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O5875

Sigma-Aldrich

Oxytetracycline hydrochloride

Synonym(s):
5-Hydroxytetracycline hydrochloride
Empirical Formula (Hill Notation):
C22H24N2O9 · HCl
CAS Number:
Molecular Weight:
496.89
Beilstein:
3853107
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

form

powder or crystals

Quality Level

shelf life

4 yr

impurities

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

color

yellow

solubility

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

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

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General description

Chemical structure: tetracycline

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.

Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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