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Tobramycin

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Name

Tobramycin

EINECS 251-322-5
CAS No. 32986-56-4 Density 1.52 g/cm3
PSA 268.17000 LogP -2.79430
Solubility 50 mg/mL in water Melting Point 178 °C
Formula C18H37N5O9 Boiling Point 775.436 °C at 760 mmHg
Molecular Weight 467.52 Flash Point 422.8 °C
Transport Information N/A Appearance White powder
Safety 26-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 32986-56-4 (Tobramycin) Hazard Symbols IrritantXi
Synonyms

D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyl-(1-4))-2-deoxy- ; Deoxykanamycin B ; Gotabiotic ; Nebramycin ; O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyl-(1-6))-2-deoxy-L-streptamine;O-3-Amino-3-deoxy-alpha-D-lucopyranosyl-(1-6)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ibohexopyranosyl-(1-4))-2-deoxy-D-streptamine;Tobamycin Base;Sulfate sterile;

Article Data 10

Tobramycin Synthetic route

23155-02-4

fosfomycin

32986-56-4

tobramycin

tobramycin sulfate

32986-56-4

tobramycin

Conditions
ConditionsYield
Stage #1: tobramycin sulfate
Stage #2: With trifluoroacetic acid In water
32986-56-4

tobramycin

207857-15-6

1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine

guanidinoboc10-tobramycin

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water at 20℃; for 72h;100%
32986-56-4

tobramycin

207857-15-6

1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine

290360-48-4

C73H127N15O29

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water at 20℃; for 72h;100%
32986-56-4

tobramycin

468065-22-7

O-3-azido-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[2,6-diazido-2,3,6-trideoxy-α-D-ribo-hexopyranosyl-(1→4)]-1,3-diazido-1,2,3-trideoxy-D-myo-inositol

Conditions
ConditionsYield
With TEA; triflic azide; copper(II) sulfate In methanol; dichloromethane100%
With triflic azide; triethylamine; zinc(II) chloride In methanol; dichloromethane; water at 20℃;92%
With triflic azide; copper(II) sulfate; triethylamine83%
With triflic azide; triethylamine; zinc(II) chloride In methanol; dichloromethane; water Inert atmosphere;
With triflic azide; zinc(II) chloride In methanol; dichloromethane; water Inert atmosphere;
32986-56-4

tobramycin

24424-99-5

di-tert-butyl dicarbonate

172950-21-9

di-tert-butyl ((1S,3R,4S,5S,6R)-4-(((2S,3R,4S,5S,6R)-4-((tert-butoxycarbonyl)amino)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,5S,6R)-3-((tert-butoxycarbonyl)amino)-6-(((tert-butoxycarbonyl)methyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate)

Conditions
ConditionsYield
With triethylamine In water at 60℃; for 0.666667h;98%
With triethylamine In methanol; water at 55℃;98%
With triethylamine In methanol; water at 55℃;97%
32986-56-4

tobramycin

5-benzoyl-3-(cyclopent-1-en-1-yl)-5-phenyl-1,5-dihydro-4H-pyrazol-4-one

C25H41N5O10

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 24h; Solvent;92%
32986-56-4

tobramycin

501-53-1

benzyl chloroformate

61093-69-4

1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-3'-deoxykanamycin B

Conditions
ConditionsYield
With sodium carbonate90%
With sodium carbonate In water
With sodium carbonate In acetone at 0℃;
32986-56-4

tobramycin

65162-83-6

N-(benzyloxycarbonyloxy)phthalimide

6'-N-benzyloxycarbonyltobramycin

Conditions
ConditionsYield
With potassium carbonate In methanol; water at 20℃; for 18h;64%

azidoacetic acid succinimidyl ester

32986-56-4

tobramycin

1220984-19-9

6'-N-azidoacetyl tobramycin

Conditions
ConditionsYield
With potassium carbonate In methanol; water for 20h;63%

Tobramycin Chemical Properties

Molecular structure of Tobramycin (CAS NO.32986-56-4) is:

Product Name: Tobramycin
CAS Registry Number: 32986-56-4
IUPAC Name: 4-amino-2-[4,6-diamino-3-[3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol
Molecular Weight: 467.51448 [g/mol]
Molecular Formula: C18H37N5O9
XLogP3-AA: -6.2
H-Bond Donor: 10
H-Bond Acceptor: 14 
EINECS: 251-322-5
Refractive index: 143 ° (C=4, H2O)
Storage temp.: 2-8°C
Solubility: H2O: 50 mg/mL, clear, faintly yellow
Melting Point: 178 °C
Surface Tension: 92.6 dyne/cm
Density: 1.52 g/cm3
Flash Point: 422.8 °C
Enthalpy of Vaporization: 128.66 kJ/mol
Boiling Point: 775.4 °C at 760 mmHg
Vapour Pressure: 9.05E-28 mmHg at 25°C
Product Categories: Oligosaccharide Compounds; Aminoglycosides (Antibiotics for Research and Experimental Use); Antibiotics for Research and Experimental Use; Biochemistry; Intermediates & Fine Chemicals; Oligosaccharides; Pharmaceuticals; Peptide Synthesis/Antibiotics

Tobramycin Uses

 Tobramycin (CAS NO.32986-56-4) is used to treat various types of bacterial infections, particularly Gram-negative infections. It is also combined with dexamethasone as an ophthalmic solution.

Tobramycin Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo intravenous 37714ug/kg (37.714mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED American Journal of Kidney Diseases. Vol. 23, Pg. 118, 1994.
mouse LD50 intramuscular 440mg/kg (440mg/kg)   Yakkyoku. Pharmacy. Vol. 27, Pg. 1467, 1976.
mouse LD50 intraperitoneal 445mg/kg (445mg/kg)   Journal of International Medical Research. Vol. 2, Pg. 100, 1974.
mouse LD50 intravenous 72500ug/kg (72.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Antibiotiki. Vol. 29, Pg. 361, 1984.
mouse LD50 oral > 11500mg/kg (11500mg/kg)   Yakkyoku. Pharmacy. Vol. 27, Pg. 1467, 1976.
mouse LD50 subcutaneous 367mg/kg (367mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Toxicology and Applied Pharmacology. Vol. 25, Pg. 398, 1973.
pig LD50 subcutaneous 676mg/kg (676mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Toxicology and Applied Pharmacology. Vol. 25, Pg. 398, 1973.
rat LD50 intramuscular 913mg/kg (913mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 107, 1977.
rat LD50 intraperitoneal 1030mg/kg (1030mg/kg)   Journal of International Medical Research. Vol. 2, Pg. 100, 1974.
rat LD50 intravenous 104mg/kg (104mg/kg)   Journal of International Medical Research. Vol. 2, Pg. 100, 1974.
rat LD50 oral > 7500mg/kg (7500mg/kg)   Yakkyoku. Pharmacy. Vol. 27, Pg. 1467, 1976.
rat LD50 subcutaneous 969mg/kg (969mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION Toxicology and Applied Pharmacology. Vol. 22, Pg. 332, 1972.

Tobramycin Consensus Reports

EPA Genetic Toxicology Program.

Tobramycin Safety Profile

Safty information about Tobramycin (CAS NO.32986-56-4) is:
Poison by intravenous and subcutaneous routes. Moderately toxic by intramuscular and intraperitoneal routes. An experimental teratogen. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 2
RTECS: WK2100000
F: 3-10

Tobramycin Specification

Tobramycin , its cas register number is 32986-56-4. It also can be called Tobramycin [USAN:INN:BAN:JAN] ; Tobradex ; Tobrasone ; 1-Epitobramycin ; 3'-Deoxykanamycin B ; 4-(2,6-Diamino-2,3,6-trideoxy-alpha-D-glycopyranosyl)-6-(3-amino-3-deoxy-alpha-D-glycopyranosyl)-2-deoxystreptamine ; Aktob ; D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyl-(1-4))-2-deoxy- ; Deoxykanamycin B ;  Gotabiotic ; Nebramycin ; O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyl-(1-6))-2-deoxy-L-streptamine ; O-3-Amino-3-deoxy-alpha-D-lucopyranosyl-(1-6)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ibohexopyranosyl-(1-4))-2-deoxy-D-streptamine ; Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-tyrideoxy-alpha-D-ribohexopyranosyl-(1-6))-2-deoxy-, D- ; Tenebrimycin ; Tenemycin ; Tobacin ; Tobi ; Tobracin ; Tobradistin ; Tobralex ; Tobramaxin ; Tobramicin ; Tobramicina ; Tobramitsetin ; Tobramycetin ; Tobramycine ; Tobramycinum ; Tobrased ; Tobrex ; D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribo-hexopyranosyl-(1-4))-2-deoxy- ; Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribohexopyranosyl-(1-6))-2-deoxy-, D- . It is a white solid. Like other aminoglycosides, In genetically susceptible individuals, it can cause deafness or a loss of equilibrioception (vertigo) .It can also be highly toxic to the kidneys, particularly if multiple doses accumulate over a course of treatment. For these reasons, when it is given parenterally, it is usually dosed by body weight. Various formulae exist for calculating tobramycin dosage.

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