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O2756

Sigma-Aldrich

Oxytetracycline hemicalcium salt

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About This Item

Linear Formula:
C22H24N2O9 · 1/2Ca
CAS Number:
Molecular Weight:
480.47
EC Number:
MDL number:
UNSPSC Code:
51101500
PubChem Substance ID:

solubility

formic acid: 50 mg/mL, very slightly hazy, orange to very deep orange

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

[Ca++].CN(C)[C@H]1[C@@H]2[C@@H](O)C3C(=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1[O-])C(=O)c4c(O)cccc4[C@@]3(C)O.CN(C)[C@H]5[C@@H]6[C@@H](O)C7C(=C(O)[C@]6(O)C(=O)C(C(N)=O)=C5[O-])C(=O)c8c(O)cccc8[C@@]7(C)O

InChI

1S/2C22H24N2O9.Ca/c2*1-21(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;/h2*4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31);/q;;+2/p-2/t2*12?,13-,14+,17+,21-,22+;/m11./s1

InChI key

KIPLYOUQVMMOHB-JOFVZRTQSA-L

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). It 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. 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

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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D F Babcock et al.
The Journal of biological chemistry, 254(17), 8117-8120 (1979-09-10)
Conditions are described that allow chlortetracycline, a fluorescent probe of membrane-associated Ca2+, to monitor the content of the major exchangeable pool of intracellular Ca2+ present in the isolated rat hepatocyte. Chlortetracycline fluorescence is decreased in cells whose Ca2+ content is

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