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Merck
CN

O4636

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:
6153-64-6
Molecular Weight:
496.46
NACRES:
NA.85
PubChem Substance ID:
24898000
UNSPSC Code:
51284038
EC Number:
201-212-8
MDL number:
MFCD00151234

Key Documents

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Product Name

Oxytetracycline dihydrate, Assay (anhydrous basis) 95.0%-102.0%

InChI key

IBZHEBHGZFICKS-IFLJXUKPSA-N

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

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

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

mode of action

protein synthesis | interferes

Quality Level

200

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Analysis Note

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

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

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.
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.

General description

Chemical structure: tetracycline

Other Notes

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

pictograms

Health hazardEnvironment
GHS08,GHS09

signalword

Warning

Hazard Classifications

Aquatic Chronic 2 - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
0000442951
0000442951
0000341549
0000341549
0000205327

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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
S S Yang et al.
Journal of microbiology, immunology, and infection = Wei mian yu gan ran za zhi, 34(4), 235-242 (2002-02-05)
This study examined whether the production of oxytetracycline by Streptomyces rimosus TM-55 (CCRC 960061) would be improved with calcium alginate immobilization in submerged fermentation compared with free cells. Results showed that in 1-mL culture broth, free cells produced 121 to
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
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