Molecular structure of pseudoephedrine
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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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Brain Fever. - book reviews
From Commonweal, 6/1/96 by Alice McDermott

The problem at the heart of this witty, energetic fifth novel by the author of Due East and The Distance between Us is not that its narrator, Tim Rooney, is a madman: bug-eyed geniuses giving diabolically brilliant accounts of themselves are not unknown in literature. The problem is that Tim Rooney ("middle-aged failed academic, failed musician, failed husband") is mentally ill--a far less romantic assessment, and one more likely to be associated in the contemporary reader's mind with emotional pain and ruined lives. Those associations belie the wit and energy and exuberance of Rooney's careening account, in an endearing Southern drawl, of a horrendous mental breakdown.

Tim Rooney has broken down before. Seven years ago he returned to his father's house in Due East, South Carolina--site of the author's four previous novels--to "have a crackup." "I took a whiz in the front row of Our Lady of Perpetua' Help at the midnight Mass. I made various claims to be the Christ child and Blaise Pascal and Bobby What's-hisname, the sympathetic one on 'Dallas.'" He has lived through "the Clozapine years, the lithium years, the Prozac years" and, as the novel begins, has "reentered sanity." He plans to marry Mary Faith Rapple, the lovely young girl next door and to adopt her eleven-year-old son, Jesse, whom he adores.

But then Mary Faith arrives at his house on Holy Thursday evening in a new Easter outfit and asks that he bring her to church Easter morning. She is an atheist. He is, if not a good Catholic, a tenacious one. Suddenly, the shadow of his illness descends: the hallucinations, the buzzing sound, the chill. Brain fever.

He calls off the wedding ("I cannot be responsible for a false conversion"), and then loses his own faith on Holy Saturday when he wakes in his sister Dottie's bed--Dottie, the youngest of the Rooney offspring, who drowned herself at twenty-one. On Easter Monday morning, he stuffs $15,000 into his socks and heads for New York City. "With a new clarity, sharper even than the Drixoral variety," he knows he must find Bernadette, his wife from a six-day marriage that ended twenty years ago.

It is not surprising that religion should be a catalyst for Rooney's breakdown. His father was a musician prone to violence, but his mother was an activist Catholic. "She lined her children up at the kitchen table to write appeals to her congressman for civil rights and human rights and poverty rights and the right to be as right about the moral issues of the day as she always happened to be." Rooney himself believed a statue of the Blessed Mother smiled at him as a child.

Leaving Due East, Rooney is followed by a black man in a black truck--a guardian angel? In Charleston he picks up Angela Bliss, a beautiful hitchhiker running away from her own wedding. Angela is remarkably nonplussed by Rooney, even as he nearly drowns them both, even as he grows more and more paranoid about being followed. When they reach New York, she brings him, blacked-out and raving, to a loft in Soho owned by two more Southerners, Velma and Fred. In the morning, Rooney explains away his deranged behavior by telling them he is an actor testing a role, and Velma and Fred, in what is either incredible naivete or unsurpassed Southern hospitality, invite him to stay on.

In the course of his forty-day descent into insanity, Rooney has bouts of clarity, bouts of memory, bouts of joy and panic and lust and regret. Sayers is remarkably skillful in seamlessly moving him back and forth, from one state to the other, in delineating his transformation from charming eccentric--he reminds everyone of Kramer from "Seinfeld"--to deranged street creature or, as he would have it, outlaw.

Rooney soon discovers that his guardian angel is G.B. Bright, his former student, and that Bright has been asked by Father Berkeley, Rooney's pastor in Due East, to keep an eye on him. G.B. does more than that, he rescues Rooney from the street, drinks with him, feeds him as he deteriorates, bathes and changes him when he becomes incontinent, even, with a wisdom that mysteriously eludes all the other characters, attempts to get him to a doctor.

Meanwhile, back in Due East, Father Berkeley has enlisted Mary Faith in a quest to rescue Rooney, telling her, "You have the chance to make a choice now. You can chose not to take on the nursing of a man who will have these...incidents all his life." She and Jesse head for New York with the old priest, who is certain that on the fortieth day of his madness, Rooney will take his own life.

Instead, there is a reunion. Having found Bernadette, Rooney has moved on to confront larger reasons for guilt: his sister's suicide, his mother's loss of faith, Bosnia. Ensconced in Washington Square Park, clothes in tatters, feet bleeding, feverish, he engages the crowds in a mad chant: Bosnia Bosnia--"so many souls to save,"--and that's where Mary Faith and Jesse find him.

As in her previous novels, Sayers's voice is so engaging, so precise and funny and strong, that it is unfortunate here to find her subject undermining it. It is not that the author lacks sympathy for her character's situation--Mary Faith acknowledges and embodies the pain Rooney's illness can cause--or that her story needs more pathos, more seriousness. It is rather that she, like Angela and Velma, seems slow to recognize that this loquacious Southern eccentric is in the throes of a serious illness, and that our understanding of mental illness, like our knowledge of tuberculosis and cancer, has changed forever its usefulness as a literary device.

Alice McDermott is the author of At Weddings and Wakes (1992) among other novels. She lives in Pittsburgh.

COPYRIGHT 1996 Commonweal Foundation
COPYRIGHT 2004 Gale Group

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