Chlortetracycline hydrochloride Chemical Properties

Melting point:

210-215 °C (dec.)(lit.)

alpha 

D23 -240°

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

1 M NaOH: soluble50mg/mL

form 

Powder

color 

faint yellow to yellow

pka

3.3(at 25℃)

Water Solubility 

Soluble in water

Sensitive 

Light Sensitive

Merck 

13,2211

BRN 

3858364

CAS DataBase Reference

64-72-2(CAS DataBase Reference)

EPA Substance Registry System

Chlortetracycline hydrochloride (64-72-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

RTECS 

QI7800000

HazardClass 

3

HS Code 

29413020

Toxicity

LD50 orally in rats: 10300 mg/kg (Goldenthal)

MSDS

• Language:English Provider:[4S-(4alpha,4aalpha,5aalpha,6beta,12aalpha)]-7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide monohydrochloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Chlortetracycline hydrochloride Usage And Synthesis

Description

Chlortetracycline was found in the culture broth of Streptomyces aureofaciens by Duggar et al. of Lederle Laboratories in 1948 and named aureomycin. It shows a wider range of antibiotic activity than the earlier antibiotics, penicillins, and streptomycins and as great as that of chloramphenicol. Its activity covers grampositive and gram-negative bacteria as well as Rickettsia and Chlamydiae. Chlortetracycline has been replaced by other tetracyclines in clinical use and is used now used as a feed additive to promote the growth of livestock.

Chemical Properties

Yellow Solid

Uses

antibacterial, antiamebic, Ca chelator, hepatotoxic; inhibits protein synthesis

Uses

Chlortetracycline is an antibiotic substance isolated from the substrate of Streptomyces aureofaciens. Chlortetracycline is an antimicrobial and antibacterial.

Uses

An antimicrobial and antibacterial. This compound contains an undetermined amount of epi-chlortetracycline

Uses

Chlortetracycline hydrochloride is a salt prepared from chlortetracycline taking advantage of the basic dimethylamino group which protonates and readily forms the salt in hydrochloric acid solutions. The hydrochloride is the preferred formulation for pharmaceutical applications. Like all tetracyclines, chlortetracycline shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal sub-units, blocking protein synthesis.

brand name

Aureomycin (Lederle).

General Description

Chlortetracycline (Aureomycin hydrochloride) was isolatedby Duggar in 1948 from S. aureofaciens. This compound,which was produced in an extensive search for new antibiotics,was the first of the group of highly successful tetracyclines.It soon became established as a valuable antibioticwith broad-spectrum activities.
It is used in medicine chiefly as the acid salt of the compoundwhose systematic chemical designation is 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide.The hydrochloride salt is a crystallinepowder with a bright yellow color, which suggested itsbrand name, Aureomycin. It is stable in air but slightly photosensitiveand should be protected from light. It is odorlessand bitter. One gram of the hydrochloride salt will dissolvein about 75 mL of water, producing a pH of about 3. It isonly slightly soluble in alcohol and practically insoluble inother organic solvents.
Oral and parenteral forms of chlortetracycline are nolonger used because of the poor bioavailability and inferiorpharmacokinetic properties of the drug. It is still marketed inointment forms for topical and ophthalmic use.

Purification Methods

Purify the salt by dissolving 1g rapidly in 20mL of hot water, cooling rapidly to 40o, treating with 0.1mL of 2M HCl, and chilling in an ice-bath. The process is repeated twice. It is also recrystallised from Me2NCHO/Me2CO. [Stephens et al. J Am Chem Soc 76 3568 1954, UV: McCormick et al. J Am Chem Soc 79 2849 1975, Beilstein 14 IV 2631.]

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