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C4881

Sigma-Aldrich

Chlortetracycline hydrochloride

≥91.0% dry basis (HPLC)

Synonym(s):

7-Chlorotetracycline hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C22H23ClN2O8 · HCl
CAS Number:
64-72-2
Molecular Weight:
515.34
Beilstein:
3858364
EC Number:
200-591-7
MDL number:
MFCD00082440
UNSPSC Code:
51101500
PubChem Substance ID:
24892735
NACRES:
NA.85

Quality Level

200

Assay

≥91.0% dry basis (HPLC)

form

powder

pKa (25 °C)

3.3
7.4
9.3

mp

210-215 °C (dec.) (lit.)

solubility

1 M NaOH: 50 mg/mL

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]2CC3C(=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c4c(O)ccc(Cl)c4[C@@]3(C)O

InChI

1S/C22H23ClN2O8.ClH/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21;/h4-5,7-8,15,26,28-29,32-33H,6H2,1-3H3,(H2,24,31);1H/t7?,8-,15-,21-,22-;/m0./s1

InChI key

CBHYYLPALVVVEY-LYNLVHCPSA-N

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General description

Chemical structure: tetracycline

Application

Chlortetracycline was used in fluorescence assays to detect the Ca+2 influx required for the completion of acrosome reaction in human spermatozoa.

Biochem/physiol Actions

Chlortetracycline is an antibiotic produced by some strains of Streptomyces aureofaciens. It inhibits protein synthesis (elongation) by preventing binding of aminoacyl-tRNA to the 30S subunit. It is effective against Gram-positive and to a lesser degree Gram-negative bacteria than tetracycline.
Mode of Resistance: Loss of cell wall permeability.

Other Notes

If stored frozen, chlortetracycline hydrochloride is expected to remain stable at least four years.

Pictograms

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Warning

Hazard Classifications

Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - Skin Sens. 1 - 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A H Amin et al.
Human reproduction (Oxford, England), 11(4), 741-745 (1996-04-01)
This study was designed to compare three different fluorescent probes to assay the acrosome reaction in human spermatozoa: chlortetracycline (CTC), mannosylated bovine serum albumin (BSA) labelled with fluorescein (MAF), and quinacrine (QN). Normal human sperm ejaculates were washed and allowed
Y H Choi et al.
Biology of reproduction, 59(6), 1328-1333 (1998-11-26)
Cyclodextrin, which stimulates cholesterol efflux from cells, was examined for its ability to induce capacitation of mouse spermatozoa. A chemically defined, protein-free medium was used for in vitro fertilization of cumulus-free mouse eggs. Fertilization did not occur in modified Krebs-Ringer
Kenneth N Agwuh et al.
The Journal of antimicrobial chemotherapy, 58(2), 256-265 (2006-07-04)
The pharmacokinetics of tetracyclines and glycylcyclines are described in three groups. Group 1, the oldest group, represented by tetracycline, oxytetracycline, chlortetracycline, demeclocycline, lymecycline, methacycline and rolitetracycline is characterized by poor absorption after food. Group 2, represented by doxycycline and minocycline
Claudia Cerella et al.
Annals of the New York Academy of Sciences, 1099, 490-493 (2007-04-21)
Many studies suggest that endoplasmic reticulum (ER) Ca2+ pool rather than cytosolic Ca2+ may play a crucial role in triggering apoptosis. In this study, we performed an image analysis of cells loaded with the fluorescent dye chlortetracycline (CTC) to in
A E Oliver et al.
Biophysical journal, 78(4), 2116-2126 (2000-03-29)
The effect of temperature on the binding equilibria of calcium-sensing dyes has been extensively studied, but there are also important temperature-related changes in the photophysics of the dyes that have been largely ignored. We conducted a systematic study of thermal
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