Tobramycin Sulfate | CAS#49842-07-1 | antibiotic

Tobramycin Sulfate
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 561624

CAS#: 49842-07-1 (sulfate)

Description: Tobramycin is an effective antibiotic commonly used in the management and treatment of various systemic and ocular infections. As an aminoglycoside antibiotic, tobramycin is active against aerobic gram-negative bacteria, including Pseudomonas aeruginosa. Tobramycin binds to the 16s ribosomal RNA component of the bacterial 30s ribosomal unit, inhibiting the initiation step of translation. By binding to the A-site, tobramycin induces mistranslation and causes transfer RNA to misread the codon, thus causing incorrect delivery of aminoacyl units. Incorrectly synthesized proteins build up inside the cell, disrupting the cell membrane and various cellular processes; this mechanism of action designates tobramycin as a bactericidal agent.

Chemical Structure

Tobramycin Sulfate

CAS# 49842-07-1 (sulfate)

Instruction

Theoretical Analysis

MedKoo Cat#: 561624
Name: Tobramycin Sulfate
CAS#: 49842-07-1 (sulfate)
Chemical Formula: C18H39N5O13S
Exact Mass: 0.00
Molecular Weight: 565.590
Elemental Analysis: C, 38.23; H, 6.95; N, 12.38; O, 36.77; S, 5.67

Price and Availability

Size	Price	Availability
250mg	USD 250	2 Weeks
1g	USD 450	2 Weeks
5g	USD 1050	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 32986-56-4 (free base) 79645-27-5 (sulfate deleted) 49842-07-1 (sulfate)

Synonym: Tobramycin Sulfate; Dartobcin; Nebcine; Tobraneg; Tobrasix;

IUPAC/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 Sulfate

InChi Key: ZEUUPKVZFKBXPW-TWDWGCDDSA-N

InChi Code: InChI=1S/C18H37N5O9.H2O4S/c19-3-9-8(25)2-7(22)17(29-9)31-15-5(20)1-6(21)16(14(15)28)32-18-13(27)11(23)12(26)10(4-24)30-18;1-5(2,3)4/h5-18,24-28H,1-4,19-23H2;(H2,1,2,3,4)/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+;/m0./s1

SMILES Code: O[C@H]1[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@H](CN)[C@@H](O)C[C@H]3N)[C@@H](N)C[C@H]2N)O[C@H](CO)[C@@H](O)[C@@H]1N.O=S(O)(O)=O

Appearance: Solid powder

Purity: >95% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Certificate of Analysis:

View CoA: current batch, Lot# C23B08B18

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 565.59 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Rosalia M, Chiesa E, Tottoli EM, Dorati R, Genta I, Conti B, Pisani S. Tobramycin Nanoantibiotics and Their Advantages: A Minireview. Int J Mol Sci. 2022 Nov 15;23(22):14080. doi: 10.3390/ijms232214080. PMID: 36430555; PMCID: PMC9692674.

2: Fiel SB, Roesch EA. The use of tobramycin for Pseudomonas aeruginosa: a review. Expert Rev Respir Med. 2022 May;16(5):503-509. doi: 10.1080/17476348.2022.2057951. Epub 2022 Apr 4. PMID: 35320051.

3: Schwarz C, Taccetti G, Burgel PR, Mulrennan S. Tobramycin safety and efficacy review article. Respir Med. 2022 Apr-May;195:106778. doi: 10.1016/j.rmed.2022.106778. Epub 2022 Feb 25. PMID: 35249787.

4: Elborn JS, Blasi F, Haworth CS, Ballmann M, Tiddens HAWM, Murris-Espin M, Chalmers JD, Cantin AM. Bronchiectasis and inhaled tobramycin: A literature review. Respir Med. 2022 Feb;192:106728. doi: 10.1016/j.rmed.2021.106728. Epub 2022 Jan 1. PMID: 34998112.

5: Mah FS, Karpecki PM. Review of Loteprednol Etabonate 0.5%/Tobramycin 0.3% in the Treatment of Blepharokeratoconjunctivitis. Ophthalmol Ther. 2021 Dec;10(4):859-875. doi: 10.1007/s40123-021-00401-x. Epub 2021 Oct 27. PMID: 34708391; PMCID: PMC8589901.

6: Karki K, Sigdel S, Kafle S. Is it Worth Adding Systemic Antibiotics to Inhalational Tobramycin Therapy to Treat Pseudomonas Infections in Cystic Fibrosis? Cureus. 2021 Aug 20;13(8):e17326. doi: 10.7759/cureus.17326. PMID: 34567873; PMCID: PMC8451513.

7: Le T, Lord L, Pignataro S, Simioni D, Cheah R. Evaluating the Impact of Education on Pharmacist Tobramycin Dose Recommendations for Cystic Fibrosis and a Review of Perceptions on Pharmacist-Led Charting. J Pharm Pract. 2022 Dec;35(6):903-910. doi: 10.1177/08971900211018419. Epub 2021 May 20. PMID: 34013814.

8: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Tobramycin. 2021 Feb 15. PMID: 30000174.

9: Alemu BM, Worku T. Efficacy of azithromycin 1% and 1.5% ophthalmic solutions compared to tobramycin 0.3% eye drops: A systematic review and meta-analysis. SAGE Open Med. 2020 Sep 18;8:2050312120958846. doi: 10.1177/2050312120958846. PMID: 32995001; PMCID: PMC7502802.

10: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Tobramycin. 2019 Apr 12. PMID: 31643824.

11: Hamed K, Debonnett L. Tobramycin inhalation powder for the treatment of pulmonary Pseudomonas aeruginosa infection in patients with cystic fibrosis: a review based on clinical evidence. Ther Adv Respir Dis. 2017 May;11(5):193-209. doi: 10.1177/1753465817691239. Epub 2017 Feb 17. PMID: 28470103; PMCID: PMC5933546.

12: Vazquez-Espinosa E, Marcos C, Alonso T, Giron RM, Gomez-Punter RM, Garcia- Castillo E, Zamora E, Cisneros C, Garcia J, Valenzuela C, Ancochea J. Tobramycin inhalation powder (TOBI Podhaler) for the treatment of lung infection in patients with cystic fibrosis. Expert Rev Anti Infect Ther. 2016;14(1):9-17. doi: 10.1586/14787210.2016.1118344. Epub 2015 Dec 4. PMID: 26559549.

13: Vázquez-Espinosa E, Girón RM, Gómez-Punter RM, García-Castillo E, Valenzuela C, Cisneros C, Zamora E, García-Pérez FJ, Ancochea J. Long-term safety and efficacy of tobramycin in the management of cystic fibrosis. Ther Clin Risk Manag. 2015 Mar 12;11:407-15. doi: 10.2147/TCRM.S75208. PMID: 25792839; PMCID: PMC4362982.

14: Somayaji R, Parkins MD. Tobramycin inhalation powder: an efficient and efficacious therapy for the treatment of Pseudomonas aeruginosa infection in cystic fibrosis. Ther Deliv. 2015 Feb;6(2):121-37. doi: 10.4155/tde.14.94. PMID: 25690082.

15: Shteinberg M, Elborn JS. Use of inhaled tobramycin in cystic fibrosis. Adv Ther. 2015 Jan;32(1):1-9. doi: 10.1007/s12325-015-0179-3. Epub 2015 Jan 27. PMID: 25620537.

16: de Velde F, Emonts M, Verbruggen S, van der Sijs H. High tobramycin serum concentrations after tobramycin inhalation in a child with renal failure. J Antimicrob Chemother. 2014 Nov;69(11):3163-4. doi: 10.1093/jac/dku260. Epub 2014 Jul 7. PMID: 25006239.

17: Lam J, Vaughan S, Parkins MD. Tobramycin Inhalation Powder (TIP): An Efficient Treatment Strategy for the Management of Chronic Pseudomonas Aeruginosa Infection in Cystic Fibrosis. Clin Med Insights Circ Respir Pulm Med. 2013 Nov 13;7:61-77. doi: 10.4137/CCRPM.S10592. PMID: 24324354; PMCID: PMC3836451.

18: Uttley L, Harnan S, Cantrell A, Taylor C, Walshaw M, Brownlee K, Tappenden P. Systematic review of the dry powder inhalers colistimethate sodium and tobramycin in cystic fibrosis. Eur Respir Rev. 2013 Dec;22(130):476-86. doi: 10.1183/09059180.00001513. PMID: 24293463; PMCID: PMC9639188.

19: Tappenden P, Harnan S, Uttley L, Mildred M, Carroll C, Cantrell A. Colistimethate sodium powder and tobramycin powder for inhalation for the treatment of chronic Pseudomonas aeruginosa lung infection in cystic fibrosis: systematic review and economic model. Health Technol Assess. 2013 Dec;17(56):v-xvii, 1-181. doi: 10.3310/hta17560. PMID: 24290164; PMCID: PMC4781138.

20: McKeage K. Tobramycin inhalation powder: a review of its use in the treatment of chronic Pseudomonas aeruginosa infection in patients with cystic fibrosis. Drugs. 2013 Nov;73(16):1815-27. doi: 10.1007/s40265-013-0141-0. PMID: 24194436.

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