O5875

Oxytetracycline hydrochloride

• Synonym(s): 5-Hydroxytetracycline hydrochloride
• Empirical Formula (Hill Notation): C₂₂H₂₄N₂O₉ · HCl
• CAS Number: 2058-46-0
• Molecular Weight: 496.89
• Beilstein/REAXYS Number: 3853107
• EC Number: 218-161-2
• MDL number: MFCD00135815
• UNSPSC Code: 51284039
• PubChem Substance ID: 24898027
• NACRES: NA.85

Properties

• form: powder or crystals
• Quality Level: 200
• 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
• 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
• 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
• InChI key: UBDNTYUBJLXUNN-IFLJXUKPSA-N

Description

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.

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[1] and antibiotic susceptibilities of Mycoplasma bovis isolates[2].

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.

Other Notes

10g,50g,100g

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

Safety Information

• Pictograms: GHS08
• signalword: Warning
• hcodes: H361fd
• pcodes: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Repr. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)