Ondansetron Hydrochloride

Modify Date: 2024-01-02 11:49:50

Ondansetron Hydrochloride Structure
Ondansetron Hydrochloride structure
Common Name Ondansetron Hydrochloride
CAS Number 99614-01-4 Molecular Weight 329.824
Density 1.27g/cm3 Boiling Point 546ºC at 760mmHg
Molecular Formula C18H20ClN3O Melting Point 178.5-179.5ºC
MSDS N/A Flash Point 284ºC

 Use of Ondansetron Hydrochloride


Ondansetron is a serotonin 5-HT3 receptor antagonist used mainly as anantiemetic (to treat nausea and vomiting), often following chemotherapy.Target: 5- HT ReceptorIC50 Value: in vitro: 5-HT evoked transient inward currents (EC50 = 3.4 microM; Hill coefficient = 1.8) that were blocked by the 5-HT3 receptor antagonist ondansetron (IC50 = 103 pM) [1]. The 5-HT3A receptor antagonist ondansetron (0.3 nM) reversibly inhibited the 5-HT (30 microM) signal by 70% and at 3 nM it abolished the response [2].in vivo: Acute ondansetron administration at the lowest dose (0.1 mg/kg, IP) tested had no effect, while other doses (0.33 and 1 mg/kg, IP) produced improvements in auditory gating [3]. Different doses of ondansetron were injected intraperitoneally (i.p.) at fixed times during the day to determine both the sublethal (TD50) and lethal (LD50) doses, which were, respectively, 3.7 +/- 0.6 mg/kg and 4.6 +/- 0.5 mg/kg [4]. ondansetron (0.25-1.0 mg/kg, subcutaneously) given before the challenge dose of ethanol (2.4 g/kg, intraperitoneally) injection, significantly and dose dependently attenuated the expression of sensitization. In addition, ondansetron (1.0 mg/kg, subcutaneously) given before ethanol injection on days 1, 4, 7, and 10 significantly blocked the development (days 1, 4, 7, and 10), and expression (day 15) of sensitization to the locomotor stimulant effect of ethanol injection [5]. Toxicity: Ondansetron may be safe in lower doses used to prevent nausea and vomiting in radiation treatment or postoperatively. However, as there is a report that a lower dose of ondansetron prolonged the QT interval in healthy volunteers, this needs to be clarified by the FDA [6].

 Names

Name ondansetron hydrochloride
Synonym More Synonyms

 Ondansetron Hydrochloride Biological Activity

Description Ondansetron is a serotonin 5-HT3 receptor antagonist used mainly as anantiemetic (to treat nausea and vomiting), often following chemotherapy.Target: 5- HT ReceptorIC50 Value: in vitro: 5-HT evoked transient inward currents (EC50 = 3.4 microM; Hill coefficient = 1.8) that were blocked by the 5-HT3 receptor antagonist ondansetron (IC50 = 103 pM) [1]. The 5-HT3A receptor antagonist ondansetron (0.3 nM) reversibly inhibited the 5-HT (30 microM) signal by 70% and at 3 nM it abolished the response [2].in vivo: Acute ondansetron administration at the lowest dose (0.1 mg/kg, IP) tested had no effect, while other doses (0.33 and 1 mg/kg, IP) produced improvements in auditory gating [3]. Different doses of ondansetron were injected intraperitoneally (i.p.) at fixed times during the day to determine both the sublethal (TD50) and lethal (LD50) doses, which were, respectively, 3.7 +/- 0.6 mg/kg and 4.6 +/- 0.5 mg/kg [4]. ondansetron (0.25-1.0 mg/kg, subcutaneously) given before the challenge dose of ethanol (2.4 g/kg, intraperitoneally) injection, significantly and dose dependently attenuated the expression of sensitization. In addition, ondansetron (1.0 mg/kg, subcutaneously) given before ethanol injection on days 1, 4, 7, and 10 significantly blocked the development (days 1, 4, 7, and 10), and expression (day 15) of sensitization to the locomotor stimulant effect of ethanol injection [5]. Toxicity: Ondansetron may be safe in lower doses used to prevent nausea and vomiting in radiation treatment or postoperatively. However, as there is a report that a lower dose of ondansetron prolonged the QT interval in healthy volunteers, this needs to be clarified by the FDA [6].
Related Catalog
References

[1]. Brown AM, et al. Ion permeation and conduction in a human recombinant 5-HT3 receptor subunit (h5-HT3A). J Physiol. 1998 Mar 15;507 ( Pt 3):653-65.

[2]. Barann M, et al. Recombinant human 5-HT3A receptors in outside-out patches of HEK 293 cells: basic properties and barbiturate effects. Naunyn Schmiedebergs Arch Pharmacol. 2000 Sep;362(3):255-65.

[3]. Wildeboer KM, et al. Ondansetron results in improved auditory gating in DBA/2 mice through a cholinergic mechanism. Brain Res. 2009 Dec 1;1300:41-50.

[4]. Khedhaier A, et al. Circadian rhythms in toxic effects of the serotonin antagonist ondansetron in mice. Chronobiol Int. 2003 Nov;20(6):1103-16.

[5]. Umathe SN, et al. The 5-HT3 receptor antagonist, ondansetron, blocks the development and expression of ethanol-induced locomotor sensitization in mice. Behav Pharmacol. 2009 Feb;20(1):78-83.

[6]. Doggrell SA, et al. Cardiac safety concerns for ondansetron, an antiemetic commonly used for nausea linked to cancer treatment and following anaesthesia. Expert Opin Drug Saf. 2013 May;12(3):421-31.

 Chemical & Physical Properties

Density 1.27g/cm3
Boiling Point 546ºC at 760mmHg
Melting Point 178.5-179.5ºC
Molecular Formula C18H20ClN3O
Molecular Weight 329.824
Flash Point 284ºC
Exact Mass 329.129486
PSA 39.82000
LogP 3.93050
Storage condition −20°C
Water Solubility H2O: >5 mg/mL

 Safety Information

Hazard Codes T: Toxic;
Risk Phrases R25
Safety Phrases 45-37/39-26
RIDADR UN 2811 6
WGK Germany 3
RTECS FE6375500
Packaging Group II
Hazard Class 6.1(a)
HS Code 29339900

 Synthetic Route

~90%

Ondansetron Hydrochloride Structure

Ondansetron Hyd...

CAS#:99614-01-4

Literature: WO2005/37822 A1, ; Page/Page column 12 ;

~78%

Ondansetron Hydrochloride Structure

Ondansetron Hyd...

CAS#:99614-01-4

Literature: WO2005/37822 A1, ; Page/Page column 12 ;

~93%

Ondansetron Hydrochloride Structure

Ondansetron Hyd...

CAS#:99614-01-4

Literature: YUHAN CORPORATION Patent:   WO2005/37822 A1, 2005 ; Location in patent: Page/Page column 12 ;

 Synonyms

UNII:2999F27MAD
(R)-Ondansetron Hydrochloride Dihydrate
4H-CARBAZOL-4-ONE,1,2,3,9-TETRAHYDRO-9-METHYL-3-[(2-METHYL-1H-IMIDAZOL-1-YL)METHYL]-,HYDROCHLORIDE (1:1)
9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-1,2,3,9-tetrahydro-4H-carbazol-4-one
LSUREMONOETHANOLAMID
Ondansetron HCl
1,2,3,9-Tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one hydrochloride
OEA,oleoylethanolamide
N-(Hydroxyethyl)oleamide
9-Methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-1,2,3,9-tetrahydro-4H-carbazol-4-one hydrochloride
[3H]-Oleoylethanolamide
oleic acid ethanolamide
ONDANSETRON HCL DIHYDRATE
9-methyl-3-[(2-methyl-1h-imidazol-1-yl)methyl]-1,2,3,9-tetrahydro-4h-carbazol-4-onhydrochlorid
Ondansetron HCl (Zofran)
4H-carbazol-4-one, 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-, monohydrochloride
oleic monoethanolamide
Ondansetron (hydrochloride)
ONDANSETRONHYDROCHLORIDE
ONDANSETRON HCL DIHYDRATE IMP. E (EP): 1H-IMIDAZOLE, CRM STANDARD
Ondansetron hydrochloride (Zofran)
oleic acid-N-monoethanolamide
N-(2-Hydroxyethyl)oleamide
OEA
Oleoylethanolamide
[3H]-Ondansetron hydrochloride
4H-Carbazol-4-one, 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-, hydrochloride (1:1)
ODANSETRON HYDROCHLORIDE DIHYDRATE
Ondansetron Hydrochloride
Oleyl monoethanolamide
OLEAMIDE MEA
9-méthyl-3-[(2-méthyl-1H-imidazol-1-yl)méthyl]-1,2,3,9-tétrahydro-4H-carbazol-4-one chlorhydrate
Oleoylmonoethanolamide
9-Methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-1,2,3,9-tetrahydro-4H-carbazol-4-one hydrochloride (1:1)
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