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
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
- Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.
- 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 inhibitorEscherichia coli (strain K12) U30S ribosomal protein S9 inhibitorEscherichia coli (strain K12) N16S ribosomal RNA inhibitorEnteric 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.
- 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 Integrate drug-drug
interactions in your softwareAcenocoumarol 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. Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - 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 show 10 more
- 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
- External Links
- Human Metabolome Database
- HMDB0014596
- KEGG Drug
- D06885
- PubChem Compound
- 54680675
- PubChem Substance
- 46505301
- ChemSpider
- 21251443
- 21272
- ChEBI
- 59589
- ChEMBL
- CHEMBL2106071
- ZINC
- ZINC000004212626
- Therapeutic Targets Database
- DAP000882
- PharmGKB
- PA164771235
- Wikipedia
- Clomocycline
Clinical Trials
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
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

- 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
- 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
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