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Merck
CN

74749

Tetracycline hydrochloride

pharmaceutical secondary standard; traceable to USP, PhEur and BP

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About This Item

Empirical Formula (Hill Notation):
C22H24N2O8 · HCl
CAS Number:
Molecular Weight:
480.90
EC Number:
200-593-8
UNSPSC Code:
41116000
MDL number:
Beilstein/REAXYS Number:
3844873
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agency

traceable to BP 480, traceable to Ph. Eur. T060000, traceable to USP 1651009

mp

220-223 °C (lit.)

storage temp.

2-8°C

SMILES string

Cl.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.ClH/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);1H/t9-,10-,15-,21+,22-;/m0./s1

InChI key

XMEVHPAGJVLHIG-FMZCEJRJSA-N

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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.

signalword

Warning

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Tam Nguyen et al.
FP essentials, 407, 11-16 (2013-04-23)
New drugs are available for managing several common skin disorders. For psoriasis, topical corticosteroids remain the first-line therapy, but topical vitamin D3 analogs, such as calcipotriene, now have a role. They are as effective as medium-potency topical steroids but without
Chong-Yue Zhong et al.
Poultry science, 92(6), 1552-1559 (2013-05-21)
Riemerella anatipestifer (RA) is one of the most important pathogens of 1- to 8-wk-old ducklings that severely affects the development of the duck industry in China. Every year, antibiotic medicines including tetracycline and doxycycline are used in the duck industry.
Biyang Deng et al.
Food chemistry, 134(4), 2350-2354 (2013-02-28)
A novel and sensitive determination for tetracycline (TC) in crucian carp muscle was developed by using capillary electrophoresis coupled with electrochemiluminescence (ECL) detection. The conditions affected separation and detection were examined in detail. The linearity range of TC concentration was
Leslie Cuthbertson et al.
Chemistry & biology, 20(2), 232-240 (2013-02-27)
The ligands that interact with the vast majority of small-molecule binding transcription factors are unknown, a significant gap in our understanding of sensory perception by cells. TetR-family regulators (TFRs) are found in most prokaryotes and are involved in regulating virtually
Anjiang Tan et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(17), 6766-6770 (2013-04-10)
Transgene-based genetic sexing methods are being developed for insects of agricultural and public health importance. Male-only rearing has long been sought in sericulture because males show superior economic characteristics, such as better fitness, lower food consumption, and higher silk yield.

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