doxycycline   Click here for help

GtoPdb Ligand ID: 6464

Synonyms: BMY-28689 | Monodox® | Vibramycin®
Approved drug PDB Ligand Immunopharmacology Ligand Antimalarial Ligand
doxycycline is an approved drug (FDA (1967), UK (2000))
Compound class: Synthetic organic
Comment: Doxycycline is a tetracycline based antibiotic. It has been repurposed as a low-potency human metalloprotease inhibitor for periodontitis and is also used as an antimalarial therapy.
There are a number of salt forms in PubChem. The chemical structure we show here matches that of the consensus structure in PubChem, listed in the links table below. The DrugBank, ChEBI, ChEMBL and PDB entries for doxycycline show a different structure.
Doxycycline is one of the key access group antibacterials on the World Health Organization's Model List of Essential Medicines (link provided in the Classification table, under the Summary tab below).

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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Canonical SMILES CN(C1C(=O)C(=C(C2(C1C(O)C1C(C)c3cccc(c3C(=C1C2=O)O)O)O)O)C(=O)N)C
Isomeric SMILES CN([C@@H]1C(=O)C(=C([C@@]2([C@H]1[C@@H](O)[C@@H]1[C@@H](C)c3cccc(c3C(=C1C2=O)O)O)O)O)C(=O)N)C
InChI InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25-27,30,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1
InChI Key SGKRLCUYIXIAHR-AKNGSSGZSA-N
Immunopharmacology Comments
Broad-spectrum proteinase inhibitors such as doxycycline might prove of therapeutic value, in particular in the confined microenvironment of the joint space, based on evidence that shows that doxycycline can slow the progression of joint-space narrowing in patients with knee OA [1].