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Phenylephrine



Phenylephrine
Systematic (IUPAC) name
3-(1-hydroxy-2-methylamino-ethyl)phenol
Identifiers
CAS number 59-42-7
61-76-7 (hydrochloride)
ATC code C01CA06 R01AA04, R01AB01, R01BA03, S01FB01, S01GA05
PubChem 6041
DrugBank APRD00365
Chemical data
Formula C9H13NO2 
Mol. mass 167.205 g/mol
Pharmacokinetic data
Bioavailability 38% through GI tract
Protein binding 95%
Metabolism Hepatic (monoamine oxidase)
Half life 2.1 to 3.4 hours
Excretion  ?
Therapeutic considerations
Pregnancy cat.

B2(AU) C(US)

Legal status

OTC(US)

Routes Oral, intranasal, ophthalmic, intravenous, intramuscular

Phenylephrine or Neo-Synephrine is an α-adrenergic receptor agonist used primarily as a decongestant, as an agent to dilate the pupil and to increase blood pressure. Phenylephrine has recently been marketed as a substitute for pseudoephedrine, (e.g. Pfizer's Sudafed (Original Formulation)) but there are recent claims that oral phenylephrine may be no more effective as a decongestant than placebo. [1]

Additional recommended knowledge

Contents

Uses

Decongestant

Phenylephrine is used as a decongestant, available as an oral medicine or as a nasal spray. Phenylephrine is now the most common over-the-counter (OTC) decongestant; oxymetazoline is a more common nasal spray.[citation needed] Pseudoephedrine was historically more common, although its notoriety as a methamphetamine precursor has led some governments to restrict its sale.

Oral phenylephrine is extensively metabolised by monoamine oxidase [1], an enzyme which is present in the gastrointestinal tract and the liver. Therefore, compared to orally-taken pseudoephedrine, it has a reduced and variable bioavailability of only up to 38 percent [2] [3], and is therefore less effective than a nasal decongestant. Because phenylephrine is a direct selective α-adrenergic receptor agonist, it does not cause the release of endogenous noradrenaline like pseudoephedrine does. Therefore, phenylephrine is less likely to cause side-effects like central nervous system stimulation, insomnia, anxiety, irritability and restlessness.

Some popular cold remedies containing phenylephrine: Canada's hot lemon Neocitran, the United Kingdom's Lemsip, and the United States' Alka-Seltzer Cold Effervescent formula, Sudafed PE Non-Drowsy Nasal Decongestant, Robitussin CF, Tylenol Sinus, and DayQuil Capsules.

As a nasal spray, phenylephrine is available in 1% and 0.5% concentrations. It suffers some rebound congestion effects, although to a lesser degree than oxymetazoline.

Mydriatic

Phenylephrine is used as an eye drop to dilate the pupil to facilitate visualization of the retina. It is often used in combination with tropicamide. Narrow angle glaucoma is a contraindication to phenylephrine use.

Vasopressor

Phenylephrine is sometimes used as a vasopressor to increase the blood pressure in unstable patients with hypotension. Such use is more common in anesthesia or critical care practices; phenylephrine is especially useful in counteracting the hypotensive effect of epidural and subarachnoid anesthetics. It also has the advantage of not being inotropic or chronotropic, and so it strictly elevates the blood pressure without increasing the heart rate or contractility. This is especially useful if the heart is already tachycardic and/or has a cardiomyopathy.

Side effects

The primary side effect of phenylephrine is hypertension. Patients with congestion and hypertension are typically advised to avoid products containing phenylephrine.

Patients with a history of epilepsy and on anticonvulsant medication should not take this substance. The drug interaction might produce seizures.

Pregnancy

Phenylephrine is in the FDA pregnancy category C.

Legal issues

Pseudoephedrine and phenylephrine are both used as decongestants; and until recently, pseudoephedrine was much more commonly available in the United States. This has changed because provisions of the Combat Methamphetamine Epidemic Act of 2005 placed restrictions on the sale of pseudoephedrine products to prevent the clandestine manufacture of methamphetamine. Since 2004, phenylephrine has been increasingly marketed as a substitute for pseudoephedrine; some manufacturers have changed the active ingredients of products to avoid the restrictions on sales. [2] Phenylephrine has been off patent for a long time; there are many generic brands available.

Questions about effectiveness

Pharmacists Leslie Hendeles and Randy Hatton of the University of Florida suggested in 2006 that oral phenylephrine is ineffective as a decongestant at the 10 mg dose used, arguing that the studies used for the regulatory approval of the drug in the United States in 1976 were inadequate to prove effectiveness at the 10 mg dose and safety at higher doses. [3] Other pharmacists have expressed concerns over phenylephrine's effectiveness as a nasal decongestant [1] and other clinicians have indicated concern for regulatory actions that reduce the availability of pseudoephedrine. [4] [5] A subsequent metaanalysis by the same researchers concluded that there is insufficient evidence for its effectiveness. [6] The matter is still under debate, though the Food and Drug Administration has stood by its 1976 approval. [2]

References

http://www.theannals.com/cgi/content/abstract/aph.1H679v1

  1. ^ a b UF press release on the Hendles letter
  2. ^ a b Hilenmeyer, K. All stuffed up Southwest Florida Herald-Tribune (30 January 2007)
  3. ^ Heldeles, L. and Hatton, R. Oral phenylephrine: An ineffective replacement for pseudoephedrine? Journal of Allergy and Clinical Immunology, Volume 118, Issue 1, Pages 279-280
  4. ^ Eccles, R. Phenylephrine an ineffective replacement for pseudoephedrine in response to the methamphetamine problem in the USA. bmj.com. (May 2006)
  5. ^ Eccles, R. Substitution of phenylephrine for pseudoephedrine as a nasal decongestant. An illogical way to control methamphetamine abuse. British Journal of Clinical Pharmacology 63. p10. (January 2007)
  6. ^ Hatton, R.C. et al. Efficacy and Safety of Oral Phenylephrine: A Systematic Review and Meta-Analysis Annals of Pharmacotherapy (published online Jan 2007)

See also

  • Drugs.com - Phenylephrine
  • MedlinePlus DrugInfo uspdi-202460
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Phenylephrine". A list of authors is available in Wikipedia.
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