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T3383

Tetracycline hydrochloride

≥95% (European Pharmacopoeia HPLC assay), meets EP testing specifications

Synonym(s):

4-Epitetracycline hydrochloride, Achromycin hydrochloride

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25 g

Available to ship TODAYfromMILWAUKEE

$83.60
100 g

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$281.00

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:
24900135
EC Number:
200-593-8
Beilstein/REAXYS Number:
3844873
MDL number:
MFCD00078142

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agency

meets EP testing specifications

Quality Segment

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

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.

Disclaimer

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.

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1 of 1

This Item
1651009T0600000BP480
Tetracycline hydrochloride ≥95% (European Pharmacopoeia HPLC assay), meets EP testing specifications

Sigma-Aldrich

T3383

Tetracycline hydrochloride

Tetracycline hydrochloride United States Pharmacopeia (USP) Reference Standard

USP

1651009

Tetracycline hydrochloride

Tetracycline hydrochloride European Pharmacopoeia (EP) Reference Standard

T0600000

Tetracycline hydrochloride

Tetracycline hydrochloride British Pharmacopoeia (BP) Reference Standard

BP480

Tetracycline hydrochloride

description

≥95% (European Pharmacopoeia HPLC assay), meets EP testing specifications

description

United States Pharmacopeia (USP) Reference Standard

description

European Pharmacopoeia (EP) Reference Standard

description

British Pharmacopoeia (BP) Reference Standard

mode of action

protein synthesis | interferes

mode of action

-

mode of action

-

mode of action

-

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

antibiotic activity spectrum

-

antibiotic activity spectrum

-

antibiotic activity spectrum

-

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

-

assay

≥95% (European Pharmacopoeia HPLC assay)

assay

-

assay

-

assay

-

form

powder

form

-

form

-

form

crystalline powder

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

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Signal Word

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

WGK

WGK 2

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

PPE (personal protective equipment)

dust mask type N95 (US), Eyeshields, Gloves

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Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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