Molecular structure of pseudoephedrine
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Drixoral

Pseudoephedrine is a sympathomimetic amine commonly used as a decongestant. The salts pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in many over-the-counter preparations either as single-ingredient preparations, or more commonly in combination with antihistamines and/or paracetamol/ibuprofen. more...

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This agent is often referred to by consumers as Sudafed, which is the trademark for a common brand of pseudoephedrine hydrochloride. Other brand names include Afrinol, Novafed, and Cenafed.

Unlike antihistamines, which modify the systemic histamine-mediated allergic response, pseudoephedrine only serves to relieve nasal congestion commonly associated with colds or allergies. The advantage of oral pseudoephedrine over topical nasal preparations, such as oxymetazoline, is that it does not cause rebound congestion (rhinitis medicamentosa). However, the disadvantage of oral pseudoephedrine is that it can cause high blood pressure.

Nomenclature

Pseudoephedrine is the International Nonproprietary Name (INN) of the (1S,2S)- diastereomer of ephedrine (which has 1R,2S- configuration). Equivalent names are (+)-pseudoephedrine and D-pseudoephedrine. (Reynolds, 1989)

(-)-Pseudoephedrine or L-pseudoephedrine then designates the enantiomer of pseudoephedrine.

Chemistry

Pseudoephedrine, a phenethylamine, is a structural isomer of the popular weightloss/energy supplement and asthma medication, ephedrine. Ephedrine is an alkaloid extracted from the Ephedra plant, which produces it naturally as a racemic mixture. That is, ephedrine molecules occur as two "mirror images," inasmuch as a pair of hands do (See the article on entantiomers). The pharmacologic properties of each "reflection" often share similarities and differences. The (-) or levorotatory isomer is a very potent sympathomimetic amine and anorectic, thus responsible for the amphetamine-like stimulation that is characteristic of Ephedra products. The (+) or dextrorotatoryisomer, aka pseudoephedrine, is far less potent as a stimulant. However, it retains much of ephedrine's ability to open airways and nasal passages.

Mode of action

Pseudoephedrine is a sympathomimetic amine - that is, its principal mechanism of action relies on its indirect action on the adrenergic receptor system. Whilst it may have weak agonist activity at α- and β-adrenergic receptors, the principal mechanism is to displace noradrenaline from storage vesicles in presynaptic neurons. The displaced noradrenaline is released into the neuronal synapse where it is free to activate the aforementioned postsynaptic adrenergic receptors.

The vasoconstriction that pseudoephedrine produces is believed to be principally an α-adrenergic receptor response. Whilst all sympathomimetic amines, to some extent, have decongestant action; pseudoephedrine shows greater selectivity for the nasal mucosa and a lower affinity for central nervous system (CNS) adrenergic-receptors than other sympathomimetic amines. (+)-(1S,2S)-pseudoephedrine shows far lower CNS activity than other Ephedra alkaloids, ephedrine, and (-)-(1R,2R)-pseudoephedrine.

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Cough suppressants
From Gale Encyclopedia of Medicine, 4/6/01 by Nancy Ross-Flanigan

Definition

Cough suppressants are medicines that prevent or stop coughing.

Purpose

Cough suppressants act on the center in the brain that controls the cough reflex. They are meant to be used only to relieve dry, hacking coughs associated with colds and flu. They should not be used to treat coughs that bring up mucus or the chronic coughs associated with smoking, asthma, emphysema or other lung problems.

Many cough medicines contain cough suppressants along with other ingredients. Some combinations of ingredients may cancel each other's effects. One example is the combination of cough suppressant with an expectorant -- a medicine that loosens and clears mucus from the airways. The cough suppressant interferes with the ability to cough up the mucus that the expectorant loosens.

Description

The cough suppressant described here, dextromethorphan, is an ingredient in many cough medicines, such as Vicks Formula 44, Drixoral Cough Liquid Caps, Sucrets Cough Control, Benylin DM and some Robitussin products. These medicines come in capsule, tablet, lozenge, and liquid forms and are available without a physician's prescription.

Recommended dosage

Regular (short-acting) capsules, lozenges, syrups, or tablets:

Adults and children over 12

10-30 mg every 4-8 hours, as needed.

Children 6-12

5-15 mg every 4-8 hours, as needed.

Children 2-6

2.5-7.5 mg every 4-8 hours, as needed.

Children under 6 should not be given lozenges containing dextromethorphan because of the high dose of dextromethorphan in each lozenge. Children under 2

Check with child's physician.

Children under 6 should not be given lozenges containing dextromethorphan.

For extended-release oral suspension

Adults and children over 12

60 mg every 12 hours, as needed.

Children 6-12

30 mg every 12 hours, as needed.

Children 2-6

15 mg every 12 hours, as needed.

Children under 2

Check with child's physician.

Precautions

Do not take more than the recommended daily dosage of dextromethorphan.

Dextromethorphan is not meant to be used for coughs associated with smoking, asthma, emphysema, chronic bronchitis, or other lung conditions. It also should not be used for coughs that produce mucus.

A lingering cough could be a sign of a serious medical condition. Coughs that last more than 7 days or are associated with fever, rash, sore throat, or lasting headache should have medical attention. Call a physician as soon as possible.

People with phenylketonuria should be aware that some products with dextromethorphan also contain the artificial sweetener aspartame, which breaks down in the body to phenylalanine.

Anyone who has asthma or liver disease should check with a physician before taking dextromethorphan.

Women who are pregnant or breastfeeding or who plan to become pregnant should check with their physicians before taking dextromethorphan.

The dye tartrazine is an ingredient in some cough suppressant products. This dye causes allergic reactions in some people, especially those who are allergic to aspirin.

Side effects

Side effects are rare, but may include nausea, vomiting, stomach upset, slight drowsiness, and dizziness.

Interactions

Patients who take monoamine oxidase inhibitors (MAO inhibitors) should be aware that the co-administration of products containing dextromethorphan can cause dizziness, fainting, fever, nausea and possibly coma. Do not take dextromethorphan unless a physician permits the use of the two drugs together.

When dextromethorphan is taken with medicines that cause drowsiness, this effect may be enhanced.

Key Terms

Asthma
A disease in which the air passages of the lungs become inflamed and narrowed.
Bronchitis
Inflammation of the air passages of the lungs.
Chronic
A word used to describe a long-lasting condition. Chronic conditions often develop gradually and involve slow changes.
Emphysema
An irreversible lung disease in which breathing becomes increasingly difficult.
Mucus
Thick fluid produced by the moist membranes that line many body cavities and structures.
Phenylketonuria (PKU)
A genetic disorder in which the body lacks an important enzyme. If untreated, the disorder can lead to brain damage and mental retardation.

Further Reading

Gale Encyclopedia of Medicine. Gale Research, 1999.

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