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Merck

O5875

Oxytetracycline hydrochloride

Synonym(s):

5-Hydroxytetracycline hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C22H24N2O9 · HCl
CAS Number:
2058-46-0
Molecular Weight:
496.89
UNSPSC Code:
51284039
NACRES:
NA.85
PubChem Substance ID:
24898027
EC Number:
218-161-2
Beilstein/REAXYS Number:
3853107
MDL number:
MFCD00135815

InChI key

UBDNTYUBJLXUNN-IFLJXUKPSA-N

InChI

1S/C22H24N2O9.ClH/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);1H/t12-,13-,14+,17+,21-,22+;/m1./s1

SMILES string

Cl.CN(C)[C@H]1[C@@H]2[C@@H](O)[C@H]3C(=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c4c(O)cccc4[C@@]3(C)O

form

powder or crystals

impurities

≤3.5% total of impurities (related substances (HPLC))

color

yellow

solubility

soluble

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

mode of action

protein synthesis | interferes

Quality Level

200

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Application

Oxytetracycline is a tetracycline analog isolated from the actinomycete Streptomyces rimosus. Oxytetracycline is an antibiotic indicated for treatment of infections caused by Gram positive and Gram negative microorganisms such as Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae, and Diplococcus pneumoniae. It is used in studies on the oxytetracycline-resistance gene (otrA). Oxytetracycline hydrochloride is used to study phagosome-lysosome (P-L) fusion in P388D1 cells and antibiotic susceptibilities of Mycoplasma bovis isolates.

Biochem/physiol Actions

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.
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. 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.

General description

Chemical structure: tetracycline
Freely soluble in water, sparingly soluble in Ethanol (96%). Solution in water becomes turbid on standing owing to the precipitation of chromatograms.

Other Notes

10g,50g,100g
Keep container tightly closed in a dry and well-ventilated place.Store under inert gas. Light sensitive.Air sensitive.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361fd

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000409197
0000409197
0000409198
0000409198
0000409196

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A M Kroon et al.
Cancer letters, 25(1), 33-40 (1984-11-01)
The mitochondrial genetic system is indispensable for the biosynthesis of the enzyme complexes involved in aerobic energy generation. Tetracyclines inhibit the expression of only the mitochondrial genes because they specifically block mitochondrial protein synthesis. A salient feature is that this
A Thomas et al.
The Veterinary record, 153(14), 428-431 (2003-10-30)
The susceptibilities of 40 recent Belgian field isolates of Mycoplasma bovis to 10 antimicrobial agents were assessed. Tiamulin was the most active antimicrobial agent against M bovis, with an initial inhibitory concentration (IIC50) of 0.06 microg/ml, but it is not
M Y Wells et al.
Infection and immunity, 56(12), 3209-3215 (1988-12-01)
Fusion of lysosomes with phagosomes containing Ehrlichia risticii, an obligate intracellular parasite, was evaluated in P388D1 murine macrophagelike cells. Lysosomes in cells ranging in infectivity from 30 to 70% were labeled cytochemically with acid phosphatase or via endocytosis of thorium
Marina Karpov et al.
Water research, 145, 136-145 (2018-08-21)
Abiotic mechanisms of oxytetracycline degradation by redox-active minerals, Fe(III)-saturated montmorillonite (Fe-SWy) and birnessite (δ-MnO2), were studied to better understand the environmental behavior of tetracycline antibiotics in aqueous systems. Kinetics of dissipation (adsorption, oxidation and formation of transformation products (TPs)), was
Ali Molaei et al.
PloS one, 12(7), e0180663-e0180663 (2017-07-07)
Oxytetracycline (OTC) and sulfamethoxazole (SMX) are two of most widely used antibiotics in livestock and poultry industry. After consumption of antibiotics, a major portion of these compounds is excreted through the feces and urine of animals. Land application of antibiotic-treated
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