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O4636

Sigma-Aldrich

Oxytetracycline dihydrate

Assay (anhydrous basis) 95.0%-102.0%

Synonyme(s) :

5-Hydroxytetracycline dihydrate, Oxytetracycline, Oxytetracycline Anhydrous

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About This Item

Formule empirique (notation de Hill):
C22H24N2O9 · 2H2O
Numéro CAS:
6153-64-6
Poids moléculaire :
496.46
Numéro CE :
201-212-8
Numéro MDL:
MFCD00151234
Code UNSPSC :
51284038
ID de substance PubChem :
24898000
Nomenclature NACRES :
NA.85

Niveau de qualité

200

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria

Mode d’action

protein synthesis | interferes

Chaîne SMILES 

O.[H][C@@]12[C@@H](O)[C@@]3([H])C(C(=O)c4c(O)cccc4[C@@]3(C)O)=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C

InChI

1S/C22H24N2O9.H2O/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29;/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31);1H2/t12-,13-,14+,17+,21-,22+;/m1./s1

Clé InChI

IBZHEBHGZFICKS-IFLJXUKPSA-N

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Description générale

Chemical structure: tetracycline

Application

Oxytetracycline is a tetracycline analog isolated from the actinomycete Streptomyces rimosus. It is used in studies on the oxytetracycline-resistance gene (otrA) and is used for fluorescence measurements of hepatocytes.

Actions biochimiques/physiologiques

Oxytetracycline inhibits translation, which results in cell death. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome, inhibiting protein synthesis (elongation). The binding is reversible in nature. Oxytetracycline is lipophilic so it can easily pass through a cell membrane and passively diffuses through channels in the bacterial membrane.
Antibiotic produced by Streptomyces rimosus.
Mode of Action: Inhibits protein synthesis (elongation) by preventing binding of aminoacyl-tRNA to the 30S subunit.
Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Mode of Resistance: Active efflux, ribosome protection, tetracycline inactivation.

Remarque sur l'analyse

solubility very slightly solube in water, it dissolves in dilute acid and alkaline solutions

Autres remarques

10g,50g
Keep container tightly closed in a dry and well-ventilated place.

Pictogrammes

Health hazardEnvironment
GHS08,GHS09

Mention d'avertissement

Warning

Mentions de danger

H361d,H411

Classification des risques

Aquatic Chronic 2 - Repr. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Marc Cherlet et al.
The Analyst, 128(7), 871-878 (2003-08-05)
Tetracycline antibiotics are commonly used in veterinary medicine because of their broad spectrum activity and cost effectiveness. Oxytetracycline (OTC) is one of the most important members of this antibiotic family. The purpose of this study was to develop and validate
A L Cinquina et al.
Journal of chromatography. A, 987(1-2), 227-233 (2003-03-05)
High-performance liquid chromatography with diode-array detection (HPLC-DAD) was optimised and validated for the determination of tetracyclines in bovine milk and tissues. Milk and tissue samples were extracted and purified using a solid-phase extraction HLB Oasis cartridge and analysed using HPLC-DAD
Bent Halling-Sørensen et al.
Chemosphere, 50(10), 1331-1342 (2003-02-15)
The fate of oxytetracyclines (OTCs) in soil interstitial water was investigated and the structure of a number of degradation products elucidated in a time-related experiment. A previously developed separation method for LC-MS-MS able to base separate and quantify OTC and
B Shiels et al.
Journal of cell science, 110 ( Pt 13), 1441-1451 (1997-07-01)
The control of differentiation through time is critical for the correct ordering of sequential developmental events. A timing mechanism based on the number of mitotic divisions has been proposed for both higher eukaryote and protozoan parasite cellular differentiation. However, the
D F Babcock et al.
The Journal of biological chemistry, 254(17), 8117-8120 (1979-09-10)
Conditions are described that allow chlortetracycline, a fluorescent probe of membrane-associated Ca2+, to monitor the content of the major exchangeable pool of intracellular Ca2+ present in the isolated rat hepatocyte. Chlortetracycline fluorescence is decreased in cells whose Ca2+ content is
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