Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C10H14O4 |
| Molecular Weight | 198.2158 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(OCC(O)CO)C=CC=C1
InChI
InChIKey=HSRJKNPTNIJEKV-UHFFFAOYSA-N
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
| Molecular Formula | C10H14O4 |
| Molecular Weight | 198.2158 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Guaifenesin is an expectorant the action of which promotes or facilitates the removal of secretions from the respiratory tract. The precise mechanism of action of guaifenesin is not known; however, it is thought to act as an expectorant by increasing the volume and reducing the viscosity of secretions in the trachea and bronchi. In turn, this may increase the efficiency of the cough reflex and facilitate removal of the secretions. Guaifenesin is over-the-counter drug for the treatment of cough and common cold.
Approval Year
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | MUCINEX Approved UseUses helps loosen phlegm (mucus) and thin bronchial secretions to rid the bronchial passageways of bothersome mucus and make coughs more productive Launch Date2002 |
|||
| Palliative | MUCINEX Approved UseUses helps loosen phlegm (mucus) and thin bronchial secretions to rid the bronchial passageways of bothersome mucus and make coughs more productive Launch Date2002 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.7 μg/mL |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
GUAIFENESIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.2 μg × h/mL |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
GUAIFENESIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1 h |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
GUAIFENESIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
400 mg 6 times / day steady, oral Highest studied dose Dose: 400 mg, 6 times / day Route: oral Route: steady Dose: 400 mg, 6 times / day Sources: |
healthy, 31. 3 years (range: 19–50 years) Health Status: healthy Age Group: 31. 3 years (range: 19–50 years) Sex: M+F Sources: |
Other AEs: Headache, Sore throat... Other AEs: Headache Sources: Sore throat Indigestion Nose bleed Eye infection |
1200 mg 2 times / day steady, oral Highest studied dose|Recommended Dose: 1200 mg, 2 times / day Route: oral Route: steady Dose: 1200 mg, 2 times / day Sources: |
healthy, 31. 3 years (range: 19–50 years) Health Status: healthy Age Group: 31. 3 years (range: 19–50 years) Sex: M+F Sources: |
Other AEs: Headache, Sore throat... Other AEs: Headache Sources: Sore throat Indigestion Nose bleed Eye infection |
600 mg 2 times / day multiple, oral Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: |
unhealthy, 63.7 years Health Status: unhealthy Age Group: 63.7 years Sex: M+F Sources: |
Disc. AE: Vomiting, Diarrhea... AEs leading to discontinuation/dose reduction: Vomiting (1 patient) Sources: Diarrhea (1 patient) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Eye infection | 400 mg 6 times / day steady, oral Highest studied dose Dose: 400 mg, 6 times / day Route: oral Route: steady Dose: 400 mg, 6 times / day Sources: |
healthy, 31. 3 years (range: 19–50 years) Health Status: healthy Age Group: 31. 3 years (range: 19–50 years) Sex: M+F Sources: |
|
| Headache | 400 mg 6 times / day steady, oral Highest studied dose Dose: 400 mg, 6 times / day Route: oral Route: steady Dose: 400 mg, 6 times / day Sources: |
healthy, 31. 3 years (range: 19–50 years) Health Status: healthy Age Group: 31. 3 years (range: 19–50 years) Sex: M+F Sources: |
|
| Indigestion | 400 mg 6 times / day steady, oral Highest studied dose Dose: 400 mg, 6 times / day Route: oral Route: steady Dose: 400 mg, 6 times / day Sources: |
healthy, 31. 3 years (range: 19–50 years) Health Status: healthy Age Group: 31. 3 years (range: 19–50 years) Sex: M+F Sources: |
|
| Nose bleed | 400 mg 6 times / day steady, oral Highest studied dose Dose: 400 mg, 6 times / day Route: oral Route: steady Dose: 400 mg, 6 times / day Sources: |
healthy, 31. 3 years (range: 19–50 years) Health Status: healthy Age Group: 31. 3 years (range: 19–50 years) Sex: M+F Sources: |
|
| Sore throat | 400 mg 6 times / day steady, oral Highest studied dose Dose: 400 mg, 6 times / day Route: oral Route: steady Dose: 400 mg, 6 times / day Sources: |
healthy, 31. 3 years (range: 19–50 years) Health Status: healthy Age Group: 31. 3 years (range: 19–50 years) Sex: M+F Sources: |
|
| Eye infection | 1200 mg 2 times / day steady, oral Highest studied dose|Recommended Dose: 1200 mg, 2 times / day Route: oral Route: steady Dose: 1200 mg, 2 times / day Sources: |
healthy, 31. 3 years (range: 19–50 years) Health Status: healthy Age Group: 31. 3 years (range: 19–50 years) Sex: M+F Sources: |
|
| Headache | 1200 mg 2 times / day steady, oral Highest studied dose|Recommended Dose: 1200 mg, 2 times / day Route: oral Route: steady Dose: 1200 mg, 2 times / day Sources: |
healthy, 31. 3 years (range: 19–50 years) Health Status: healthy Age Group: 31. 3 years (range: 19–50 years) Sex: M+F Sources: |
|
| Indigestion | 1200 mg 2 times / day steady, oral Highest studied dose|Recommended Dose: 1200 mg, 2 times / day Route: oral Route: steady Dose: 1200 mg, 2 times / day Sources: |
healthy, 31. 3 years (range: 19–50 years) Health Status: healthy Age Group: 31. 3 years (range: 19–50 years) Sex: M+F Sources: |
|
| Nose bleed | 1200 mg 2 times / day steady, oral Highest studied dose|Recommended Dose: 1200 mg, 2 times / day Route: oral Route: steady Dose: 1200 mg, 2 times / day Sources: |
healthy, 31. 3 years (range: 19–50 years) Health Status: healthy Age Group: 31. 3 years (range: 19–50 years) Sex: M+F Sources: |
|
| Sore throat | 1200 mg 2 times / day steady, oral Highest studied dose|Recommended Dose: 1200 mg, 2 times / day Route: oral Route: steady Dose: 1200 mg, 2 times / day Sources: |
healthy, 31. 3 years (range: 19–50 years) Health Status: healthy Age Group: 31. 3 years (range: 19–50 years) Sex: M+F Sources: |
|
| Diarrhea | 1 patient Disc. AE |
600 mg 2 times / day multiple, oral Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: |
unhealthy, 63.7 years Health Status: unhealthy Age Group: 63.7 years Sex: M+F Sources: |
| Vomiting | 1 patient Disc. AE |
600 mg 2 times / day multiple, oral Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: |
unhealthy, 63.7 years Health Status: unhealthy Age Group: 63.7 years Sex: M+F Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Sensitive spectrophotometric method for quantitation of guaifenesin and dropropizine in their dosage forms. | 2010 |
|
| Spontaneous dissolution of a guaifenesin stone. | 2005-08 |
|
| Dextromethorphan-induced delirium and possible methadone interaction. | 2005-03 |
|
| Ephedrine- and guaifenesin-induced nephrolithiasis. | 2004-12 |
|
| Pseudoephedrine and guaifenesin urolithiasis: widening the differential diagnosis of radiolucent calculi on abdominal radiograph. | 2004-09-08 |
|
| Bilateral guaifenesin ureteral calculi. | 2004-01 |
|
| Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001-11 |
|
| Guaifenesin- and ephedrine-induced stones. | 1999-11 |
|
| Abuse of guaifenesin-containing medications generates an excess of a carboxylate salt of beta-(2-methoxyphenoxy)-lactic acid, a guaifenesin metabolite, and results in urolithiasis. | 1999-07 |
|
| Fulminant hepatic failure associated with clarithromycin. | 1996-02 |
|
| Affective disorder following use of phenylpropanolamine. | 1990-03 |
|
| Hypertension in bulls and steers anesthetized with guaifenesin-thiobarbiturate-halothane combination. | 1986-07 |
|
| Potentiating effects of chlorpromazine on the paralysis and toxicity induced by guaiacal glyceryl ether in rats. | 1972-12 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021282s021,021585s012,021620s011lbl.pdf
Curator's Comment: Guaifenesin can also be given in syrup form.
1 tablet every 12 hours (adults and children 12 years of age and over).
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/10424525
Sputum or mucus simulants were analyzed untreated and after the addition of guaifenesin at 1:5 volume to volume ratio for a contact period of 60 s. The concentration of guaifenesin was 20 mg/mL.
| Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 17:55:16 GMT 2025
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| Record UNII |
495W7451VQ
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| Record Status |
Validated (UNII)
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WHO-VATC |
QR05CA03
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NCI_THESAURUS |
C29767
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CFR |
21 CFR 522.1086
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WHO-VATC |
QM03BX90
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CFR |
21 CFR 341.78
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CFR |
21 CFR 341.18
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CFR |
21 CFR 522.1085
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WHO-ATC |
R05CA03
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100000090413
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DTXSID5023114
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Guaifenesin
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93-14-1
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CHEMBL980
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5032
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C29081
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GUAIFENESIN
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D006140
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m5861
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1301007
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| Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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METABOLITE -> PARENT |
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PARENT -> METABOLITE |
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| Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
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