Tobramycin supplier | CasNO.32986-56-4

Name
Tobramycin
EINECS 251-322-5
CAS No. 32986-56-4
Article Data10
CAS DataBase
Density 1.52 g/cm³
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
Appearance White powder
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
PSA 268.17000
LogP -2.79430

Synthetic route

: 23155-02-4
fosfomycin

: 32986-56-4
tobramycin

: tobramycin sulfate

: 32986-56-4
tobramycin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With TEA; triflic azide; copper(II) sulfate In methanol; dichloromethane	100%
With triflic azide; triethylamine; zinc(II) chloride In methanol; dichloromethane; water at 20℃;	92%
With triflic azide; copper(II) sulfate; triethylamine	83%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium carbonate	90%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 32986-56-4
tobramycin

: 24424-99-5
di-tert-butyl dicarbonate

: C33H61N5O15

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 32986-56-4
tobramycin

: 108-24-7
acetic anhydride

: 144727-30-0
penta-N-penta-O-acetyltobramycin

Conditions

Conditions	Yield
With pyridine

: 32986-56-4
tobramycin

: 501-53-1
benzyl chloroformate

: 6'-N-benzyloxycarbonyltobramycin

Conditions

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

: 32986-56-4
tobramycin

: 56-65-5
ATP

: C28H49N10O15P

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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 NO_x.
Hazard Codes: Irritant Xi
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.

Product Name

Tobramycin

Synthetic route

Tobramycin Chemical Properties

Tobramycin Uses

Tobramycin Toxicity Data With Reference

Tobramycin Consensus Reports

Tobramycin Safety Profile

Tobramycin Specification

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