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Chlortetracycline hydrochloride

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Chlortetracycline hydrochloride Basic information
Chlortetracycline hydrochloride Chemical Properties
  • Melting point:210-215 °C (dec.)(lit.)
  • alpha D23 -240°
  • storage temp. 2-8°C
  • solubility 1 M NaOH: soluble50mg/mL
  • form Powder
  • color faint yellow to yellow
  • pka3.3(at 25℃)
  • Water Solubility Soluble in water
  • Sensitive Light Sensitive
  • Merck 13,2211
  • BRN 3858364
  • CAS DataBase Reference64-72-2(CAS DataBase Reference)
  • EPA Substance Registry SystemChlortetracycline 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
  • ToxicityLD50 orally in rats: 10300 mg/kg (Goldenthal)
MSDS
Chlortetracycline hydrochloride Usage And Synthesis
  • Chemical PropertiesYellow Solid
  • Usesantibacterial, antiamebic, Ca chelator, hepatotoxic; inhibits protein synthesis
  • UsesChlortetracycline is an antibiotic substance isolated from the substrate of Streptomyces aureofaciens. Chlortetracycline is an antimicrobial and antibacterial.
  • UsesChlortetracycline 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.
  • UsesAn antimicrobial and antibacterial. This compound contains an undetermined amount of epi-chlortetracycline
  • brand nameAureomycin (Lederle).
  • General DescriptionChlortetracycline (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 MethodsPurify 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.]
Chlortetracycline hydrochloride Preparation Products And Raw materials
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