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HomeProduct name listGranisetron Hydrochloride

Granisetron Hydrochloride

Synonym(s):1-Methyl-N-[(3-endo)-9-methyl-9-azabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide hydrochloride;Granisetron hydrochloride

  • CAS NO.:107007-99-8
  • Empirical Formula: C18H25ClN4O
  • Molecular Weight: 348.87
  • MDL number: MFCD01747034
  • EINECS: 634-603-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-21 22:41:43
Granisetron Hydrochloride Structural

What is Granisetron Hydrochloride?

Description

Granisetron hydrochloride is the second selective 5HT-3-antagonist approved for the management of nausea and vomiting induced by cancer chemotherapy.Like ondansetron, granisetron hydrochloride is superior to metoclopramide in both efficacy and side effect profile. The compound appears to be effective both as a prophylactic agent and in blocking vomiting once started.

Chemical properties

White to Off-White Crystalline Sold

Originator

SmithKline Beecham (United Kingdom)

The Uses of Granisetron Hydrochloride

anticoagulant

The Uses of Granisetron Hydrochloride

A specific serotonin (5HT3) receptor antagonist. Used as an antiemetic. Granisetron HCl is a serotonin 5-HT3 receptor antagonist used as an antiemetic to treat nausea and vomiting following chemothera py. Its main effect is to reduce the activity of the vagus nerve. It does not have much effect on vomiting due to motion sickness. This drug does not have any effect on dopamine receptors or muscarini c receptor

The Uses of Granisetron Hydrochloride

These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

What are the applications of Application

Granisetron hydrochloride is a SR-3 antagonist

Manufacturing Process

A solution of 1-(phenylmethyleneamino)isatin (1.354 g, 0.0054 mol) and endo-3-amino-9-methyl-9-azabicyclo[3.3.1]nonane (0.832 g, 0.0054 mol) in dry THF (25 ml) under argon was heated to reflux for 5 hours. The solution was cooled and evaporated and the residual traces of THF were azeotropically removed with dichloromethane. The residue was triturated with ether to give the intermediate 2-(benzylidenehydrazino)-α-oxophenyl-(9-methyl-9- azabicyclo[3.3.1]non-3-yl)carboxamide as an orange powder (1.583 g, 73%).
Sodium hydride (50 mg, 60% dispersion in oil) was added to a solution of the 2-(benzylidenehydrazino)-α-oxophenyl-(9-methyl-9-azabicyclo[3.3.1]non-3-yl) carboxamide in dry THF (2.3 ml) under argon at -50°C. The resultant solution was warmed to 0°C over 20 min then cooled to -30°C and treated with methyl iodide (0.020 ml). The solution was allowed to warm to room temperature and stirred for 24 hours then filtered. The filtrate was evaporated to dryness, and triturated with chloroform to give the 2-(N-methylbenzylidenehydrazo)-α- oxophenyl-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)carboxamide as a light coloured powder (50 mg, 38%). Further trituration of the mother liquor gave a further crop, (37 mg, 28%, after recrystallisation from chloroform).
A solution of 2-(N-methylbenzylidenehydrazo)-α-oxophenyl-(9-methyl-9- azabicyclo[3.3.1]non-3-yl)carboxamide (37 mg) in methanol (1 ml) was treated with 2 N hydrochloric acid (0.1 ml) and left at room temperature for several hours. Evaporation of the solvent gave the crude product as a brown oil (36 mg). HPLC and MS analysis confirmed the structure and indicated a quantitative yield of endo-N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-1- methylindazole-3-carboxamide (Ganisetron).
In practice it is usually used as hydrochloride.

brand name

Kytril (Roche).

Therapeutic Function

Serotonin antagonist

General Description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Biological Activity

5-HT 3 receptor antagonist that possesses potent antiemetic activity.

Biochem/physiol Actions

Granisetron hydrochloride is a serotonin 5-HT3 receptor antagonist and antiemetic.

Pharmacology

Granisetron Hydrochloride is a highly selective 5-HT3 receptor antagonist with good preventive and therapeutic effects on nausea and vomiting caused by radiotherapy, chemotherapy and surgery. Factors such as radiotherapy, chemotherapy and surgery can cause enterochromaffin cells to release 5-HT, and 5-HT can activate 5-HT3 receptors in the central or vagus nerve and cause gag reflex. The mechanism of this product to control nausea and vomiting is to inhibit the occurrence of nausea and vomiting by antagonizing the 5-HT3 receptors in the central chemoreceptor area and peripheral vagus nerve endings.

Pharmacokinetics

After intravenous injection of 20 or 40 μg/kg of this product in healthy subjects, the average peak plasma concentration was 13.7 and 42.8 μg/L, and the plasma elimination half-life was about 3.1-5.9 hours. Granisetron hydrochloride is widely distributed in the body, the serum protein binding rate is about 65%, and most of it is rapidly metabolized. The main metabolic pathway is N-dealkylation and aromatic epoxidation and then conjugated. It is excreted in feces and urine.

Veterinary Drugs and Treatments

Granisetron is an alternative to other 5-HT3 receptor antagonists (e.g., ondansetron or dolasetron) for the treatment of severe vomiting or prophylaxis before administering antineoplastic drugs such as cisplatin that can cause severe vomiting.

storage

Desiccate at +4°C

Properties of Granisetron Hydrochloride

Melting point: 290-292°C
storage temp.  Room temp
solubility  H2O: >10mg/mL
form  solid
color  white to off-white
Merck  14,4536
CAS DataBase Reference 107007-99-8(CAS DataBase Reference)

Safety information for Granisetron Hydrochloride

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral

Computed Descriptors for Granisetron Hydrochloride

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