doxycycline

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 0.43
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (1967))
IUPAC Name
(4S,4aR,5S,5aR,6R,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
International Nonproprietary Names
INN number INN
2125 doxycycline
Synonyms
BMY-28689 | Monodox® | Vibramycin®
Comments
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 prophylactic 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 and ChEMBL entries for doxycycline show a different structure.
Doxycycline is one of the key antibacterials in the WHO 20th Essential Medicines List (2017).
Database Links
CAS Registry No. 564-25-0 (source: PubChem)
ChEBI CHEBI:50845
ChEMBL Ligand CHEMBL1433
DrugBank Ligand DB00254
GtoPdb PubChem SID 178103078
PubChem CID 54671203
Search Google for chemical match using the InChIKey SGKRLCUYIXIAHR-AKNGSSGZSA-N
Search Google for chemicals with the same backbone SGKRLCUYIXIAHR
Search PubMed clinical trials doxycycline
Search PubMed titles doxycycline
Search PubMed titles/abstracts doxycycline
Search UniChem for chemical match using the InChIKey SGKRLCUYIXIAHR-AKNGSSGZSA-N
Search UniChem for chemicals with the same backbone SGKRLCUYIXIAHR
Wikipedia Doxycycline