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Key Documents

O4636

Sigma-Aldrich

Oxytetracycline dihydrate

Assay (anhydrous basis) 95.0%-102.0%

Synonym(s):

5-Hydroxytetracycline dihydrate, Oxytetracycline, Oxytetracycline Anhydrous

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About This Item

Empirical Formula (Hill Notation):
C22H24N2O9 · 2H2O
CAS Number:
Molecular Weight:
496.46
EC Number:
MDL number:
UNSPSC Code:
51284038
PubChem Substance ID:
NACRES:
NA.85

Quality Level

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

protein synthesis | interferes

SMILES string

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

InChI key

IBZHEBHGZFICKS-IFLJXUKPSA-N

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General description

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.

Biochem/physiol Actions

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.

Analysis Note

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

Other Notes

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

Pictograms

Health hazardEnvironment

Signal Word

Warning

Hazard Statements

Hazard Classifications

Aquatic Chronic 2 - Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
L H Hansen et al.
Applied and environmental microbiology, 67(1), 239-244 (2001-01-03)
Combining the high specificity of bacterial biosensors and the resolution power of fluorescence-activated cell sorting (FACS) provided qualitative detection of oxytetracycline production by Streptomyces rimosus in soil microcosms. A plasmid containing a transcriptional fusion between the tetR-regulated P(tet) promoter from
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

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