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targets (3)
for drugs
Identification
Name Clomocycline
Accession Number DB00453 (APRD00343)
Type small molecule
Groups approved
Description

Clomocycline is a tetracycline antibiotic.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Chlormethylenecycline
Clomociclina [INN-Spanish]
Clomocyclinum [INN-Latin]
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Tetracyclines
CAS number 1181-54-0
Weight Average: 508.906
Monoisotopic: 508.124858115
Chemical Formula C23H25ClN2O9
InChI Key InChIKey=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
Plain Text
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(O)C=CC(Cl)=C1[C@@]3(C)O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Tetracyclines
Substructures
  • Tetracyclines
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Naphthalenes
  • Phenols and Derivatives
  • Amino Ketones
  • Phenylpropenes
  • Benzene and Derivatives
  • Aminals and Derivatives
  • Aryl Halides
  • Halobenzenes
  • Aliphatic and Aryl Amines
  • Alcohols and Polyols
  • Aromatic compounds
  • Cinnamaldehydes
  • Ketenes and Derivatives
  • Phenyl Esters
  • Enols
  • Ketones
Pharmacology
Indication For the treatment and management of Brucellosis, mycoplasma infection, acne vulgaris, chlamydial infection;Chronic bronchitis
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.
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
Toxicity Not Available
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Pathway Name SMPDB ID
Smp00262 Clomocycline Pathway SMP00262
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 1.77e+00 g/l ALOGPS
logP -0.45 ALOGPS
logP -3.3 ChemAxon
logS -2.5 ALOGPS
pKa (strongest acidic) 0.013 ChemAxon
pKa (strongest basic) 8.23 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 10 ChemAxon
hydrogen donor count 7 ChemAxon
polar surface area 187.86 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 124.99 ChemAxon
polarizability 49.29 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D06885 Link_out
PubChem Compound 5464321 Link_out
PubChem Substance 46505301 Link_out
ChemSpider 4576619 Link_out
ChEBI 59589 Link_out
ChEMBL 59589 Link_out
Therapeutic Targets Database DAP000882 Link_out
PharmGKB PA164771235 Link_out
Wikipedia http://en.wikipedia.org/wiki/Clomocycline Link_out
ATC Codes
  • J01AA11
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. 30S ribosomal protein S4

Pharmacological action: yes
Actions: inhibitor

Also functions as a rho-dependent antiterminator of rRNA transcription, increasing the synthesis of rRNA under conditions of excess protein, allowing a more rapid return to homeostasis. Binds directly to RNA polymerase

Organism class: bacterial
UniProt ID: P0A7V8 Link_out
Gene: rpsD
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
  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. Pubmed

2. 30S ribosomal protein S9

Pharmacological action: unknown
Actions: inhibitor

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

Organism class: bacterial
UniProt ID: P0A7X3 Link_out
Gene: rpsI
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
  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. Pubmed

3. 16S rRNA

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.

Gene Sequence: FASTA

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. Pubmed
  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. Pubmed
  3. Toledo H, Lopez-Solis R: Tetracycline resistance in Chilean clinical isolates of Helicobacter pylori. J Antimicrob Chemother. 2010 Mar;65(3):470-3. Epub 2009 Dec 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19