Granisetron
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Granisetron
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CAS No:
109889-09-0
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Formula:
C18H24N4O
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Chemical Name:
Granisetron
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Synonyms:
1H-Indazole-3-carboxamide,1-methyl-N-[(3-endo)-9-methyl-9-azabicyclo[3.3.1]non-3-yl]-;1H-Indazole-3-carboxamide,1-methyl-N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-,endo-;9-Azabicyclo[3.3.1]nonane,1H-indazole-3-carboxamide deriv.;1-Methyl-N-[(3-endo)-9-methyl-9-azabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide;Granisetron;BRL 43694;BRL 43964;Kevatril;endo-Granisetron;Sustol;APF 530;Sancuso;121061-98-1;2407911-98-0
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CAS No:
Description
White to yellowish white crystalline powder, odorless, soluble in water, hard to dissolve in methanol, extremely hard to dissolve in ethanol, almost insoluble in ether. Melting Point: 290~292℃. ChEBI: A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 1-methyl-1H-indazole-3-carboxylic acid with the primary amino group of (3-endo)-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine. A sele tive 5-HT3 receptor antagonist, it is used (generally as the monohydrochlor
Solid
The serotonin type 3 (5-HT3) receptor antagonists are potent antiemetics used for prevention of postsurgical or chemotherapy induced nausea and vomiting and for some agents as therapy of diarrhea-predominant irritable bowel syndrome. The 5-HT3 receptor antagonists are associated with a low rate of transient serum enzyme elevations during therapy, but have been only rarely implicated in cases of clinically apparent liver injury.|A serotonin receptor (5HT-3 selective) antagonist that has been used as an antiemetic for cancer chemotherapy patients.
Characteristics
50.16000
1.47
1.33±0.1 g/cm3(Predicted)
219
532.0±40.0 °C(Predicted)
275.6±27.3 °C
1.690
4.34e-01 g/L
Safety Information
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P305+P351+P338, P330, P337+P313, and P501|Aggregated GHS information provided by 53 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
The 5-HT3 receptor antagonists have been linked to occasional instances of serum enzyme elevations during therapy, but these are generally mild and asymptomatic, resolving rapidly. Because they are used at the time of surgery and with chemotherapy, instances of liver injury arising after their use have been reported, but other drugs or factors may have played a role in the published cases. The rate of serum enzyme elevations with 5-HT3 receptor antagonist therapy has ranged from 1% to 8% and has generally been no greater than that observed with placebo therapy. While moderate serum enzyme elevations during 5-HT3 receptor antagonist therapy have been described, there have been have been only rare and isolated reports of clinically apparent acute liver injury with jaundice attributed to these agents. The onset of injury has been within 1 to 2 weeks of exposure and the pattern of injury hepatocellular and without immunoallergic or autoimmune features. Instances of recurrence after re-exposure have been published. No instances of acute liver failure, chronic hepatitis or vanishing bile duct syndrome have been attributed to the 5-HT3 receptor antagonists.
Drug Information
The serotonin type 3 (5-HT3) receptor antagonists are potent antiemetics used for prevention of postsurgical or chemotherapy induced nausea and vomiting and for some agents as therapy of diarrhea-predominant irritable bowel syndrome. The 5-HT3 receptor antagonists are associated with a low rate of transient serum enzyme elevations during therapy, but have been only rarely implicated in cases of clinically apparent liver injury.
Gastrointestinal Agents
Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)|Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS. (See all compounds classified as Serotonin Antagonists.)
1-Methyl-N-(endo-9-Methyl-9-Azabicyclo(3.3.1)non-3-yl)-1H-Indazole-3-Carboxamide
Granisetron Use and Manufacturing
Anti-emetic.Launched by GSK's predecessor Britain SmithKline pharmaceutical company in the early 90s,Granisetron is an anti-nausea drug for the prevention and treatment of nausea and vomiting caused by chemotherapy and radiotherapy, with 6 ~ 11 time the anti-nausea effect of Ondansetron. Through blocking effect on the upper small intestine stomach centripetal nerve fibers and solitary nucleus or 5 - HT3 receptor in vomiting chemical feeling area, it suppresses nausea and vomiting caused by anti
Computed Properties
Molecular Weight:312.4
XLogP3:2.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:312.19501140
Monoisotopic Mass:312.19501140
Topological Polar Surface Area:50.2
Heavy Atom Count:23
Complexity:442
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Granisetron is a selective 5-hydroxytryptamine 3 (5HT3) receptor antagonist with little or no affinity for other serotonin receptors (including 5-HT1, 5-HT1A, 5-HTIB/C, 5-HT2), alpha1, alpha2, or beta adrenergic receptors, dopamine D2, or histamine H1, benzodiazepines, picrotoxin, or opioid receptors. During chemotherapy that can induce emesis, mucosal enterochromaffin cells can release serotonin, which stimulates 5-HT3 receptors. This can cause vagal afferent discharges, which can induce emesis. Animal studies have shown that granisetron, when bound to the 5-HT3 receptor, can block serotonergic stimulation and subsequent emesis caused by administration of emetogenic stimuli (such as cisplatin).
Registered Holders
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SYN-TECH CHEM AND PHARM CO LTD
Active
United States
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Fujian South Pharmaceutical Co., Ltd.
Active
China
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Yichang Humanwell Pharmaceutical Co., Ltd.
Active
China
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