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Chlortetracycline

CAS No.
57-62-5
Chemical Name:
Chlortetracycline
Synonyms
CHLOROTETRACYCLINE;Clortetraciclina;Chlortetracyclin;Chlortetracycline Premix;aureomykoin;Aurofac;flamycin;duomycin;acronize;Biovetin
CBNumber:
CB5408663
Molecular Formula:
C22H23ClN2O8
Molecular Weight:
478.88
MDL Number:
MFCD00864876
MOL File:
57-62-5.mol
Last updated:2023-11-09 20:36:52

Chlortetracycline Properties

Melting point 168-169°
alpha D23 -275.0° (methanol)
Boiling point 821.1±65.0 °C(Predicted)
Density 1.2833 (rough estimate)
refractive index 1.6000 (estimate)
storage temp. 2-8°C
solubility DMF: Soluble; DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble
form A solid
pka pKa 3.3 (Uncertain)
Water Solubility 0.63g/L(25 ºC)
LogP -0.620
FDA 21 CFR 556.150; 558.128; 558.4
CAS DataBase Reference 57-62-5(CAS DataBase Reference)
FDA UNII WCK1KIQ23Q
ATC code A01AB21,D06AA02,J01AA03,S01AA02
EPA Substance Registry System Chlortetracycline (57-62-5)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P330-P501
Hazard Codes  Xn
Risk Statements  22
WGK Germany  1
RTECS  QI7750000
NFPA 704
0
1 0

Chlortetracycline price More Price(9)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 17776 Chlortetracycline Selective Supplement suitableformicrobiology 57-62-5 5vials $72.1 2024-03-01 Buy
Cayman Chemical 23302 Chlortetracycline ≥98% 57-62-5 5mg $177 2024-03-01 Buy
Cayman Chemical 23302 Chlortetracycline ≥98% 57-62-5 25mg $831 2024-03-01 Buy
American Custom Chemicals Corporation API0001975 CHLOROTETRACYCLINE 95.00% 57-62-5 1G $945.95 2021-12-16 Buy
AK Scientific S042 Chlortetracycline 57-62-5 5mg $294 2021-12-16 Buy
Product number Packaging Price Buy
17776 5vials $72.1 Buy
23302 5mg $177 Buy
23302 25mg $831 Buy
API0001975 1G $945.95 Buy
S042 5mg $294 Buy

Chlortetracycline Chemical Properties,Uses,Production

Description

Chlortetracycline (Brand name: Aureomycin) is the 7-chloro substitution derivative of the tetracycline and has a golden color. As a veterinary medicine, chlortetracycline is commonly used for the treatment of conjunctivitis of cats. It can also be used in the treatment of infections occurring in the urinary tract, respiratory tract, and the intestines. Its mechanism of action is through inhibiting the protein synthesis, inhibiting the binding of aminoacyl-tRNA to the mRNA-ribosome complex through binding to the 30S ribosome subunit.

Originator

Aureomycin, Lederle, US ,1948

Uses

Chlortetracycline was the first reported member of the tetracycline class, isolated from Streptomyces aureofaciens in 1948. Chlortetracyclines heralded the early wave of antibiotic discoveries from microbes and after 50 years are still widely used as pharmaceuticals. Chlortetracycline is a pigment and, like most pigments, is extremely sensitive to environmental and storage conditions. Commercial chlortetracycline may contain significant levels of degradation products.

Definition

ChEBI: A member of the class of tetracyclines with formula C22H23ClN2O8 isolated from Streptomyces aureofaciens.

Indications

Chlorotetracycline, an antibiotic with a broad spectrum of action, causes a bacteriostatic effect with respect to Gram-positive (staphylococci, including those that produce penicillinase; streptococci, pneumococci; clostridia, listeria, and anthrax bacillus) and Gram-negative microorganisms (gonococci, whooping cough bacillus, colon bacillus, enterobacteria, klebisella, salmonella, shigella), as well as Rickettsia, chlamydia, mycoplasma, and spirochaeta. Blue-pus bacillus, proteus, serracia, most strains of Bacteroides fragilis, most fungi, and small viruses are resistant to this drug. It is used for pneumonia, bronchitis, empyema of the lungs, angina, cholecystitis, whooping cough, endocarditis, endometritis, intestinal infections, prostatitis, syphilis, gonorrhea, brucellosis, osteomyelitis, purulent infections of soft tissues, and others caused by microorganisms sensitive to this drug. Synonyms of this drug are aureomycin, biomycin, xanthomycin, and others.

Manufacturing Process

The following process description is taken from US Patent 2,987,449. An appropriate S. aureofaciens strain such as mutant S1308 (ATCC No. 12,748) is grown aerobically in a suitable inoculum medium. A typical medium used to grow the primary inoculum is prepared according to the following formula: sucrose, 20.0 g; corn steep liquor, 16.5 ml, ammonium sulfate, 2.0 g; calcium carbonate, 7.0 g; and water to 1,000 ml.
A 100 ml aliquot of this medium is placed in a 500 mi Erlenmeyer flask and sterilized by autoclaving for 20 minutes under 15 psi pressure. Spores of mutant strain S. aureofaciens S1308 (ATCC No. 12,748) are washed from an agar slant into the flask with sterile distilled water to form a suspension containing approximately 108 spores per milliliter. A 1.0 ml portion of this suspension is used to inoculate the fermentation media in the example which follows. A fermentation medium consisting of the following ingredients was prepared.
25 ml aliquots of this fermentation medium were placed in each of two 250 ml Erlenmeyer flasks and 0.5 ml of lard oil was added to each flask. Then 0.002 mg/ml of riboflavin was added to one flask, the other flask being retained as a control. The flasks were sterilized in an autoclave for 20 minutes under 15 psi pressure, then cooled to room temperature (25°±5°C). At this point, a 1.0 ml portion of inoculum of mutant strain S. aureofaciens S1308 (ATCC No. 12,748) was added to each of the two flasks. The flasks were incubated at25°C for 120 hours on a rotary shaker operating at 180 rpm. Upon completion of the fermentation period the mashes were assayed for 7-chlorotetracycline content.
The increase in production due to the addition of riboflavin was very noticeable in the above example. A similar effect was reported for cupric sulfate pentahydrate addition according to US Patent 3,050,446.

Therapeutic Function

Antibacterial

Antimicrobial activity

It is slightly less active than tetracycline against many bacteria, with the exception of Gram-positive organisms.

Pharmaceutical Applications

7-Chlortetracycline. A fermentation product of certain strains of Streptomyces aureofaciens. Formulated as the hydrochloride or the free base for oral or topical application.

Pharmacokinetics

Oral absorption:30–60%
Cmax 500 mg oral:2.5–7 mg/L:
Plasma half-life: 5–6 h
Volume of distribution: c.2 L/kg
Plasma protein binding: 47–65%
Absorption is relatively poor compared with other tetracyclines. It undergoes rapid metabolism and is largely eliminated by biliary excretion, with only a small proportion eliminated via the kidney. Despite this, chlortetracycline is not recommended for patients in renal failure, since accumulation occurs as a consequence of the half-life increase to approximately 7–11 h.

Clinical Use

Its uses are those common to the group. It has also been used topically in the management of recurrent aphthous ulcers of the mouth, but experience is limited and the mechanism of action is unknown.

Side effects

Side effects are typical of the group. Contact hypersensitivity has been reported with topical application to abraded skin and varicose ulcers.

Safety Profile

Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of Cland NOx. See also TETRACYCLINE.

Synthesis

Chlorotetracyline, 7-chloro-4-dimethylamino-1,4,4a,5,5a,6,11,12aoxtahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacencarboxamide (32.3.1), is obtained biosynthetically as a result of the activity of a microorganism, the actinomycete S. aureofaciens.

Veterinary Drugs and Treatments

There are a variety of approved chlortetracycline products for use in food animals. It may also be useful in treating susceptible infections in dogs, cats, birds and small mammals (not Guinea pigs). For more information, refer to the Doses section below.

Purification Methods

Aureomycin is dehydrated by azeotropic distillation of its solution with toluene. On cooling, the anhydrous material crystallises out and is recrystallised from *C6H6, then dried under vacuum at 100o over paraffin wax. (If it is crystallised from MeOH, it contains MeOH which is not removed on drying.) [Stephens et al. J Am Chem Soc 76 3568 1954, Laskin & Chan Biochem Biophys Res Commun 14 137 1964]. [Beilstein 14 IV 2631.]

Chlortetracycline Preparation Products And Raw materials

Global( 178)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Lingding Biotechnology Co., Ltd.
+86-18031140164 +86-19933155420 erin@hbldbiotech.com China 882 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21700 55
Shanghai Yingrui Biopharma Co., Ltd.
+86-21-33585366 - 03@ sales03@shyrchem.com CHINA 738 60
Hefei TNJ Chemical Industry Co.,Ltd.
+86-0551-65418679 +86-18949832763 info@tnjchem.com China 2989 55
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29914 58
Hubei Jusheng Technology Co.,Ltd.
18871490254 linda@hubeijusheng.com CHINA 28180 58
Cangzhou Wanyou New Material Technology Co.,Ltd
18631714998 sales@czwytech.com CHINA 906 58
Chongqing Chemdad Co., Ltd
+86-023-61398051 +8613650506873 sales@chemdad.com China 39916 58
CONIER CHEM AND PHARMA LIMITED
+8618523575427 sales@conier.com China 47465 58
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000 marketing@targetmol.com United States 19892 58

View Lastest Price from Chlortetracycline manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Chlortetracycline pictures 2024-03-26 Chlortetracycline
57-62-5
US $0.00 / Kg/Bag 2Kg/Bag 99% up, High Density 20 tons Sinoway Industrial co., ltd.
Chlortetracycline pictures 2023-11-09 Chlortetracycline
57-62-5
US $50.00 / KG 1KG 99% 9000kg/per month Hebei Lingding Biotechnology Co., Ltd.
Chlortetracycline Hydrochloride pictures 2023-03-06 Chlortetracycline Hydrochloride
57-62-5
US $200.70 / Kg/Bag 10g 99% 10000kg Hebei Guanlang Biotechnology Co,.LTD
  • Chlortetracycline pictures
  • Chlortetracycline
    57-62-5
  • US $0.00 / Kg/Bag
  • 99% up, High Density
  • Sinoway Industrial co., ltd.
acronize aureocina aureomycina-377 biomitsin chlortetracycline chrysomykine duomycin flamycin ydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,[4s-(4alpha,4aalpha,5a 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 Acronize PD Aureocarmyl Aureociclin Aureomicina Aureomycin-R Aurofac Chlortetracycline (15%) 10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-ydro-6 7-chlorotetracycline Aurofac 10 Biomycin A Biovetin Chlortetracyclinum Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S-(4alpha,4aalpha,5aalpha,6beta,12aalpha))- Streptomyces aureofaciens antibiotic CHLORTETRACYCLINE HCL ( VETERINARY) auromycin Chlorotetracycline HCL(Vet) ChlorotetracyclineF.G.powder F.G.granulated Chlorotetracyclinebaseand/orunspecifiedsalts 2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S,4aS,5aS,6S,12aS)- aureomycine chlortetracycline,calcium salt Feed aureomycin powder Chlorotetracycline, Chlortetracycline Uromycin Chlortetracycline Selective Supplement,Chlorotetracycline, Chlortetracycline Chlortetracycline, AureoMycin Chlortetracycline base AureoMycin, Chlorotetracycline, BioMycin (4S,4aS,5aS,6S,12aS)-7-Chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide Chlortetracycline USP/EP/BP CHLORTETRACYCLINE CA Chlorotetracyclin Animals Pharmaceutical 7-Chlorotetracycline Feed Additive Chlortetracycline CAS 57-62-5 Chlorotetracycline (API) aureomykoin CHLOROTETRACYCLINE Clortetraciclina Chlortetracyclin Chlortetracycline Premix Chlortetracycline HCG Paracetamol Impurity 41 Lymecycline EP Impurity G(Chlortetracycline) 57-62-5 C22H23CIN2O8 C22H23ClN2O3