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Clomocycline

 

Therapeutic use

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

Dosage and Administration

 

Toxicology

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 273mg/kg (273mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 501, 1978.
mouse LD50 intravenous 115mg/kg (115mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 501, 1978.
mouse LD50 oral 2830mg/kg (2830mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 501, 1978.

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.

Clomocycline at as inhibitor of 30S ribosomal protein S4. It 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 [1,2].

 

Taken from http://pathman.smpdb.ca/pathways/SMP00262/pathway?level=1

Microbiology

 

Resistance

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.

 


Medicinal Chemistry

CAS number: 1181-54-0   EINECS:

Molecular Formula: C23H25ClN2O9

Average mass: 508.905609 Da

Monoisotopic mass: 508.124847 Da

Systematic name: (2Z,4S,4aS,5aS,6S,12aS)-7-Chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-2-{hydroxy[(hydroxymethyl)amino]methylene}-6-methyl-4a,5a,6,12a-tetrahydro-1,3,12(2H,4H,5H)-tetracenetrione

SMILES: Clc1c4c(c(O)cc1)C(\O)=C3\C(=O)[C@]2(O)C(=O)/C(C(=O)[C@@H](N(C)C)[C@@H]2C[C@@H]3[C@@]4(O)C)=C(\O)NCO

Std. 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/h4-5,8-9,16,25,27-29,33-35H,6-7H2,1-3H3/b21-14-/t8-,9-,16-,22-,23-/m0/s1

ACD/LogP: 9.432 # of Rule of 5 Violations: 4
ACD/LogD (pH 5.5): 8.18 ACD/LogD (pH 7.4): 6.54
ACD/BCF (pH 5.5): 486721.60 ACD/BCF (pH 7.4): 11230.94
ACD/KOC (pH 5.5): 180738.60 ACD/KOC (pH 7.4): 4170.48
#H bond acceptors: 11 #H bond donors: 7
#Freely Rotating Bonds: 9 Polar Surface Area: 187.86 Å2
Index of Refraction: 1.738 Molar Refractivity: 120.109 cm3
Molar Volume: 298.406 cm3 Polarizability: 47.615 10-24cm3
Surface Tension: 102.208999633789 dyne/cm Density: 1.705 g/cm3
Flash Point: 401.142 C Enthalpy of Vaporization: 113.231 kJ/mol
Boiling Point: 739.677 C at 760 mmHg Vapour Pressure: 0 mmHg at 25C

 


1. 1.Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006, 5(12), 993-6.

2. 2.Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006, 5(10),821-34.

 

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