Clomocycline

Identification

Generic Name

Clomocycline

DrugBank Accession Number

DB00453

Background

Clomocycline is a tetracycline used to treat bacterial infections.

Type

Small Molecule

Groups

Experimental

Structure

Similar Structures

Weight: Average: 508.906
Monoisotopic: 508.124858115
Chemical Formula: C₂₃H₂₅ClN₂O₉

Synonyms

Chlormethylenecycline
Clomociclina
Clomocyclina
Clomocycline
Clomocyclinum

Pharmacology

Indication

For the treatment and management of Brucellosis, mycoplasma infection, acne vulgaris, chlamydial infection;Chronic bronchitis

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Clomocycline is a tetracycline antibiotic that is commonly prescribed by medical doctors for infections and to treat acne. It may also be used to treat urinary tract infections, gum disease, and other bacterial infections such as gonorrhea and chlamydia. Clomocycline is also used commonly as a prophylactic treatment for infection by Bacillus anthracis (anthrax). It is also effective against Yersinia pestis and malaria and is also prescribed for the treatment of Lyme disease. Clomocycline inhibits cell growth by inhibiting translation. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. The binding is reversible in nature. Cells become resistant to Clomocycline by at least two mechanisms: efflux and ribosomal protection. In efflux, a resistance gene encodes a membrane protein that actively pumps Clomocycline out of the cell. This is the mechanism of action of the tetracycline resistance gene on the artificial plasmid pBR322. In ribosomal protection, a resistance gene encodes a protein which binds to the ribosome and prevents Clomocycline from acting on the ribosome.

Mechanism of action

Clomocycline inhibits cell growth by inhibiting translation. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. The binding is reversible in nature. Clomocycline is lipophilic and can easily pass through the cell membrane or passively diffuses through porin channels in the bacterial membrane.

Target	Actions	Organism
A30S ribosomal protein S4	inhibitor	Escherichia coli (strain K12)
U30S ribosomal protein S9	inhibitor	Escherichia coli (strain K12)
N16S ribosomal RNA	inhibitor	Enteric bacteria and other eubacteria

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Pathway	Category
Clomocycline Action Pathway	Drug action

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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Acenocoumarol	Clomocycline may increase the anticoagulant activities of Acenocoumarol.
Acitretin	The risk or severity of pseudotumor cerebri can be increased when Acitretin is combined with Clomocycline.
Alitretinoin	The risk or severity of pseudotumor cerebri can be increased when Alitretinoin is combined with Clomocycline.
Almasilate	Almasilate can cause a decrease in the absorption of Clomocycline resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminium	Aluminium can cause a decrease in the absorption of Clomocycline resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminium phosphate	Aluminium phosphate can cause a decrease in the absorption of Clomocycline resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminum hydroxide	Aluminum hydroxide can cause a decrease in the absorption of Clomocycline resulting in a reduced serum concentration and potentially a decrease in efficacy.
Ambroxol	The risk or severity of methemoglobinemia can be increased when Clomocycline is combined with Ambroxol.
Amoxicillin	The therapeutic efficacy of Amoxicillin can be decreased when used in combination with Clomocycline.
Ampicillin	The therapeutic efficacy of Ampicillin can be decreased when used in combination with Clomocycline.

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Food Interactions

Not Available

Chemical Identifiers

UNII: YP0241BU76
CAS number: 1181-54-0
InChI Key: GJGDLRSSCNAKGL-KMVLDZISSA-N
InChI: InChI=1S/C23H25ClN2O9/c1-22(34)8-6-9-16(26(2)3)18(30)14(21(33)25-7-27)20(32)23(9,35)19(31)12(8)17(29)13-11(28)5-4-10(24)15(13)22/h4-5,8-9,16,27-28,30-31,34-35H,6-7H2,1-3H3,(H,25,33)/t8-,9-,16-,22-,23-/m0/s1
IUPAC Name: (4S,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-N-(hydroxymethyl)-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(=O)NCO)=C(O)[C@H]2N(C)C)C(=O)C1=C(C(Cl)=CC=C1O)[C@@]3(C)O

References

General References

Not Available

External Links

Human Metabolome Database: HMDB0014596
KEGG Drug: D06885
PubChem Compound: 54680675
PubChem Substance: 46505301
ChemSpider: 21251443
RxNav: 21272
ChEBI: 59589
ChEMBL: CHEMBL2106071
ZINC: ZINC000004212626
Therapeutic Targets Database: DAP000882
PharmGKB: PA164771235
Wikipedia: Clomocycline

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers: Not Available
Packagers: Not Available
Dosage Forms: Not Available
Prices: Not Available
Patents: Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
logP	0.2	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.77 mg/mL	ALOGPS
logP	-0.45	ALOGPS
logP	-3.3	Chemaxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	2.95	Chemaxon
pKa (Strongest Basic)	9.04	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	10	Chemaxon
Hydrogen Donor Count	7	Chemaxon
Polar Surface Area	187.86 Å²	Chemaxon
Rotatable Bond Count	3	Chemaxon
Refractivity	124.99 m³·mol^-1	Chemaxon
Polarizability	48.79 Å³	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.6317
Blood Brain Barrier	-	0.9659
Caco-2 permeable	-	0.5295
P-glycoprotein substrate	Substrate	0.8364
P-glycoprotein inhibitor I	Non-inhibitor	0.846
P-glycoprotein inhibitor II	Inhibitor	0.551
Renal organic cation transporter	Non-inhibitor	0.8954
CYP450 2C9 substrate	Non-substrate	0.7461
CYP450 2D6 substrate	Non-substrate	0.8278
CYP450 3A4 substrate	Substrate	0.6882
CYP450 1A2 substrate	Non-inhibitor	0.8305
CYP450 2C9 inhibitor	Non-inhibitor	0.8343
CYP450 2D6 inhibitor	Non-inhibitor	0.8658
CYP450 2C19 inhibitor	Non-inhibitor	0.8104
CYP450 3A4 inhibitor	Non-inhibitor	0.8207
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.5532
Ames test	Non AMES toxic	0.7312
Carcinogenicity	Non-carcinogens	0.8924
Biodegradation	Not ready biodegradable	0.9951
Rat acute toxicity	2.4234 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9898
hERG inhibition (predictor II)	Inhibitor	0.5484

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
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. 30S ribosomal protein S4

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

General Function: Translation repressor activity, nucleic acid binding
Specific Function: One of two assembly initiator proteins for the 30S subunit, it binds directly to 16S rRNA where it nucleates assembly of the body of the 30S subunit.With S5 and S12 plays an important role in trans...
Gene Name: rpsD
Uniprot ID: P0A7V8
Uniprot Name: 30S ribosomal protein S4
Molecular Weight: 23468.915 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Details2. 30S ribosomal protein S9

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

General Function: Trna binding
Specific Function: The C-terminal tail plays a role in the affinity of the 30S P site for different tRNAs. Mutations that decrease this affinity are suppressed in the 70S ribosome.
Gene Name: rpsI
Uniprot ID: P0A7X3
Uniprot Name: 30S ribosomal protein S9
Molecular Weight: 14856.105 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Details3. 16S ribosomal RNA

Kind

Nucleotide

Organism

Enteric bacteria and other eubacteria

Pharmacological action

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Toledo H, Lopez-Solis R: Tetracycline resistance in Chilean clinical isolates of Helicobacter pylori. J Antimicrob Chemother. 2010 Mar;65(3):470-3. doi: 10.1093/jac/dkp457. Epub 2009 Dec 24. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 03, 2023 08:08

Clomocycline

Identification

Structure for Clomocycline (DB00453)

Pharmacology

Interactions

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

References

References