ambroxol   

GtoPdb Ligand ID: 10692

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 [4-5,7-8,15], and in clinical trial subjects [12,16]. 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 dissassociation, leaving the enzyme free to function normally.
2D Structure
Click here for structure editor
Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
InChI Key JBDGDEWWOUBZPM-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes
Prodrug bromhexine
IUPAC Name
4-[(2-amino-3,5-dibromophenyl)methylamino]cyclohexan-1-ol
Database Links
ChEMBL Ligand CHEMBL1477775
GtoPdb PubChem SID 404859139
PubChem CID 2132
Search Google for chemical match using the InChIKey JBDGDEWWOUBZPM-UHFFFAOYSA-N
Search Google for chemicals with the same backbone JBDGDEWWOUBZPM
Search UniChem for chemical match using the InChIKey JBDGDEWWOUBZPM-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone JBDGDEWWOUBZPM