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Tobramycin

Tobramycin Structure
CAS No.
32986-56-4
Chemical Name:
Tobramycin
Synonyms
Tobramycin Base;Tobramycine;tobra;nebcin;tobrex;Tobramax;nf6;obracin;Tobracin;nebicina
CBNumber:
CB7154445
Molecular Formula:
C18H37N5O9
Molecular Weight:
467.52
MOL File:
32986-56-4.mol
MSDS File:
SDS
Modify Date:
2024/6/7 16:07:22

Tobramycin Properties

Melting point 178 °C
alpha D20 +129° (c = 1 in water)
Boiling point 570.01°C (rough estimate)
Density 1.3458 (rough estimate)
refractive index 143 ° (C=4, H2O)
storage temp. Keep in dark place,Inert atmosphere,2-8°C
solubility H2O: 50 mg/mL, clear, faintly yellow
pka pKa 6.7 (Uncertain);8.3 (Uncertain);9.9 (Uncertain)
form White to off-white solid
color white to off-white
Water Solubility Soluble in water
Merck 14,9490
BRN 1357507
Stability Hygroscopic

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS08
Signal word  Warning
Hazard statements  H361f
Precautionary statements  P201-P202-P280-P308+P313-P405-P501
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-37/39
WGK Germany  2
RTECS  WK2100000
3-10
HS Code  29419090
Toxicity LD50 in mice, rats (mg/kg): 441, 969 s.c. (Welles)
NFPA 704
0
2 0

Tobramycin price More Price(7)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) T4014 Tobramycin Aminoglycoside antibiotic 32986-56-4 100MG ₹13163.2 2022-06-14 Buy
Sigma-Aldrich(India) T4014 Tobramycin Aminoglycoside antibiotic 32986-56-4 500MG ₹36729.23 2022-06-14 Buy
Sigma-Aldrich(India) PHR1079 Tobramycin Pharmaceutical Secondary Standard; Certified Reference Material 32986-56-4 1G ₹10002.3 2022-06-14 Buy
TCI Chemicals (India) T2503 Tobramycin 32986-56-4 5G ₹9700 2022-05-26 Buy
TCI Chemicals (India) T2503 Tobramycin 32986-56-4 25G ₹23800 2022-05-26 Buy
Product number Packaging Price Buy
T4014 100MG ₹13163.2 Buy
T4014 500MG ₹36729.23 Buy
PHR1079 1G ₹10002.3 Buy
T2503 5G ₹9700 Buy
T2503 25G ₹23800 Buy

Tobramycin Chemical Properties,Uses,Production

Description

Tobramycin is one component (factor 6) of a mixture produced by fermentation of Streptomyces tenebrari us. Lacking the C-3′ hydroxyl group, it is not a substrate for APH(3′)-1 and APH(3′)-II and so has an intrinsically broader spectrum than kanamycin. It is a substrate, however, for adenylation at C-2′ by ANT (2′) and acetylation at C-3 by AAC(3)-I and AAC(3)-II and at C-2′ by AAC(2′).

Chemical Properties

White or almost white powder.

Uses

Tobramycin is an aminoglycoside antibiotic.

Indications

Tobramycin is highly active with respect to Gram-negative microorganisms (blue-pus bacillus and gastric bacilli, rabbit fever, serratia, providencia, enterobacteria, proteus, salmonella, shigella), as well as Gram-positive microorganisms (staphylococci, including those resistant to penicillin and some cephalosporins), and a few strains of streptococci.
It is used for severe bacterial infections: peritonitis, sepsis, meningitis, osteomyelitis, endocarditis, pneumonia, pleural empyema, pulmonary abscess, purulent skin infections and soft tissue infections, and infections of the urinary tract caused by microorganisms that are sensitive to the drug. Synonyms of this drug are nebicine, obracine, and others.

Definition

ChEBI: A amino cyclitol glycoside that is kanamycin B lacking the 3-hydroxy substituent from the 2,6-diaminoglucose ring.

Antimicrobial activity

In-vitro activity against Ps. aeruginosa is usually somewhat greater than that of gentamicin; against other organisms activity is similar or a little lower. Other Pseudomonas species are generally resistant, as are streptococci and most anaerobic bacteria. Other organisms usually susceptible in vitro include Acinetobacter, Legionella and Yersinia spp. Alkaligenes, Flavobacterium spp. and Mycobacterium spp. are resistant. It exhibits bactericidal activity at concentrations close to the MIC and bactericidal synergy typical of aminoglycosides in combination with penicillins or cephalosporins.

Acquired resistance

It is inactivated by many aminoglycoside-modifying enzymes that inactivate gentamicin. However, AAC(3′)-I does not confer tobramycin resistance and AAC(3′)-II confers a lower degree of tobramycin resistance than of gentamicin resistance. Conversely, ANT(4′) confers tobramycin but not gentamicin resistance, as do some types of AAC(6′). Overproduction of APH(3′), conferring a low degree of resistance to tobramycin (MIC 8 mg/L), but not gentamicin (MIC 2 mg/L), was ascribed to ‘trapping’ rather than phosphorylation.
Resistance rates are generally similar to those of gentamicin, although they may vary locally because of the prevalence of particular enzyme types.

Biological Activity

Pharmacologically, tobramycin is quite similar to gentamicin. The drug is somewhat more active against Ps. aeruginosa than gentamicin. Tobramycin also acts synergistically with penicillin, but to a lesser degree than gentamicin.

Clinical Use

Severe infections caused by susceptible micro-organisms Ps. aeruginosa infections, including chronic pulmonary infections in cystic fibrosis (administration by injection or nebulizer)
For practical purposes use is identical to that of gentamicin, except possibly for Pseudomonas infection, where it has somewhat greater activity against gentamicin-susceptible and some gentamicin-resistant strains. Its value as a substitute for gentamicin in the speculative treatment of severe undiagnosed infection is offset by its lower activity against other organisms that may be implicated.
It has been used extensively to treat Ps. aeruginosa infections in patients with cystic fibrosis.

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Tobramycin (350 mg) Tobramycin (350 mg)L0E077970ug/mg(an) TobraMycin Base API Tobramycin, Antibiotic for Culture Media Use Only TOBRAMYCIN (RE-EXPORT OF REJECTED MATERIAL RETURN TO VENDOR) 1-epitobramycin 3’-deoxykanamycinb 4-[2,6-diamino-2,3,6-trideoxy-alpha-d-glycopyranosyl]-6-[3-amino-3-deoxy-alpha 6-trideoxy-alpha-d-ribo-hexopyranosyl-(1-4))-2-deoxy- d-6-trideoxy-alpha-d-ribohexopyranosyl-(1-6))-2-deoxy d-6-tyrideoxy-alpha-d-ribohexopyranosyl-(1-6))-2-deoxy O-[3-AMINO-3-DEOXY-ALPHA-D-GLUCOPYRANOSYL-(1->6)]-O-[2,6-DIAMINO-2,3,6-TRIDEOXY-ALPHA-D-RIBOHEXOPYRANOSYL-(1->4)]-2-DEOXY-D-STREPTAMINE Tobramycin, Free Base TobramycinSulphate49842-07-1/Base O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(2,6- O-3-Amino-3-deoxy-a-D-glucopyranosyl-(1-6)-O-[2,6-diamino-2,3,6-trideoxy-a-D-ribo-hexopyranosyl-(1-4)]-2-deoxy-D-streptamine >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- o-[3-amino-3-deoxy-α-d-glucopyranosyl-(1→6)]-o-[2,6-diamino-2,3,6-trideoxy-α-d-ribohexopyranosyl-(1→4)]-2-deoxy-d-streptamine D-Streptamine, O-3-amino-3-deoxy-a-D-glucopyranosyl-(16)-O-[2,6-diamino-2,3,6-trideoxy-a-D-ribo-hexopyranosyl-(14)]-2-deoxy- (9CI) NSC 180514 O-3-Amino-3-deoxy-a-D-glucopyranosyl-(14)-O-[2,6-diamino-2,3,6-trideoxy-a-D-ribo-hexopyranosyl-(16)]-2-deoxystreptamine Streptamine, O-3-amino-3-deoxy-a-D-glucopyranosyl-(14)-O-[2,6-diamino-2,3,6-trideoxy-a-D-ribo-hexopyranosyl-(16)]-2-deoxy-, D- (8CI) Tobracin Tobramaxin Tobramycetin Tobramycin (base and/or unspecified salts) O-[3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1→6)]-O-[2,6-diamino-2,3,6-trideoxy-alpha-D-ribohexopyranosyl-(1→4)]-2-deoxy-D-streptamine O-3-Amino-3-deoxy-α-D-glucopyranosyl-(1-6)-O-[2,6-diamino-2,3,6-trideoxy-a -D-ribo-hexopyranosyl-(1-4)]-2-deoxy-D-streptamine deoxykanamycinb -d-glycopyranosyl]-2-deoxystreptamine distobram gernebcin lpha-d-ribohexopyranosyl-(1-4)]-2-deoxy-d-streptamine nebicina nebramycin6 nebramycinfactor6 nebramycinvi nf6 o-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1-6)-o-[2,6-diamino-2,3,6-trideoxy-a obracin obramycin streptamine,o-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1-4)-o-(2,6-diamino-2,3, tobradistin tobralex (2S,3R,4S,5S,6R)-4-amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxy-oxan-2-yl]oxy-2-hydroxy-cyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol O-[3-Amino-3-deoxy-a-D-glucopyranosyl-(1[R]6)]-O-[2,6-diamino-2,3,6-trideoxy-a-D-ribohexopyranosyl-(1[R]4)]-2-deoxy-D-streptamine O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,3,6-trideoxy-alpha-D-ribohexopyranosyl-(1-4))-2-deoxy-D-streptamine TOBRAMYCIN Tobramycin,O-[3-Amino-3-deoxy-α-D-glucopyranosyl-(1→6)]-O-[2,6-diamino-2,3,6-trideoxy-α-D-ribohexopyranosyl-(1→4)]-2-deoxy-D-streptamine Tobramycin, Free Base - CAS 32986-56-4 - Calbiochem Tobramycin, potency: ≥900μG/mg,98% Tobramycin CRS Tobramycin for identification CRS D-Streptamine, O-3-amino-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[2,6-diamino-2,3,6-trideoxy-α-D-ribo-hexopyranosyl-(1→4)]-2-deoxy- (2S,3R,4S,5S,6R)-4-amino-2-(((1S,2S,3R,4S,6R)-4,6-diamino-3-(((2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,5-diol Tobramycin solution in Water, 100μg/mL Tobramycin-[13C6] pentaacetate salt O-[3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1->