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Substance Name: Guaifenesin [USAN:USP:INN:BAN:JAN]
RN: 93-14-1
UNII: 495W7451VQ
InChIKey: HSRJKNPTNIJEKV-UHFFFAOYSA-N

Note

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

Molecular Formula

  • C10-H14-O4

Molecular Weight

  • 198.2166
 

Classification Codes

  • Drug / Therapeutic Agent
  • Expectorant
  • Expectorants
  • Respiratory System Agents

Names and Synonyms

Name of Substance

  • Glyceryl guaiacolate
  • Guaifenesin
  • Guaifenesin [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Guaifenesin

Synonyms

  • (+-)-3-(o-Methoxyphenoxy)-1,2-propanediol
  • (component of) Deconsal II
  • 1,2,3-Propanetriol, ether with 2-methoxyphenol
  • 1,2-Dihydroxy-3-(2-methoxyphenoxy)propane
  • 1,2-Propanediol, 3-(2-methoxyphenoxy)-
  • 1,2-Propanediol, 3-(2-methoxyphenoxy)- (+-)-
  • 1,2-Propanediol, 3-(o-methoxyphenoxy)-
  • 2-G
  • 2/G
  • 3-(2-Methoxyphenoxy)-1,2-propanediol
  • 3-(o-Methoxyphenoxy)-1,2-propanediol
  • 3-o-Methoxyphenoxypropane 1:2-diol
  • 4-06-00-05576 (Beilstein Handbook Reference)
  • Aeronesin
  • Aether glycerinoguaiacolicus
  • AI3-24947
  • alpha-Glyceryl guaiacol ether
  • alpha-Glyceryl guaiacolate ether
  • Amonidrin
  • Aresol
  • Breonesin
  • BRN 2049375
  • Bronchol
  • Calmipan
  • Cortussin
  • Creson
  • Dilyn
  • Dorassin
  • EINECS 202-222-5
  • Flartussin
  • G 87
  • Gaiamar
  • GGE
  • GGG
  • Glycerin guaiacolate
  • Glycerin monoguaiacol ether
  • Glycerinmonoguaiacol ether
  • Glycero-guaiacol ether
  • Glycerol alpha-(2-methoxyphenyl) ether
  • Glycerol alpha-(o-methoxyphenyl) ether
  • Glycerol alpha-(o-methoxyphenyl)ether
  • Glycerol alpha-guaiacyl ether
  • Glycerol alpha-guiacyl ether
  • Glycerol alpha-monoguaiacol ether
  • Glycerol guaiacolate
  • Glycerol mono(2-methoxyphenyl) ether
  • Glycerol mono(2-methoxyphenyl)ether
  • Glycerol-alpha-guajakolether
  • Glycerol-alpha-guajakolether [Czech]
  • Glycerol-alpha-monoguaiacol ether
  • Glyceryl guaiacol
  • Glyceryl guaiacolate
  • Glyceryl guaiacyl ether
  • Glyceryl guaicolate
  • Glyceryl guiacolate
  • Glycerylguaiacol
  • Glycotuss
  • Gnaifenesin
  • Guaia-rom
  • Guaiacol glycerin ether
  • Guaiacol glycerol ether
  • Guaiacol glyceryl ether
  • Guaiacolglicerinetere
  • Guaiacolic acid, ester with glycerol
  • Guaiacuran
  • Guaiacurane
  • Guaiacyl glyceryl ether
  • Guaiamar
  • Guaianesin
  • Guaicol glycerine ether
  • Guaicol glyceryl ether
  • Guaifenesin
  • Guaifenesina
  • Guaifenesina [INN-Spanish]
  • Guaifenesine
  • Guaifenesine [INN-French]
  • Guaifenesinum
  • Guaifenesinum [INN-Latin]
  • Guaiphenesin
  • Guaiphenesine
  • Guaiphesin
  • Guajacol-alpha-glycerinether
  • Guajacol-glycerinaether
  • Guajacol-glycerinaether [German]
  • Guajacuran
  • Guajamar
  • Guanar
  • Guayanesin
  • Guiaphenesin
  • Gvaja
  • HSDB 3089
  • Hustodil
  • Hustosil
  • Hytuss
  • Metfenossidiolo
  • Methoxypropanediol
  • Methphenoxydiol
  • Metossipropandiolo
  • Mintosyl
  • Miocaina
  • Miocurin
  • Miorelax
  • Mucinex
  • Mucostop
  • Muskurelax
  • My 301
  • MY-301
  • Myocain
  • Myocaine
  • Myorelax
  • Myoscain
  • Myoscaine
  • Neuroton
  • Neurotone
  • NSC 62112
  • o-Methoxyphenyl glyceryl ether
  • Oresol
  • Oreson
  • Propanosedyl
  • Reduton
  • Relaxil G
  • Relaxyl-G
  • Reorganin
  • Resil
  • Respenyl
  • Respil
  • Resyl
  • Ritussin
  • Robitussin
  • Sirotol
  • SL-90
  • Tenntuss
  • Tolyn
  • Trecid
  • Tulyl
  • Tulyn
  • Tussin
  • UNII-495W7451VQ
  • XL-90

Systematic Names

  • 1,2-Propanediol, 3-(2-methoxyphenoxy)-
  • 1,2-Propanediol, 3-(o-methoxyphenoxy)-
  • Guaifenesin

Mixture Names

  • Bayer Select Head & Chest Cold
  • Brexin EX
  • Brondecon
  • Bronkaid Caplets
  • Congestac
  • Contac Cough & Sore Throat Formula
  • Contac Cough Formula
  • Coricidin Syrup
  • Dilor G
  • Dimacol
  • Donatuss
  • Entex
  • Guaifenesin
  • Histalet X Tablets
  • Hycotuss
  • Isoclor Expectorant C
  • Kwelcof
  • Lufyllin-GG
  • Mucinex D
  • Mucinex DM
  • Naldecon-CX
  • Naldecon-DX
  • Naldecon-EX
  • Nasatab LA
  • Neothylline-GG
  • Organidin NR
  • Pneumomist
  • Pneumotussin HC
  • Polaramine Expectorant
  • PV Tussin Tablet
  • Q-Tussin
  • Robitussin
  • Robitussin CF
  • Robitussin Cold & Cough
  • Robitussin DM
  • Robitussin PE
  • Robitussin Severe Congestion
  • Ru-Tuss DE Tablets
  • Ru-Tuss Expectorant
  • Slo-Phyllin GG
  • Sudafed Cold and Cough
  • Sudafed Cough Syrup
  • Tedral Expectorant
  • Theolair Plus
  • Triaminic
  • Tussar SF
  • Tussar-2
  • Tussi-Organidin DM NR
  • Tussi-Organidin DM-S NR
  • Tussi-Organidin NR
  • Tussi-Organidin-S NR

Registry Numbers

CAS Registry Number

  • 93-14-1

FDA UNII

  • 495W7451VQ

Other Registry Numbers

  • 12041-73-5
  • 128707-44-8
  • 1336-67-0

System Generated Number

  • 0000093141

Structure Descriptors

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

InChIKey

HSRJKNPTNIJEKV-UHFFFAOYSA-N

Smiles

COc1ccccc1OCC(O)CO

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 335mg/kg (335mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 54, Pg. 688, 1958.
mouse LD50 intramuscular 2210mg/kg (2210mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 429, 1974.
mouse LD50 intraperitoneal 495mg/kg (495mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 398, 1972.
mouse LD50 intravenous 400mg/kg (400mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 429, 1974.
mouse LD50 oral 690mg/kg (690mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 398, 1972.
mouse LD50 subcutaneous 800mg/kg (800mg/kg) AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)" Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 1355, 1965.
rabbit LD50 oral 2553mg/kg (2553mg/kg)   Applied Therapeutics. Vol. 9, Pg. 55, 1967.
rat LD50 intramuscular 4gm/kg (4000mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 429, 1974.
rat LD50 intraperitoneal 1gm/kg (1000mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) Archives Internationales de Pharmacodynamie et de Therapie. Vol. 191, Pg. 147, 1971.
rat LD50 intravenous 360mg/kg (360mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

KIDNEY, URETER, AND BLADDER: HEMATURIA
Proceedings of the Society for Experimental Biology and Medicine. Vol. 85, Pg. 323, 1954.
rat LD50 oral 1510mg/kg (1510mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA
Pharmacological Research Communications. Vol. 1, Pg. 413, 1969.
rat LD50 subcutaneous 2550mg/kg (2550mg/kg)   Drugs in Japan Vol. 6, Pg. 210, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 78.5 deg C   EXP
log P (octanol-water) 1.39 (none)   EXP
Water Solubility 5.00E+04 mg/L 25 EXP
Vapor Pressure 1.52E-06 mm Hg 25 EST
Henry's Law Constant 4.44E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.10E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.