Welcome to DrugBank 4.0! If you prefer, you can still go back to version 3.0.
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
SaltsNot Available
Brand names
NameCompany
Duratuss GNot Available
Ganidin NRNot Available
HustosilNot Available
HytussNot Available
MucinexNot Available
RobitussinNot Available
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
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 KeyInChIKey=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
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
    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 °CPhysProp
    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
    Spectra
    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
    Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12