Streptomycesfradiae. Structurally, neomycin sulfate may be represented as follows:Chemically, i...
Active IngredientNeomycin sulfate
Dosage FormTablet
RouteOral
Strength500mg
Market StatusPrescription
CompanyOman Pharm Products; Teva; X Gen Pharms

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


Protein Synthesis Inhibitors

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Aminoglycosides [CS]; Aminoglycoside Antibacterial [EPC]