Granisetron

Title: Granisetron
CAS Registry Number: 109889-09-0
CAS Name: 1-Methyl-N-[(3-endo)-9-methyl-9-azabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide
Molecular Formula: C18H24N4O
Molecular Weight: 312.41
Percent Composition: C 69.20%, H 7.74%, N 17.93%, O 5.12%
Literature References: Specific serotonin (5HT3) receptor antagonist. Prepn: F. D. King, EP 200444; idem, US 4886808 (1986, 1989 both to Beecham). 5HT3 receptor binding study: G. J. Kilpatrick et al., Nature 330, 746 (1987). Series of articles on pharmacology and clinical trials to prevent chemotherapy-induced emesis: Semin. Oncol. 22, Suppl. 10, 1-30 (1995).
Derivative Type: Hydrochloride
CAS Registry Number: 107007-99-8
Manufacturers' Codes: BRL-43694A
Trademarks: Kytril (SKB)
Molecular Formula: C18H24N4O.HCl
Molecular Weight: 348.87
Percent Composition: C 61.97%, H 7.22%, N 16.06%, O 4.59%, Cl 10.16%
Properties: White to off-white solid, mp 290-292°. Readily sol in water at 20°.
Melting point: mp 290-292°
Therap-Cat: Antiemetic.
Keywords: Antiemetic; Serotonin Receptor Antagonist.
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Granisetron
Granisetron.svg
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Systematic (IUPAC) name
1-methyl-N-((1R,3r,5S)-9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)-1H-indazole-3-carboxamide
Clinical data
Trade names Kytril
AHFS/Drugs.com monograph
MedlinePlus a601211
Pregnancy cat. B1 (AU)
Legal status Prescription Only (S4) (AU) POM (UK) -only (US)
Routes Oral, intravenous, transdermal
Pharmacokinetic data
Bioavailability 60%
Protein binding 65%
Metabolism Hepatic
Half-life 3–14 hours
Excretion Renal 11–12%, faecal 38%
Identifiers
CAS number 109889-09-0 YesY
ATC code A04AA02
PubChem CID 3510
IUPHAR ligand 2300
DrugBank DB00889
ChemSpider 10482033 YesY
UNII WZG3J2MCOL YesY
KEGG D04370 YesY
ChEBI CHEBI:5537 N
ChEMBL CHEMBL519643 N
Chemical data
Formula C18H24N4O 
Mol. mass 312.41 g/mol
 N (what is this?)  (verify)

Granisetron is a serotonin 5-HT3 receptor antagonist used as an antiemetic to treat nausea and vomiting following chemotherapy. Its main effect is to reduce the activity of the vagus nerve, which is a nerve that activates the vomiting center in the medulla oblongata. 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.

Granisetron was developed by chemists working at the British drug company Beecham around 1988 and is available as a generic. It is produced by Roche Laboratories under the trade name Kytril. The drug was approved in the United Kingdom in 1991 and in United States in 1994 by the FDA.

A granisetron transdermal patch with the trade name Sancuso was approved by the US FDA on September 12, 2008.[1] Sancuso is manufactured by ProStrakan, Inc., a pharmaceutical company headquartered in Bedminster, NJ, with global headquarters in Scotland.

Granisetron is metabolized slowly by the liver, giving it a longer than average half-life. One dose usually lasts 4 to 9 hours and is usually administered once or twice daily. This drug is removed from the body by the liver and kidneys.