T3383
Tetracycline hydrochloride
≥95% (European Pharmacopoeia HPLC assay)
Synonym(s):
4-Epitetracycline hydrochloride, Achromycin hydrochloride
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About This Item
Empirical Formula (Hill Notation):
C22H24N2O8 · HCl
CAS Number:
Molecular Weight:
480.90
Beilstein:
3844873
EC Number:
MDL number:
UNSPSC Code:
51101500
PubChem Substance ID:
NACRES:
NA.76
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Quality Level
Assay
≥95% (European Pharmacopoeia HPLC assay)
form
powder
storage condition
(Keep container tightly closed in a dry and well-ventilated place.)
color
yellow
mp
220-223 °C (lit.)
antibiotic activity spectrum
Gram-negative bacteria
Gram-positive bacteria
Mode of action
protein synthesis | interferes
storage temp.
−20°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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General description
Chemical structure: tetracycline
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.
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.
Caution
This product should be frozen below 0°C and protected from light and moisture. In these conditions, the product has been shown to retain activity for 4 years. Stock solutions should be stored at -20°C and are stable at 37°C for 4 days.
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.
Other Notes
Keep container tightly closed in a dry and well-ventilated place.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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 Code
11 - Combustible Solids
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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