Guaifenesin

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Guaifenesin
Guaifenesin.svg
Guaifenesin molecule spacefill.png
Clinical data
Pronunciation /ɡwaɪˈfɛnɪsɪn/ [1]
Trade names Mucinex, others
Other namesGlyceryl guaiacolate
AHFS/Drugs.com Monograph
MedlinePlus a682494
License data
Routes of
administration 		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Metabolism Kidney
Elimination half-life 1–5 hours [3]
Identifiers
  • (RS)-3-(2-methoxyphenoxy)propane-1,2-diol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.002.021 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C10H14O4
Molar mass 198.218 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
  • O(c1ccccc1OC)CC(O)CO
  • 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 Yes check.svgY
  • Key:HSRJKNPTNIJEKV-UHFFFAOYSA-N Yes check.svgY
   (verify)

Guaifenesin, also known as glyceryl guaiacolate, is an expectorant medication taken by mouth and marketed as an aid to eliminate sputum from the respiratory tract. Chemically, it is an ether of guaiacol and glycerine. It may be used in combination with other medications. [4] A 2014 study found that guaifenesin has no effect on sputum production or clearance in upper respiratory infections. [5] [6]

Contents

Side effects may include dizziness, sleepiness, skin rash, and nausea. [4] While it has not been properly studied in pregnancy, it appears to be safe. [7] It is believed to work by making airway secretions more liquid. [4]

Guaifenesin has been used medically since at least 1933. [8] It is available as a generic medication and over the counter. [4] [7] In 2021, it was the 288th most commonly prescribed medication in the United States, with more than 600,000 prescriptions. [9] [10]

Medical use

Guaifenesin is used to try to help with coughing up thick mucus, and is sometimes combined with the antitussive (cough suppressant) dextromethorphan, such as in Mucinex DM or Robitussin DM. [11] It is also combined with ephedrine in Primatene and Bronkaid tablets for symptomatic relief of asthma.

A Cochrane review identified only three clinical trials assessing guaifenesin for the treatment of acute cough, with one finding significant benefit and the other two trials finding that it was not effective. [12]

Side effects

Although generally well-tolerated, side-effects of guaifenesin may include an allergic reaction (rare), nausea, vomiting, dizziness or headache. [13] [14]

Pharmacology

Mechanism of action

Guaifenesin is thought to act as an expectorant by increasing the volume and reducing the viscosity of secretions in the trachea and bronchi. It may aid in the flow of respiratory tract secretions, allowing ciliary movement to carry the loosened secretions upward toward the pharynx. [15] Thus, it may increase the efficiency of the cough reflex and facilitate removal of the secretions.

History

Similar medicines derived from the guaiac tree were in use as a generic remedy by American indigenous peoples when explorers reached North America in the 16th century. The Spanish encountered guaiacum wood "when they conquered Santo Domingo; it was soon brought back to Europe, where it acquired an immense reputation in the sixteenth century as a cure for syphilis and certain other diseases..." [16]

The 1955 edition of the Textbook of Pharmacognosy states: "Guaiacum has a local stimulant action which is sometimes useful in sore throat. The resin is used in chronic gout and rheumatism, whilst the wood is an ingredient in the compound concentrated solution of sarsaparilla, which was formerly much used as an alternative in syphilis." [16]

In the US, guaifenesin was first approved by the Food and Drug Administration (FDA) in 1952. Although previously deemed "Generally Regarded as Safe" in its original approval, the drug received a New Drug Application for the extended-release version, which received approval on 12 July 2002. [17] Because of this, the FDA then issued letters to other manufacturers of timed-release guaifenesin to stop marketing their unapproved versions, leaving Adams Respiratory Therapeutics in control of the market. In 2007, Adams was acquired by Reckitt Benckiser. [18] [19] The drug is now sold over-the-counter by many companies, alone and in combination. [20]

Society and culture

Brand names

Guaifenesin is taken by mouth, [4] and is supplied as a tablet, a capsule, an extended-release (long-acting) tablet, dissolving granules, and a syrup. [14] It is available under many brand names, as either the sole active ingredient or part of a combination drug. [14] Drugs combined with guaifenesin in over-the-counter preparations include the cough-suppressant dextromethorphan, analgesics such as paracetamol/acetaminophen, and decongestants such as ephedrine, pseudoephedrine, or phenylephrine. [14]

Economics

In 2014, sales of guaifenesin were estimated to be approximately $135 million per year in the United States. [6]

Veterinary use

Guaifenesin's neurological properties first became known in the late 1940s. Guaifenesin is a centrally acting muscle relaxant used routinely in large-animal veterinary surgery. Guaifenesin is used in combination with, for example, ketamine, since guaifenesin does not provide analgesia or produce unconsciousness. [21] [22] In horses, the drug's biological half-life is 77 minutes. Premeditation with xylazine (1.1 mg/kg) can reduced the dose required from 163 mg/kg (in geldings) to just 88 mg/kg. [22]

Related Research Articles

<span class="mw-page-title-main">Recreational use of dextromethorphan</span> Cough suppressant drug susceptible to misuse.

Dextromethorphan, or DXM, a common active ingredient found in many over-the-counter cough suppressant cold medicines, is used as a recreational drug and entheogen for its dissociative effects. It has almost no psychoactive effects at medically recommended doses. However, dextromethorphan has powerful dissociative properties when administered in doses well above those considered therapeutic for cough suppression. Recreational use of DXM is sometimes referred to in slang form as "robo-tripping", whose prefix derives from the Robitussin brand name, or "Triple Cs", which derives from the Coricidin brand whose tablets are printed with "CC+C" for "Coricidin Cough and Cold". However, this brand presents additional danger when used at recreational doses due to the presence of chlorpheniramine.

<span class="mw-page-title-main">Pseudoephedrine</span> Pharmaceutical drug

Pseudoephedrine (PSE) is a sympathomimetic drug of the phenethylamine and amphetamine chemical classes. It may be used as a nasal/sinus decongestant, as a stimulant, or as a wakefulness-promoting agent in higher doses.

<span class="mw-page-title-main">Ephedrine</span> Medication and stimulant

Ephedrine is a central nervous system (CNS) stimulant that is often used to prevent low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is of unclear benefit in nasal congestion. It can be taken by mouth or by injection into a muscle, vein, or just under the skin. Onset with intravenous use is fast, while injection into a muscle can take 20 minutes, and by mouth can take an hour for effect. When given by injection it lasts about an hour and when taken by mouth it can last up to four hours.

<span class="mw-page-title-main">Over-the-counter drug</span> Medication available without a prescription

Over-the-counter (OTC) drugs are medicines sold directly to a consumer without a requirement for a prescription from a healthcare professional, as opposed to prescription drugs, which may be supplied only to consumers possessing a valid prescription. In many countries, OTC drugs are selected by a regulatory agency to ensure that they contain ingredients that are safe and effective when used without a physician's care. OTC drugs are usually regulated according to their active pharmaceutical ingredient (API) and strengths of final products.

<span class="mw-page-title-main">Cold medicine</span> Medication taken to relieve cold symptoms

Cold medicines are a group of medications taken individually or in combination as a treatment for the symptoms of the common cold and similar conditions of the upper respiratory tract. The term encompasses a broad array of drugs, including analgesics, antihistamines and decongestants, among many others. It also includes drugs which are marketed as cough suppressants or antitussives, but their effectiveness in reducing cough symptoms is unclear or minimal.

A decongestant, or nasal decongestant, is a type of pharmaceutical drug that is used to relieve nasal congestion in the upper respiratory tract. The active ingredient in most decongestants is either pseudoephedrine or phenylephrine. Intranasal corticosteroids can also be used as decongestants and antihistamines can be used to alleviate runny nose, nasal itch, and sneezing.

Vicks NyQuil is a brand of over-the-counter medication manufactured by Procter & Gamble intended for the relief of various symptoms of the common cold. All medications within the NyQuil imprint contain sedating antihistamines, hypnotics, and/or alcohol, and are intended to be taken before sleep. Its daytime counterpart is antihistamine-free DayQuil, formulated to avoid drowsiness. NyQuil is also used as a sleep aid. NyQuil was first marketed in the United States in 1966.

<span class="mw-page-title-main">Benadryl</span> Brand of various antihistamine medications

Benadryl is a brand of various antihistamine medications used to stop allergies, whose content varies in different countries, but which includes some combination of diphenhydramine, acrivastine, and/or cetirizine.

Vicks DayQuil is an over-the-counter combination medication product used for the temporary relief of common cold and flu symptoms. DayQuil is available in several formulations.

<span class="mw-page-title-main">Promethazine</span> Sedating Antihistamine

Promethazine, sold under the brand name Phenergan among others, is a first-generation antihistamine, antipsychotic, sedative, and antiemetic used to treat allergies, insomnia, and nausea. It may also help with some symptoms associated with the common cold and may also be used for sedating people who are agitated or anxious, an effect that has led to some recreational use. Promethazine is taken by mouth (oral), as a rectal suppository, or by injection into a muscle (IM).

<span class="mw-page-title-main">Coricidin</span> Brand name for a cough and pain medicine

Coricidin, Coricidin 'D' (decongestant), or Coricidin HBP, is the name of an over-the-counter cough and cold drug containing dextromethorphan and chlorpheniramine maleate. Introduced by Schering-Plough in 1949 as one of the first antihistamines, it is now owned by Bayer. Varieties of Coricidin may also contain acetaminophen and guaifenesin.

Dimetapp is an American brand of over-the-counter cold and allergy medicines that is manufactured by Foundation Consumer Brands. At one point, Dimetapp as a household word referred to a single combination preparation marketed to relieve symptoms of the common cold, containing brompheniramine and phenylephrine. Variants were created, including Dimetapp DM with the addition of dextromethorphan. Dimetapp Elixir and Colour Free Elixir are intended to relieve nasal congestion, runny nose, itchy watery eyes and sneezing, whereas Dimetapp DM and Dimetapp DM Colour Free Elixir are intended for colds with dry coughs and also to treat whooping cough. Early Dimetapp was flavored with cherry and plum as they were readily available during the time, setting a precedent for its purple color; however, the flavor has been described as a grape candy.

<span class="mw-page-title-main">Dextromethorphan</span> Cough suppressant, anti-depressent, and dissociative drug

Dextromethorphan (DXM), sold under the trade name Robitussin among others, is a cough suppressant used in many cough and cold medicines. It affects serotonin, norepinephrine, NMDA, and sigma-1 receptors in the brain, all of which have been implicated in the pathophysiology of depression. In 2022, the FDA approved the combination dextromethorphan/bupropion to serve as a rapid acting antidepressant in patients with major depressive disorder.

<span class="mw-page-title-main">Benylin</span> Brand of medications

Benylin is a brand name owned by Kenvue for a range of cough, cold and flu medications. Some Benylin products also contain codeine, which is used to treat pain, cough and diarrhea.

Mucoactive agents are a class of chemical agents that aid in the clearance of mucus or sputum from the upper and lower airways, including the lungs, bronchi, and trachea. Mucoactive drugs include expectorants, mucolytics, mucoregulators, and mucokinetics. These medications are used in the treatment of respiratory diseases that are complicated by the oversecretion or inspissation of mucus. These drugs can be further categorized by their mechanism of action.

<span class="mw-page-title-main">Pentoxyverine</span> Antitussive / cough suppressant

Pentoxyverine (rINN) or carbetapentane is an antitussive commonly used for cough associated with illnesses like common cold. It is sold over-the-counter as Solotuss, or in combination with other medications, especially decongestants. One such product is Certuss, a combination of guaifenesin and pentoxyverine. The drug has been available in the form of drops, suspensions and suppositories.

<span class="mw-page-title-main">Oxomemazine/guaifenesin</span> Combination drug

Oxomemazine/guaifenesin is a sedative antihistamine plus expectorant. It is a combination of oxomemazine and guaifenesin.

Guaifenesin/phenylephrine is a combination of the drugs guaifenesin and phenylephrine and is a preparation against the symptoms of cold, flu and allergy. Guaifenesine is an expectorant, phenylephrine is a decongestant. The drug is sold under the brand name Entex and as generic brands. Entex La is 400 mg guaifenesin and 30 mg phenylephrine hydrochloride. Entex Pse is 600 mg guaifenesin and 120 mg phenylephrine hydrochloride. Both are extended release products, meaning that the non-active ingredients are chosen to dissolve slowly to provide a prolonged therapeutic effect.

<span class="mw-page-title-main">Moguisteine</span> Chemical compound

Moguisteine is a non-narcotic, peripherally acting antitussive. In a small double-blind, randomized controlled trial, 200 mg of moguisteine suspension taken 3 times daily significantly reduced the frequency of coughing in patients with COPD, compared to placebo. It has also been studied in small trials in comparison to codeine and dextromethorphan, and has similar efficacy to both. It has not been approved for use in the United States.

Guaifenesin/codeine is a fixed-dose combination cold medicine used for the treatment of cough. It contains guaifenesin, an expectorant; and codeine, as the phosphate, an opioid antitussive. It is taken by mouth.

References

  1. ↑ "Guaifenesin Definition & Meaning". Merriam-Webster.
  2. ↑ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA . Retrieved 22 October 2023.
  3. ↑ Aluri JB, Stavchansky S (1993). "Determination of guaifenesin in human plasma by liquid chromatography in the presence of pseudoephedrine". J Pharm Biomed Anal. 11 (9): 803–808. doi:10.1016/0731-7085(93)80072-9. PMID   8218524.
  4. 1 2 3 4 5 "Guaifenesin: Monograph for Professionals". Drugs.com, American Society of Health-System Pharmacists. 23 January 2023. Retrieved 30 July 2023.
  5. ↑ Hoffer-Schaefer A, Rozycki HJ, Yopp MA, Rubin BK (May 2014). "Guaifenesin has no effect on sputum volume or sputum properties in adolescents and adults with acute respiratory tract infections". Respiratory Care. 59 (5): 631–636. doi: 10.4187/respcare.02640 . PMID   24003241.
  6. 1 2 O'Connell OJ (May 2014). "Is extended-release guaifenesin no better than a placebo?". Respir Care. 59 (5): 788–9. doi:10.4187/respcare.03319. PMID   24789023.
  7. 1 2 Weiner CP, Rope K (2013). The Complete Guide to Medications During Pregnancy and Breastfeeding: Everything You Need to Know to Make the Best Choices for You and Your Baby . St. Martin's Press. p. PT282. ISBN   9781250037206.
  8. ↑ Riviere JE, Papich MG (2013). Veterinary Pharmacology and Therapeutics. John Wiley & Sons. p. 287. ISBN   9781118685907.
  9. ↑ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  10. ↑ "Guaifenesin – Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  11. ↑ "Guaifenesin DM". WebMD.com.
  12. ↑ Smith SM, Schroeder K, Fahey T (November 2014). "Over-the-counter (OTC) medications for acute cough in children and adults in community settings". Cochrane Database Syst Rev. 2014 (11): CD001831. doi:10.1002/14651858.CD001831.pub5. PMC   7061814 . PMID   25420096.
  13. ↑ "Guaifenesin Side Effects". Drugs.com. 3 July 2023. Retrieved 30 July 2023.
  14. 1 2 3 4 "Guaifenesin". MedlinePlus, United States National Library of Medicine. 15 January 2022. Retrieved 30 July 2023.
  15. ↑ Gutierrez, K. (2007). Pharmacotherapeutics: Clinical Reasoning in Primary Care. W.B. Saunders Co.
  16. 1 2 Wallis TE (1955). Textbook of Pharmacognosy .
  17. ↑ "Drug Approval Package: Mucinex (Guaifenesin) NDA #21-282". accessdata.fda.gov. 25 November 2002. Retrieved 26 October 2022.
  18. ↑ "Announcements RB Press release - 10/12/2007". Archived from the original on 15 July 2011. Retrieved 16 November 2010.
  19. ↑ Goldstein J (25 May 2007). "FDA Bumps Phlegm-Fighters From Market". The Wall Street Journal. Retrieved 16 November 2010.
  20. ↑ "Guaifenesin (Oral Route) Description and Brand Names". Mayo Clinic. Retrieved 27 July 2021.
  21. ↑ Tranquilli WJ, Thurmon JC, Grimm KA, eds. (2007). "Centrally Acting Muscle Relaxants". Lumb and Jones' Veterinary Anesthesia and Analgesia (2nd ed.). Blackwell Publishing.
  22. 1 2 Valverde A (April 2013). "Balanced anesthesia and constant-rate infusions in horses". Vet Clin North Am Equine Pract. 29 (1): 89–122. doi:10.1016/j.cveq.2012.11.004. PMID   23498047.
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