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Merck

T4062

Tetracycline hydrochloride

meets USP testing specifications

Synonyme(s) :

Tetracycline HCL

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A propos de cet article

Formule empirique (notation de Hill) :
C22H24N2O8 · HCl
Numéro CAS:
64-75-5
Poids moléculaire :
480.90
UNSPSC Code:
51284043
NACRES:
NA.76
PubChem Substance ID:
24900192
EC Number:
200-593-8
Beilstein/REAXYS Number:
3844873
MDL number:
MFCD00078142

Principaux documents

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Nom du produit

Tetracycline hydrochloride, meets USP testing specifications

InChI key

XMEVHPAGJVLHIG-FMZCEJRJSA-N

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

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

agency

USP/NF
meets USP testing specifications

assay

≥900 (Units in µg/mg)

form

crystalline powder

optical activity

[α]/D -255 to 240° (Specific rotation )

storage condition

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

impurities

≤4.0%

color

yellow

mp

220-223 °C (lit.)

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

application(s)

pharmaceutical (small molecule)

mode of action

protein synthesis | interferes

storage temp.

−20°C

Quality Level

200

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Catégories apparentées

Application

Tetracycline is a broad spectrum polyketide antibiotic with clinical uses in treating bacterial infections such as Rocky Mountain spotted fever, typush fever, tick fevers, Q fever, and Brill-Zinsser disease and to treat upper respiratory infections and acne. It has been used in studies of multidrug resistance and potential side effects including acute pancreatitis. It is recommended for use in cell culture applications at 10 mg/L.

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. Light sensitive.

Preparation Note

The product is freely soluble in water, soluble in methanol and ethanol but is insoluble in ether and hydrocarbons. In water, the product yields a clear, yellow-orange solution with heating and in 95% ethanol, 50 mg dissolved in 4 mL with heating yields a clear, yellow-green solution. Tetracycline is rapidly destroyed by alkali hydroxide solutions and standing water solutions become turbid due to hydrolysis and precipitation. The potency of tetracycline is reduced in solutions with pH below 2.

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

Classe de stockage

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
0000457913
0000457913
0000417204
0000417204
0000397382

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Zhijie Li et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(13), 5004-5009 (2013-03-12)
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