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D-Mannitol
Systematic (IUPAC) name
(2R,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexol
Identifiers
CAS number 69-65-8
ATC code A06AD16 B05BC01 B05CX04
PubChem 453
DrugBank APRD01083
ChemSpider 6015
Chemical data
Formula C 6H14O6  
Mol. mass 182.172
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability ~7%
Metabolism Hepatic, negligible.
Half life 100 minutes
Excretion Renal: 90%
Therapeutic considerations
Pregnancy cat. C: (USA)
Legal status
Routes Intravenous
Oral
 Yes check.svgY(what is this?)  (verify)

Mannitol is an organic compound with the formula (C6H8(OH)6). This polyol is used as an osmotic diuretic agent and a weak renal vasodilator. It was originally isolated from the secretions of the flowering ash, called manna after their resemblance to the Biblical food, and is also be referred to as mannite and manna sugar.[1]

Contents

Chemistry

Mannitol is a sugar alcohol, that is, it is derived from a sugar by reduction. Other sugar alcohols include xylitol and sorbitol. Aqueous solutions of mannitol are mildly acidic and sometimes such solutions are treated to raise the pH. Chemical Abstracts Registry Numbers for mannitol are 123897-58-5, 69-65-8 (D-Mannitol), 75398-80-0, 85085-15-0, and 87-78-5 (mannitol with unspecified stereochemistry).

Uses

Medical applications

Mannitol is used clinically to reduce acutely raised intracranial pressure until more definitive treatment can be applied, e.g., after head trauma. This use is controversial,[2][3][4] though reference to it is still made in texts published as recently as 2009.[5] It is also used to treat patients with oliguric renal failure. It is administered intravenously, and is filtered by the glomeruli of the kidney, but is incapable of being resorbed from the renal tubule, resulting in decreased water and Na+ reabsorption via its osmotic effect. Consequently, mannitol increases water and Na+ excretion, thereby decreasing extracellular fluid volume.

Mannitol can also be used to open the blood-brain barrier by temporarily shrinking the tightly coupled endothelial cells that make up the barrier. This makes mannitol indispensable for delivering various drugs directly to the brain (e.g., in the treatment of Alzheimer's disease). Mannitol is commonly used in the circuit prime of a heart lung machine during cardiopulmonary bypass. The presence of mannitol preserves renal function during the times of low blood flow and pressure, while the patient is on bypass. The solution prevents the swelling of endothelial cells in the kidney, which may have otherwise reduced blood flow to this area and resulted in cell damage.

Mannitol is also being developed by an Australian pharmaceutical company as a treatment for cystic fibrosis and bronchiectasis and as a diagnostic test for airway hyperresponsiveness. The mannitol is orally inhaled as a dry powder through what is known as an osmohaler and osmotically draws water into the lungs to thin the thick, sticky mucus characteristic of cystic fibrosis. This is intended to make it easier for the sufferer to cough the mucus up during physiotherapy. The critical characteristic of the mannitol is its particle size distribution.

Mannitol is also the first drug of choice for the treatment of acute glaucoma in veterinary medicine. It is administered as a 20% solution IV. It dehydrates the vitreous humor and thus lower the intraocular pressure. However, it requires an intact blood-ocular barrier to work.[6]

Mannitol can also be used to temporarily encapsulate a sharp object (such as a helix on a lead for an artificial pacemaker) while it is passed through the venous system. Because the mannitol dissolves readily in blood, the sharp point will become exposed at its destination.

Mannitol may be administered in cases of severe Ciguatera poisoning. Severe ciguatoxin, or "tropical fish poisoning" can produce stroke-like symptoms.

Mannitol is the primary ingredient of Mannitol Salt Agar, a bacterial growth medium, and is used in others.

In oral doses larger than 20 g, mannitol acts as an osmotic laxative, and is sometimes sold as a laxative for children.

In foods

Mannitol is also used as a sweetener for people with diabetes. Since mannitol has a positive heat of solution, it is used as a sweetener in "breath-freshening" candies, the cooling effect contributing to the fresh feel. The pleasant taste and mouthfeel of mannitol also makes it a popular excipient for chewable tablets.[7]

In illicit drugs

Mannitol is sometimes used as an adulterant or cutting agent for heroin, methamphetamines or other illicit drugs. In popular culture, when it is used in this manner, it is often referred to as baby laxative.[8]

Controversy

The three studies[9][10][11] which initially found that high-dose mannitol was effective in cases of severe head injury have been the subject of a recent investigation.[12] Although several authors are listed with Dr. Julio Cruz, it is unclear whether the authors had knowledge of how the patients were recruited. Further, the Federal University of São Paulo, which Dr. Cruz gave as his affiliation, has never employed him. Currently, therefore, the Cochrane review recommending high-dose mannitol[13] has been withdrawn pending re-evaluation, as there is some evidence that mannitol may worsen cerebral edema.[14]

See also

References

  1. ^ Cooley's Cyclopaedia of Practical Receipts, 6th ed. (1880)
  2. ^ http://ijntonline.com/June08/abstracts/abs4.PDF
  3. ^ http://ceaccp.oxfordjournals.org/cgi/content/full/6/2/79
  4. ^ http://www.ncbi.nlm.nih.gov/pubmed/17727664
  5. ^ PreTest Surgery, 12th Edition, 2009.
  6. ^ Veterinary Class Notes, Ophthalmology, The Ohio State University, provided by David Wilkie, DVM, DACVO
  7. ^ Weiner, Myra L.; Lois A. Kotkoskie (1999). Excipient Toxicity and Safety. pp. 370. ISBN 0824782100, 9780824782108.  
  8. ^ An interview on the History Channel show Gangland showed a man claiming to be the chief methamphetamine "cooker" for the Pagans MC in Philadelphia, who stated that he used mannitol, a "baby laxative", as a "cut" for methamphetamine. He stated that in his hands the drug began as a purple color, and became first dark pink, then light pink, finally white as successive adulterations were done with mannitol. In the interview he stated that people snorting a line of the powder would need to go to the bathroom as a result of using it. He said that they incorrectly believed that this was the result of the potency of the drug, but it was actually caused by the added mannitol.
  9. ^ Cruz J, Minoja G, Okuchi K. Improving clinical outcomes from acute subdural hematomas with the emergency preoperative administration of high doses of mannitol: a randomized trial. Neurosurgery. 2001 Oct;49(4):864-71. PMID 11564247
  10. ^ Cruz J, Minoja G, Okuchi K. Major clinical and physiological benefits of early high doses of mannitol for intraparenchymal temporal lobe hemorrhages with abnormal pupillary widening: a randomized trial. Neurosurgery. 2002 Sep;51(3):628-37; discussion 637-8. PMID 12188940
  11. ^ Cruz J, Minoja G, Okuchi K, Facco E. Successful use of the new high-dose mannitol treatment in patients with Glasgow Coma Scale scores of 3 and bilateral abnormal pupillary widening: a randomized trial. J Neurosurg. 2004 Mar;100(3):376-83. PMID 15035271
  12. ^ Roberts I, Smith R, Evans S. Doubts over head injury studies. BMJ. 2007 Feb 24;334(7590):392-4. PMID 17322250
  13. ^ Wakai A, Roberts I, Schierhout G. Mannitol for acute traumatic brain injury. Cochrane Database Syst Rev. 2005 Oct 19;(4):CD001049. PMID 16235278
  14. ^ Kaufmann AM, Cardoso ER. Aggravation of vasogenic cerebral edema by multiple-dose mannitol. J Neurosurg. 1992 Oct;77(4):584-9. PMID 1527619

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