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Tetracycline hydrochloride

Name: Tetracycline hydrochloride
Brand: SIAL

meets USP testing specifications

Synonym(s):

Tetracycline HCL

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About This Item

Empirical Formula (Hill Notation):

C₂₂H₂₄N₂O₈ · HCl

CAS Number:

64-75-5

Molecular Weight:

480.90

UNSPSC Code:

51284043

NACRES:

NA.76

PubChem Substance ID:

24900192

EC Number:

200-593-8

Beilstein/REAXYS Number:

3844873

MDL number:

MFCD00078142

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Properties

Quality Segment

200

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

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

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.

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. Light sensitive.

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This Item	PHR1041	T3383	T7660
Sigma-Aldrich T4062 Tetracycline hydrochloride	Supelco PHR1041 Tetracycline hydrochloride	Sigma-Aldrich T3383 Tetracycline hydrochloride	Sigma-Aldrich T7660 Tetracycline hydrochloride
description meets USP testing specifications	description Pharmaceutical Secondary Standard; Certified Reference Material	description ≥95% (European Pharmacopoeia HPLC assay), meets EP testing specifications	description powder, BioReagent, suitable for cell culture
antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria	antibiotic activity spectrum -	antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria	antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria
mode of action protein synthesis \| interferes	mode of action -	mode of action protein synthesis \| interferes	mode of action protein synthesis \| interferes
Quality Level 200	Quality Level 300	Quality Level 200	Quality Level 200
assay ≥900 (Units in µg/mg)	assay -	assay ≥95% (European Pharmacopoeia HPLC assay)	assay -
application(s) pharmaceutical (small molecule)	application(s) pharmaceutical (small molecule)	application(s) -	application(s) -
form crystalline powder	form -	form powder	form powder

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Pictograms

GHS08,GHS07,GHS09

Signal Word

Warning

Hazard Codes

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

11 - Combustible Solids

Flash Point (°F)

Not applicable

Flash Point (°C)