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
References
1. Brandt KD, Mazzuca SA, Katz BP, Lane KA, Buckwalter KA, Yocum DE, Wolfe F, Schnitzer TJ, Moreland LW, Manzi S et al.. (2005)
Effects of doxycycline on progression of osteoarthritis: results of a randomized, placebo-controlled, double-blind trial.
Arthritis Rheum, 52 (7): 2015-25. [PMID:15986343]
2. Dahl EL, Rosenthal PJ. (2007)
Multiple antibiotics exert delayed effects against the Plasmodium falciparum apicoplast.
Antimicrob Agents Chemother, 51 (10): 3485-90. [PMID:17698630]
3. Dahl EL, Shock JL, Shenai BR, Gut J, DeRisi JL, Rosenthal PJ. (2006)
Tetracyclines specifically target the apicoplast of the malaria parasite Plasmodium falciparum.
Antimicrob Agents Chemother, 50 (9): 3124-31. [PMID:16940111]
4. García RA, Pantazatos DP, Gessner CR, Go KV, Woods Jr VL, Villarreal FJ. (2005)
Molecular interactions between matrilysin and the matrix metalloproteinase inhibitor doxycycline investigated by deuterium exchange mass spectrometry.
Mol Pharmacol, 67 (4): 1128-36. [PMID:15665254]
5. Sepper R, Konttinen YT, Ding Y, Takagi M, Sorsa T. (1995)
Human neutrophil collagenase (MMP-8), identified in bronchiectasis BAL fluid, correlates with severity of disease.
Chest, 107 (6): 1641-7. [PMID:7781360]
6. Tan KR, Magill AJ, Parise ME, Arguin PM, Centers for Disease Control and Prevention. (2011)
Doxycycline for malaria chemoprophylaxis and treatment: report from the CDC expert meeting on malaria chemoprophylaxis.
Am J Trop Med Hyg, 84 (4): 517-31. [PMID:21460003]