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56391-57-2

Basic Information
CAS No.: 56391-57-2
Name: Netilmicin sulfate
Molecular Structure:
Molecular Structure of 56391-57-2 (Netilmicin sulfate)
Formula: C21H41N5O7.2.5(H2SO4)
Molecular Weight: 720.80
Synonyms: Netilmicinum [INN-Latin];Netilmicin sulfate [USAN:JAN];Netillin;(2R,3R,4R,5R)-2-[(1S,2R,3R,4S,6R)-4-amino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-6-ethylamino-2-hydroxy-cyclohexyl]oxy-5-methyl-4-methylamino-oxane-3,5-diol;56391-56-1;Neomycin Trisulfate;Nelitmicin sulfate;Netilmicin Sulfate Sterile and non-sterile;Sch-20569;D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl(1-4))-2-deoxy-N(sup 1)-ethyl-;Netilmicin sulphate;1-N-Aethylsisomicin;Nettacin;NTL;Certomycin;Zetamicin;Netromycin (TN);Vectacin;Netilyn;NTL sulfate;Netilmicine [INN-French];
EINECS: 260-147-3
Density: 1.32 g/cm3
Melting Point: >194oC (dec.)
Boiling Point: 684.3 °C at 760 mmHg
Flash Point: 367.7 °C
Solubility: Easily soluble in water, almost insoluble in alcohol or ether
Appearance: white to light yellow powder
Hazard Symbols: ToxicT,IrritantXi
Risk Codes: 61-20/21/22-60
Safety: 53-36/37/39-45-37/39-36-26
Transport Information:
PSA: 814.36000
LogP: 1.50400
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Specification

The IUPAC name of this chemical is (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4-amino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-6-(ethylamino)-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol; sulfuric acid. With the CAS registry number  56391-57-2 and EINECS  260-147-3, it is also named as Certomycin. The product's categories are Active Pharmaceutical Ingredients; Intermediates & Fine Chemicals; Pharmaceuticals. It is white to light yellow powder which is easily soluble in water, almost insoluble in alcohol or ether. Additionally, this chemical should be sealed in the container and stored at the temperature of 2-8 °C.

The other characteristics of this product can be summarized as:(1)ACD/LogP: -1.90; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): -8.43; (4)ACD/LogD (pH 7.4): -6.85; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 12; (10)#H bond donors: 11; (11)#Freely Rotating Bonds: 14; (12)Polar Surface Area: 80.81 Å2; (13)Enthalpy of Vaporization: 114.8 kJ/mol; (14)Vapour Pressure: 1.1E-21 mmHg at 25°C; (15)Rotatable Bond Count: 16; (16)Exact Mass: 1440.438094; (17)MonoIsotopic Mass: 1440.438094; (18)Topological Polar Surface Area: 814; (19)Heavy Atom Count: 91; (20)Complexity: 754.

Preparation of Netilmicin sulfate: It can be obtained by the following reaction:

Uses of Netilmicin sulfate: It is an aminoglycoside antibiotic with action similar to gentamicin, but less ear and kidney toxicity. It is used in the treatment of serious infections caused by gram-negative bacteria.

When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. And it may cause harm to the unborn child. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) Avoid exposure - obtain special instructions before use.

People can use the following data to convert to the molecule structure. 
1. Smiles:O([C@H]1[C@@H](C[C@@H]([C@H]([C@@H]1O)O[C@H]1OC(=CC[C@H]1N)CN)N)NCC)[C@@H]1[C@@H]([C@@H](NC)[C@@](C)(O)CO1)O.S(O)(O)(=O)=O.O([C@H]1[C@@H](C[C@H](N)[C@H]([C@@H]1O)O[C@H]1OC(=CC[C@H]1N)CN)NCC)[C@@H]1[C@@H]([C@H]([C@@](C)(O)CO1)NC)O.S(O)(O)(=O)=O.S(O)(O)(=O)=O.S(O)(O)(=O)=O.S(O)(O)(=O)=O
2. InChI:InChI=1/2C21H41N5O7.5H2O4S/c2*1-4-26-13-7-12(24)16(32-19-11(23)6-5-10(8-22)31-19)14(27)17(13)33-20-15(28)18(25-3)21(2,29)9-30-20;5*1-5(2,3)4/h2*5,11-20,25-29H,4,6-9,22-24H2,1-3H3;5*(H2,1,2,3,4)/t2*11-,12+,13-,14+,15-,16-,17+,18-,19-,20-,21+;;;;;/m11...../s1

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 63100ug/kg (63.1mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.
mouse LD50 intraperitoneal 189mg/kg (189mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Antimicrobial Agents and Chemotherapy. Vol. 10, Pg. 827, 1976.
mouse LD50 intravenous 22mg/kg (22mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.
mouse LD50 subcutaneous 68900ug/kg (68.9mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.
rat LD50 intramuscular 167mg/kg (167mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.
rat LD50 intraperitoneal 231mg/kg (231mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.
rat LD50 intravenous 40700ug/kg (40.7mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.
rat LD50 oral > 10gm/kg (10000mg/kg)   Yakkyoku. Pharmacy. Vol. 36, Pg. 1249, 1985.
rat LD50 subcutaneous 169mg/kg (169mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.