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PHR1041 Sigma-Aldrich

Tetracycline hydrochloride

Pharmaceutical Secondary Standard; Certified Reference Material

  • CAS Number 64-75-5

  • Empirical Formula (Hill Notation) C22H24N2O8 · HCl

  • Molecular Weight 480.90

  •  Beilstein Registry 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,
grade   certified reference material
  pharmaceutical secondary standard
InChI Key   XMEVHPAGJVLHIG-FMZCEJRJSA-N
form   neat
mp   220-223 °C(lit.)
format   neat
pharmacopeia traceability   traceable to BP 480
  traceable to PhEur T060000
  traceable to USP 1651009

Description

Analysis Note

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. These secondary standards offer multi-traceability to the USP, EP (PhEur) and BP primary standards, where they are available. This product was designed, produced and verified for accuracy and stability in accordance with ISO/IEC 17025:2005 (AClass Cert AT-1467), ISO GUIDES 34:2009 (AClass Cert AR-1470).

Application

Tetracycline is a broad spectrum polyketide antibiotic with clinical uses in treating bacterial infections such as Rocky Mountain spotted fever, typush fever, tick fevers, Q fever, and Brill-Zinsser disease and to treat upper respiratory infections and acne. It has been used in studies of multidrug resistance and potential side effects including acute pancreatitis. It is recommended for use in cell culture applications at 10 mg/L.

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.

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.

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Safety & Documentation

Safety Information

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