General
Preferred name
GUAIFENESIN
Synonyms
Glycerol guaiacolate ()
Guaiphenesin ()
Guaiacol glyceryl ether ()
guaifenesin, Elan ()
Humabid ()
Hustosil ()
Glyceryl Guaiacolate ()
Nirolex For Chesty Cough Decongestant ()
Robitussin ()
Franolyn Chesty ()
NSC-62112 ()
Gecolate ()
Mucinex ()
Guaifensin ()
CVT-2534 ()
Famel ()
Liqufruta ()
Methphenoxydiol ()
Tixylix Chesty Cough ()
Amonidron ()
Guaifenesin ()
Guaifenesin-d3 ()
P&D ID
PD002316
CAS
93-14-1
12041-73-5
1189924-85-3
Tags
natural product
drug
available
Approved by
FDA
First approval
2002
Drug Status
investigational
approved
vet_approved
Max Phase
Phase 4
Drug indication
Expectorant
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PHARMACODYNAMICS
Guaifenesin is categorized as an expectorant that acts by enhancing the output of phlegm (sputum) and bronchial secretions via decreasing the adhesiveness and surface tension of such material [F4516]. Furthermore, guaifenesin elicits an increased flow of less viscous gastric secretions that subsequently promote ciliary action - all actions that ultimately change dry, unproductive coughing to coughs that are more productive and less frequent [F4516]. Essentially, by decreasing the viscosity and adhesiveness of such secretions, guaifenesin enhances the efficacy of mucociliary activity in removing accumulated secretions from the upper and lower airway [F4516].
ROE
After administration, guaifenesin is metabolized and then largely excreted in the urine [A177676, L6079, L6100, F4522, F4525].
INDICATION
Guaifenesin is an expectorant that is indicated for providing temporary symptomatic relief from congested chests and coughs which may be due to a cold, bronchitis, and/or other breathing illnesses [FDA Label, F4510, L6079].
TOXICITY
The most prevalent signs and symptoms associated with an overdose of guaifenesin have been nausea and vomiting [L6100].; ; Although adequate and well-controlled studies in pregnant women have not been performed, the Collaborative Perinatal Project monitored 197 mother-child pairs exposed to guaifenesin during the first trimester [L6100]. An increased occurrence of inguinal hernias was found in the neonates [L6100]. However, congenital defects were not strongly associated with guaifenesin use during pregnancy in 2 large groups of mother-child pairs [L6100].; ; Moreover, guaifenesin is excreted in breast milk in small quantities [L6100]. Subsequently, caution should be exercised by balancing the potential benefit of treatment against any possible risks [L6100].; ; Additionally, an LD50 value of 1510 mg/kg (rat, oral) has been reported for guaifenesin [MSDS].
METABOLISM
After the oral administration of 400 mg guaifenesin, the agent experiences rapid hydrolysis (more than 60% of the dose hydrolyzed over a range of seven hours) with β-(2-methoxyphenoxy)-lactic acid found as the major urinary metabolite but no parent drug detectable in the urine [A177676, L6100]. Moreover, it has been observed that guaifenesin also experiences both oxidation and demethylation [A177676]. In particular, the medication is quickly metabolized hepatically by way of oxidation to β-(2-methoxyphenoxy)-lactic acid [A177676]. Furthermore, guaifenesin is also demethylated by O-demethylase in liver microsomes to the point where about 40% of an administered dose is excreted as this metabolite in the urine within 3 hours [A177676]. In fact, O-demethylase appears to be the primary enzyme for the metabolism of guaifenesin and the primary metabolites of the substance are β-(2-methoxyphenoxy)-lactic acid and the demethylated hydroxyguaifenesin, both of which are themselves inactive moieties [A177676].
ABSORPTION
Studies have shown that guaifenesin is well absorbed from and along the gastrointestinal tract after oral administration [A177634, F4522, L6100].
HALF-LIFE
The half-life in plasma observed for guaifenesin is approximately one hour [A177676, L6079, L6100, F4522, F4525].
DESCRIPTION
The approved drug is a racemic mixture of enantiomers; R-guaifenesin and S-guaifenesin. We show the non-stereo structure to represent the mixture.
(GtoPdb)
MOA
Although the exact mechanism of action of guaifenesin may not yet be formally or totally elucidated, it is believed that expectorants like guaifenesin function by increasing mucus secretion [A177661]. Moreover, it is also further proposed that such expectorants may also act as an irritant to gastric vagal receptors, and recruit efferent parasympathetic reflexes that can elicit glandular exocytosis that is comprised of a less viscous mucus mixture [A177661]. Subsequently, these actions may provoke coughing that can ultimately flush difficult to access, congealed mucopurulent material from obstructed small airways to facilitate a temporary improvement for the individual [A177661].; ; Consequently, while it is generally proposed that guaifenesin functions as an expectorant by helping to loosen phlegm (mucus) and thin bronchial secretions to rid the bronchial passageways of bothersome mucus and make coughs more productive, there has also been research to suggest that guaifenesin possesses and is capable of demonstrating anticonvulsant and muscle relaxant effects to some degree possibly by acting as an NMDA receptor antagonist [A177652].
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Compound Sets
17
ChEMBL Approved Drugs
ChEMBL Drugs
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMatrix
Guide to Pharmacology
MedChem Express Bioactive Compound Library
NCATS Inxight Approved Drugs
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
The Spectrum Collection
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
39
Molecular Weight
198.09
Hydrogen Bond Acceptors
4
Hydrogen Bond Donors
2
Rotatable Bonds
5
Ring Count
1
Aromatic Ring Count
1
cLogP
0.43
TPSA
58.92
Fraction CSP3
0.4
Chiral centers
1.0
Largest ring
6.0
QED
0.72
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Immunology/Inflammation
Target
Mucin
Source data
