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Key Documents

T4062

Sigma-Aldrich

Tetracycline hydrochloride

meets USP testing specifications

Synonyme(s) :

Tetracycline HCL

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About This Item

Formule empirique (notation de Hill):
C22H24N2O8 · HCl
Numéro CAS:
Poids moléculaire :
480.90
Numéro Beilstein :
3844873
Numéro CE :
Numéro MDL:
Code UNSPSC :
51284043
ID de substance PubChem :
Nomenclature NACRES :
NA.76

Agence

USP/NF
meets USP testing specifications

Niveau de qualité

Pureté

≥900 (Units in µg/mg)

Forme

crystalline powder

Activité optique

[α]/D -255 to 240° (Specific rotation )

Conditions de stockage

(Keep container tightly closed in a dry and well-ventilated place. Light sensitive.)

Impuretés

≤4.0%

Couleur

yellow

Pf

220-223 °C (lit.)

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria

Application(s)

pharmaceutical (small molecule)

Mode d’action

protein synthesis | interferes

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

XMEVHPAGJVLHIG-FMZCEJRJSA-N

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Description générale

Chemical structure: tetracycline

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.

Actions biochimiques/physiologiques

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.

Attention

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.

Notes préparatoires

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.

Autres remarques

Keep container tightly closed in a dry and well-ventilated place. Light sensitive.

Pictogrammes

Health hazardExclamation markEnvironment

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves


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Consulter la Bibliothèque de documents

Shruti Sharma et al.
Nature communications, 10(1), 3105-3105 (2019-07-17)
Fas plays a major role in regulating ligand-induced apoptosis in many cell types. It is well known that several cancers demonstrate reduced cell surface levels of Fas and thus escape a potential control system via ligand-induced apoptosis, although underlying mechanisms
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
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
Olivier Marion et al.
Bioorganic & medicinal chemistry, 17(3), 1006-1017 (2008-02-01)
A series of simplified thiomarinol derivatives was prepared by way of catalytic enantioselective inverse electron demand hetero [4+2] cycloaddition/allylboration tandem reaction. As a preliminary evaluation, these analogs were tested for antimicrobial activity using a standard disk diffusion assay. Whereas amide
Leslie Cuthbertson et al.
Chemistry & biology, 20(2), 232-240 (2013-02-27)
The ligands that interact with the vast majority of small-molecule binding transcription factors are unknown, a significant gap in our understanding of sensory perception by cells. TetR-family regulators (TFRs) are found in most prokaryotes and are involved in regulating virtually

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