NAV

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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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.

TargetActionsOrganism
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
PathwayCategory
Clomocycline Action PathwayDrug 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.
DrugInteraction
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interactions in your software
AcenocoumarolClomocycline may increase the anticoagulant activities of Acenocoumarol.
AcitretinThe risk or severity of pseudotumor cerebri can be increased when Acitretin is combined with Clomocycline.
AlitretinoinThe risk or severity of pseudotumor cerebri can be increased when Alitretinoin is combined with Clomocycline.
AlmasilateAlmasilate can cause a decrease in the absorption of Clomocycline resulting in a reduced serum concentration and potentially a decrease in efficacy.
AluminiumAluminium can cause a decrease in the absorption of Clomocycline resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminium phosphateAluminium phosphate can cause a decrease in the absorption of Clomocycline resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Clomocycline resulting in a reduced serum concentration and potentially a decrease in efficacy.
AmoxicillinThe therapeutic efficacy of Amoxicillin can be decreased when used in combination with Clomocycline.
AmpicillinThe therapeutic efficacy of Ampicillin can be decreased when used in combination with Clomocycline.
ArticaineThe risk or severity of methemoglobinemia can be increased when Clomocycline is combined with Articaine.
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Food Interactions
Not Available

Categories

ATC Codes
J01AA11 — Clomocycline
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Tetracyclines
Sub Class
Not Available
Direct Parent
Tetracyclines
Alternative Parents
Naphthacenes / Anthracenecarboxylic acids and derivatives / Tetralins / Aryl ketones / 1-hydroxy-2-unsubstituted benzenoids / Aralkylamines / Cyclohexenones / Aryl chlorides / Vinylogous acids / Tertiary alcohols
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Substituents
1-hydroxy-2-unsubstituted benzenoid / Alcohol / Alkanolamine / Amine / Amino acid or derivatives / Anthracene carboxylic acid or derivatives / Aralkylamine / Aromatic homopolycyclic compound / Aryl chloride / Aryl halide
show 27 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
tetracyclines (CHEBI:59589)
Affected organisms
  • Enteric bacteria and other eubacteria

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
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
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP0.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.77 mg/mLALOGPS
logP-0.45ALOGPS
logP-3.3Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)2.95Chemaxon
pKa (Strongest Basic)9.04Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count7Chemaxon
Polar Surface Area187.86 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity124.99 m3·mol-1Chemaxon
Polarizability48.79 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6317
Blood Brain Barrier-0.9659
Caco-2 permeable-0.5295
P-glycoprotein substrateSubstrate0.8364
P-glycoprotein inhibitor INon-inhibitor0.846
P-glycoprotein inhibitor IIInhibitor0.551
Renal organic cation transporterNon-inhibitor0.8954
CYP450 2C9 substrateNon-substrate0.7461
CYP450 2D6 substrateNon-substrate0.8278
CYP450 3A4 substrateSubstrate0.6882
CYP450 1A2 substrateNon-inhibitor0.8305
CYP450 2C9 inhibitorNon-inhibitor0.8343
CYP450 2D6 inhibitorNon-inhibitor0.8658
CYP450 2C19 inhibitorNon-inhibitor0.8104
CYP450 3A4 inhibitorNon-inhibitor0.8207
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5532
Ames testNon AMES toxic0.7312
CarcinogenicityNon-carcinogens0.8924
BiodegradationNot ready biodegradable0.9951
Rat acute toxicity2.4234 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9898
hERG inhibition (predictor II)Inhibitor0.5484
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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
No
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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