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PHR1079

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Tobramycin

Pharmaceutical Secondary Standard; Certified Reference Material

Synonym(s):

Nebramycin Factor 6, 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

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About This Item

Empirical Formula (Hill Notation):
C18H37N5O9
CAS Number:
32986-56-4
Molecular Weight:
467.51
Beilstein/REAXYS Number:
1357507
EC Number:
251-322-5
MDL number:
MFCD00077885
UNSPSC Code:
41116107
PubChem Substance ID:
329823102
NACRES:
NA.24

grade

certified reference material
pharmaceutical secondary standard

Quality Level

300

agency

traceable to BP 333
traceable to Ph. Eur. T1500000
traceable to USP 1667508

API family

tobramycin

CofA

current certificate can be downloaded

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@@H](N)[C@H]3O)[C@H]2O)[C@H](N)C[C@@H]1O

InChI

1S/C18H37N5O9/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/h5-18,24-28H,1-4,19-23H2/t5-,6+,7+,8-,9+,10+,11+,12+,13+,14-,15+,16-,17+,18+/m0/s1

InChI key

NLVFBUXFDBBNBW-SNGYORCQSA-N

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General description

Certified pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to pharmacopeia primary standards. Tobramycin is an aminoglycoside antibiotic effective in treating infections caused by Gram negative bacteria.

Application

These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.
Tobramycin may be used as a pharmaceutical reference standard for the determination of the analyte in drug dosage forms by high performance liquid chromatography.

Biochem/physiol Actions

Tobramycin is an aminoglycoside.
Mode of Action: Binds to 70S ribosomal subunit; inhibits translocation; elicits miscoding.
Spectrum of Activity: Gram negative bacteria. Not effective against Enterococci.

Analysis Note

These secondary standards offer multi-traceability to the USP, EP (PhEur) and BP primary standards, where they are available.

Other Notes

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.
Values of analytes vary lot to lot.

Footnote

To see an example of a Certificate of Analysis for this material enter LRAA5713 in the slot below. This is an example certificate only and may not be the lot that you receive.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361f

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
LRAC4285
LRAC0046
LRAC7886
LRAA5713
LRAB8291

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Sigma-Aldrich

B5264

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Development of molecular imprinted nanosensor for determination of tobramycin in pharmaceuticals and foods
Yola M, et al.
Talanta, 120(2), 318-324 (2014)
A liquid-chromatographic method for the determination of tobramycin
Dash AK and Suryanarayanan R
Journal of Pharmaceutical and Biomedical Analysis, 9(3), 237-245 (1991)
A simple and rapid high-performance liquid chromatographic method for determining tobramycin in pharmaceutical formulations by direct UV detection
Ruckmani K, et al.
Pharmaceutical Methods, 2(2), 117-123 (2011)
Determination of aminoglycosides in pharmaceutical formulations-II. High-performance liquid chromatography
Fabre H, et al.
Journal of Pharmaceutical and Biomedical Analysis, 7(12), 1711-1718 (1989)
Yifat Berkov-Zrihen et al.
Organic letters, 15(24), 6144-6147 (2013-11-15)
A short site-selective strategy for the activation and derivatization of alcohols of the clinically important aminoglycoside tobramycin is reported. The choice of amine protecting group affected the site-selective conversion of secondary alcohols of tobramycin into leaving groups. Temperature-dependent, chemoselective sequential
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