ambroxol   Click here for help

GtoPdb Ligand ID: 10692

Approved drug
ambroxol is an approved drug
Compound class: Synthetic organic
Comment: Ambroxol stimulates the synthesis and release of surfactant in the respiratory tract and acts as a mucoactive/expectorant drug. This action appears to be associated with ambroxol's regulation of glucosylceramide levels, via modulation of non-lysosomal glucosylceramidase (GCase) beta 2 (GBA2; Q9HCG7). Ambroxol is reported to act as a small molecule chaperone for GCase proteins that can increase the stability and function of mutant and wild-type GCases in in vitro and in vivo models [4-5,7-8,17], and in clinical trial subjects [12,18]. Ambroxol binds to nascent GCase proteins (at the enzyme active site) within the endoplasmic reticulum, and this action facilitates transport to the lysosome [1,4]. The acidic lysosomal environment provokes ambroxol disassociation, leaving the enzyme free to function normally.

SARS-CoV-2 and COVID-19: Evidence presented in a preprint suggests that ambroxol (and its prodrug bromhexine) directly disrupts the protein-protein interaction between the SARS-CoV-2 spike protein and ACE2 [14]. This action is reported to inhibit the cytopathic effects induced by SARS-CoV-2 infection in vitro, which is suggestive of potential prophylactic and/or therapeutic use of these drugs against COVID-19.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 58.28
Molecular weight 375.98
XLogP 2.9
No. Lipinski's rules broken 0
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Canonical SMILES OC1CCC(CC1)NCc1cc(Br)cc(c1N)Br
Isomeric SMILES OC1CCC(CC1)NCc1cc(Br)cc(c1N)Br
InChI InChI=1S/C13H18Br2N2O/c14-9-5-8(13(16)12(15)6-9)7-17-10-1-3-11(18)4-2-10/h5-6,10-11,17-18H,1-4,7,16H2
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes
Prodrug bromhexine
IUPAC Name Click here for help
Database Links Click here for help
ChEMBL Ligand CHEMBL1477775
GtoPdb PubChem SID 404859139
PubChem CID 2132
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