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Chlortetracycline

Chlortetracycline structure

CAS No:
57-62-5
Formula:
C22H23ClN2O8
Chemical Name:
Chlortetracycline
Synonyms:
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)-;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-;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-(4α,4aα,5aα,6β,12aα)]-;(4S,4aS,5aS,6S,12aS)-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;Acronize PD;Aureocina;Aureomykoin;Biomycin;7-Chlorotetracycline;Chlortetracycline;7-Chlortetracycline;Chrysomykine;CTC;Duomycin;Flamycin;Aureomycin;Chlortetracyclin;Aurofac 10;Biomycin a;Aurofac;Aureociclin;Aureocarmyl;Aureomicina;Tri-chlortetracycline;Uromycin;CTC (antibiotic);Chrusomykine;Orospray;Centraureo;Aureomycin 100G;Chlorocyclinum;A-Mycin;Chloratet 50;7-Chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-naphthacenecarboxamide;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;4-(Dimethylamino)-7-chloro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4,5,6,12a,4a,5a-hexahydronaphthacene-2-carboxamide;96066-24-9;96968-60-4;98271-27-3;103651-17-8;856305-72-1;879633-99-5;1236363-43-1
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Chlorotetracycline (7-Chlorotetracycline) is a specific and potent calcium ionophore antibiotic, inhibits binding of aminoacyl-tRNA to ribosomes.

Chlortetracycline is a member of the class of tetracyclines with formula C22H23ClN2O8 isolated from Streptomyces aureofaciens. It has a role as an antiprotozoal drug, a fluorescent probe, a calcium ionophore and an antibacterial drug. It is a member of monochlorobenzenes, a tertiary amino compound, a tertiary alcohol, a monocarboxylic acid amide, a tertiary alpha-hydroxy ketone and a member of tetracyclines. It is a conjugate acid of a chlortetracycline(1-).|Chlortetracycline is a tetracycline antibiotic, and historically the first member of this class to be identified. It was discovered in 1945 by the scientist, Benjamin Minge Duggar, working at Lederle Laboratories under the supervision of Yellapragada Subbarow. He discovered that this antibiotic was the product of an actinomycete strain he cultured and obtained from a soil sample from a field in Missouri. The organism was named Streptomyces aureofaciens due to its gold-hued color.|A TETRACYCLINE with a 7-chloro substitution.

Chlortetracycline Basic Attributes

Molecular Weight：

478.88

Exact Mass：

478.88

EC Number：

200-341-7

UNII：

WCK1KIQ23Q

DSSTox ID：

DTXSID9022811

ATC Code：

S01AA02|A - Alimentary tract and metabolism|D - Dermatologicals|J - Antiinfectives for systemic use|S - Sensory organs

Characteristics

PSA：

181.62000

XLogP3：

-0.53

Appearance：

Golden yellow crystal powder

Density：

1.52 g/cm³

Melting Point：

168.5 °C

Boiling Point：

821.1±65.0 °C at 760 mmHg

Flash Point：

450.4±34.3 °C

Refractive Index：

1.745

Water Solubility：

0.63g/L(25 ºC)

Storage Conditions：

2-8°C

Specific rotation：

D23 -275.0° (methanol)

Dissociation Constants：

7.435

Collision Cross Section：

203.9 Å² [M+H]+ [CCS Type: TW]|199 Å² [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|210.5 Å² [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|202.55 Å² [M-H]-

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

RTECS Number：

QI7750000

Marks：

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 129 companies from 2 notifications to the ECHA C&L Inventory.

Toxicity

Toxicity Summary：

The acute oral LD50 in mice is 2314mg/kg [MSDS].The most common adverse effects of tertacylines are gastrointestinal disturbances, and staining of teeth and bone. Some occurences of dental hypoplasia and bone deformity have been noted. In pregnant women tetracyclines may produce hepatotoxicity.

Protein Binding：

Chlortetracline is 50-55% bound to plasma proteins.

Drug Information

Drug Indication：

Used in the manufacuring of medicated animal feeds.|FDA Label

Pharmacology：

Tetracycline antibiotics are bacteriostatic agents which act to inhibit bacterial growth and reproduction.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)|Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

Absorption：

Chortetracycline reaches peak plasma concentation in about 3 hours. Its oral bioavailability is 25-30%.|Chlortetracycline is mainly eliminated in feces. Renal function does not appear to affect the rate of elimination.|Chlortetracycline has a volume of distribution of 100 liters.

Metabolism/Metabolites：

Chlortetracycline is not known to undergo significant metabolism.

Biological Half-Life：

The half-life of Chlortetracycline is 5.6 hours.

Mechanism of Action：

Chlortetracycline, like other tetracyclines, competes for the A site of the bacterial ribosome. This binding competes with tRNA carrying amino acids preventing the addition of more amino acids to the peptide chain. This inhibition of protein synthesis ultimately inhibits growth and reproduction of the bacterial cell as necessary proteins cannot be synthesized.

MeSH Entry Terms：

4-Epimer Chlortetracycline

Chlortetracycline Use and Manufacturing

Methods of Manufacturing

It is produced by fermentation of Streptomyces aureofacieus. The fermentation broth is acidified and filtered to obtain a precipitate, which is dissolved in ethanol and then acid precipitated to obtain a crude product. After dissolution and salt formation, hydrochloride crystals are obtained.

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.

Manufacturing Info：

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)-: ACTIVE

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients|Veterinary Drug -> ANTIMICROBIAL_AGENT; -> JECFA Functional Classes|Polyketides [PK] -> Linear tetracyclines [PK07]|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Food Additive Classes：

Veterinary Drug -> ANTIMICROBIAL_AGENT;

Computed Properties

Molecular Weight:478.9
XLogP3:-1.3
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:2
Exact Mass:478.1142934
Monoisotopic Mass:478.1142934
Topological Polar Surface Area:182
Heavy Atom Count:33
Complexity:1010
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Methanol

Drug Function and Efficacy

This product is a broad-spectrum antibacterial agent with bactericidal effect at high concentrations. Many Rickettsia, Mycoplasma, Chlamydia, atypical mycobacteria, and spirochetes are also sensitive to this product. This product is better than Gram-positive bacteria for Gram-negative bacteria, but Enterococcus is resistant to it. Others such as Actinomycetes, Bacillus anthracis, Listeria monocytogenes, Clostridium, Nocardia, Vibrio, Brucella, Campylobacter, and Yersinia are sensitive to this product. This product has certain antibacterial activity against Neisseria gonorrhoeae, but penicillin-resistant Neisseria gonorrhoeae is also resistant to doxycycline. There is cross-resistance between this product and different varieties of tetracycline antibiotics. The mechanism of action of this product is that the drug can specifically bind to the A position of the 30S subunit of the bacterial ribosome, inhibit the growth of the peptide chain and affect the synthesis of bacterial proteins. Animal experiments have confirmed that this product is teratogenic. In vitro experiments have shown that this product may cause mutations at a certain concentration.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Doxycycline Hydrochloride Tablets
Ingredients	Tetracycline antibiotics. This product is a broad-spectrum antibacterial agent with bactericidal effects at high concentrations. Many Rickettsia, Mycoplasma, Chlamydia, atypical mycobacteria, and spirochetes are also sensitive to this product. This product is more effective against Gram-positive bacteria than Gram-negative bacteria, but Enterococcus is resistant to it. Others such as Actinomycetes, Bacillus anthracis, Listeria monocytogenes, Clostridium, Nocardia, Vibrio, Brucella, Campylobacter, and Yersinia are sensitive to this product. This product has certain antibacterial activity against Neisseria gonorrhoeae, but penicillin-resistant Neisseria gonorrhoeae is also resistant to doxycycline. Due to the widespread use of tetracyclines over the years, common clinical pathogens have become seriously resistant to this product, including Gram-positive bacteria such as Staphylococcus and most Gram-negative bacilli. There is cross-resistance between this product and different varieties of tetracycline antibiotics. The mechanism of action of this product is that the drug can specifically bind to the A position of the bacterial ribosome 30S subunit, inhibiting the growth of the peptide chain and affecting the synthesis of bacterial protein. Animal experiments have confirmed that this product is teratogenic. In vitro tests have shown that this product may be mutagenic at a certain concentration.
Indication	1. This product can inhibit the activity of plasma prothrombin, so patients receiving anticoagulant therapy need to adjust the dose of anticoagulants. 2. When barbiturates, phenytoin or carbamazepine are used with this product, the above drugs can induce the activity of microsomal enzymes and cause a decrease in the blood concentration of doxycycline, so the dose of doxycycline must be adjusted.
Specifications	0.1g (calculated as C22H24N2O8) (plain tablet)
Manufacturer	Harbin Pharmaceutical Group Pharmaceutical Factory No.6

Chlortetracycline Hydrochloride Eye Ointment
Ingredients	The main ingredient is chlortetracycline.
Indication	Not yet clear.
Specifications	0.50%
Manufacturer	Henan Daxin Pharmaceutical Co., Ltd.

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