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Encyclopedia > Ondansetron
Ondansetron chemical structure
Ondansetron
Systematic (IUPAC) name
9-methyl-3-[(2-methyl-1H-imidazol-1-yl)
methyl]-1,2,3,9-tetrahydrocarbazol-4-one
Identifiers
CAS number 99614-02-5
ATC code A04AA01
PubChem 4595
DrugBank APRD00481
Chemical data
Formula C18H19N3O 
Mol. weight 325.9 g/mol
Pharmacokinetic data
Bioavailability ~60%
Protein binding 70%-76%
Metabolism Hepatic (CYP3A4, CYP1A2, CYP2D6)
Half life 5.7 hours
Excretion Renal
Therapeutic considerations
Pregnancy cat.

B1(AU) B(US) Ondansetron structure. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A division of the Anatomical Therapeutic Chemical Classification System A Alimentary tract and metabolism A04A Antiemetics and antinauseants A04AA Serotonin (5-HT3) antagonists A04AA01 Ondansetron A04AA02 Granisetron A04AA03 Tropisetron A04AA04 Dolasetron A04AD Other antiemetics A04AD01 Scopolamine A04AD02 Cerium oxalate A04AD04 Chlorobutanol A04AD05 Metopimazine A04AD10 Dronabinol A04AD11 Nabilone A04AD51 Scopolamine, combinations... PubChem is a database of chemical molecules . ... DrugBank is a database available at the University of Alberta that provides information about thousands of products. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Atomic mass 15. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Many drugs are bound to Blood plasma proteins. ... Overview of the citric acid cycle The citric acid cycle, one of the central metabolic pathways in aerobic organisms. ... The liver is an organ in living beings, including humans. ... Cytochrome P450 3A4 (abbreviated CYP3A4) (EC 1. ... This page is a candidate for speedy deletion. ... Cytochrome P450 2D6 (abbreviated CYP2D6, EC 1. ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... Excretion is the biological process by which an organism chemically separates waste products from its body. ... The kidneys are bean-shaped excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... Motto: None Anthem: Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney English (de facto 1) Government Constitutional monarchy (federal)  - Queen Elizabeth II  - Governor-General Michael Jeffery  - Prime Minister John Howard Independence from the UK   - Constitution 1 January 1901   - Statute of Westminster 11 December 1931... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Legal status

S4(AU) POM(UK) -only(US) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... Motto: None Anthem: Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney English (de facto 1) Government Constitutional monarchy (federal)  - Queen Elizabeth II  - Governor-General Michael Jeffery  - Prime Minister John Howard Independence from the UK   - Constitution 1 January 1901   - Statute of Westminster 11 December 1931... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Routes Oral, rectal, IV, IM

Ondansetron (INN) (IPA: [ɒnˈdænsɛˌtrɒn]) is a serotonin 5-HT3 receptor antagonist used mainly to treat nausea and vomiting following chemotherapy. Its effects are thought to be on both peripheral and central nerves. One part is to reduce the activity of the vagus nerve, which is a nerve that activates the vomiting center in the medulla oblongata, the other is a blockage of serotonin receptors in the chemoreceptor trigger zone. It does not have much effect on vomiting due to motion sickness. This drug does not have any effect on dopamine receptors or muscarinic receptors. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Four 500mg acetaminophen/paracetamol suppositories A suppository is a medicine that is inserted either into the rectum (rectal suppository) or into the vagina (vaginal suppository) where it melts. ... Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... Intramuscular injection is the injection of a substance directly into a muscle. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... For information on how to read IPA transcriptions of English words see here. ... Serotonin (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system (CNS) and enterochromaffin cells in the gastrointestinal tract. ... For other uses, see Nausea (disambiguation). ... Vomiting (also throwing up or emesis) is the forceful expulsion of the contents of ones stomach through the mouth. ... Chemotherapy is the use of chemical substances to treat disease. ... The vagus nerve (also called pneumogastric nerve or cranial nerve X) is the tenth of twelve paired cranial nerves, and is the only nerve that starts in the brainstem (within the medulla oblongata) and extends, through the jugular foramen, down below the head, to the abdomen. ... The medulla oblongata is the lower portion of the brainstem. ... The Chemoreceptor trigger zone (CTZ) is an area of the brain which receives inputs from blood-borne drugs or hormones, and communicates with the Vomit Centre, to initiate vomiting. ... This article or section is in need of attention from an expert on the subject. ... Amanita muscaria from which muscarine was isolated Acetylcholine - natural agonist of muscarinic and nicotinic receptors. ...


The drug is administered 1–3 times daily, depending on the severity of nausea and/or vomiting. The normal dose for adults and children over the age of 12, is 8 mg initially, followed by a second dose of 8 mg, eight hours later. The drug is then administered once every 12 hours, usually not for more than 2-3 days. Following oral administration, it takes about 1.5–2 hours to reach maximum plasma concentrations. This drug is removed from the body by the liver and kidneys. The liver is an organ in living beings, including humans. ... The kidneys are bean-shaped excretory organs in vertebrates. ...


It is currently marketed by GlaxoSmithKline (GSK) under the trade name Zofran®; other manufacturers include Cipla Ltd. (Emeset), Gedeon Richter Ltd. (Emetron), and Zentiva a.s. (Ondemet). On May 29, 2006, Baxter Healthcare received tentative approval [1] to market its own label of Ondansetron Injection, USP, 8 mg/50 mL and 32 mg/50 mL iso-osmotic sodium chloride solution, after GSK's patent expires on December 24, 2006. GlaxoSmithKline plc (LSE: GSK NYSE: GSK) is a British based pharmaceutical, biologicals, and healthcare company. ... Cipla is an Indian pharmaceutical company, best-known for manufacturing cheap anti-AIDS drugs. ... Gedeon Richter Ltd. ... Baxter, Incorporated (NYSE: BAX), is a global Medical Instruments & Supplies company, with headquarters in Deerfield, IL. // History A detailed history of Baxter can be found at on the Baxter Company Website Management Robert L. Parkinson Jr. ...

Contents

History

Ondansetron was developed around 1984 by scientists working at Glaxo's laboratories in London. After several attempts the company successfully filed for U.S. patent protection for the drug in 1986. U.S. Patent 4,695,578 was granted in September 1987 while U.S. Patent 4,753,789 was granted in June 1988. U.S. Patent 5,578,628, a divisional patent of U.S. Patent 4,753,789, was granted in November 26, 1996. Ondansetron was granted Food and Drug Administration (FDA) approval as Zofran in January 1991. Glaxo did pediatric research on Zofran's uses, and gained patent extension as a result. Consequently U.S. exclusivity is now set to end December 24, 2006. London (pronounced ) is the capital city of the United Kingdom and the largest city of England (strangely, England has no constitutional existence within the United Kingdom, and therefore cannot be said to have a capital). ... The Food and Drug Administration (FDA) is an agency of the United States Department of Health and Human Services and is responsible for regulating food (humans and animal), dietary supplements, drugs (human and animal), cosmetics, medical devices (human and animal) and radiation emitting devices (including non-medical devices), biologics, and...


Clinical uses

  • Chemotherapy-induced nausea and vomiting
    • 5-HT3 receptor antagonists are the primary drugs used to treat and prevent chemotherapy-induced nausea and vomiting. Many times they are given intravenously about 30 minutes before beginning therapy.
  • Post-operative and post-radiation nausea and vomiting
  • Is a possible therapy for nausea and vomiting due to acute or chronic medical illness or acute gastroenteritis

Although highly effective, its high cost limits its use to controlling postoperative nausea and vomiting (PONV) and chemotherapy-induced nausea and vomiting (CINV). It is also used off-label to treat hyperemesis gravidarum in pregnant women, but there is no conclusive data available on its safety in pregnancy, especially during the first trimester. It is also often used to treat cyclic vomiting syndrome although there have been no formal trials to confirm efficacy, case reports suggest it can be helpful in some cases. Nausea and vomiting caused by chemotherapy; stomach upset may trigger a strong urge to vomit, or forcefully eliminate what is in the stomach. ... Gastroenteritis involves diarrhea or vomiting, with noninflammatory infection of the upper small bowel, or inflammatory infection of the colon, both part of the gastrointestinal tract. ... Postoperative nausea and vomiting is an unpleasant complication affecting about a third of the 10% of the population undergoing general anaesthesia each year. ... Nausea and vomiting caused by chemotherapy; stomach upset may trigger a strong urge to vomit, or forcefully eliminate what is in the stomach. ... Hyperemesis gravidarum (from the Latin for extreme vomiting of the pregnant woman) is a severe form of morning sickness. ... This article or section contains information that has not been verified and thus might not be reliable. ...


Clinical effect of ondansetron (and other drugs from the same group) can be potentiated by combining it with dexamethasone. Dexamethasone is a potent synthetic member of the glucocorticoid class of steroid hormones. ...


Adverse effects

Ondansetron is a well-tolerated drug with few side effects. Headache, constipation, and dizziness are the most commonly reported side effects associated with its use. There have been no significant drug interactions reported with this drug's use. It is broken down by the hepatic cytochrome P450 system and it has little effect on the metabolism of other drugs broken down by this system. Cytochrome P450 Oxidase (CYP2E1) Cytochrome P450 oxidase (commonly abbreviated CYP) is a generic term for a large number of related, but distinct, oxidative enzymes (EC 1. ...


Media

Harvard Medical School Associate Professor Emeritus of Psychiatry Lester Grinspoon discussed ondansetron in a 1997 interview about cannabis with the Australian Broadcasting Corporation: [2] Shield of Harvard Medical School Harvard Medical School (HMS) is one of the graduate schools of Harvard University. ... Lester Grinspoon. ... A Cannabis sativa plant Look up marijuana in Wiktionary, the free dictionary. ... The Australian Broadcasting Corporation or ABC (formerly the Australian Broadcasting Commission) is Australias national non-profit public broadcaster. ...


Q: I presume the pharmaceutical companies would not be enormously in favour of marijuana suddenly appearing on the scene as a major competitor?


A: No. Take ondansetron for example. The drug company is paid almost $20 for an eight milligram pill. A marijuana cigarette, which is just as effective, if not more so, will cost around 30 cents. Is it any wonder the drug companies are concerned about marijuana becoming legally available.


See also

Granisetron is used to prevent nausea and vomiting caused by cancer chemotherapy and radiation therapy. ... Dolasetron is a drug used to treat nausea following chemotherapy. ... Alosetron is a 5-HT3 antagonist used for the management of severe diarrhoea-predominant irritable bowel syndrome (IBS) in women only. ...

References

 - 4,695,578 - 4,753,789 - 5,578,628 

  Results from FactBites:
 
Ondansetron - Wikipedia, the free encyclopedia (630 words)
Ondansetron (INN) (IPA: [ɒnˈdænsɛˌtrɒn]) is a serotonin 5-HT receptor antagonist used mainly to treat nausea and vomiting following chemotherapy.
Ondansetron was developed around 1984 by scientists working at Glaxo's laboratories in London.
Ondansetron was granted Food and Drug Administration (FDA) approval as Zofran in January 1991.
Ondansetron for Anxiety & Novel Applications (2268 words)
Ondansetron, an antiemetic with anxiolytic properties, has been shown to be effective for treatment of social phobia in a double-blind, placebo-controlled study.
Ondansetron is a selective 5-hydroxytryptamine(3) (5-HT(3)) receptor antagonist that has been introduced to clinical practice as an antiemetic for cancer treatment-induced and anesthesia-related nausea and vomiting.
Ondansetron in all the doses tested (0.01, 0.1 and 1 mg/kg i.p.) showed significant anxiolytic action as compared to naive mice, but it was less potent as compared to a well-known anxiolytic, diazepam (1 mg/kg).
  More results at FactBites »

 
 

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