31741

Tetracycline hydrochloride

VETRANAL^®, analytical standard

• Empirical Formula (Hill Notation): C₂₂H₂₄N₂O₈ · HCl
• CAS Number: 64-75-5
• Molecular Weight: 480.90
• Beilstein: 3844873
• EC Number: 200-593-8
• MDL number: MFCD00078142
• UNSPSC Code: 41116107
• PubChem Substance ID: 329753913
• E Number: E701
• NACRES: NA.24

Properties

• grade: analytical standard
• Quality Level: 100
• product line: VETRANAL^®
• shelf life: limited shelf life, expiry date on the label
• technique(s): HPLC: suitable; gas chromatography (GC): suitable
• mp: 220-223 °C (lit.)
• application(s): cleaning products; cosmetics; food and beverages; forensics and toxicology; personal care; pharmaceutical (small molecule)
• format: neat
• 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

Description

General description

Tetracycline hydrochloride (TCH) 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 also helps as an alternate drug for penicillin.

Application

Tetracycline (TCH) 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. TCH is also used as a reference standard in LC/MS/MS method for tetracycline residue analysis in biological samples.

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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.

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.

Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Pictograms: GHS08,GHS07,GHS09
• Signal Word: Warning
• Hazard Statements: H315,H319,H335,H361fd,H410
• Precautionary Statements: P202 - P261 - P273 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• 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