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Merck

31741

Tetracycline hydrochloride

VETRANAL®, analytical standard

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About This Item

Formule empirique (notation de Hill) :
C22H24N2O8 · HCl
Numéro CAS:
64-75-5
Poids moléculaire :
480.90
NACRES:
NA.24
E Number:
E701
PubChem Substance ID:
329753913
UNSPSC Code:
41116107
EC Number:
200-593-8
MDL number:
MFCD00078142
Beilstein/REAXYS Number:
3844873

Nom du produit

Tetracycline hydrochloride, VETRANAL®, analytical standard

InChI key

XMEVHPAGJVLHIG-FMZCEJRJSA-N

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

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

grade

analytical standard

product line

VETRANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

220-223 °C (lit.)

application(s)

cleaning products
cosmetics
food and beverages
forensics and toxicology
personal care
pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

Quality Level

100

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Catégories apparentées

Application

Tetracycline (TCH) 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. TCH is also used as a reference standard in LC/MS/MS method for tetracycline residue analysis in biological samples.

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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.

Disclaimer

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.

General description

Tetracycline hydrochloride (TCH) 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 also helps as an alternate drug for penicillin.

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.

Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

signalword

Warning

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Classe de stockage

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
BCCM9536
BCCG3225
BCCC9767
BCBX5586
BCBW2124

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Consulter la Bibliothèque de documents

A molecular imprinted membrane for molecular discrimination of tetracycline hydrochloride.
Trotta, F., et al.
Journal of Membrane Science, 254.1, 13-19 (2005)
Yasuhiro Igarashi et al.
Journal of natural products, 74(4), 670-674 (2011-03-11)
A new spirotetronate-class polyketide, maklamicin (1), was isolated from the culture extract of an endophytic actinomycete of the genus Micromonospora. The structure and relative configuration of 1 were elucidated by interpretation of NMR and other spectroscopic data, and the absolute
Ruiling Qi et al.
Colloids and surfaces. B, Biointerfaces, 110, 148-155 (2013-05-29)
Fabrication of nanofiber-based drug delivery system with controlled release property is of general interest in biomedical sciences. In this study, we prepared an antibiotic drug tetracycline hydrochloride (TCH)-loaded halloysite nanotubes/poly(lactic-co-glycolic acid) composite nanofibers (TCH/HNTs/PLGA), and evaluated the drug release and
T Bouchery et al.
Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases, 19(2), 131-140 (2013-02-13)
Symbiotic associations between eukaryotes and microorganisms are frequently observed in nature, and range along the continuum between parasitism and mutualism. The genus Wolbachia contains well-known intracellular bacteria of arthropods that induce several reproductive phenotypes that benefit the transmission of the
Zhijie Li et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(13), 5004-5009 (2013-03-12)
Reported here is a piggyBac transposon-based expression system for the generation of doxycycline-inducible, stably transfected mammalian cell cultures for large-scale protein production. The system works with commonly used adherent and suspension-adapted mammalian cell lines and requires only a single transfection
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