Ligand id: 6464

Name: doxycycline

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 9
Hydrogen bond donors 6
Rotatable bonds 2
Topological polar surface area 181.62
Molecular weight 444.15
XLogP 0.39
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

No information available.
Summary of Clinical Use
Doxycycline is used to treat a wide range of bacterial infections. These include acne, urinary tract infections, intestinal infections, eye infections, gonorrhea, chlamydia, periodontitis (gum disease), lesions caused by rosacea, anthrax, and to treat infections resulting from by mite, tick, or lice infestations.
It is also used to prevent malaria (particularly useful in areas where chloroquine or multidrug-resistant P. falciparum are found) and as an effective treatment for severe malaria, when used as a combination therapy [6]. It should not be used as a monotherapy for malaria treatment due to a delayed antimalarial effect (see MOA for more details).
Marketed formulations may contain doxycycline hyclate or doxycycline monohydrate.
Mechanism Of Action and Pharmacodynamic Effects
Antibacterial MMOA is reversible binding to the 30S ribosomal subunits to block binding of aminoacyl tRNA to mRNA and thereby inhibit bacterial protein synthesis. Human MMOA is pan-MMP inhibition but some specificity for MMP7and MMP8 is evident, and is associated with reducing inflammation and elevated levels of proinflammatory cytokines.
In Plasmodium, pharmacological concentrations of the compound kill the parasite in the lifecycle after treatment starts. It is thought that doxycycline inhibits the production of proteins encoded by the apicoplast genome, leading to a subsequent loss of apicoplast function and a possible explanation for the delayed antimalarial effect [3].
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