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Tobramycin (Synonyms: Deoxykanamycin B, Distobram, Gernebcin, NSC 180514)

Catalog No.GC18130 Copy One-Click Copy Product Info

Tobramycin is a parenterally administered aminoglycoside antibiotic with significant antibacterial activity against aerobic Gram-negative bacteria such as Pseudomonas aeruginosa.

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Tobramycin Chemical Structure

Cas No.: 32986-56-4

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10mM (in 1mL Water)
$35.00
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100mg
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500mg
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1g
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5g
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10g
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25g
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Sample solution is provided at 25 µL, 10mM.



Description of Tobramycin

Tobramycin is a parenterally administered aminoglycoside antibiotic with significant antibacterial activity against aerobic Gram-negative bacteria such as Pseudomonas aeruginosa[1]. Tobramycin exerts its bactericidal effect by irreversibly binding to the bacterial 30S ribosomal subunit, thereby inhibiting protein synthesis[2]. Tobramycin is commonly used to treat conditions such as ocular infections, respiratory tract infections in patients with cystic fibrosis, and urinary tract infections[3,4].

In vitro, treatment of 96 clinically isolated P. aeruginosa strains with Tobramycin (0.39-25μg/mL) for 18h resulted in MICs ≤ 3.12μg/mL for 83/96 strains on Mueller Hinton agar, while its bacteriostatic activity was stronger in Mueller Hinton broth (MIC values were 2-8 times lower)[5]. Pretreatment of human lung microvascular endothelial cells (HLMVEC) with Tobramycin (0.5mM) for 24h significantly inhibited platelet-induced T-cell migration (inhibition rate 66.5%)[6].

In vivo, combined administration of Tobramycin (30mg/kg; once daily; s.c.) and Furanone C-30 (1mg/kg) to BALB/c mice implanted with a pre-infected P. aeruginosa silicone tube for up to 48h significantly reduced the bacterial load on the silicone implant. The synergistic clearance effect was significantly superior to monotherapy[7]. Intratracheal single-dose administration of Tobramycin (250μg/mouse) on the first day after NMRI mice were infected with Klebsiella pneumoniae significantly increased the survival rate within 8 days post-infection by 33% compared to the untreated control group[8]. Treatment of CBA/Ca mice with Tobramycin (200mg/kg/day; s.c. for 14 days) resulted in gap detection deficits in the gap pre-pulse inhibition of the acoustic startle (GPIAS) test in 36% of the mice, indicating tinnitus-like behavior. This behavior was most pronounced at 2 weeks post-administration and gradually diminished over time[9].

References:
[1] FIEL S B, ROESCH E A. The use of tobramycin for Pseudomonas aeruginosa: A review[J]. Expert Review of Respiratory Medicine, 2022, 16(5): 503-509.
[2] KRAUS L, DUCHARDT-FERNER E, BRÄUCHLE E, et al. Development of a novel tobramycin dependent riboswitch[J]. Nucleic Acids Research, 2023, 51(20): 11375-11385.
[3] CHEER S M, WAUGH J, NOBLE S. Inhaled Tobramycin (TOBI®): A review of its use in the management of Pseudomonas aeruginosa infections in patients with cystic fibrosis[J]. Drugs, 2003, 63(22): 2501-2520.
[4] NEU H C. Tobramycin: an overview[J]. The Journal of Infectious Diseases, 1976, S3-S19.
[5] MEYER R D, YOUNG L S, ARMSTRONG D. Tobramycin (nebramycin factor 6): in vitro activity against Pseudomonas aeruginosa[J]. Applied Microbiology, 1971, 22(6): 1147-1151.
[6] GZIUT M, MACGREGOR H J, NEVELL T G, et al. Anti‐inflammatory effects of tobramycin and a copper–tobramycin complex with superoxide dismutase‐like activity[J]. British Journal of Pharmacology, 2013, 168(5): 1165-1181.
[7] CHRISTENSEN L D, VAN GENNIP M, JAKOBSEN T H, et al. Synergistic antibacterial efficacy of early combination treatment with tobramycin and quorum-sensing inhibitors against Pseudomonas aeruginosa in an intraperitoneal foreign-body infection mouse model[J]. Journal of Antimicrobial Chemotherapy, 2012, 67(5): 1198-1206.
[8] VAN‘T VEEN A, MOUTON J W, GOMMERS D, et al. Pulmonary surfactant as vehicle for intratracheally instilled tobramycin in mice infected with Klebsiella pneumoniae[J]. British Journal of Pharmacology, 1996, 119(6): 1145.
[9] LONGENECKER R J, GU R, HOMAN J, et al. Development of Tinnitus and Hyperacusis in a mouse model of Tobramycin Cochleotoxicity[J]. Frontiers in Molecular Neuroscience, 2021, 14: 715952.

Protocol of Tobramycin

Cell experiment [1]:

Cell lines

HLMVEC (human lung microvascular endothelial cells)

Preparation Method

Tobramycin (0.5mM) was co-incubated with HLMVEC for 24h, followed by co-culturing thrombin-activated platelets with pretreated HLMVEC to induce T cell migration. The migration inhibition effect was assessed by counting the number of T cells that migrated to the lower chamber of the Transwell.

Reaction Conditions

0.5mM; 24h

Applications

Tobramycin treatment significantly inhibited platelet-induced T cell migration (inhibition rate 66.5%).
Animal experiment [2]:

Animal models

CBA/Ca mice

Preparation Method

Mice were given subcutaneous injections of Tobramycin (200mg/kg/day) for 14 days. Gap prepulse inhibition of the acoustic startle reflex was used to assess behavioral evidence of tinnitus. GPIAS assessments were collected before (baseline), as well as at weeks 2, 6, 10, 14, and 18 from the start of Tobramycin treatment.

Dosage form

200mg/kg/day; 14 days; s.c.

Applications

Tobramycin treatment resulted in gap detection defects in 36% of mice in the GPIAS test, exhibiting tinnitus-like behavior, which was most pronounced 2 weeks after administration and gradually decreased over time.

References:
[1] GZIUT M, MACGREGOR H J, NEVELL T G, et al. Anti‐inflammatory effects of tobramycin and a copper–tobramycin complex with superoxide dismutase‐like activity[J]. British Journal of Pharmacology, 2013, 168(5): 1165-1181.
[2] LONGENECKER R J, GU R, HOMAN J, et al. Development of Tinnitus and Hyperacusis in a mouse model of Tobramycin Cochleotoxicity[J]. Frontiers in Molecular Neuroscience, 2021, 14: 715952.

Chemical Properties of Tobramycin

Cas No. 32986-56-4 SDF
Synonyms Deoxykanamycin B, Distobram, Gernebcin, NSC 180514
Chemical Name (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-hydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol
Canonical SMILES C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(CC(C(O3)CN)O)N)N
Formula C18H37N5O9 M.Wt 467.52369
Solubility ≥ 46.8mg/mL in Water Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Tobramycin

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 2.1389 mL 10.6946 mL 21.3893 mL
5 mM 427.8 μL 2.1389 mL 4.2779 mL
10 mM 213.9 μL 1.0695 mL 2.1389 mL
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Review for Tobramycin

Average Rating: 5 ★★★★★ (Based on Reviews and 6 reference(s) in Google Scholar.)

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