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32986-56-4

Basic Information
CAS No.: 32986-56-4
Name: Tobramycin
Molecular Structure:
Molecular Structure of 32986-56-4 (Tobramycin)
Formula: C18H37N5O9
Molecular Weight: 467.51
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;
EINECS: 251-322-5
Density: 1.52 g/cm3
Melting Point: 178 °C
Boiling Point: 775.436 °C at 760 mmHg
Flash Point: 422.8 °C
Solubility: 50 mg/mL in water
Appearance: White powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
Transport Information:
PSA: 268.17000
LogP: -2.79430
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%
32986-56-4

tobramycin

142-72-3, 92123-19-8

magnesium acetate

68244-01-9

3-N-acetyltobramycin

Conditions
ConditionsYield
With Tmed buffer; ATP In water for 12h; aminoglycoside phosphotransferase;62%
32986-56-4

tobramycin

62210-73-5

N-<<(benzyloxy)carbonyl>oxy>-5-norbornene-2,3-dicarboximide

24424-99-5

di-tert-butyl dicarbonate

C36H59N5O15

Conditions
ConditionsYield
Stage #1: tobramycin With zinc(II) acetate dihydrate In dimethyl sulfoxide at 21℃;
Stage #2: N-<<(benzyloxy)carbonyl>oxy>-5-norbornene-2,3-dicarboximide In dimethyl sulfoxide at 21℃; for 24h;
Stage #3: di-tert-butyl dicarbonate In dimethyl sulfoxide at 21℃; for 4h;
57%
32986-56-4

tobramycin

24424-99-5

di-tert-butyl dicarbonate

C33H61N5O15

Conditions
ConditionsYield
Stage #1: tobramycin With zinc(II) acetate dihydrate In dimethyl sulfoxide at 21℃;
Stage #2: di-tert-butyl dicarbonate In dimethyl sulfoxide at 21℃; for 5h;
53%
32986-56-4

tobramycin

40371-52-6

N-[(S)-4-benzyloxycarbonylamino-2-hydroxy-butyryloxy]succinimide

1312471-07-0

6'-N-CbzAHB tobramycin

Conditions
ConditionsYield
Stage #1: tobramycin With zinc diacetate In water; N,N-dimethyl-formamide at 20℃; for 16h;
Stage #2: N-[(S)-4-benzyloxycarbonylamino-2-hydroxy-butyryloxy]succinimide In water; N,N-dimethyl-formamide for 24h;
31%
32986-56-4

tobramycin

93801-70-8

2,4-dinitrophenylthioglycolic acid N-hydroxy succinimide ester

93801-67-3

N-{(2R,3S,5R,6R)-5-Amino-6-[(1R,2S,3S,4R,6S)-4,6-diamino-3-((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyloxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl}-2-(2,4-dinitro-phenylsulfanyl)-acetamide

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 0℃; for 2h; pH=10.76;28.3%
32986-56-4

tobramycin

108-24-7

acetic anhydride

A

33985-51-2

1,3,2',6',3''-penta-N-acetyltobramycin

B

1,2',6',3''-tetra-N-acetyltobramycin

C

1,3,2',6'-tetra-N-acetyltobramycin

D

1,2',6'-tri-N-acetyltobramycin

Conditions
ConditionsYield
In methanol for 0.166667h; Ambient temperature; Yields of byproduct given;A 26.9%
B n/a
C n/a
D n/a
In methanol for 0.166667h; Ambient temperature; Yields of byproduct given;A n/a
B 7.4%
C n/a
D n/a
In methanol for 0.166667h; Ambient temperature; Yield given. Yields of byproduct given;
32986-56-4

tobramycin

13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

[2-[4-amino-3-(4-amino-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-benzyloxycarbonylamino-2-hydroxy-cyclohexyloxy]-6-(benzyloxycarbonylamino-methyl)-5-hydroxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Conditions
ConditionsYield
Stage #1: tobramycin With zinc diacetate In dimethyl sulfoxide for 12h;
Stage #2: N-(Benzyloxycarbonyloxy)succinimide In dimethyl sulfoxide for 2h;
25%
32986-56-4

tobramycin

[[(tetramethyl-4,4-difluoro-4-bora-3a,4a-diazaindacene)methyl]phenoxy]ethyl (4-nitrophenyl) carbonate

C40H58BF2N7O12

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Darkness;17%
32986-56-4

tobramycin

1195-16-0, 768351-04-8

N-acetyl-DL-homocysteinethiolactone

2-Acetylamino-N-{(2R,3S,5R,6R)-5-amino-6-[(1R,2S,3S,4R,6S)-4,6-diamino-3-((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyloxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl}-4-mercapto-butyramide

Conditions
ConditionsYield
In water for 30h; pH=10.12-10.25; Yield given;
32986-56-4

tobramycin

1195-16-0, 768351-04-8

N-acetyl-DL-homocysteinethiolactone

70-11-1

α-bromoacetophenone

C32H52N6O12S

Conditions
ConditionsYield
With hydrogenchloride 1.) 20110.12-10.25, 30 min; 2.) pH=7.5, water, THF, 0 deg C, 2 h; Yield given. Multistep reaction;
32986-56-4

tobramycin

108-24-7

acetic anhydride

144727-30-0

penta-N-penta-O-acetyltobramycin

Conditions
ConditionsYield
With pyridine
32986-56-4

tobramycin

501-53-1

benzyl chloroformate

6'-N-benzyloxycarbonyltobramycin

Conditions
ConditionsYield
With benzotriazol-1-ol; triethylamine 1.) dioxane, RT, 30 min, 2.) dioxane, water, RT, 20 h; Yield given. Multistep reaction;
32986-56-4

tobramycin

C28H49N10O15P

Conditions
ConditionsYield
at 37℃; aminoglycoside-4'-nucleotidyltransferaze of Bacillus brevis, MgCl2, potassium phosphate buffer (pH 6.0);
32986-56-4

tobramycin

(2S,3R,5S,6R)-4-Azido-2-[(2S,3R,4S,6R)-4,6-diazido-3-((2R,3R,5S,6R)-3-azido-6-azidomethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyloxy]-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

Conditions
ConditionsYield
With triflic azide; triethylamine; zinc(II) chloride In methanol; dichloromethane; water
32986-56-4

tobramycin

103842-08-6

3,2',6'-tris(N-benzyloxycarbonyl)-3'-deoxy-3''-N-(trifluoroacetyl)kanamycin B

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: Zn(OAc)2*2H2O / dimethylsulfoxide / 12 h
1.2: 25 percent / dimethylsulfoxide / 2 h
2.1: 60 percent / dimethylsulfoxide / 2 h
View Scheme
32986-56-4

tobramycin

C21H43N7O11

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: Zn(OAc)2*2H2O / dimethylsulfoxide / 12 h
1.2: 25 percent / dimethylsulfoxide / 2 h
2.1: 60 percent / dimethylsulfoxide / 2 h
3.1: 11 mg / tetrahydrofuran; H2O / 96 h / 20 °C
4.1: aq. NaOH / methanol / 20 h
5.1: 4.5 mg / H2 / 10 percent Pd/C / dioxane; H2O; acetic acid / 0.67 h
View Scheme
32986-56-4

tobramycin

533923-31-8

C53H67N7O19

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: Zn(OAc)2*2H2O / dimethylsulfoxide / 12 h
1.2: 25 percent / dimethylsulfoxide / 2 h
2.1: 60 percent / dimethylsulfoxide / 2 h
3.1: 11 mg / tetrahydrofuran; H2O / 96 h / 20 °C
4.1: aq. NaOH / methanol / 20 h
View Scheme
32986-56-4

tobramycin

533923-30-7

C62H70F3N7O21

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: Zn(OAc)2*2H2O / dimethylsulfoxide / 12 h
1.2: 25 percent / dimethylsulfoxide / 2 h
2.1: 60 percent / dimethylsulfoxide / 2 h
3.1: 11 mg / tetrahydrofuran; H2O / 96 h / 20 °C
View Scheme
Raw Materials
23155-02-4
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Chemistry

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

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.

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.

Consensus Reports

EPA Genetic Toxicology Program.

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

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.