Guaifenesin

Identification

Name
Guaifenesin
Accession Number
DB00874  (APRD01005)
Type
Small Molecule
Groups
Approved, Vet Approved
Description

An expectorant that also has some muscle relaxing action. It is used in many cough preparations. [PubChem]

Structure
Thumb
Synonyms
  • Glyceryl guaiacolate
  • guaiphenesin
  • Hustosil
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MucinexTablet, extended release600 mg/1OralAphena Pharma Solutions Tennessee, Inc.2012-07-03Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
7 Select Mucus ReliefTablet, extended release600 mg/1Oral7 Eleven2014-10-26Not applicableUs
Adult TussinSyrup100 mg/5mLOralRite Aid2013-09-212017-11-14Us
Adult Tussin Chest CongestionSolution200 mg/10mLOralHyvee1997-06-25Not applicableUs
Air PowerTablet200 mg/1OralSchwabe North America, Inc2003-05-19Not applicableUs
Air-powerTablet200 mgOralEnzymatic Therapy, Inc.1997-03-202002-08-08Canada
AkinSolution100 mg/5mLOralSouthern Sales & Service, Inc.2015-01-01Not applicableUs
AuroMucus - Childrens Chest CongestionSolution100 mg/5mLOralAurohealth LLC2015-08-24Not applicableUs
Aurotussin Mucus plus Chest Congestion (ORIGINAL)Liquid200 mg/10mLOralAurohealth LLC2015-06-26Not applicableUs
Balminil ExpectorantSyrup100 mgOralTeva1979-12-31Not applicableCanada
Balminil Expectorant (sucrose Free)Syrup100 mgOralTeva1979-12-31Not applicableCanada
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
GuaifenesinTablet, extended release1200 mg/1OralKroger2017-08-21Not applicableUs
GuaifenesinTablet200 mg/1OralContract Pharmacy Services Pa2010-10-062017-08-29Us
GuaifenesinTablet, extended release600 mg/1OralOhm Laboratories Inc2017-11-15Not applicableUs
Guaifenesin Extended ReleaseTablet, extended release1200 mg/1OralSam's West, Inc2017-10-31Not applicableUs
Guaifenesin Extended ReleaseTablet, extended release1200 mg/1OralChain Drug Marketing Association2017-10-15Not applicableUs
MucusTablet, extended release600 mg/1OralMc Kesson2017-10-15Not applicableUs
MucusTablet, extended release600 mg/1OralMc Kesson (Health Mart)2017-10-15Not applicableUs
MucusTablet, extended release600 mg/1OralKroger2017-09-07Not applicableUs
MucusTablet, extended release600 mg/1OralChain Drug Marketing Association2017-11-15Not applicableUs
Mucus Extended ReleaseTablet, extended release1200 mg/1OralWalgreens2017-08-21Not applicableUs
International/Other Brands
Duratuss G / Ganidin (Cypress) / Hustosil (Kyoto Yakuhin) / Hytuss (Hyrex) / Robitussin (Wyeth) / Scot-tussin Expectorant / Sinumist-SR
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
7 select Tussin DMGuaifenesin (200 mg/10mL) + Dextromethorphan hydrobromide (20 mg/10mL)SolutionOral7 Eleven2016-05-31Not applicableUs
Acetaminophen, Dextromethorphan Hydrobromide, Guaifenesin, Phenylephrine HydrochlorideGuaifenesin (100 mg/1) + Acetaminophen (325 mg/1) + Dextromethorphan hydrobromide (10 mg/1) + Phenylephrine hydrochloride (5 mg/1)Tablet, coatedOralAAA Pharmaceutical, Inc.2012-12-22Not applicableUs
Acetaminophen, Dextromethorphan Hydrobromide, Guaifenesin, Phenylephrine HydrochlorideGuaifenesin (200 mg/1) + Acetaminophen (325 mg/1) + Dextromethorphan hydrobromide (10 mg/1) + Phenylephrine hydrochloride (5 mg/1)Tablet, coatedOralAAA Pharmaceutical, Inc.2012-12-28Not applicableUs
Acetaminophen, Dextromethorphan Hydrobromide, Guaifenesin, Phenylephrine HydrochlorideGuaifenesin (200 mg/1) + Acetaminophen (325 mg/1) + Dextromethorphan hydrobromide (10 mg/1) + Phenylephrine hydrochloride (5 mg/1)Tablet, coatedOralAAA Pharmaceutical, Inc.2012-12-28Not applicableUs
Acetaminophen, Dextromethorphan Hydrobromide, Guaifenesin, Phenylephrine HydrochlorideGuaifenesin (200 mg/1) + Acetaminophen (325 mg/1) + Dextromethorphan hydrobromide (10 mg/1) + Phenylephrine hydrochloride (5 mg/1)Tablet, coatedOralAAA Pharmaceutical, Inc.2012-12-28Not applicableUs
Acetaminophen, Guaifenesin, Phenylephrine HydrochlorideGuaifenesin (200 mg/1) + Acetaminophen (325 mg/1) + Phenylephrine hydrochloride (5 mg/1)Tablet, coatedOralAAA Pharmaceutical, Inc.2012-12-28Not applicableUs
Actidom DmxGuaifenesin (200 mg/5mL) + Dextromethorphan hydrobromide (30 mg/5mL) + Phenylephrine hydrochloride (10 mg/5mL)SolutionOralActipharma, Inc2015-08-13Not applicableUs
ActinelGuaifenesin (200 mg/5mL) + Dextromethorphan hydrobromide (15 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)SolutionOralActipharma, Inc2014-09-24Not applicableUs
Actinel PediatricGuaifenesin (50 mg/5mL) + Dextromethorphan hydrobromide (5 mg/5mL) + Pseudoephedrine hydrochloride (15 mg/5mL)SolutionOralActipharma, Inc2014-09-24Not applicableUs
Adult CF CoughGuaifenesin (100 mg/5mL) + Dextromethorphan hydrobromide (10 mg/5mL) + Phenylephrine hydrochloride (5 mg/5mL)LiquidOralMeijer Distribution2006-08-112017-11-22Us
Categories
UNII
495W7451VQ
CAS number
93-14-1
Weight
Average: 198.2158
Monoisotopic: 198.089208936
Chemical Formula
C10H14O4
InChI Key
HSRJKNPTNIJEKV-UHFFFAOYSA-N
InChI
InChI=1S/C10H14O4/c1-13-9-4-2-3-5-10(9)14-7-8(12)6-11/h2-5,8,11-12H,6-7H2,1H3
IUPAC Name
3-(2-methoxyphenoxy)propane-1,2-diol
SMILES
COC1=CC=CC=C1OCC(O)CO

Pharmacology

Indication

Used to assist the expectoration of phlegm from the airways in acute respiratory tract infections.

Structured Indications
Pharmacodynamics

Guaifenesin is an expectorant which increases the output of phlegm (sputum) and bronchial secretions by reducing adhesiveness and surface tension. The increased flow of less viscous secretions promotes ciliary action and changes a dry, unproductive cough to one that is more productive and less frequent. By reducing the viscosity and adhesiveness of secretions, guaifenesin increases the efficacy of the mucociliary mechanism in removing accumulated secretions from the upper and lower airway.

Mechanism of action

Guaifenesin may act as an irritant to gastric vagal receptors, and recruit efferent parasympathetic reflexes that cause glandular exocytosis of a less viscous mucus mixture. Cough may be provoked. This combination may flush tenacious, congealed mucopurulent material from obstructed small airways and lead to a temporary improvement in dyspnea or the work of breathing.

Absorption

Rapidly absorbed from the GI tract

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Rapidly hydrolyzed (60% within seven hours) and then excreted in the urine, with beta-(2-methoxyphenoxy)-lactic acid as its major urinary metabolite.

Route of elimination
Not Available
Half life

1 hour

Clearance
Not Available
Toxicity

LD50 1510 mg/kg (rat, oral)

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
  • Take with a full glass of water.
  • Take without regard to meals.

References

Synthesis Reference

Wilfred P. Shum, Harry Mazurek, Jian Chen, "Process for producing enantiomerically enriched guaifenesin." U.S. Patent US5495052, issued August, 1949.

US5495052
General References
Not Available
External Links
Human Metabolome Database
HMDB04998
KEGG Drug
D00337
PubChem Compound
3516
PubChem Substance
46508004
ChemSpider
3396
ChEBI
5551
ChEMBL
CHEMBL980
PharmGKB
PA449818
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Guaifenesin
ATC Codes
R05CA03 — Guaifenesin
AHFS Codes
  • 48:16.00 — Expectorants
FDA label
Download (394 KB)
MSDS
Download (73.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
1CompletedTreatmentMucociliary Clearance1
2CompletedTreatmentAcute Respiratory Infections1
2CompletedTreatmentAcute Rhinitis1
2RecruitingTreatmentChronic Rhinitis1
2WithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections / Sinusitis1
2, 3CompletedTreatmentAcute Upper Respiratory Tract Infections1
3Unknown StatusTreatmentViral Infections of the Upper Respiratory Tract1
4CompletedPreventionAcute Upper Respiratory Track Infection1
4CompletedTreatmentAcute Respiratory Infections / Acute Rhinosinusitis1
4CompletedTreatmentAcute maxillary sinusitis caused by M. catarrhalis / Acute Respiratory Infections / Bronchitis1
Not AvailableCompletedNot AvailableBronchitis2
Not AvailableCompletedTreatmentInfection NOS1
Not AvailableCompletedTreatmentPneumonia1
Not AvailableCompletedTreatmentUpper Back Pain1
Not AvailableRecruitingTreatmentFilamentary Keratitis1

Pharmacoeconomics

Manufacturers
  • Reckitt benckiser inc
Packagers
Dosage forms
FormRouteStrength
TabletOral200 mg
KitOral
Solution / dropsOral
Suspension / dropsOral
LiquidOral100 mg
GranuleOral
SolutionOral100 mg/5mL
ElixirOral
Capsule, liquid filledOral
Capsule; kitOral
SuppositoryRectal
TabletOral
CapsuleOral
TabletOral100 mg/1
SyrupOral100 mg
LiquidOral200 mg
TabletOral400 mg
Solution / dropsNasal
TabletOral400 mg/1
Tablet, film coatedOral
Tablet, coatedOral
SyrupOral100 mg/5mL
SolutionOral
SyrupOral200 mg/10mL
LiquidOral300 mg/15mL
Tablet, extended releaseOral600 mg/1
Tablet, orally disintegratingOral100 mg/1
SyrupOral20 mg
LiquidOral20 mg
LiquidOral5 g/100mL
SyrupOral50 mg/5mL
LiquidOral200 mg/5mL
GranuleOral100 mg/1
Tablet, multilayer, extended releaseOral600 mg
Tablet, extended releaseOral1200 mg/1
SolutionOral100 mg
Tablet, extended releaseOral
Tablet, coatedOral400 mg/1
Tablet, film coatedOral400 mg/1
Kit
TabletOral200 mg/1
SyrupOral200 mg/5mL
SyrupOral200 mg
Capsule, coatedOral
Powder, for solutionOral
SyrupOral
Kit; tabletOral
LiquidOral
Capsule, gelatin coatedOral
LiquidOral200 mg/10mL
SolutionOral200 mg/10mL
LiquidOral100 mg/5mL
SuspensionOral
Prices
Unit descriptionCostUnit
Diabetic Tussin Max St 10-200 mg/5ml Liquid 118ml Bottle15.99USD bottle
Naldecon Senior EX 200 mg/5ml Syrup 118ml Bottle15.99USD bottle
P-ephed w/guaifen tablet1.21USD tablet
P-ephedrine-guaifen la tablet1.14USD tablet
Guaifen/p-ephed tablet sa1.01USD tablet
Organidin nr 200 mg tablet0.89USD tablet
Mucinex dm er 1200-60 mg tablet0.8USD tablet
Pseudoephedrine-guaifen tr tablet0.76USD tablet
Humibid e 400 mg tablet0.74USD tablet
Mucinex d er tablet0.73USD tablet
P-ephed w/guaifen tablet sr0.67USD tablet
Pseudoephedrine-guaif sr tablet0.63USD tablet
Guaifenesin/p-ephedrine tablet0.62USD tablet
P-ephed-guaifen tablet la0.6USD tablet
Kid's mucinex mini-melts pack0.57USD each
Mucinex cough mini-melt pack0.57USD each
Mucinex d tablet0.54USD tablet
Organidin NR 100 mg/5ml Liquid0.49USD ml
Codeine 10 mg-guai 300 mg liq0.46USD ml
Mucinex er 600 mg tablet0.44USD tablet
Mucinex 600 mg tablet0.42USD tablet
Mucinex full force nasal spray0.42USD ml
Mucinex moisture smart nas spr0.42USD ml
Tussi-Organidin NR 300-10 mg/5ml Liquid0.39USD ml
Mucus relief 400 mg tablet0.37USD tablet
Codeine-guaifen 10 mg-200 mg liq0.28USD ml
Guaifenesin 200 mg tablet0.28USD tablet
Guaifenesin-dm 400-20 mg tablet0.25USD tablet
Robitussin coughgels0.25USD each
Diabetic tussin ex 400 tablet0.2USD tablet
G-fenesin dm 20-400 mg caplet0.2USD caplet
Organ-i nr 200 mg tablet0.2USD tablet
G-fenesin 400 mg caplet0.19USD caplet
Guaifenesin 400 mg tablet0.16USD tablet
Chest congestion relief tablet0.15USD tablet
Guaifen p-ephed caplet er0.15USD caplet
Fenesin dm ir tablet0.13USD tablet
Fenesin pe ir tablet0.13USD tablet
Guaifenesin nr liquid0.13USD ml
Fenesin ir 400 mg tablet0.1USD tablet
Guaifenesin-dm nr liquid0.1USD ml
Guaifenesin-DM 100-10 mg/5ml Liquid0.09USD ml
Robitussin dm to go liquid0.09USD ml
Guaiacol liquid purified0.08USD ml
Guaifenesin dac oral solution0.08USD ml
Guaifenesin nr 100 mg/5 ml0.08USD ml
Children's mucinex cough liq0.06USD ml
Mucinex cold liquid0.06USD ml
Naldecon-dx senior0.06USD ml
Child's mucinex 100 mg/5 ml lq0.05USD ml
Guiatuss-dm syrup0.05USD ml
Adlt robitussin cough-cold-flu0.04USD ml
Adt robitussin cough-cold d lq0.04USD ml
Adult robitussin cough syrup0.04USD ml
Guiatuss DAC 30-10-100 mg/5ml Solution0.04USD ml
Robitussin chest congest syrup0.04USD ml
Robitussin cough & cold liquid0.04USD ml
Robitussin cough-cold liquid0.04USD ml
Robitussin cough-cong syrup0.04USD ml
Robitussin dm max liquid0.04USD ml
Robitussin long-acting liq0.04USD ml
Robitussin pe head & chest liq0.04USD ml
Robitussin-cough-chest-cong lq0.04USD ml
Robitussin-dm cough syrup0.04USD ml
Scot-tussin 100 mg/5 ml liq0.04USD ml
Guiatuss ac syrup0.03USD ml
Guiatuss-dac syrup0.03USD ml
Sb cough control syrup0.03USD ml
Guaifenesin ac cough syrup0.02USD ml
Guaifenesin dm syrup0.02USD ml
Guiatuss dm syrup0.02USD ml
Guiatuss-pe syrup0.02USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6372252No2000-04-282020-04-28Us
US6955821No2000-04-282020-04-28Us
US7838032No2000-04-282020-04-28Us
US9549907No2015-11-132035-11-13Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)78.5-79British Patent 628,497.
boiling point (°C)215 °C at 1.90E+01 mm HgPhysProp
water solubility5E+004 mg/L (at 25 °C)MERCK INDEX (1996)
logP1.39SMITH,JT & VINJAMOORI,DT (1995)
Predicted Properties
PropertyValueSource
Water Solubility14.9 mg/mLALOGPS
logP0.76ALOGPS
logP0.34ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity51.24 m3·mol-1ChemAxon
Polarizability20.59 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9231
Blood Brain Barrier-0.8631
Caco-2 permeable-0.6755
P-glycoprotein substrateSubstrate0.5523
P-glycoprotein inhibitor INon-inhibitor0.7979
P-glycoprotein inhibitor IINon-inhibitor0.9002
Renal organic cation transporterNon-inhibitor0.88
CYP450 2C9 substrateNon-substrate0.8348
CYP450 2D6 substrateNon-substrate0.8535
CYP450 3A4 substrateNon-substrate0.6853
CYP450 1A2 substrateInhibitor0.6013
CYP450 2C9 inhibitorNon-inhibitor0.9592
CYP450 2D6 inhibitorNon-inhibitor0.9616
CYP450 2C19 inhibitorNon-inhibitor0.9328
CYP450 3A4 inhibitorNon-inhibitor0.9481
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9445
Ames testNon AMES toxic0.7677
CarcinogenicityNon-carcinogens0.9215
BiodegradationReady biodegradable0.7769
Rat acute toxicity2.0868 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9171
hERG inhibition (predictor II)Non-inhibitor0.8735
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.98 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-00di-3900000000-022756bf476e39b7c0be
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0hb9-2900000000-261d308d57fa6814ad4e
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Anisoles
Direct Parent
Anisoles
Alternative Parents
Phenoxy compounds / Methoxybenzenes / Alkyl aryl ethers / Secondary alcohols / 1,2-diols / Primary alcohols / Hydrocarbon derivatives
Substituents
Phenoxy compound / Methoxybenzene / Anisole / Alkyl aryl ether / Monocyclic benzene moiety / Secondary alcohol / 1,2-diol / Ether / Organic oxygen compound / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on June 13, 2005 07:24 / Updated on January 14, 2018 10:04