C4881

Sigma-Aldrich

Chlortetracycline hydrochloride

≥91.0% dry basis (HPLC)

Synonym(s):
7-Chlorotetracycline hydrochloride
Empirical Formula (Hill Notation):
C22H23ClN2O8 · HCl
CAS Number:
Molecular Weight:
515.34
Beilstein/REAXYS Number:
3858364
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

Quality Level

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

Mode of action

protein synthesis | interferes

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

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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Related Categories

General description

Chemical structure: tetracycline

Packaging

5, 25, 100 g in glass bottle

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

Signal Word

Warning

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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...
Lindsay Gillan et al.
Theriogenology, 63(2), 445-457 (2005-01-01)
Most laboratory methods used to evaluate semen quality have not correlated highly with fertilizing capacity. The discovery of a variety of fluorochromes and compounds conjugated to fluorescent probes has enabled a more widespread analysis of sperm attributes, and in conjunction...
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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