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Tetracycline hydrochloride

Pharmaceutical Secondary Standard; Certified Reference Material

  • CAS Number 64-75-5

  • Empirical Formula (Hill Notation) C22H24N2O8 · HCl

  • Molecular Weight 480.90

  •  Beilstein/REAXYS Number 3844873

  •  EC Number 200-593-8

  •  MDL number MFCD00078142

  •  PubChem Substance ID 329823071

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Properties

Related Categories Additional Standards, Analytical Standards, Analytical/Chromatography, Chromatography, Drugs & Metabolites,
Quality Level   300
grade   certified reference material
  pharmaceutical secondary standard
form   neat
application(s)   HPLC: suitable
  gas chromatography (GC): suitable
mp   220-223 °C (lit.)
Featured Industry   Pharmaceutical (small molecule)
format   neat
pharmacopeia traceability   traceable to BP 480
  traceable to PhEur T060000
  traceable to USP 1651009
SMILES string   Cl.CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c4c(O)cccc4[C@@]3(C)O
InChI   1S/C22H24N2O8.ClH/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28;/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30);1H/t9-,10-,15-,21+,22-;/m0./s1
InChI key   XMEVHPAGJVLHIG-FMZCEJRJSA-N

Description

General description

Tetracycline hydrochloride is a broad-spectrum antibiotic, effective against both Gram-negative and Gram-positive microorganisms. Its aqueous solution has effective as a root canal irrigant for the removal of smear layer.
Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Application

Tetracycline hydrochloride may be used as a pharmaceutical reference standard for the determination of the analyte in pharmaceutical formulations by kinetic spectrophotometric method.

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.

Biochem/physiol Actions

Mode of Action: Tetracycline passively diffuses through proin channels in the cell membrane, binding to 30S ribosomes and inhibits protein synthesis by preventing access of aminoacyl tRNA to the acceptor site on the mRNA-ribosome complex. It also binds to the bacterial 50S ribosomal subunit, altering the membrane and causing intracellular components to leak from bacterial cells. The inhibitory effects can be reversed by washing, suggesting that it is the reversibly bound antibiotic, and not the irreversibly bound drug, that is responsible for antibacterial action.

Mode of Resistance: The effects are inactivated via a loss of cell wall permeability.

Antimicrobial spectrum: Includes a wide range of antimicrobial activity against gram-positive and gram-negative bacteria.

Caution

This product should be frozen below 0°C and protected from light and moisture. In these conditions, the product has been shown to retain activity for 4 years. Stock solutions should be stored at -20°C and are stable at 37°C for 4 days.

Preparation Note

The product is freely soluble in water, soluble in methanol and ethanol but is insoluble in ether and hydrocarbons. In water, the product yields a clear, yellow-orange solution with heating and in 95% ethanol, 50 mg dissolved in 4 mL with heating yields a clear, yellow-green solution. Tetracycline is rapidly destroyed by alkali hydroxide solutions and standing water solutions become turbid due to hydrolysis and precipitation. The potency of tetracycline is reduced in solutions with pH below 2.

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.

Footnote

To see an example of a Certificate of Analysis for this material enter LRAA7192 in the slot below. This is an example certificate only and may not be the lot that you receive.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
WGK 2
RTECS 
QI9100000

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

LC/MS/MS Analysis of Tetracycline Antibiotics on Kromasil® Eternity™ C18

From our library of Articles, Sigma-Aldrich presents LC/MS/MS Analysis of Tetracycline Antibiotics on Kromasil® Eternity™ C18
Keywords: Antibiotics, Chromatography, High performance liquid chromatography, Liquid chromatography mass spectrometry, Mass spectrometry, Metabolites

Peer-Reviewed Papers
15

References

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