Chlortetracycline

Identification

Summary

Chlortetracycline is the first tetracycline antibiotic most commonly used for veterinary purposes.

Generic Name

Chlortetracycline

DrugBank Accession Number

DB09093

Background

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.

Type

Small Molecule

Groups

Approved, Investigational, Vet approved

Structure

Similar Structures

Weight: Average: 478.88
Monoisotopic: 478.114293429
Chemical Formula: C₂₂H₂₃ClN₂O₈

Synonyms

Chlortetracycline
Chlortétracycline
Chlortetracyclinum
Clortetraciclina

Pharmacology

Indication

Used in the manufacuring of medicated animal feeds ^Label.

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Associated Conditions

Contraindications & Blackbox Warnings

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Pharmacodynamics

Tetracycline antibiotics are bacteriostatic agents which act to inhibit bacterial growth and reproduction ².

Mechanism of action

Chlortetracycline, like other tetracyclines, competes for the A site of the bacterial ribosome ². 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.

Target	Actions	Organism
A16S ribosomal RNA	inhibitor	Enteric bacteria and other eubacteria
A30S ribosomal protein S3	inhibitor	Escherichia coli (strain K12)
A30S ribosomal protein S8	inhibitor	Escherichia coli (strain K12)
A30S ribosomal protein S19	inhibitor	Escherichia coli (strain K12)
A30S ribosomal protein S14	inhibitor	Escherichia coli (strain K12)
A30S ribosomal protein S7	inhibitor	Escherichia coli (strain K12)
UADP-ribosylation factor 1	inhibitor	Humans
UCatalase	inhibitor	Micrococcus luteus
UEphrin type-B receptor 1	inhibitor	Humans
UPancreatic triacylglycerol lipase	inhibitor	Humans
UProtein-arginine deiminase type-4	inhibitor	Humans

Absorption

Chortetracycline reaches peak plasma concentation in about 3 hours ¹. Its oral bioavailability is 25-30%.

Volume of distribution

Chlortetracycline has a volume of distribution of 100 liters ¹.

Protein binding

Chlortetracline is 50-55% bound to plasma proteins ¹.

Metabolism

Chlortetracycline is not known to undergo significant metabolism ¹.

Route of elimination

Chlortetracycline is mainly eliminated in feces ¹. Renal function does not appear to affect the rate of elimination.

Half-life

The half-life of Chlortetracycline is 5.6 hours ¹.

Clearance

Not Available

Adverse Effects

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Toxicity

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 ². In pregnant women tetracyclines may produce hepatotoxicity.

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Acetylcysteine	The therapeutic efficacy of Acetylcysteine can be decreased when used in combination with Chlortetracycline.
Ambroxol	The risk or severity of methemoglobinemia can be increased when Chlortetracycline is combined with Ambroxol.
Articaine	The risk or severity of methemoglobinemia can be increased when Chlortetracycline is combined with Articaine.
Benzocaine	The risk or severity of methemoglobinemia can be increased when Chlortetracycline is combined with Benzocaine.
Benzyl alcohol	The risk or severity of methemoglobinemia can be increased when Chlortetracycline is combined with Benzyl alcohol.
Bupivacaine	The risk or severity of methemoglobinemia can be increased when Chlortetracycline is combined with Bupivacaine.
Butacaine	The risk or severity of methemoglobinemia can be increased when Chlortetracycline is combined with Butacaine.
Butamben	The risk or severity of methemoglobinemia can be increased when Chlortetracycline is combined with Butamben.
Capsaicin	The risk or severity of methemoglobinemia can be increased when Chlortetracycline is combined with Capsaicin.
Chloroprocaine	The risk or severity of methemoglobinemia can be increased when Chlortetracycline is combined with Chloroprocaine.

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Food Interactions

No interactions found.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Chlortetracycline bisulfate	1D06KZ672I	27823-62-7	GQUMQTDURIYYIA-MRFRVZCGSA-N
Chlortetracycline calcium complex	NR4B2SX17S	57122-99-3	BRXWPGYMDYZZNU-NAUDNZITSA-L
Chlortetracycline hydrochloride	O1GX33ON8R	64-72-2	CBHYYLPALVVVEY-MRFRVZCGSA-N

International/Other Brands

Aueromycin

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Aureomycin - Ont Top 3%	Ointment	3 %	Topical	Wyeth Ayerst Canada Inc.	1997-10-24	2000-08-02
Aureomycin Ont 3%	Ointment	3 %	Topical	Lederle Cyanamid Canada Inc.	1952-12-31	1997-11-24
Aureomycin Ont Oph 1%	Ointment	1 %	Ophthalmic	Lederle Cyanamid Canada Inc.	1955-12-31	1997-01-14

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
ขี้ผึ้งทรามัยซิน ใส่แผล	Ointment	3 %w/w	Topical	บริษัท แลชแมน จำกัด จำกัด	1986-01-16	Not applicable
ขี้ผึ้งใส่แผล ฮีโร่มัยซิน	Ointment	3 %w/w	Topical	บริษัท ฮีโร่มัยซิน ฟาร์ม่า จำกัด จำกัด	2003-04-23	Not applicable
ออริโอมัยซิน *	Ointment	3 %w/w	Topical	บริษัท อินเตอร์ไทย ฟาร์มาซูติเคิ้ล แมนูแฟคเจอริ่ง จำกัด จำกัด	1998-01-30	Not applicable
โคบาล มัยซิน ออยเม้นท์	Ointment	3 %w/w	Topical	บริษัท ไบร์วู๊ดฟาร์มาซูติคอล จำกัด	1987-08-03	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Aureocort 1 mg/g + 30 mg/g Salbe	Chlortetracycline hydrochloride (30 mg/g) + Triamcinolone acetonide (1 mg/g)	Ointment	Topical	Dermapharm Gmb H	1966-09-28	Not applicable
ไทรไมซิน ออยท์เมนท์	Chlortetracycline (5 MG/1G) + Chloramphenicol (5 MG/1G) + Neomycin (5 MG/1G)	Ointment	Topical	บริษัท สหแพทย์เภสัช จำกัด	2017-01-25	2020-08-24

Chemical Identifiers

UNII: WCK1KIQ23Q
CAS number: 57-62-5
InChI Key: CYDMQBQPVICBEU-XRNKAMNCSA-N
InChI: InChI=1S/C22H23ClN2O8/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)/t7-,8-,15-,21-,22-/m0/s1
IUPAC Name: (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
SMILES: [H][C@@]12C[C@@]3([H])C(=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C)C(=O)C1=C(O)C=CC(Cl)=C1[C@@]3(C)O

References

General References

Agwuh KN, MacGowan A: Pharmacokinetics and pharmacodynamics of the tetracyclines including glycylcyclines. J Antimicrob Chemother. 2006 Aug;58(2):256-65. Epub 2006 Jul 1. [Article]
49, 50. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 614, 629). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]

External Links

KEGG Drug: D07689
KEGG Compound: C06571
PubChem Compound: 54708735
PubChem Substance: 310265020
ChemSpider: 10469370
RxNav: 2408
ChEBI: 27644
ChEMBL: CHEMBL404520
ZINC: ZINC000019701769
PDBe Ligand: CTC
Wikipedia: Chlortetracycline

PDB Entries

2fj1 / 2tct / 2y6r / 3egz / 4v2g / 5tui / 6qjw / 6umw

FDA label

Download (218 KB)

MSDS

Download (179 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Terminated	Treatment	Osteomyelitis	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Cream
Cream	Ophthalmic	1 %
Ointment	Topical	3 %
Solution / drops		20 ML
Ointment	Ophthalmic	1 %
Ointment	Ophthalmic
Ointment	Ophthalmic	10 mg/g
Ointment	Topical	3 %w/w
Capsule		250 mg
Ointment	Topical

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	Decomposes at 210-215	MSDS

Predicted Properties

Property	Value	Source
Water Solubility	0.259 mg/mL	ALOGPS
logP	-0.13	ALOGPS
logP	-2.9	Chemaxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.99	Chemaxon
pKa (Strongest Basic)	9.04	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	9	Chemaxon
Hydrogen Donor Count	6	Chemaxon
Polar Surface Area	181.62 Å²	Chemaxon
Rotatable Bond Count	2	Chemaxon
Refractivity	118.99 m³·mol^-1	Chemaxon
Polarizability	45.61 Å³	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

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Details1. 16S ribosomal RNA

Kind

Nucleotide

Organism

Enteric bacteria and other eubacteria

Pharmacological action

Yes

Actions

Inhibitor

In prokaryotes, the 16S rRNA is essential for recognizing the 5' end of mRNA and hence positioning it correctly on the ribosome. The 16S rRNA has a characteristic secondary structure in which half of the nucleotides are base-paired. The 16S rRNA sequence has been highly conserved and is often used for evolutionary and species comparative analysis.

References

Nawaz M, Sung K, Khan SA, Khan AA, Steele R: Biochemical and molecular characterization of tetracycline-resistant Aeromonas veronii isolates from catfish. Appl Environ Microbiol. 2006 Oct;72(10):6461-6. [Article]
Domingue GJ Sr: Cryptic bacterial infection in chronic prostatitis: diagnostic and therapeutic implications. Curr Opin Urol. 1998 Jan;8(1):45-9. [Article]
Pringle M, Fellstrom C, Johansson KE: Decreased susceptibility to doxycycline associated with a 16S rRNA gene mutation in Brachyspira hyodysenteriae. Vet Microbiol. 2007 Jul 20;123(1-3):245-8. Epub 2007 Feb 25. [Article]
Rasmussen B, Noller HF, Daubresse G, Oliva B, Misulovin Z, Rothstein DM, Ellestad GA, Gluzman Y, Tally FP, Chopra I: Molecular basis of tetracycline action: identification of analogs whose primary target is not the bacterial ribosome. Antimicrob Agents Chemother. 1991 Nov;35(11):2306-11. [Article]

Details2. 30S ribosomal protein S3

Kind: Protein
Organism: Escherichia coli (strain K12)
Pharmacological action: Yes
Actions: Inhibitor

General Function: Structural constituent of ribosome
Specific Function: Binds the lower part of the 30S subunit head. Binds mRNA in the 70S ribosome, positioning it for translation (By similarity).Plays a role in mRNA unwinding by the ribosome, possibly by forming part...
Gene Name: rpsC
Uniprot ID: P0A7V3
Uniprot Name: 30S ribosomal protein S3
Molecular Weight: 25983.07 Da

References

Buck MA, Cooperman BS: Single protein omission reconstitution studies of tetracycline binding to the 30S subunit of Escherichia coli ribosomes. Biochemistry. 1990 Jun 5;29(22):5374-9. [Article]

Details3. 30S ribosomal protein S8

Kind: Protein
Organism: Escherichia coli (strain K12)
Pharmacological action: Yes
Actions: Inhibitor

General Function: Structural constituent of ribosome
Specific Function: One of the primary rRNA binding proteins, it binds directly to 16S rRNA central domain where it helps coordinate assembly of the platform of the 30S subunit.Protein S8 is a translational repressor ...
Gene Name: rpsH
Uniprot ID: P0A7W7
Uniprot Name: 30S ribosomal protein S8
Molecular Weight: 14126.435 Da

References

Buck MA, Cooperman BS: Single protein omission reconstitution studies of tetracycline binding to the 30S subunit of Escherichia coli ribosomes. Biochemistry. 1990 Jun 5;29(22):5374-9. [Article]

Details4. 30S ribosomal protein S19

Kind: Protein
Organism: Escherichia coli (strain K12)
Pharmacological action: Yes
Actions: Inhibitor

General Function: Trna binding
Specific Function: In the E.coli 70S ribosome in the initiation state (PubMed:12809609) it has been modeled to contact the 23S rRNA of the 50S subunit forming part of bridge B1a; this bridge is broken in the model wi...
Gene Name: rpsS
Uniprot ID: P0A7U3
Uniprot Name: 30S ribosomal protein S19
Molecular Weight: 10430.235 Da

References

Buck MA, Cooperman BS: Single protein omission reconstitution studies of tetracycline binding to the 30S subunit of Escherichia coli ribosomes. Biochemistry. 1990 Jun 5;29(22):5374-9. [Article]

Details5. 30S ribosomal protein S14

Kind: Protein
Organism: Escherichia coli (strain K12)
Pharmacological action: Yes
Actions: Inhibitor

General Function: Structural constituent of ribosome
Specific Function: Binds 16S rRNA, required for the assembly of 30S particles and may also be responsible for determining the conformation of the 16S rRNA at the A site.
Gene Name: rpsN
Uniprot ID: P0AG59
Uniprot Name: 30S ribosomal protein S14
Molecular Weight: 11580.36 Da

References

Buck MA, Cooperman BS: Single protein omission reconstitution studies of tetracycline binding to the 30S subunit of Escherichia coli ribosomes. Biochemistry. 1990 Jun 5;29(22):5374-9. [Article]

Details6. 30S ribosomal protein S7

Kind: Protein
Organism: Escherichia coli (strain K12)
Pharmacological action: Yes
Actions: Inhibitor

General Function: Trna binding
Specific Function: One of the primary rRNA binding proteins, it binds directly to 16S rRNA where it nucleates assembly of the head domain of the 30S subunit. Is located at the subunit interface close to the decoding ...
Gene Name: rpsG
Uniprot ID: P02359
Uniprot Name: 30S ribosomal protein S7
Molecular Weight: 20018.91 Da

References

Buck MA, Cooperman BS: Single protein omission reconstitution studies of tetracycline binding to the 30S subunit of Escherichia coli ribosomes. Biochemistry. 1990 Jun 5;29(22):5374-9. [Article]

Details7. ADP-ribosylation factor 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Receptor signaling protein activity
Specific Function: GTP-binding protein that functions as an allosteric activator of the cholera toxin catalytic subunit, an ADP-ribosyltransferase. Involved in protein trafficking among different compartments. Modula...
Gene Name: ARF1
Uniprot ID: P84077
Uniprot Name: ADP-ribosylation factor 1
Molecular Weight: 20696.62 Da

References

Macia E, Vazquez-Rojas M, Robiolo A, Fayad R, Abelanet S, Mus-Veteau I, Fontaine-Vive F, Mehiri M, Luton F, Franco M: Chlortetracycline, a Novel Arf Inhibitor That Decreases the Arf6-Dependent Invasive Properties of Breast Cancer Cells. Molecules. 2021 Feb 12;26(4). pii: molecules26040969. doi: 10.3390/molecules26040969. [Article]

Details8. Catalase

Kind: Protein
Organism: Micrococcus luteus
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Metal ion binding
Specific Function: Decomposes hydrogen peroxide into water and oxygen; serves to protect cells from the toxic effects of hydrogen peroxide.
Gene Name: katA
Uniprot ID: P29422
Uniprot Name: Catalase
Molecular Weight: 56905.52 Da

References

Ren L, Wang Q, Du Y, Xu P, Zong W: Research on the Impact and Mechanism for the Inhibition of Micrococcus Catalase Activity by Typical Tetracyclines. Biomed Res Int. 2020 Oct 13;2020:5085369. doi: 10.1155/2020/5085369. eCollection 2020. [Article]

Details9. Ephrin type-B receptor 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Receptor tyrosine kinase which binds promiscuously transmembrane ephrin-B family ligands residing on adjacent cells, leading to contact-dependent bidirectional signaling into neighboring cells. The signaling pathway downstream of the receptor is referred to as forward signaling while the signaling pathway downstream of the ephrin ligand is referred to as reverse signaling. Cognate/functional ephrin ligands for this receptor include EFNB1, EFNB2 and EFNB3. During nervous system development, regulates retinal axon guidance redirecting ipsilaterally ventrotemporal retinal ganglion cells axons at the optic chiasm midline. This probably requires repulsive interaction with EFNB2. In the adult nervous system together with EFNB3, regulates chemotaxis, proliferation and polarity of the hippocampus neural progenitors. In addition to its role in axon guidance plays also an important redundant role with other ephrin-B receptors in development and maturation of dendritic spines and synapse formation. May also regulate angiogenesis. More generally, may play a role in targeted cell migration and adhesion. Upon activation by EFNB1 and probably other ephrin-B ligands activates the MAPK/ERK and the JNK signaling cascades to regulate cell migration and adhesion respectively. Involved in the maintenance of the pool of satellite cells (muscle stem cells) by promoting their self-renewal and reducing their activation and differentiation (By similarity).
Specific Function: Atp binding
Gene Name: EPHB1
Uniprot ID: P54762
Uniprot Name: Ephrin type-B receptor 1
Molecular Weight: 109884.175 Da

References

Ahmed MS, Wang P, Nguyen NUN, Nakada Y, Menendez-Montes I, Ismail M, Bachoo R, Henkemeyer M, Sadek HA, Kandil ES: Identification of tetracycline combinations as EphB1 tyrosine kinase inhibitors for treatment of neuropathic pain. Proc Natl Acad Sci U S A. 2021 Mar 9;118(10). pii: 2016265118. doi: 10.1073/pnas.2016265118. [Article]

Details10. Pancreatic triacylglycerol lipase

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Triglyceride lipase activity
Specific Function: Not Available
Gene Name: PNLIP
Uniprot ID: P16233
Uniprot Name: Pancreatic triacylglycerol lipase
Molecular Weight: 51156.48 Da

References

ROKOS J, MALEK P, BURGER M, PROCHAZKA P, KOLC J: The effect of divalent metals on the inhibition of pancreatic lipase by chlortetracycline. Antibiot Chemother (Northfield). 1959 Oct;9:600-8. [Article]

Details11. Protein-arginine deiminase type-4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Protein-arginine deiminase activity
Specific Function: Catalyzes the citrullination/deimination of arginine residues of proteins such as histones, thereby playing a key role in histone code and regulation of stem cell maintenance. Citrullinates histone...
Gene Name: PADI4
Uniprot ID: Q9UM07
Uniprot Name: Protein-arginine deiminase type-4
Molecular Weight: 74078.65 Da

References

Knuckley B, Luo Y, Thompson PR: Profiling Protein Arginine Deiminase 4 (PAD4): a novel screen to identify PAD4 inhibitors. Bioorg Med Chem. 2008 Jan 15;16(2):739-45. Epub 2007 Oct 13. [Article]

Carriers

Details1. Serum albumin

Kind: Protein
Organism: Humans
Pharmacological action: No

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
Molecular Weight: 69365.94 Da

References

Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. doi: 10.1159/000136629. [Article]

Drug created at September 16, 2015 17:03 / Updated at December 02, 2023 07:01

Chlortetracycline

Identification

Structure for Chlortetracycline (DB09093)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

References

References

References

References

References

References

References

References

References

References

Carriers

References