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Merck

T3258

Tetracycline

98.0-102.0% (HPLC)

Synonym(s):

Tetracycline Hydrate

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About This Item

Empirical Formula (Hill Notation):
C22H24N2O8 · xH2O
CAS Number:
60-54-8
Molecular Weight:
444.43 (anhydrous basis)
UNSPSC Code:
51284017
NACRES:
NA.85
PubChem Substance ID:
24900120
EC Number:
200-481-9
Beilstein/REAXYS Number:
2230417
MDL number:
MFCD00151232

Product Name

Tetracycline, 98.0-102.0% (HPLC)

InChI key

OFVLGDICTFRJMM-WESIUVDSSA-N

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

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

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

Quality Level

200

Gene Information

human ... CYP1A2(1544), TERT(7015)

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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.

General description

Chemical structure: tetracycline

Other Notes

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

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000504483
0000504483
0000485090
0000485090
0000480313

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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
Vanessa G Allen et al.
Antimicrobial agents and chemotherapy, 55(2), 703-712 (2010-11-26)
Surveillance of gonococcal antimicrobial resistance and the molecular characterization of the mechanisms underlying these resistance phenotypes are essential in order to establish correct empirical therapies, as well as to describe the emergence of new mechanisms in local bacterial populations. To
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