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T3258

Sigma-Aldrich

Tetracycline

98.0-102.0% (HPLC)

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Synonym(s):
Tetracycline Hydrate
Empirical Formula (Hill Notation):
C22H24N2O8 · xH2O
CAS Number:
Molecular Weight:
444.43 (anhydrous basis)
Beilstein:
2230417
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

Quality Level

Assay

98.0-102.0% (HPLC)

form

powder or crystals

storage condition

(Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.)

color

faint yellow to dark yellow

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

CN(C)[C@H]1[C@@H]2C[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/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1

InChI key

OFVLGDICTFRJMM-WESIUVDSSA-N

Gene Information

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This Item
87128T3383T8032
Tetracycline 98.0-102.0% (HPLC)

Sigma-Aldrich

T3258

Tetracycline

Tetracycline 98.0-102.0% (HPLC)

Sigma-Aldrich

87128

Tetracycline

form

powder or crystals

form

powder or crystals

form

powder

form

powder

storage condition

(Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.)

storage condition

-

storage condition

(Keep container tightly closed in a dry and well-ventilated place.)

storage condition

(Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.)

color

faint yellow to dark yellow

color

faint yellow to dark yellow

color

yellow

color

faintly yellow to yellow

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

mode of action

protein synthesis | interferes

mode of action

protein synthesis | interferes

mode of action

protein synthesis | interferes

mode of action

protein synthesis | interferes

General description

Chemical structure: tetracycline

Biochem/physiol Actions

Mode of Action: Tetracycline passively diffuses through proin channels in the cell membrane, binding to 30S ribosomes and inhibits protein synthesis by preventing access of aminoacyl tRNA to the acceptor site on the mRNA-ribosome complex. It also binds to the bacterial 50S ribosomal subunit, altering the membrane and causing intracellular components to leak from bacterial cells. The inhibitory effects can be reversed by washing, suggesting that it is the reversibly bound antibiotic, and not the irreversibly bound drug, that is responsible for antibacterial action.

Mode of Resistance: The effects are inactivated via a loss of cell wall permeability.

Antimicrobial spectrum: Includes a wide range of antimicrobial activity against gram-positive and gram-negative bacteria.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - 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

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Maulik Thaker et al.
Cellular and molecular life sciences : CMLS, 67(3), 419-431 (2009-10-29)
Resistance to tetracycline emerged soon after its discovery six decades ago. Extensive clinical and non-clinical uses of this class of antibiotic over the years have combined to select for a large number of resistant determinants, collectively termed the tetracycline resistome.
Jennifer M Adams-Haduch et al.
Antimicrobial agents and chemotherapy, 52(11), 3837-3843 (2008-08-30)
A total of 49 unique clinical isolates of multidrug-resistant (MDR) Acinetobacter baumannii identified at a tertiary medical center in Pittsburgh, Pennsylvania, between August 2006 and September 2007 were studied for the genetic basis of their MDR phenotype. Approximately half of
Lucia Pallecchi et al.
Antimicrobial agents and chemotherapy, 51(8), 2720-2725 (2007-06-06)
A survey carried out in 2005 among members of a healthy population of children living in Bolivia and Peru revealed that fecal carriage of Escherichia coli strains resistant to expanded-spectrum cephalosporins was remarkably increased compared to that observed in the
Zhijie Li et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(13), 5004-5009 (2013-03-12)
Reported here is a piggyBac transposon-based expression system for the generation of doxycycline-inducible, stably transfected mammalian cell cultures for large-scale protein production. The system works with commonly used adherent and suspension-adapted mammalian cell lines and requires only a single transfection
Andrew E Simor et al.
Antimicrobial agents and chemotherapy, 51(11), 3880-3886 (2007-08-29)
Mupirocin resistance in Staphylococcus aureus is increasingly being reported in many parts of the world. This study describes the epidemiology and laboratory characterization of mupirocin-resistant methicillin-resistant S. aureus (MRSA) strains in Canadian hospitals. Broth microdilution susceptibility testing of 4,980 MRSA

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