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Identification
NameGuaifenesin
Accession NumberDB00874  (APRD01005)
Typesmall molecule
Groupsapproved
Description

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

Structure
Thumb
Synonyms
SynonymLanguageCode
Glyceryl guaiacolateNot AvailableNot Available
guaiphenesinNot AvailableNot Available
HustosilNot AvailableNot Available
RobitussinNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
Duratuss GNot Available
GanidinCypress
HustosilKyoto Yakuhin
HytussHyrex
MucinexReckitt Benckiser
RobitussinWyeth
Scot-tussin ExpectorantNot Available
Sinumist-SRNot Available
Brand mixtures
Brand NameIngredients
Babys Own Cough SyrAmmonium Chloride + Guaifenesin + Pyrilamine Maleate
Benylin 4 Flu - SyrupAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Benylin Codeine 3.3mg de SyrCodeine Phosphate + Guaifenesin + Pseudoephedrine Hydrochloride
BiocotronDextromethorphan + Guaifenesin
Broncho Tuss AdultGuaifenesin + L-Ephedrine Hydrochloride + Sodium Camsylate
Broncho Tuss InfantGuaifenesin + L-Ephedrine Hydrochloride + Sodium Camsylate
Bronchodex PediatriqueDextromethorphan Hydrobromide + Guaifenesin + Pheniramine Maleate + Pseudoephedrine Hydrochloride
Calmylin #3 SyrDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Calmylin Codeine D-E SyrCodeine Phosphate + Guaifenesin + Pseudoephedrine Hydrochloride
Calmylin Cough and Flu LiqAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Centracol Pediatrique - SyrDextromethorphan Hydrobromide + Guaifenesin + Pheniramine Maleate + Pseudoephedrine Hydrochloride
Cheracol Cough SyrupAlcohol Anhydrous + Ammonium Chloride + Codeine Phosphate + Guaifenesin
Cold Aid for BirdsAmmonium Chloride + Glycerine + Guaifenesin + Oil of Anise + Sodium Bicarbonate
Cold and Respiratory Aid for HamstersAmmonium Chloride + Glycerine + Guaifenesin + Oil of Anise + Sodium Bicarbonate
Cough and Flu SyrupAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Cough Syr W.Cod. Pseudoephed.Hcl GuaifenesinCodeine Phosphate + Guaifenesin + Pseudoephedrine Hydrochloride
Cough Syrup Dm Decongestant ExpectorantDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Cough Syrup Dm ExpectorantDextromethorphan Hydrobromide + Guaifenesin
Cough Syrup Dm-D-EDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Cough Syrup Dm-EDextromethorphan Hydrobromide + Guaifenesin
Cough Syrup Dm-ExpectorantDextromethorphan Hydrobromide + Guaifenesin
Cough Syrup W.Guaifenesin W.DextromethorphanDextromethorphan Hydrobromide + Guaifenesin
Creo Grippe Enfants SupCamphor + Eucalyptol + Guaifenesin
Creo Grippe Sup AdultesCamphor + Eucalyptol + Guaifenesin
Dayquil LiquicapsAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Daytime Cold & Flu Liquid CapsulesAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Daytime Liquid - LiqAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Dimetane Expectorant LiqBrompheniramine Maleate + Guaifenesin + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetane Expectorant-C SyrBrompheniramine Maleate + Codeine Phosphate + Guaifenesin + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetane Expectorant-Dc SyrBrompheniramine Maleate + Guaifenesin + Hydrocodone Bitartrate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dm Cough Syrup ExpectorantDextromethorphan Hydrobromide + Guaifenesin
Dm Expectorant Cough SyrupDextromethorphan Hydrobromide + Guaifenesin
Dm Plus Decongestant Plus Expector.Ex.St.SyrDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Dm Plus Decongestant Plus Expectorant Cough SyrupDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Dm Plus Expectorant SyrupDextromethorphan Hydrobromide + Guaifenesin
Dm-D-Expectorant Cough and Cold SyrupDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Dymetadrine 25 - TabEphedrine Hydrochloride + Guaifenesin
Entex LaGuaifenesin + Phenylpropanolamine Hydrochloride
Entex La Tablets SrtGuaifenesin + Phenylpropanolamine Hydrochloride
Ephedrine Ii with GuaifenesinEphedrine Racemic (Ephedrine Hydrochloride) + Guaifenesin
Ephedrine V with GuaifenesinEphedrine Hydrochloride + Guaifenesin
Guaiacol Plus PwrAmmonium Chloride + Guaifenesin + Potassium Iodide
I D M Expectorant TabGuaifenesin + Potassium Iodide + Pyrilamine Maleate + Theophylline
I.D.M. SolutionGuaifenesin + L-Ephedrine Hydrochloride + Potassium Iodide + Pyrilamine Maleate
Koffex Dm + Decongestant + ExpectorantDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Koffex Dm + Decongestant + Expectorant Extra StrengthDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Koffex Dm + ExpectorantDextromethorphan Hydrobromide + Guaifenesin
Koffex Dm + Expectorant Extra StrengthDextromethorphan Hydrobromide + Guaifenesin
Koffex Dm-D-E - LiqDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Mielocol SyrupAralia Racemosa + Eucalyptol + Guaifenesin + Honey + Poplar Bud + Sanguinaria Canadensis + White Pine + Wild Cherry
Nezger TabAcetylsalicylic Acid + Diphenylpyraline Hydrochloride + Guaifenesin + Phenylephrine Hydrochloride
Novahistex Dh ExpectorantGuaifenesin + Hydrocodone Bitartrate + Phenylephrine Hydrochloride
Novahistex Dm Expectorant with DecongestantDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Novahistex Expectorant with DecongestantGuaifenesin + Pseudoephedrine Hydrochloride
Novahistine Dm Expectorant with DecongestantDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Ornade Expectorant Cough FormulaChlorpheniramine Maleate + Guaifenesin + Phenylpropanolamine Hydrochloride
Pharmitussin DmDextromethorphan Hydrobromide + Guaifenesin
Pulmorex Expectorant LiqAmmonium Chloride + Diphenhydramine Hydrochloride + Guaifenesin
Pulmosirum Plus ExpectorantAmmonium Chloride + Beechwood Creosote + Cocillana + Eucalyptus Oil + Guaiacol + Guaifenesin + Ipecac + Lobelia Inflata + Menthol + Myroxylon Balsamum + White Pine
Quiex-K1 SyrAminophylline + Guaifenesin + Potassium Iodide
Regular Strength Tylenol Cold Chest CongestionAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Robitussin Syrup with CodeineCodeine Phosphate + Guaifenesin + Pheniramine Maleate
Sudafed Cold and Flu Gel CapsAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Tri-Anamine Expect Antihist Decong SyrupGuaifenesin + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Triaminic Decongest+Expect Liqui-Gels CapGuaifenesin + Pseudoephedrine Hydrochloride
Triaminic DM Daytime SyrDextromethorphan Hydrobromide + Guaifenesin + Phenylpropanolamine Hydrochloride
Triaminic DM Expectorant SyrChlorpheniramine Maleate + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Triaminic Expectorant Dh SyrupGuaifenesin + Hydrocodone Bitartrate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Triaminic Expectorant SyrChlorpheniramine Maleate + Guaifenesin + Pseudoephedrine Hydrochloride
Tussin Cough Medicine Dm Antitussive Expectorant DecongestantDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Vicks Cough Syrup New ImprovedCarbetapentane Citrate + Ephedrine + Guaifenesin
Categories
CAS number93-14-1
WeightAverage: 198.2158
Monoisotopic: 198.089208936
Chemical FormulaC10H14O4
InChI KeyHSRJKNPTNIJEKV-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
Mass Specshow(7.98 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenol Ethers
Direct parentAnisoles
Alternative parentsAlkyl Aryl Ethers; Secondary Alcohols; 1,2-Diols; Primary Alcohols; Polyamines
Substituentsalkyl aryl ether; secondary alcohol; polyol; 1,2-diol; primary alcohol; ether; polyamine; alcohol
Classification descriptionThis compound belongs to the anisoles. These are organic compounds contaiing a methoxybenzene or a derivative thereof.
Pharmacology
IndicationUsed to assist the expectoration of phlegm from the airways in acute respiratory tract infections.
PharmacodynamicsGuaifenesin 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 actionGuaifenesin 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.
AbsorptionRapidly absorbed from the GI tract
Volume of distributionNot Available
Protein bindingNot 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.

SubstrateEnzymesProduct
Guaifenesin
Not Available
beta-(2-methoxyphenoxy)-lactic acidDetails
Route of eliminationNot Available
Half life1 hour
ClearanceNot Available
ToxicityLD50 1510 mg/kg (rat, oral)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9231
Blood Brain Barrier - 0.8631
Caco-2 permeable - 0.6755
P-glycoprotein substrate Substrate 0.5523
P-glycoprotein inhibitor I Non-inhibitor 0.7979
P-glycoprotein inhibitor II Non-inhibitor 0.9002
Renal organic cation transporter Non-inhibitor 0.88
CYP450 2C9 substrate Non-substrate 0.8348
CYP450 2D6 substrate Non-substrate 0.8535
CYP450 3A4 substrate Non-substrate 0.6853
CYP450 1A2 substrate Inhibitor 0.6013
CYP450 2C9 substrate Non-inhibitor 0.9592
CYP450 2D6 substrate Non-inhibitor 0.9616
CYP450 2C19 substrate Non-inhibitor 0.9328
CYP450 3A4 substrate Non-inhibitor 0.9481
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9445
Ames test Non AMES toxic 0.7677
Carcinogenicity Non-carcinogens 0.9215
Biodegradation Ready biodegradable 0.7769
Rat acute toxicity 2.0868 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9171
hERG inhibition (predictor II) Non-inhibitor 0.8735
Pharmacoeconomics
Manufacturers
  • Reckitt benckiser inc
Packagers
Dosage forms
FormRouteStrength
LiquidOral
SyrupOral
Prices
Unit descriptionCostUnit
Diabetic Tussin Max St 10-200 mg/5ml Liquid 118ml Bottle15.99USDbottle
Naldecon Senior EX 200 mg/5ml Syrup 118ml Bottle15.99USDbottle
P-ephed w/guaifen tablet1.21USDtablet
P-ephedrine-guaifen la tablet1.14USDtablet
Guaifen/p-ephed tablet sa1.01USDtablet
Organidin nr 200 mg tablet0.89USDtablet
Mucinex dm er 1200-60 mg tablet0.8USDtablet
Pseudoephedrine-guaifen tr tablet0.76USDtablet
Humibid e 400 mg tablet0.74USDtablet
Mucinex d er tablet0.73USDtablet
P-ephed w/guaifen tablet sr0.67USDtablet
Pseudoephedrine-guaif sr tablet0.63USDtablet
Guaifenesin/p-ephedrine tablet0.62USDtablet
P-ephed-guaifen tablet la0.6USDtablet
Kid's mucinex mini-melts pack0.57USDeach
Mucinex cough mini-melt pack0.57USDeach
Mucinex d tablet0.54USDtablet
Organidin NR 100 mg/5ml Liquid0.49USDml
Codeine 10 mg-guai 300 mg liq0.46USDml
Mucinex er 600 mg tablet0.44USDtablet
Mucinex 600 mg tablet0.42USDtablet
Mucinex full force nasal spray0.42USDml
Mucinex moisture smart nas spr0.42USDml
Tussi-Organidin NR 300-10 mg/5ml Liquid0.39USDml
Mucus relief 400 mg tablet0.37USDtablet
Codeine-guaifen 10 mg-200 mg liq0.28USDml
Guaifenesin 200 mg tablet0.28USDtablet
Guaifenesin-dm 400-20 mg tablet0.25USDtablet
Robitussin coughgels0.25USDeach
Diabetic tussin ex 400 tablet0.2USDtablet
G-fenesin dm 20-400 mg caplet0.2USDcaplet
Organ-i nr 200 mg tablet0.2USDtablet
G-fenesin 400 mg caplet0.19USDcaplet
Guaifenesin 400 mg tablet0.16USDtablet
Chest congestion relief tablet0.15USDtablet
Guaifen p-ephed caplet er0.15USDcaplet
Fenesin dm ir tablet0.13USDtablet
Fenesin pe ir tablet0.13USDtablet
Guaifenesin nr liquid0.13USDml
Fenesin ir 400 mg tablet0.1USDtablet
Guaifenesin-dm nr liquid0.1USDml
Guaifenesin-DM 100-10 mg/5ml Liquid0.09USDml
Robitussin dm to go liquid0.09USDml
Guaiacol liquid purified0.08USDml
Guaifenesin dac oral solution0.08USDml
Guaifenesin nr 100 mg/5 ml0.08USDml
Children's mucinex cough liq0.06USDml
Mucinex cold liquid0.06USDml
Naldecon-dx senior0.06USDml
Child's mucinex 100 mg/5 ml lq0.05USDml
Guiatuss-dm syrup0.05USDml
Adlt robitussin cough-cold-flu0.04USDml
Adt robitussin cough-cold d lq0.04USDml
Adult robitussin cough syrup0.04USDml
Guiatuss DAC 30-10-100 mg/5ml Solution0.04USDml
Robitussin chest congest syrup0.04USDml
Robitussin cough & cold liquid0.04USDml
Robitussin cough-cold liquid0.04USDml
Robitussin cough-cong syrup0.04USDml
Robitussin dm max liquid0.04USDml
Robitussin long-acting liq0.04USDml
Robitussin pe head & chest liq0.04USDml
Robitussin-cough-chest-cong lq0.04USDml
Robitussin-dm cough syrup0.04USDml
Scot-tussin 100 mg/5 ml liq0.04USDml
Guiatuss ac syrup0.03USDml
Guiatuss-dac syrup0.03USDml
Sb cough control syrup0.03USDml
Guaifenesin ac cough syrup0.02USDml
Guaifenesin dm syrup0.02USDml
Guiatuss dm syrup0.02USDml
Guiatuss-pe syrup0.02USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States63722522000-04-282020-04-28
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point78.5-79British Patent 628,497.
boiling point215 °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 solubility1.49e+01 g/lALOGPS
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 area58.92ChemAxon
rotatable bond count5ChemAxon
refractivity51.24ChemAxon
polarizability20.59ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
Spectra1D NMR2D NMR
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 ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00337
PubChem Compound3516
PubChem Substance46508004
ChemSpider3396
PharmGKBPA449818
Drug Product Database2242892
RxListhttp://www.rxlist.com/cgi/generic2/guaifen.htm
Drugs.comhttp://www.drugs.com/guaifenesin.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/tus1463.shtml
WikipediaGuaifenesin
ATC CodesR05CA03
AHFS Codes
  • 48:16.00
PDB EntriesNot Available
FDA labelshow(394 KB)
MSDSshow(73.4 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12